Description
House Rules
Amenities
Bed and Baths
Location
Community
Upcoming Events
Reviews
Host Family

Out of Office

Name: FIFA World Cup on Jumbotron
Start: 2026-07-18T16:00:00+00:00
Location: The Big Chill

Out of Office

Sleeps 10 - 5 Bedrooms - 4 Baths

61 Sheepshank Ln, Santa Rosa Beach, FL 32459

📍

Watersound West!

🏖️

Private beach access via gorgeous boardwalk

🛌

5 bedrooms, 4 bathrooms

👙

Heated community pool, open year-round

🔥

Outdoor grill, kitchen, dining area seats 6

🛺

6-seater golf cart

🚲

4 bikes

☕

Keurig and standard coffee maker

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

The ultimate 30A getaway? Absolutely! Tucked inside an exclusive gated community, Out of Office in Watersound West is a 5-bedroom, 4-bath beauty, that’s all about laid-back luxury and family fun.

Start your day lounging on the dreamy front porch—hammock chairs, cozy seating, and a dining table just waiting for your evenings of al fresco dining. Head out back for grill master vibes on the spacious deck with an outdoor kitchen ready for your BBQs and sunset hangouts.

Inside, you’ll find a welcoming open space with super comfy furniture, perfect for stretching out after a beach day. The kitchen?

Fully stocked, with an island for three—whether you’re whipping up meals or grabbing takeout, it’s all easy breezy.

Upstairs, a second living area makes for the best movie night spot, complete with a big couch, chairs, and a Smart TV for all your streaming marathons.

Ready to make some memories? Your perfect vacation is just a few clicks away. Book now and let Out of Office be your home base for sunshine, relaxation, and lots of beachy fun!

Welcome! Our dedicated team at Oversee 30A, a local company, is committed to ensuring your stay is nothing short of exceptional. We strive for perfection and are just a stone's throw away should you require any assistance. Reach out to us anytime, seven days a week, with the added peace of a 24/7 emergency line.

Overview:
-Private beach access via a scenic boardwalk
-Seasonally Heated community pool (Heated November - February)
-5 bedrooms, 4 bathrooms
-Pack n play and highchair available
-Outdoor grill and dining space
-4 Complimentary bikes
-Complimentary 6 seater golf cart
-Wi-Fi
-2894 sq ft

Overnight:
- King in 1st floor primary; private bath; TV
- Queen in 1st floor guest room (barn door); shared bath; TV
- King in 2nd floor primary; private bath; TV
- King in 2nd floor guest room; shared bath; TV
- Queen in 2nd floor guest room; shared bath; TV

Check-in is 4:00 PM CST. Checkout is 10:00 AM CST.

Take the 3D walkthrough.

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House Rules

Who can stay.

10 guests maximum
No pets

What's allowed.

Check-in after 4:00 PM
Check-out before 10:00 AM
No smoking
No parties or events

Amenities

Kitchen

Dishwasher
Stove
Standard coffee maker
Microwave
Refrigerator
Toaster

Indoor

Wireless internet
Fireplace
Workspace

Complimentary Items

4 Oversee bikes
Beach chairs
Golf cart

Outdoor

Garage
Balcony

Community Amenities

Community pool

Safety Features

Carbon monoxide detector
Fire extinguisher

Bed And Bathroom

Hair dryer
Iron & board

Entertainment

Smart TV

Bed and Baths

1st Floor

bedroom

1 Queen bed

Primary Bed Bedroom

1 King bed

full bathroom

2nd Floor

bedroom

1 King bed

bedroom

1 King bed

bedroom

1 Queen bed

full bathroom

Location

Community

Watersound

Upcoming Events

Mon, July 6

Art Bar Menu Station hosted by Uniquely Clever Art

Watersound

Arts & Culture

Uniquely Clever Art hosts an Art Bar Menu Station at The Big Chill every Monday. Guests can choose from various art projects to create in the screened-in room located to the left of the jumbotron. No prior registration is necessary, though fees apply and vary by project.

Mon, July 6

FIFA World Cup on Jumbotron

Watersound

Sports & Games

FIFA World Cup matches will be broadcast on the Jumbotron until the nightly entertainment begins, after which the games will be available to watch on the televisions in the Pavilion.

Mon, July 6

Face Paint with Uniquely Clever Art

Watersound

Family Fun

Katlyn of Uniquely Clever will be providing face painting services. While there are fees associated with the activity, no prior sign-up is required to participate.

Mon, July 6

DJ Dance Party with DJ Dan

Watersound

Family Fun

DJ Dan will be hosting the Ultimate Family Dance Party, featuring a variety of popular hits. This high-energy event invites families to enjoy a night of dancing and fun in a welcoming environment.

