Ventana Breeze

Ventana Breeze

Sleeps 8 - 3 Bedrooms - 3 Baths

279 Ventana Blvd, Santa Rosa Beach, FL 32459
📍
Ventana Dunes in Blue Mountain Beach
🏝️
1 mile to Blue Mountain Beach Access
🛏️
3 bedrooms, 3 baths
🛺
Six-seater golf cart!
👙
Community pool!
🍤
Gas grill
🚲
3 bikes!
🦞
5-star restaurants
🛍️
Lots of shops, eateries

Ventana Breeze by Oversee 30A | Perfect in Walton County Awards – Three-Time Diamond Winner – Best Rental Mgmt. 2026, 2025, 2024

Welcome to Ventana Breeze, a thoughtfully designed home in Ventana Dunes of Blue Mountain Beach. This quiet cottage community keeps things simple, with a community pool, no through traffic, and an easy, laid-back feel. The beach is about a mile away at Blue Mountain Access, with Ed Walline Public Beach Access just a bit farther down the road. It’s close enough for quick trips, easy mornings, and no overthinking the day’s plan.

Getting around is half the fun here. Hop on one of the three bikes or take the golf cart and head out to Blue Mabel Smokehouse, Johnny McTighes Irish Pub, and Blue Mountain Bakery.

A stop at Blue Mountain Creamery is always a good idea. Between nearby restaurants, coffee spots, and small shops, there’s plenty to keep everyone happy without going far.

Inside, the main living space keeps things comfortable and connected, with the living room flowing right into the dining area and kitchen. It’s a great setup for shared meals, card games, or winding down after the beach.

The kitchen is fully stocked and ready for anything from quick breakfasts to full dinners, with plenty of room for everyone to gather without crowding.

The first floor includes a guest room with a king bed, private bath, and TV, ideal for guests who like a little extra privacy.

Upstairs, the primary bedroom offers its own private bath, while the bunkroom features two twin-over-full bunks and a TV, making it a fun and easy space for kids or extra guests.

Out back, a private patio with seating for four and a gas grill are perfect for relaxed evenings at home. Add in the community pool, included Wi-Fi, and a location that keeps everything within reach, and you’ve got a stay that feels easy from start to finish.

Settle into Ventana Breeze and enjoy a classic 30A getaway. Sounds dreamy, doesn’t it? With Oversee 30A as your host, the answer is yes.

Overview:
- 1 mile to beach (Blue Mountain Access)
- 1.6 miles to Ed Walline Public Beach Access
- 3-bedroom, 3 bath
- 1558 square feet
- Community pool
- Gas grill
- Wi-Fi
- Golf cart included
- 3 bikes included

Overnight:
FIRST FLOOR
Guest Room: king bed, private bath, TV
SECOND FLOOR
Primary Bedroom: king bed, private bath
Bunkroom: two twin over full bunk beds, TV

Details:
Check-in is at 4:00 PM CST and checkout is at 10:00 AM CST

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  • Hassle-free check-in.
  • Add your trip dates to get the cancellation details for this stay.

House Rules

Who can stay.

  • Guests Maximum8 guests maximum
  • No petsNo pets

What's allowed.

  • Check-inCheck-in after 4:00 PM
  • Check-outCheck-out before 10:00 AM
  • No smokingNo smoking
  • No parties or eventsNo parties or events

Amenities

Outdoor

  • BalconyBalcony

Community Amenities

  • Community poolCommunity pool

Indoor

  • Wireless internetWireless internet
  • WorkspaceWorkspace

Safety Features

  • Carbon monoxide detectorCarbon monoxide detector
  • Fire extinguisherFire extinguisher

Kitchen

  • Standard coffee makerStandard coffee maker
  • MicrowaveMicrowave
  • RefrigeratorRefrigerator
  • ToasterToaster
  • DishwasherDishwasher
  • StoveStove

Bed And Bathroom

  • Hair dryerHair dryer
  • Iron & boardIron & board

Entertainment

  • Smart TVSmart TV

Complimentary Items

  • 3 Oversee bikes3 Oversee bikes
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Bed and Baths

1st Floor

bedroom

1 King bed

full bathroom

 

2nd Floor

Primary Bedroom

1 King bed

full bathroom

 

bedroom

2 Bunk beds

full bathroom

 

Location

Upcoming Events

Wed, April 29

Battle of the Bayou Fishing Tournament & Poker Run

Santa Rosa Beach
Outdoor Activities Outdoor Activities

Early registration is open for the inaugural Battle of the Bayou, a weeklong fishing tournament and Poker Run benefiting the Point Washington Medical Clinic. The event is open to all skill levels and includes a week of fishing from any location, a Poker Run on May 2, and an Awards and Weigh-In Celebration featuring food, live music, and prizes. Fishing categories include Redfish, Trout, Bass, and Flounder, while the Poker Run features stops at Baytowne Wharf, Freeport Marina, and Nick’s Seafood. The final celebration includes a low country boil and BBQ. Various registration and ticket options are available, with early bird pricing valid until April 15.

Learn More
Wed, April 29

Contemporary Tai Chi Beginner Classes with Able

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Sifu Able leads a complimentary Tai Chi session every Wednesday at 10:00 AM in the Coastal Branch Library meeting room. This gentle exercise program focuses on enhancing balance, flexibility, and strength for participants of all ages.

Learn More
Wed, April 29

Lego Club Wednesdays

Santa Rosa Beach
Family Fun Family Fun

Lego Club takes place on Wednesdays from 3:30 pm to 4:30 pm in the Coastal Library community meeting room. Participants can create their own Lego designs while meeting new friends.

Learn More
Wed, April 29

Salty Strays

Santa Rosa Beach
Live Music Live Music

Salty Strays will perform a live musical set from 5 PM to 8 PM.

Learn More
Wed, April 29

Killer Robot Army

Santa Rosa Beach
Live Music Live Music

Papa Surf offers a full schedule of events throughout April, featuring live music nearly every night. Guests can also enjoy trivia on Mondays, karaoke on Tuesdays, and Sunday Strings.

Learn More
Wed, April 29

Dirty Bingo

Santa Rosa Beach
Sports & Games Sports & Games

Dirty Bingo is an event that offers a unique and playful twist on the traditional game. Participants can enjoy a lively atmosphere while competing for various prizes.

