Beach and Boardwalk w/ Carriage House
Beach and Boardwalk w/ Carriage House
Beach and Boardwalk w/ Carriage House
Beach and Boardwalk with Carriage House by Oversee 30A | 2025 Diamond Winner - Best Rental Management
This is not your average beach house. Designed by George Israel and just two doors from the sand, Beach and Boardwalk has 3 bedrooms, 4 bathrooms, and the carriage house, 1 bedroom and 1 bath. Full of personality, thoughtful details, and an unmistakable “wow” factor, this will feel more like an experience than just a place to stay.
Inside, it’s stylish but relaxed, filled with curated details, warm textures, and spaces that invite you to kick back and pretend you live here year-round. There’s personality around every corner, from the art to the layout.
Gulf views and breezy courtyards? Yes, and yes.
And a carriage house? Oh my goodness. The whole place feels like your own private corner of Rosemary Beach. Explore every artistic detail while enjoying modern comforts and effortless beach access, with the town center just a flip-flop stroll away.
With Oversee 30A, exceptional service meets unforgettable surroundings. You’ll be taken care of by a local team that’s around every day, with a 24/7 line if anything unexpected comes up. We make luxury feel laid-back. Just like it should.
Overview:
- Located two homes from the beach
- Private beach access
- 4 community pools
- Covered porches and stunning Gulf views from private balconies
- Unique nautical-inspired interiors
- Dining table for 6, bar seating for 3
- Fully equipped kitchen w/stainless steel appliances and gas stove
- Beach chair and umbrella service (additional fees)
- Fitness center (additional fees)
- Tennis courts (additional fees)- Beach chair and umbrella service (additional fees)
Overnight:
FIRST FLOOR
- Primary Bedroom: Queen bed, private bath, tub and glass-enclosed shower, private shuttered porch
- Guest Bedroom: Queen bed, private bath with shower
- Bunk Room: Two twin-over-twin bunks, private bath w/shower (no TV)
SECOND FLOOR
- Full bath with tub/shower combination
THIRD FLOOR
- Loft with queen bed, two elevated twin beds, TV
CARRIAGE HOUSE:
- Primary Bedroom: King bed, full private bath, TV
Check-in is 4:00 PM CST. Checkout is 10:00 AM CST.
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Take the 3D walkthrough.
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Hassle-free check-in.
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Add your trip dates to get the cancellation details for this stay.
House Rules
Who can stay.
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14 guests maximum
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No pets
What's allowed.
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Check-in after 4:00 PM
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Check-out before 10:00 AM
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No smoking
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No parties or events
Amenities
Bed and Baths
1st Floor
2nd Floor
Location
Upcoming Events
Thu, January 8
Michael Johnson
Havana Beach Bar & Grill, situated in The Pearl at Rosemary Beach, offers live music from Thursday through Saturday, 5-7 PM. Guests can enjoy their meal while listening to Michael Johnson play classic favorites on the baby grand piano in the main dining area.
Fri, January 9
Michael Johnson
Havana Beach Bar & Grill, situated in The Pearl at Rosemary Beach, offers live music from Thursday through Saturday, between 5 PM and 7 PM. Guests can enjoy their favorite classic songs, performed live by Michael Johnson on the baby grand piano in the main dining area.
Sat, January 10
Michael Johnson
Havana Beach Bar & Grill, situated in The Pearl at Rosemary Beach, offers live music from Thursday through Saturday, 5–7 PM. Guests can enjoy dinner while listening to Michael Johnson play classic songs live on the baby grand piano in the main dining area.
Sat, January 10
10th Annual Prohibition Repeal Wine Dinner
Restaurant Paradis, presented by Cryo 850, is set to host its 10th Annual Prohibition Repeal Wine Dinner on Saturday, January 10, 2026, with proceeds benefiting South Walton Academy. The event, kicking off at 6:30 p.m., will begin with an intimate cocktail hour featuring a specialty spirit served in a commemorative glass, courtesy of Buddy’s Seafood. The restaurant will be closed for the private, Gatsby, Prohibition-era celebration. Guests will then proceed to the main dining room for a four-course meal sponsored by 30A Hat Bar, 30A Home, Shore Thing Cigars, and Silver Sands Premium Outlets. Prepared by award-winning chef Mark Eichin and his culinary team, the meal will feature local produce, Gulf seafood, and fine meats. Entertainment for the evening includes an electric violinist from Violin 30A, sponsored by Inlet Beach Real Estate, a photo booth courtesy of Coastal Insurance and Shay Wiggins, florals sponsored by 30A Luxury Vacations, and photography sponsored by Swiftly Catered. Attendees will also receive a special gift to commemorate the 10-year anniversary.