Tue, July 7

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of hair styling services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, mermaid-style waves with bold color accents, and customized braids. These services are designed for those looking to express their personal style, though applicable fees will apply.

Tue, July 7

FIFA World Cup on Jumbotron

Watersound

Sports & Games

FIFA World Cup matches will be broadcast on the Jumbotron until the nightly entertainment begins, after which the games will continue to be shown on the televisions in the Pavilion.

Tue, July 7

Boukou Groove

Watersound

Live Music

Established in 2010, Boukou Groove is a New Orleans-based ensemble specializing in funk, soul, and jam music. The group features the talents of veteran vocalist and keyboardist Donnie Sundal alongside guitarist Derwin “Big D” Perkins. Their global performances are characterized by the fusion of Perkins' authentic funk guitar style and Sundal’s soulful vocals and keyboard work. This creative partnership is captured in their discography, which includes the albums A Lil’ Boukou in Your Cup from 2012, Let the Groove Ride from 2015, and their 2019 single, Never Steal Our Thunder.

Wed, July 8

Wild Sea Turtle Wednesdays!

Watersound

Family Fun

The South Walton Turtle Watch hosts Wild Sea Turtle Wednesday every Wednesday morning throughout June and July. This educational event invites people of all ages to learn about local sea turtles and their role in the coastal ecosystem. Participants can engage in activities such as painting sea turtle art, adopting a hatchling keepsake, and taking the Jr. Ocean Ranger pledge to maintain clean and dark beaches for nesting. While the event is free and open to the public, donations for craft materials are accepted. The organizing group consists of volunteers dedicated to protecting endangered sea turtles in Northwest Florida during the nesting season from May 1st to October 31st.

Wed, July 8

Face Paint with Uniquely Clever Art

Watersound

Arts & Culture

Katlyn of Uniquely Clever will be available for face painting. While fees apply for the service, no prior sign-ups are required for those wishing to participate.

Wed, July 8

Dueling Pianos Show

Watersound

Live Music

The Big Chill is hosting the Gulf Coast Interactive Dueling Pianos Show for the first time. This high-energy, family-friendly performance features all-audience requests, blending comedy and crowd participation with sing-along classics from various genres. The free show begins at 6:00 PM, and guests are encouraged to arrive early for dinner and drinks.

Thu, July 9

Farmers' Market

Watersound

Markets & Shopping

The Farmer’s Market at The Big Chill, managed by Anchored Market Ventures, takes place from 9 AM to 1 PM. This family-friendly event features a variety of local vendors offering assorted goods, including fresh produce, farm-fresh eggs, handmade jewelry, and home decor. Attendees can enjoy live music and explore on-site shops and dining options. The market is open to the public and encourages community connection through local news and newsletters.

Thu, July 9

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of styling services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, bold mermaid hair accents, and personalized custom braids. This event is designed for those looking to express their personal style through creative hair transformations. Fees apply for these services.

Thu, July 9

Tie Dye Workshop*

Watersound

Workshops & Classes

David's Tie Dye Workshop invites participants to get their hippie on from 5 PM to 8 PM. Attendees can choose from various designs, including guitars, peace signs, hearts, and swirls. A wide range of shirt sizes is available, from kids' 2T to adult 4XL, and aprons and gloves are provided for the activity. The workshop costs $25 per shirt.

Thu, July 9

Sounds Like Summer: Voices of Valor-ECTC Celebration

Watersound

Family Fun

Running from June through August 2026 at The Pavilion, this signature summer series offers families a rotating schedule of lively entertainment and community activities. Each month, attendees can enjoy whimsical children's plays, live music from 30A Songwriters Festival artists, inclusive family nights, or energetic community races hosted by Fleet Feet.

Fri, July 10

FIFA World Cup on Jumbotron

Watersound

Sports & Games

FIFA World Cup matches will be broadcast on the Jumbotron until the nightly programmed entertainment begins, after which the games will continue to be available for viewing on the televisions in the Pavilion.

Fri, July 10

Craft & Canvas Art Class hosted by Uniquely Clever *Must Pre-register

Watersound

Workshops & Classes

Uniquely Clever hosts the Craft and Canvas art class on Fridays from 5:00 PM to 6:00 PM. The class is held in the screened-in area situated to the left of the Jumbotron. Participants are required to pre-register for this event.

Fri, July 10

Face Paint with Uniquely Clever Art

Watersound

Family Fun

Katlyn of Uniquely Clever will be available for face painting. Fees apply for this activity, and no advance sign-ups are required for those wishing to participate.

Fri, July 10

DJ Dance Party w/ DJ Dan

Watersound

Family Fun

The Ultimate Family Dance Party invites families to join DJ Dan for a high-energy evening of dancing to popular hits. This family-friendly event encourages attendees of all ages to hit the stage and enjoy a vibrant atmosphere on the dance floor.