Learn More
Thu, April 30

Battle of the Bayou Fishing Tournament & Poker Run

Santa Rosa Beach
Outdoor Activities Outdoor Activities

Early registration is open for the first annual Battle of the Bayou, a weeklong fishing tournament and Poker Run that benefits the Point Washington Medical Clinic. The event welcomes anglers of all skill levels for a full week of fishing from any location, followed by a Poker Run on May 2 and a celebration featuring food, live music, and prizes. Fishing categories include Redfish, Trout, Bass, and Flounder, while the Poker Run will include stops at Baytowne Wharf, Freeport Marina, and Nick’s Seafood. The concluding awards ceremony will offer a low country boil and BBQ. Registration is currently available, with early bird pricing offered through April 15.

Learn More
Thu, April 30

Coastal Library Preschool Story Time

Santa Rosa Beach
Family Fun Family Fun

Preschool Story Time at the Coastal Branch Library takes place on Thursday mornings at 10:00 am, featuring stories, songs, crafts, and social interaction for children and their families. Participants can enjoy various tales and musical activities while meeting new friends in a welcoming environment. Following the stories, from 11:00 am until noon, parents and caretakers can socialize while children engage in educational play with different types of blocks and introductory robotics. No registration is required for this community event.

Learn More
Thu, April 30

Ribbon Cutting

Santa Rosa Beach
Sports & Games Sports & Games

YOGO Spine Co. will host a ribbon-cutting ceremony on April 30 at 12:00 PM to celebrate a significant business milestone. Community members and Chamber associates are invited to the location at 2441 US-98 STE 103 in Santa Rosa Beach to meet the team and network with fellow attendees.

Learn More
Thu, April 30

Coastal Library Game Day for Adults

Santa Rosa Beach
Sports & Games Sports & Games

The Coastal Branch Library hosts a Game Day for adults every Thursday from 1:00 PM to 4:00 PM. Community members are encouraged to bring their own card and table games to share with others in the library's meeting space. This gathering provides an opportunity for individuals to play familiar family-friendly games or learn new ones in a social setting. Interested participants can contact the library at 850-267-2809 for further details.

Learn More
Thu, April 30

Bingo Nights, Rooftop Heights

Santa Rosa Beach
Sports & Games Sports & Games

The "Not Your Grandma’s Bingo" event invites guests to join every Thursday for "Bingo with a view" at Ara Rooftop Pool & Lounge Bar, running from 5:00 to 7:00 pm. Attendees can enjoy free games, tasty cocktails, delicious bites, and breathtaking rooftop vibes. Winners receive prizes each round, encouraging guests to bring friends, press their luck, and shout "BINGO!" under the evening sky.

Learn More
Thu, April 30

Billy Garrett & Friends

Santa Rosa Beach
Live Music Live Music

Papa Surf has a busy schedule for the month of April, featuring live music almost every night. The venue also hosts trivia on Mondays, karaoke on Tuesdays, and Sunday Strings. Individuals are encouraged to choose a night to visit.

Learn More
Thu, April 30

Boukou Groove

Santa Rosa Beach
Live Music Live Music

Boukou Groove, a New Orleans-based funk, soul, and jam band established in 2010, features the talents of vocalist and keyboardist Donnie Sundal alongside guitarist Derwin Big D Perkins. The group is scheduled to perform as a duo on April 30, May 7, and May 14, while full band performances are set for April 23 and May 23. Known for their high-energy chemistry and Sundal’s soulful vocals, the band has released several projects including the albums A Lil’ Boukou in Your Cup and Let the Groove Ride, as well as the 2019 single Never Steal Our Thunder. Their recordings and live shows frequently highlight collaborations with renowned musicians such as Sam Bush and Junior Marvin.

Learn More
Thu, April 30

Redd Sings Dinner Show

Santa Rosa Beach
Live Music Live Music

Redd The Singing Bartender performs requested songs for tips. Guests are encouraged to call ahead to make dinner table reservations.

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Thu, April 30

Paint your pet

Santa Rosa Beach
Arts & Culture Arts & Culture

Idyll Hounds is hosting a Pet Portrait Edition of Paint Night on Thursday, April 30th, at 6:30 PM. Participants will receive a pre-sketched canvas of their pet along with all the necessary supplies to create their own masterpiece. Tickets for the event can be purchased through The Traveling Painter.

Learn More
Fri, May 1

Battle of the Bayou Fishing Tournament & Poker Run

Santa Rosa Beach
Outdoor Activities Outdoor Activities

Early registration is currently open for the inaugural Battle of the Bayou, a weeklong fishing tournament and Poker Run that benefits the Point Washington Medical Clinic. This event is open to anglers of all skill levels and features a full week of fishing from any location, a Poker Run on May 2, and an Awards and Weigh-In Celebration with food, live music, and prizes. Fishing categories include Redfish, Trout, Bass, and Flounder, while Poker Run stops include Baytowne Wharf, Freeport Marina, and Nick’s Seafood. The celebration includes a low country boil, BBQ, and live music, with early bird registration pricing available through April 15.

Learn More
Fri, May 1

Joy of Art Club Coastal Library

Santa Rosa Beach
Arts & Culture Arts & Culture

Artists are invited to gather on Fridays to experience the joy of creating alongside fellow creators. Participants can bring their own projects, exchange ideas, and enjoy artistic camaraderie. Potential attendees are encouraged to call the library at 850-267-2809 to confirm the schedule, as meetings are subject to change due to holidays or other conflicts.

Learn More
Fri, May 1

Crawfish Boil

Santa Rosa Beach
Food & Drink Food & Drink

Shunk Gulley Oyster Bar hosts a weekly crawfish boil every Friday from 11:00 AM to 3:00 PM under their tent. Visitors can enjoy fresh crawfish plates for $25 while experiencing a relaxed coastal atmosphere with friends and family.

Learn More
Fri, May 1

Coastal Library: Robotics and Coding for All Ages!

Santa Rosa Beach
Workshops & Classes Workshops & Classes

The Coastal Branch Library invites people of all ages to participate in robotics and coding sessions every Friday afternoon starting at 3:30 pm. Attendees can explore various kits designed for different age groups, including preschool, elementary, middle school, and high school students.