The proceeds from the dinner will go to South Walton Academy, a private, non-profit inclusion school and pediatric therapy clinic located in Santa Rosa Beach, Florida. The academy, situated at 305 Mack Bayou Road, aims to empower children through inclusive education and community engagement, serving students from preschool through 12th grade. It offers individualized education and therapeutic support like speech, occupational, and behavioral therapy. Calley Middlebrooks, founder of South Walton Academy, noted that the academy was built on the belief that every child deserves access to education and support, emphasizing the vital role of community support, like the Prohibition Repeal Dinner, in removing barriers and changing children’s lives.
Over the past decade, Restaurant Paradis’ Prohibition Dinners have successfully raised over $63,000 for various local charities, including Alaqua Animal Refuge, Beach Care Services, Destin Charity Wine Auction, Emerald Coast Children’s Advocacy Center, Food for Thought Outreach, Hannies Grannies, Neurodiversity Resource of the Panhandle, and Westonwood Ranch. Danny Cosenzi, owner of Restaurant Paradis, expressed that it has been an honor to host the charity wine dinner for the past ten years, bringing generous people together for a fabulous evening while raising money for great causes. He stated they look forward to hosting many more dinners in the future, especially to support South Walton Academy and the much-needed service it provides to the community. Guests are encouraged to dress in 1920s, Gatsby-themed attire. A limited number of tickets are available for $250 per person, which includes all food, beverage, and gratuity. Tickets can be purchased online.
Sun, January 11
30A Farmers Market
The 30A Farmers Market is held every Sunday year-round from 9 AM to 1 PM. It is located at 28 N. Barrett Square, Rosemary Beach, Florida.
Thu, January 15
Michael Johnson
Havana Beach Bar & Grill, situated in The Pearl at Rosemary Beach, offers live music from 5 to 7 PM, Thursday through Saturday. Guests can enjoy dining while Michael Johnson plays classic favorites live on the baby grand piano in the main dining area.
Fri, January 16
Michael Johnson
Havana Beach Bar & Grill, situated in The Pearl at Rosemary Beach, offers live music from Thursday through Saturday between 5 PM and 7 PM. Guests can dine while enjoying classic songs performed live by Michael Johnson on the baby grand piano in the main dining area.
Sat, January 17
Michael Johnson
Havana Beach Bar & Grill, situated in The Pearl at Rosemary Beach, features live music on Thursdays, Fridays, and Saturdays from 5 PM to 7 PM. Guests can enjoy dining while Michael Johnson plays classic favorites on the baby grand piano in the main dining area.
Sun, January 18
30A Farmers Market
The 30A Farmers Market is held every Sunday year-round, operating from 9 AM to 1 PM. It is located at 28 N. Barrett Square in Rosemary Beach, Florida.
Thu, January 22
Michael Johnson
Guests can prepare for a bold and flavorful evening at Bud & Alley’s annual Bourbon Event on January 22nd, 2026. Attendees will enjoy rich pours of top-shelf bourbons thoughtfully paired with savory, smoky bites that highlight Southern charm. This exclusive experience is designed for those who appreciate indulgence, craftsmanship, and connection. While details for the 2026 event are still being finalized, previous years featured cigars and live music, and guests can anticipate the same elevated atmosphere. Attendance will be limited to 200 guests to ensure an intimate and memorable experience.
Fri, January 23
Michael Johnson
Havana Beach Bar & Grill, located in The Pearl at Rosemary Beach, offers live music from Thursday through Saturday between 5 PM and 7 PM. Guests can enjoy dining while Michael Johnson plays classic favorites live on the baby grand piano in the main dining area.
Sat, January 24
Michael Johnson
Havana Beach Bar & Grill, situated in The Pearl at Rosemary Beach, offers live music from Thursday through Saturday between 5 PM and 7 PM. Guests can dine while enjoying classic songs performed live by Michael Johnson on the baby grand piano in the main dining area.
Sun, January 25
30A Farmers Market
The 30A Farmers Market takes place every Sunday throughout the year, running from 9 AM to 1 PM. It is situated at 28 N. Barrett Square in Rosemary Beach, Florida.
Thu, January 29
Michael Johnson
Havana Beach Bar & Grill, situated in The Pearl at Rosemary Beach, offers live music from Thursday through Saturday, 5-7 PM. Guests can enjoy dining while Michael Johnson performs classic songs live on the baby grand piano in the main dining area.