Learn More
Fri, May 1

Salt Rock Revival

Santa Rosa Beach
Live Music Live Music

Salt Rock Revival is scheduled to perform a live musical set from 6:00 PM to 9:00 PM.

Learn More
Sat, May 2

Battle of the Bayou Fishing Tournament & Poker Run

Santa Rosa Beach
Outdoor Activities Outdoor Activities

Early registration is open for the inaugural Battle of the Bayou, a weeklong fishing tournament and Poker Run that supports the Point Washington Medical Clinic. The event is open to anglers of all skill levels and includes a full week of fishing, a Poker Run on May 2, and an awards celebration featuring live music, a low country boil, and BBQ. Fishing categories include Redfish, Trout, Bass, and Flounder, while the Poker Run features stops at Baytowne Wharf, Freeport Marina, and Nick’s Seafood. Registration and ticket options are currently available, with early bird pricing valid through April 15.

Learn More
Sat, May 2

The Sunshine Wranglers

Santa Rosa Beach
Live Music Live Music

The Sunshine Wranglers will perform a live musical set from 6:00 PM until 9:00 PM.

Learn More
Sat, May 2

Alex Napier

Santa Rosa Beach
Live Music Live Music

Alex Napier performs at Papa Surf for a Saturday evening of live music and cold drinks on 30A.

Learn More
Sun, May 3

Sunday Strings w/ Black Creek String Band

Santa Rosa Beach
Live Music Live Music

Visitors can enjoy live acoustic music every Sunday afternoon at Papa Surf. The Black Creek String Band performs bluegrass, folk, and Americana music while guests relax with food and drinks on 30A.

Learn More
Sun, May 3

The Wildlife Specials

Santa Rosa Beach
Arts & Culture Arts & Culture

Audiences can watch The Wildlife Specials during its live broadcast from 1:00 PM until 4:00 PM.

Learn More
Sun, May 3

Sunday Pickin' with Mike Whitty & Friends

Santa Rosa Beach
Live Music Live Music

Sunday Pickin' at The Bay with Mike Whitty and Friends takes place every Sunday from 4-8 PM. Whitty introduces new musicians to perform each week. The performers are typically announced by Saturday, and details are available on The Bay’s Facebook or Instagram pages ahead of the event.

Learn More
Mon, May 4

Open House

Santa Rosa Beach
Workshops & Classes Workshops & Classes

The Walton Area Chamber of Commerce is hosting an open house on May 4, 2026, from 8:30 AM to 4:00 PM. This event invites current and prospective members to tour the office, meet the staff, and learn about Chamber resources in a relaxed environment. The day’s activities include a morning social with mimosas, a lunch and learn session about promotional experiences presented by A2Z Specialty Advertising, and afternoon refreshments. Attendees are encouraged to drop in at any time to network and engage with the local business community.

Learn More
Mon, May 4

Coastal Journal Writing Group Mondays

Santa Rosa Beach
Workshops & Classes Workshops & Classes

The Coastal Library Journal Writing Group meets on Mondays at 11:30 am, welcoming individuals to bring their own journals and pens for a session of reflection and self-discovery. This group focuses on healing and reconnecting with one's authentic self through the art of writing, and no prior experience is required. Participants of all levels can explore various topics, including memoir writing and tools for sparking creativity.

Learn More
Mon, May 4

The Promo Experience Lunch and Learn Presented by A2Z Specialty Advertising

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Attendees can join a free Lunch and Learn hosted by A2Z Specialty Advertising on May 4 to improve their business branding and learn about the benefits of Chamber membership. The event includes networking and a presentation designed to help local businesses grow their visibility. Seating is limited, so an RSVP is required.

Learn More
Mon, May 4

Trivia Night

Santa Rosa Beach
Sports & Games Sports & Games

Papa Surf hosts a weekly Trivia Night every Monday, featuring Super Good Trivia. Attendees can enjoy burgers and cold drinks while testing their knowledge with friends in this free-to-play event.

Learn More
Mon, May 4

Tacos, Tequila & Trivia Night

Santa Rosa Beach
Food & Drink Food & Drink

Local Cantina Westerville hosts Trivia Night every Monday at 7 PM, offering a lively atmosphere with hot tacos and cold margaritas. This weekly event is free to play and features prizes for top teams, hosted by trivia professionals. Guests can enjoy a full Tex-Mex menu, local brews, and the Mustache Ride Monday special, which includes $5 house margaritas all day. Located at 667 N Cleveland Avenue, the venue encourages groups to arrive early to secure seating and participate in a night of friendly competition and entertainment.

Learn More
Tue, May 5

Coastal Library: Music and Movement Toddler Time Tuesdays

Santa Rosa Beach
Family Fun Family Fun

Ms. Deanna and Ms. Shirles host a toddler session at the Coastal Branch Library every Tuesday at 10:00 am, featuring music and movement activities. Attendees are encouraged to contact the library at 850-267-2809 to confirm the schedule, as sessions may be affected by holiday closures or staffing changes.

Learn More
Tue, May 5

Cinco de Mayo

Santa Rosa Beach
Food & Drink Food & Drink

North Beach Social will host a Cinco de Mayo beach party on May 5, featuring live music, food, and drinks. The celebration includes carne asada tacos with sides like esquites and Spanish rice, alongside various margarita and tequila specials. Guests can enjoy an El Tesoro Tequila tasting from 4 PM to 6 PM and live music by Weston T. Hine from 6 PM to 9 PM.

Learn More
Tue, May 5

Ribbon Cutting

Santa Rosa Beach
Arts & Culture Arts & Culture

Watersound Real Estate will be welcomed to the Walton Area Chamber during a ribbon-cutting ceremony on May 5, 2026, located at 1701 E County Hwy 30A in Santa Rosa Beach. The event takes place from 12:00 PM to 2:00 PM, with the official ceremony at 1:00 PM. Attendees can network and meet the team while celebrating this business milestone.

Learn More
Tue, May 5

Chess with Mr. Owens

Santa Rosa Beach
Sports & Games Sports & Games

Chess with Mr. Owens takes place every Tuesday at 3:30 pm at the Coastal Branch Library. This program is open to individuals of all ages and skill levels, offering instruction on chess openings, endings, and special moves. Interested participants can contact the library at (850) 267-2809 for further details.

Learn More
Tue, May 5

Weston T. Hine

Santa Rosa Beach
Live Music Live Music

Weston T. Hine is scheduled to perform a live set from 6:00 PM to 9:00 PM.

Learn More
Tue, May 5

English Language Learners Class

Santa Rosa Beach
Workshops & Classes Workshops & Classes

English Language Learners classes are held every Tuesday evening at 6:30, with the exception of the second Tuesday of each month.

Learn More
Wed, May 6

Contemporary Tai Chi Beginner Classes with Able

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Sifu Able leads a complimentary Tai Chi session every Wednesday at 10:00 within the Coastal Branch Library meeting room. This gentle exercise program is designed to enhance balance, flexibility, and strength for participants of all ages, encouraging everyone to rediscover the pleasure of physical activity.

Learn More
Wed, May 6

Tai Chi with Ed

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Coastal Library is hosting an eight-week Tai Chi course specifically for seniors aged 60 and older to help improve balance and lower the risk of falls. Scheduled from Monday, February 23rd, through Wednesday, April 15th, the classes are open to all skill levels. Registration is required and can be completed by calling 850-669-0579, where Ed Rosentell will be assisting in place of Jennifer.

Learn More
Wed, May 6

Lego Club Wednesdays

Santa Rosa Beach
Family Fun Family Fun

The Lego Club gathers every Wednesday between 3:30 pm and 4:30 pm at the Coastal Library community meeting room. Participants have the opportunity to create their own Lego structures while socializing with others.

Learn More
Wed, May 6

Matt’s Jazz Jam!

Santa Rosa Beach
Live Music Live Music

Matt's Jazz Jam will be performing live from 6:00 PM to 9:00 PM.

Learn More
Thu, May 7

Coastal Library Preschool Story Time

Santa Rosa Beach
Family Fun Family Fun

Preschool Story Time at the Coastal Branch Library takes place on Thursday mornings at 10:00 am. The event features stories, songs, crafts, and opportunities for children and families to socialize. Following the story session, from 11:00 am until noon, parents and caregivers can visit while children explore various building blocks and robots. No registration is required for this program.

Learn More
Thu, May 7

Coastal Library Game Day for Adults

Santa Rosa Beach
Sports & Games Sports & Games

The library hosts a weekly Game Day for adults every Thursday from 1:00 to 4:00 pm. Community members are encouraged to bring their own card and table games to share with others in a family-friendly environment. The event offers a space for individuals to play familiar games or learn new ones. Interested parties can contact the library at 850-267-2809 for further details.

Learn More
Thu, May 7

Boukou Groove

Santa Rosa Beach
Live Music Live Music

Boukou Groove is a New Orleans funk, soul, and jam band formed in 2010 by vocalist and keyboardist Donnie Sundal alongside guitarist Derwin “Big D” Perkins. The group is scheduled to perform as a duo on April 30, May 7, and May 14, with full band shows occurring on April 23 and May 23. Throughout their career, they have released albums such as A Lil’ Boukou in Your Cup and Let the Groove Ride, often featuring collaborations with prominent artists like Sam Bush and Junior Marvin.

Learn More
Fri, May 8

Joy of Art Club Coastal Library

Santa Rosa Beach
Arts & Culture Arts & Culture

Artists are invited to gather on Fridays to create and share ideas in a collaborative environment. Participants are encouraged to bring their own artwork and engage with fellow creators. Interested individuals should contact the library at 850-267-2809 to confirm the schedule, as meeting times may change due to holidays or other conflicts.

Learn More
Fri, May 8

Crawfish Boil

Santa Rosa Beach
Food & Drink Food & Drink

Shunk Gulley Oyster Bar hosts a weekly Crawfish Boil every Friday from 11:00 AM to 3:00 PM under their outdoor tent. For $25 per plate, guests can enjoy fresh crawfish in a relaxed coastal environment suitable for both friends and families. It is an ideal way for visitors to spend a fun Friday afternoon.

Learn More
Fri, May 8

Coastal Library Robotics and Coding for All Ages!

Santa Rosa Beach
Workshops & Classes Workshops & Classes

The Coastal Branch Library invites people of all ages to participate in robotics and coding sessions held every Friday starting at 3:30 pm. Various robotic kits are available for participants ranging from preschool to high school levels to explore and build with during these afternoon events.

Learn More
Fri, May 8

The Sunshine Wranglers

Santa Rosa Beach
Live Music Live Music

The Sunshine Wranglers will perform a live musical set from 6:00 PM until 9:00 PM.

Learn More
Sat, May 9

Let's Luau!

Santa Rosa Beach
Food & Drink Food & Drink

North Beach is hosting a traditional Luau Pig Roast on Saturday, May 9, beginning at noon. The onsite BBQ will feature pig roast plates and tacos served with Hawaiian macaroni salad and vegetable skewers. Live music will be provided by Kimberly Burke from 1 PM to 4 PM and Jordan Chase from 6 PM to 9 PM. Additionally, Patron will host a Margarita Bike from 1 PM to 3 PM, allowing guests aged 21 and older to mix their own drinks.

Learn More
Sat, May 9

Jordan Chase

Santa Rosa Beach
Live Music Live Music

Jordan Chase is scheduled to perform a live set from 6:00 PM to 9:00 PM.

Learn More
Sun, May 10

Sunday Strings w/ Black Creek String Band

Santa Rosa Beach
Live Music Live Music

Guests can enjoy live acoustic performances by the Black Creek String Band every Sunday afternoon at Papa Surf. The band plays a mix of bluegrass, folk, and Americana music while visitors relax with food and drinks along 30A.

Learn More
Sun, May 10

Coconut Radio

Santa Rosa Beach
Arts & Culture Arts & Culture

Coconut Radio will be broadcasting live from 1:00 PM to 4:00 PM.

Learn More
Sun, May 10

Sunday Pickin’ with Mike Whitty & Friends

Santa Rosa Beach
Live Music Live Music

The event, "Sunday Pickin' at The Bay with Mike Whitty and Friends," takes place every Sunday from 4-8 PM. Mike brings in different musicians to perform weekly. The performers are posted by Saturday; details can be found on The Bay's social media pages.