Fri, January 30
Michael Johnson
Havana Beach Bar & Grill, situated in The Pearl at Rosemary Beach, offers live music every Thursday through Saturday from 5 PM to 7 PM. Guests can enjoy classic songs performed live by Michael Johnson on the baby grand piano in the main dining area.
Sat, January 31
Michael Johnson
Havana Beach Bar & Grill, located in The Pearl at Rosemary Beach, hosts live music every Thursday through Saturday from 5-7 PM. Patrons can enjoy some of their favorite classics played live by Michael Johnson on the baby grand piano in the main dining area.
Sun, February 1
30A Farmers Market
The 30A Farmers Market takes place every Sunday throughout the year, operating from 9 AM to 1 PM. It is situated at 28 N. Barrett Square in Rosemary Beach, Florida.
Sun, February 8
30A Farmers Market
The 30A Farmers Market is held every Sunday throughout the year, operating from 9 AM to 1 PM. It is situated at 28 N. Barrett Square in Rosemary Beach, Florida.
Thu, February 12
SOWAL Comedy Fest: Valentine’s Weekend
The SOWAL Comedy Fest, formerly known as the Sand Up Comedy Fest, is scheduled to return over Valentine’s Weekend 2026, from Thursday, February 12 through Saturday, February 14. The festival will offer three nights of stand-up comedy across three different venues in South Walton, FL (30A). This event is promoted as an ideal date weekend, featuring intimate rooms and capped attendance. Due to two consecutive years of sold-out shows, early ticket purchasing is strongly recommended. For the first time, all shows will offer reserved seating, allowing guests to choose their preferred view, whether it be front-row, center-room, or a quieter corner. The festival will feature two showtimes each night at 6:00 p.m. and 8:00 p.m.
The 2026 headliners include Peter Wong (New York, NY), known for his features on Comedy Central and Nate Bargatze’s Nateland, returning for his third year; Anjelica Scannura (New York, NY), who was recently named a Just For Laughs “New Face of Stand-Up” and is the first Canadian woman to win the Boston Comedy Festival; and Carter Deems (Atlanta, GA), an alum of MTV’s Wild ’N Out with writing credits for shows like Epic Rap Battles of History and Drop The Mic.
The venues hosting the event are SOWAL House, described as an intimate room central to South Walton’s cultural scene; Wild Olives, located at 30A’s Greenway Station with a full bar and food options; and Distillery 98, known for its craft cocktails, lively atmosphere, tours, and local art.
The SOWAL Comedy Fest also serves a purpose, as support and sponsorships benefit the SOWAL Foundation (SOFO), a nonprofit dedicated to empowering and uplifting local creatives. Beyond the festival, SOFO hosts recurring programming at SOWAL House, including film screenings, poetry gatherings, art exhibitions, creative meetups, and special monthly events. Tickets are currently on sale and can be purchased by date, venue, or headliner.
Thu, February 12
SOWAL Comedy Fest: Valentine’s Weekend
The SOWAL Comedy Fest, formerly known as the Sand Up Comedy Fest, is returning for Valentine’s Weekend 2026, running from Thursday, February 12 through Saturday, February 14. The festival will feature three nights of stand-up comedy across three venues in South Walton, FL (30A), offering an ideal date weekend escape. Due to two straight years of sold-out shows, early ticket purchase is strongly encouraged. For the first time, every show offers reserved seating selections. The 2026 headliners include Peter Wong (featured on Comedy Central and Nate Bargatze’s Nateland), Anjelica Scannura (awarded Just For Laughs “New Face of Stand-Up”), and Carter Deems (MTV’s Wild ’N Out alum). Shows run across all three nights with two showtimes (6:00 p.m. and 8:00 p.m.) at each venue. Venue highlights include SOWAL House, Wild Olives (at 30A’s Greenway Station with a full bar and food), and Distillery 98 (known for craft cocktails). Support and sponsorships benefit the SOWAL Foundation (SOFO), a nonprofit dedicated to empowering local creatives. SOFO also hosts recurring programming at SOWAL House, such as film screenings, poetry gatherings, and art exhibitions/creative meetups. Tickets are on sale now and can be purchased by date, venue, or headliner.
Sun, February 15
30A Farmers Market
The 30A Farmers Market takes place every Sunday throughout the year, from 9 AM to 1 PM. It is situated at 28 N. Barrett Square, Rosemary Beach, Florida.
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Emerald Office at Sunnyside
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