Learn More
Mon, May 11

Coastal Journal Writing Group Mondays

Santa Rosa Beach
Workshops & Classes Workshops & Classes

The Coastal Library Journal Writing Group meets on Mondays at 11:30 am. Participants are invited to bring a journal and pen for a session focused on inner wisdom, gentle reflection, and authentic self-connection. No prior writing experience is necessary, only an open heart. The group is open to both beginners and experienced journalers, covering various topics including memoir writing and tools for self-discovery and creativity.

Learn More
Mon, May 11

Trivia Night

Santa Rosa Beach
Sports & Games Sports & Games

Papa Surf hosts a weekly Trivia Night every Monday, presented by Super Good Trivia. Attendees can enjoy burgers and cold drinks while testing their knowledge with friends during this free event.

Learn More
Mon, May 11

Tacos, Tequila & Trivia Night

Santa Rosa Beach
Sports & Games Sports & Games

Local Cantina Westerville hosts a free weekly trivia night every Monday at 7 PM, featuring prizes for the top teams and a lively Tex-Mex atmosphere. Participants can enjoy $5 Mustache Ride Margaritas all day while competing in a friendly environment hosted by trivia professionals. Guests are encouraged to arrive early to secure seating and are asked to refrain from using their phones during the competition to ensure fair play.

Learn More
Tue, May 12

Coastal Library, Music and Movement Toddler Time Tuesdays

Santa Rosa Beach
Family Fun Family Fun

Ms. Deanna and Ms. Shirles lead a toddler program focused on music and movement every Tuesday at 10:00 am at the Coastal Branch Library. Participants are advised to call the library at 850-267-2809 to confirm the schedule, as sessions may be affected by holiday closures or staffing changes.

Learn More
Tue, May 12

Chess with Mr. Owens

Santa Rosa Beach
Sports & Games Sports & Games

The Coastal Branch Library hosts a weekly chess program with Mr. Owens every Tuesday at 3:30 pm. Open to all ages and skill levels, these sessions offer instruction on openings, endings, and special moves.

Learn More
Tue, May 12

Adult Writers’ Group

Santa Rosa Beach
Arts & Culture Arts & Culture

The adult writers' group gathers at the Coastal Library's meeting room on the second Tuesday of each month at 5:00 pm. This public event does not require registration and provides local writers with an opportunity to network, share their work, and support one another.

Learn More
Tue, May 12

Jared Herzog

Santa Rosa Beach
Live Music Live Music

Jared Herzog will perform a live set from 6:00 PM to 9:00 PM.

Learn More
Tue, May 12

English Language Learners Class

Santa Rosa Beach
Workshops & Classes Workshops & Classes

An English Language Learners class meets weekly on Tuesday evenings at 6:30, with the exception of the second Tuesday of each month.

Learn More
Wed, May 13

Contemporary Tai Chi Beginner Classes with Able

Santa Rosa Beach
Sports & Games Sports & Games

Sifu Able conducts a free Tai Chi class every Wednesday at 10:00 AM in the meeting room of the Coastal Branch Library. This gentle exercise program focuses on improving balance, flexibility, and strength for participants of all ages. Attendees are encouraged to join the sessions to rediscover the joy of movement.

Learn More
Wed, May 13

Tai Chi with Ed

Santa Rosa Beach
Workshops & Classes Workshops & Classes

The Coastal Library is offering an eight-week Tai Chi course starting Monday, February 23rd, and running through Wednesday, April 15th. This program is designed for seniors aged 60 and older of all experience levels to improve their balance and decrease the risk of falling. Registration is mandatory and can be completed by contacting Jennifer at 850-669-0579. Ed Rosentell will serve as the substitute instructor for Jennifer.

Learn More
Wed, May 13

Lego Club Wednesdays

Santa Rosa Beach
Family Fun Family Fun

The Coastal Library hosts a Lego Club in its community meeting room every Wednesday from 3:30 pm to 4:30 pm. This gathering provides an opportunity for individuals to create unique Lego designs and connect with others.

Learn More
Wed, May 13

Gilleran’s Island

Santa Rosa Beach
Live Music Live Music

Gilleran's Island will perform a live set from 6:00 PM to 9:00 PM.

Learn More
Thu, May 14

GENERATE

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Generate is a dynamic leads group in the Walton area designed to help local professionals build meaningful relationships and gain quality referrals. The group meets every other month for coffee and conversation, providing a welcoming environment where participants can engage in purposeful networking and share business cards through the Coffee Card Exchange. This initiative offers Chamber members a chance to learn and grow alongside one another while expanding their professional reach. By fostering these connections, the group aims to help its members energize their networking efforts and achieve collective success.

Learn More
Thu, May 14

Coastal Library Preschool Story Time

Santa Rosa Beach
Family Fun Family Fun

The Coastal Branch Library hosts Preschool Story Time every Thursday starting at 10:00 am, featuring stories, songs, and crafts. Following the stories, from 11:00 am to noon, children are invited to play with various building blocks and robots. No registration is required for this weekly event.

Learn More
Thu, May 14

Coastal Library Game Day for Adults

Santa Rosa Beach
Sports & Games Sports & Games

The library hosts a weekly Game Day for adults every Thursday from 1:00 pm to 4:00 pm. Community members are encouraged to bring their own card and table games to share with others in the library's meeting space. These sessions provide a family-friendly environment for individuals to play familiar games or learn new ones together. Interested parties can contact the library at 850-267-2809 for additional details.

Learn More
Thu, May 14

Boukou Groove

Santa Rosa Beach
Live Music Live Music

Boukou Groove is a New Orleans-based funk, soul, and jam band formed in 2010, featuring the talents of vocalist and keyboardist Donnie Sundal alongside guitarist Derwin Perkins. The group has scheduled duo performances for April 30, May 7, and May 14, with full band shows occurring on April 23 and May 23. Known for their unique chemistry and high-profile collaborations with artists such as Sam Bush and Junior Marvin, the band has produced multiple albums and singles since their debut.

Learn More
Fri, May 15

Joy of Art Club Coastal Library

Santa Rosa Beach
Arts & Culture Arts & Culture

The library invites artists to gather every Friday to experience the joy of creating alongside fellow community members. Participants are encouraged to bring their own projects, share creative ideas, and enjoy the artistic camaraderie. Because meeting times may change due to holidays or scheduling updates, individuals should contact the library at 850-267-2809 for the most current information.

Learn More
Fri, May 15

Crawfish Boil

Santa Rosa Beach
Food & Drink Food & Drink

Shunk Gulley Oyster Bar hosts a weekly crawfish boil every Friday from 11:00 AM to 3:00 PM under the venue's tent. Guests can enjoy fresh crawfish plates for $25 while experiencing a relaxed coastal atmosphere with friends and family.

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Fri, May 15

Coastal Library Robotics and Coding for all ages!

Santa Rosa Beach
Workshops & Classes Workshops & Classes

The Coastal Branch Library invites people of all ages to participate in its robotics and coding program held every Friday afternoon starting at 3:30 pm. Attendees can explore various robotic kits designed for preschool, elementary, middle, and high school students.

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Fri, May 15

Salt Rock Revival

Santa Rosa Beach
Live Music Live Music

Salt Rock Revival will perform a live set from 6 PM to 9 PM.

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Fri, May 15

Digital Graffiti

Santa Rosa Beach
Arts & Culture Arts & Culture

Alys Beach Digital Graffiti is a multi-day art festival scheduled for May 15-16, 2026, that utilizes digital technology to project original works onto the town's white walls. The event begins on Friday evening with an all-inclusive session for adults aged 21 and older, pairing art installations with food and drink presentations from regional chefs and craft producers. On Saturday night, the festival transitions to an all-ages exhibition featuring various vendors and interactive elements designed for younger guests. Recognized by National Geographic as a premier unconventional art destination, the festival provides an immersive experience at the intersection of art and architecture. Detailed information and updates are available through the event's official website and social media channels.

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Sat, May 16

Josh Drake Band

Santa Rosa Beach
Live Music Live Music

The Josh Drake Band will perform a live set from 6:00 PM to 9:00 PM.

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Sat, May 16

Digital Graffiti

Santa Rosa Beach
Arts & Culture Arts & Culture

Digital Graffiti at Alys Beach is an innovative art festival scheduled for May 15-16, 2026, where original digital works are projected onto the town’s white walls to explore the intersection of art and architecture. The event begins on Friday, May 15, from 8 PM to 11 PM, with an all-inclusive night for adults aged 21 and older, featuring art installations paired with tastings from local chefs, restaurants, and various beverage producers. The festival concludes on Saturday, May 16, from 8 PM to 11 PM, with an all-ages exhibition that includes food and beverage vendors and special activities designed for younger guests. Recognized by National Geographic as a top unconventional art destination, this immersive experience encourages audience engagement with unique interactive projections. Additional information and updates can be found on the official event website and social media platforms.

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Sun, May 17

Sunday Strings w/ Black Creek String Band

Santa Rosa Beach
Live Music Live Music

Guests at Papa Surf on 30A can enjoy live acoustic performances by the Black Creek String Band every Sunday afternoon. The band plays a mix of bluegrass, folk, and Americana music while visitors partake in food and cold drinks.

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Sun, May 17

The Wildlife Specials

Santa Rosa Beach
Arts & Culture Arts & Culture

Viewers can watch The Wildlife Specials broadcast live between 1:00 PM and 4:00 PM.

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Sun, May 17

Sunday Pickin' with Mike Whitty & Friends

Santa Rosa Beach
Live Music Live Music

Sunday Pickin’ at The Bay with Mike Whitty and Friends occurs every Sunday from 4-8 PM. Mr. Whitty invites new musicians to perform each week. The musicians are typically announced by Saturday; details can be found on The Bay’s social media pages before the event.

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Mon, May 18

Coastal Journal Writing Group Mondays

Santa Rosa Beach
Workshops & Classes Workshops & Classes

The Coastal Library Journal Writing Group meets on Mondays at 11:30 am, and attendees are encouraged to bring their own journal and pen. This session facilitates a journey into inner wisdom through gentle reflection and healing, helping participants reconnect with their authentic selves. No previous writing experience is necessary, as the group is open to anyone willing to participate with an open heart. The sessions cater to both beginners and experienced writers, covering topics such as memoir writing, self-discovery, and sparking creativity.

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Mon, May 18

Trivia Night

Santa Rosa Beach
Sports & Games Sports & Games

Papa Surf hosts a weekly Trivia Night every Monday, featuring Super Good Trivia. Guests can enjoy burgers and cold drinks while testing their knowledge with friends at this free-to-play event.

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Mon, May 18

Tacos, Tequila & Trivia Night

Santa Rosa Beach
Sports & Games Sports & Games

Local Cantina Westerville hosts a weekly Trivia Night every Monday at 7 PM at its location on 667 N Cleveland Avenue. The event is free to attend and features prizes for the top teams, alongside a full menu of Tex-Mex food and local brews. Guests can also take advantage of five-dollar Mustache Ride Margaritas, which are available all day. To ensure a good experience, attendees are advised to arrive early for seating and to keep their phones away during the trivia rounds.

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Tue, May 19

Coastal Library, Music and Movement Toddler Time Tuesdays

Santa Rosa Beach
Family Fun Family Fun

Ms. Deanna and Ms. Shirles lead a toddler session featuring music and movement every Tuesday at 10:00 am at the Coastal Branch Library. Participants are encouraged to contact the library at 850-267-2809 to confirm the schedule, as sessions may change due to holiday closures or staffing adjustments.

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Tue, May 19

Chess with Mr. Owens

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Mr. Owens hosts a chess program every Tuesday at 3:30 pm at the Coastal Branch Library. This event welcomes participants of all ages and skill levels to learn about various chess strategies, including openings, endings, and special moves. Interested individuals can call (850) 267-2809 for further details.

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Tue, May 19

Pickl’d Coast Shoppy Hour – Pickle, Shop, & Sip

Santa Rosa Beach
Live Music Live Music

Jared Herzog will perform a live show from 6:00 PM to 9:00 PM.

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Tue, May 19

English Language Learners Class

Santa Rosa Beach
Workshops & Classes Workshops & Classes

English Language Learners classes are held every Tuesday evening at 6:30, excluding the second Tuesday of each month.

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Wed, May 20

Contemporary Tai Chi Beginner Classes with Able

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Sifu Able hosts a complimentary Tai Chi class every Wednesday at 10:00 AM in the meeting room of the Coastal Branch Library. This gentle exercise program, which focuses on improving balance, flexibility, and strength, is open to individuals of all ages looking to rediscover the joy of movement.

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Wed, May 20

Monthly Roaster Tours and Coffee and Tea Classes

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Amavida Coffee is increasing its educational opportunities by hosting monthly roaster tours and tastings every third Wednesday, while also providing a variety of coffee and tea classes throughout the month.

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Wed, May 20

Tai Chi with Ed

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Seniors aged 60 and older can participate in an eight-week Tai Chi class at Coastal Library starting Monday, February 23rd, and ending Wednesday, April 15th. The program aims to improve balance and reduce the risk of falls for participants of all experience levels. Registration is mandatory and can be completed by calling Jennifer at 850-669-0579, with Ed Rosentell serving as the substitute instructor.

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Wed, May 20

Lego Club Wednesdays

Santa Rosa Beach
Sports & Games Sports & Games

Lego Club meets on Wednesdays from 3:30 pm to 4:30 pm at the Coastal Library community meeting room. Participants are invited to build their own Lego designs and connect with new friends.

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Wed, May 20

Matt's Jazz Jam!

Santa Rosa Beach
Live Music Live Music

Matt's Jazz Jam will be performing live from 6:00 PM to 9:00 PM.

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Thu, May 21

Coastal Library Preschool Story Time

Santa Rosa Beach
Food & Drink Food & Drink

The Coastal Branch Library hosts Preschool Story Time on Thursday mornings starting at 10:00 am, featuring stories, songs, and crafts for children and their families. From 11:00 am until noon, children are invited to play with various building blocks and robots while parents and caretakers socialize. This event does not require registration.

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Thu, May 21

Coastal Library Game Day for Adults

Santa Rosa Beach
Sports & Games Sports & Games

The library hosts a weekly Game Day for adults every Thursday from 1:00 to 4:00 pm. Community members are encouraged to bring their favorite card or table games to share with others in a family-friendly environment. This gathering provides an opportunity for individuals to play familiar games or learn new ones, and interested participants can contact the library at 850-267-2809 for further details.

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Thu, May 21

Donnie Sundal

Santa Rosa Beach
Live Music Live Music

Donnie Sundal performs a live musical set from 6:00 PM to 9:00 PM.

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Fri, May 22

Joy of Art Club Coastal Library

Santa Rosa Beach
Arts & Culture Arts & Culture

Artists are invited to gather every Friday to explore their creativity alongside fellow creators. Participants are encouraged to bring their own projects, share ideas, and enjoy a sense of community. Because meetings are subject to change for holidays or scheduling reasons, interested individuals should contact the library at 850-267-2809 for the most current information.

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Fri, May 22

Crawfish Boil

Santa Rosa Beach
Food & Drink Food & Drink

Every Friday from 11:00 AM to 3:00 PM, Shunk Gulley Oyster Bar hosts a crawfish boil under its outdoor tent. Patrons can enjoy fresh crawfish plates for $25 while soaking in a relaxed coastal atmosphere with family and friends. This weekly event provides a fun and casual dining experience for those looking to kick off their weekend.

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Fri, May 22

Coastal Library Robotics and Coding for all ages!

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Individuals of all ages are invited to the Coastal Branch Library on Friday afternoons at 3:30 p.m. to engage in coding and robotics activities. The library provides various exploration kits suitable for all age levels, including preschool, elementary, middle school, and high school students.

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Fri, May 22

Salt Rock Revival

Santa Rosa Beach
Live Music Live Music

Salt Rock Revival performs live from 6:00 PM to 9:00 PM.

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Sat, May 23

Boukou Groove

Santa Rosa Beach
Live Music Live Music

Boukou Groove, a New Orleans-based funk, soul, and jam ensemble, features the talents of vocalist and keyboardist Donnie Sundal alongside guitarist Derwin Perkins. The group is scheduled to perform as a duo on April 30 as well as May 7 and 14, with full band appearances set for April 23 and May 23. Since forming in 2010, the band has released several projects and often collaborates with notable musicians such as Sam Bush and Junior Marvin to enhance their live performances and recordings.

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Sun, May 24

Sunday Strings w/ Black Creek String Band

Santa Rosa Beach
Live Music Live Music

Every Sunday afternoon, Papa Surf features live acoustic music from the Black Creek String Band. Guests can enjoy a mix of bluegrass, folk, and Americana while relaxing with food and drinks on 30A.

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Sun, May 24

The Wildlife Specials

Santa Rosa Beach
Arts & Culture Arts & Culture

Viewers can watch The Wildlife Specials during the live broadcast from 1:00 PM to 4:00 PM.

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Sun, May 24

Hearts-to-Hearts with Heaven®: A Mediumship Group Reading Event

Santa Rosa Beach
Arts & Culture Arts & Culture

International psychic medium Lindsay Marino will host Heart-to-Hearts with Heaven, a mediumship group reading event, at Distillery 98 in Santa Rosa Beach, Florida. Scheduled for Sunday, May 24th, from 2:00 to 3:30 pm, the event features Marino connecting random audience members with their deceased loved ones to share messages of healing and memory. Tickets are priced at $99 and must be purchased online in advance, as the event is limited to 50 participants and no tickets will be sold at the door. Check-in begins at 1:30 pm, and while the bar will be closed during the readings, attendees may purchase drinks before the program starts. Participants are encouraged to bring a printed ticket for entry to this intimate evening of spiritual connection.

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Sun, May 24

Sunday Pickin’ with Mike Whitty & Friends

Santa Rosa Beach
Arts & Culture Arts & Culture

"Sunday Pickin’ at The Bay with Mike Whitty and Friends" occurs every Sunday from 4-8 PM. Mike Whitty invites new musicians to play each week. Details about the performers are usually posted by Saturday on The Bay’s Facebook or Instagram pages, and attendees should check those social media accounts for updates before the event.

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Sun, May 24

The Typos

Santa Rosa Beach
Live Music Live Music

The band Catch The Typos performs a live set from 6:00 PM to 9:00 PM.

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Mon, May 25

Coastal Journal Writing Group Mondays

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Participants are invited to join the Coastal Library Journal Writing Group every Monday at 11:30 am to explore their inner wisdom through reflection and the art of reconnecting with their authentic selves. No prior writing experience is necessary, only a journal, a pen, and a willingness to participate. The group welcomes both beginners and experienced writers to delve into topics such as memoir writing and creative self-discovery.

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Mon, May 25

Trivia Night

Santa Rosa Beach
Food & Drink Food & Drink

Every Monday, Papa Surf hosts a Trivia Night presented by Super Good Trivia. Participants can enjoy burgers and cold drinks while testing their knowledge with friends at this free event.

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Mon, May 25

Tacos, Tequila & Trivia Night

Santa Rosa Beach
Food & Drink Food & Drink

Local Cantina Westerville invites guests to join their weekly Trivia Night every Monday at 7 PM. This free event features a competitive showdown with prizes for the top teams, accompanied by a full Tex-Mex menu and a variety of beverages. Participants can also take advantage of the Mustache Ride Monday special, which offers house-favorite margaritas for $5 throughout the day. To ensure a great experience, visitors are encouraged to arrive early for seating and are asked to refrain from using phones during the trivia rounds.

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Tue, May 26

Coastal Library, Music and Movement Toddler Time Tuesdays

Santa Rosa Beach
Family Fun Family Fun

Ms. Deanna and Ms. Shirles host a toddler time session focused on music and movement every Tuesday at 10:00 am at the Coastal Branch Library. Participants are advised to contact the library at 850-267-2809 to confirm the schedule, as it is subject to change based on holiday closures or staffing adjustments.

Learn More
Tue, May 26

Chess with Mr. Owens

Santa Rosa Beach
Sports & Games Sports & Games

Mr. Owens hosts a weekly chess program at the Coastal Branch Library every Tuesday at 3:30 pm. Participants of all ages and skill levels are invited to learn about various strategies, including openings, endings, and special moves. Interested individuals can contact (850) 267-2809 for further details.

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Tue, May 26

Weston T. Hine

Santa Rosa Beach
Live Music Live Music

Weston T. Hine will perform a live musical set from 6:00 PM to 9:00 PM.

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Tue, May 26

English Language Learners Class

Santa Rosa Beach
Workshops & Classes Workshops & Classes

English Language Learners classes are held weekly on Tuesday evenings at 6:30, with the exception of the second Tuesday of each month.

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Wed, May 27

Contemporary Tai Chi Beginner Classes with Able

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Sifu Able leads a complimentary Tai Chi class every Wednesday at 10:00 AM in the meeting room of the Coastal Branch Library. This gentle exercise program is designed to enhance balance, strength, and flexibility for participants of all ages, helping them rediscover the joy of movement.

Learn More
Wed, May 27

Tai Chi with Ed

Santa Rosa Beach
Workshops & Classes Workshops & Classes

Seniors aged 60 and above can participate in an eight-week Tai Chi course at Coastal Library to improve their balance and reduce the risk of falling. The program, which welcomes all skill levels, begins on Monday, February 23rd, and concludes on Wednesday, April 15th. Although Ed Rosentell will be substituting for Jennifer, registration is mandatory and can be completed by calling 850-669-0579.

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Wed, May 27

Lego Club Wednesdays

Santa Rosa Beach
Family Fun Family Fun

The Coastal Library hosts a Lego Club every Wednesday from 3:30 pm to 4:30 pm in its community meeting room. Participants are invited to create their own unique designs while socializing and meeting new people.

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Wed, May 27

Matt’s Jazz Jam!

Santa Rosa Beach
Live Music Live Music

Attendees can enjoy a live performance of Matt’s Jazz Jam from 6:00 PM to 9:00 PM.

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Thu, May 28

Coastal Library Preschool Story Time

Santa Rosa Beach
Family Fun Family Fun

Coastal Library hosts Preschool Story Time every Thursday morning starting at 10:00 am. The program includes stories, music, and crafts designed to help children and families socialize. Following the story session, parents and caregivers are invited to visit from 11:00 am until noon while children play with magnet blocks and robots. No registration is required to attend this event at the Coastal Branch Library.

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Thu, May 28

Coastal Library Game Day for Adults

Santa Rosa Beach
Sports & Games Sports & Games

Adults are invited to participate in Game Day at the library every Thursday from 1:00 to 4:00 pm. Community members are encouraged to bring their favorite card or table games to share with others in a family-friendly environment. The meeting space is available for those interested in playing or learning new games, and further information can be obtained by contacting the library directly.

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Reviews - 2

joy
Mar 2026 Google

Oversee was a great company to work with during our recent trip to 30A. They managed the rental cottage we stayed at during our trip. The office staff was very helpful an responsive throughout our stay! Each bathroom included a cute little zipper pouch with necessities for the stay. The Oversee group has been one of the best rental groups we have used. They are always asking how they can improve and I think that is the mark of a business that will be successful! We look forward to staying at another property in the future.

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keith
Mar 2026 Google

We had a fantastic stay at Ventana Breeze! The home was spacious, beautifully decorated, and very comfortable for our group of four adults and four kids. It had plenty of room for everyone to spread out and relax, which made a big difference for our trip.

The location was super convenient, and the golf cart and bikes were a great bonus. They made getting around easy and fun. The public beach access is a bit of a walk, but the golf cart made it easy. The neighborhood pool was also nice.

We did run into a small issue with our door code when we first arrived (after office hours), but Oversee responded quickly and took care of us right away. Their communication was excellent throughout our stay, and they really went above and beyond to make us feel welcome.

Overall, we had a great experience and would absolutely stay here again!

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Host Family

Grayton Office

Gloria Cruz
Danny West
Ryan Pearson
Heather Silva
Madi Chendemi
Crystal	Becktel
Charles McTear
Summer McKeon
Right in the heart of Grayton Beach, the Grayton Office lets us offer quick, thoughtful support whenever you need a hand.

Office location:

Grayton Office, Florida

Contact Grayton Office
Price Tag Prices include all fees and taxes
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1 guest