Sat, July 11

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of hair styling services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, beachy mermaid hair with bold color accents, and personalized custom braids. This event is designed for those who enjoy expressing themselves through creative and stylish looks, and fees apply for the services provided.

Sat, July 11

FIFA World Cup on Jumbotron

Watersound

Sports & Games

FIFA World Cup games will be displayed on the Jumbotron until the nightly programmed entertainment begins, after which the matches will be available for viewing on the televisions in the Pavilion.

Sun, July 12

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of hair styling services designed for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, beachy mermaid hair with bold color accents, and custom braids tailored to each individual. This event provides a creative way for attendees to express themselves, though fees for the services do apply.

Mon, July 13

Art Bar Menu Station hosted by Uniquely Clever Art

Watersound

Arts & Culture

Uniquely Clever Art hosts an Art Bar Menu Station at The Big Chill on Mondays, offering guests a variety of art projects to choose from and create. The station is located in the screened-in room to the left of the jumbotron. No prior registration is necessary, though fees apply and pricing varies by project.

Mon, July 13

Face Paint with Uniquely Clever Art

Watersound

Family Fun

Katlyn of Uniquely Clever provides face painting services for attendees. While fees are required for participation, no prior registration is necessary for this event.

Tue, July 14

FIFA World Cup on Jumbotron

Watersound

Sports & Games

FIFA World Cup matches will be broadcast on the Jumbotron until the start of the nightly entertainment, at which point the games will remain available for viewing on the televisions located in the Pavilion.

Tue, July 14

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a special event featuring various hair styling services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, mermaid-style beachy waves with bold accents, and personalized custom braids. Fees apply for these services, which are designed to help participants express their inner magic.

Tue, July 14

Cam Shelton

Watersound

Live Music

Cam Shelton is a rising Nashville country artist who blends traditional country roots with modern soul and Southern rock. Having performed since age three, he is recognized for his powerful vocals, high-energy live performances, and heartfelt storytelling. Currently, his single My Grandpa and My Old Man is featured on Music Row’s Country Breakout Chart, and his music has earned over 212,000 streams on Spotify, where he was also included on the Country Hits 2026 playlist. Throughout his career, he has opened for notable artists such as Riley Green and Tracy Byrd, and his music is available across all major streaming platforms.

Wed, July 15

Wild Sea Turtle Wednesdays!

Watersound

Family Fun

South Walton Turtle Watch invites the public to attend Wild Sea Turtle Wednesday every Wednesday morning throughout June and July. This family-friendly event offers educational opportunities to learn about local sea turtles and their coastal ecosystem, as well as activities such as sea turtle art, hatchling adoption, and taking the Jr. Ocean Ranger pledge. While the event is free and open to all ages, donations are accepted for craft supplies. South Walton Turtle Watch is a volunteer organization dedicated to protecting endangered and threatened sea turtles in Northwest Florida during their nesting season from May 1st to October 31st.

Wed, July 15

FIFA World Cup on Jumbotron

Watersound

Sports & Games

FIFA World Cup matches will be displayed on the Jumbotron until the nightly scheduled entertainment begins, after which the games will continue to be available for viewing on the televisions in the Pavilion.

Wed, July 15

Face Paint with Uniquely Clever Art

Watersound

Arts & Culture

Katlyn of Uniquely Clever provides face painting services for attendees to enjoy. While fees are applicable for the activity, no prior registration is required to participate.

Wed, July 15

Family Movie Night: Lilo & Stitch 2

Watersound

Family Fun

The Big Chill hosts family movie nights where guests can gather to watch popular films on a Jumbotron under the stars. This event is designed for all ages, offering a magical evening for families to enjoy together.

Thu, July 16

Farmers Market

Watersound

Markets & Shopping

The Big Chill hosts a Farmers Market managed by Anchored Market Ventures every Tuesday from 9am to 1pm. This family-friendly event is open to the public and features a variety of local vendors offering fresh produce, farm-fresh eggs, artisanal food items, and handmade crafts such as jewelry, wood work, and home decor. Visitors can also enjoy live music and on-site dining options while shopping for local goods.

Thu, July 16

Miami Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of creative hair services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, and beachy mermaid hair with bold color accents. Additionally, guests can enjoy custom braids tailored to their individual style, with fees applicable for these services.

Thu, July 16

Tie Dye Workshop

Watersound

Workshops & Classes

David’s Tie Dye Workshop offers an opportunity for participants to create their own designs, such as guitars, peace signs, hearts, and swirls, from 5pm to 8pm. The event provides a range of shirt sizes from 2T kids to 4XL adults, along with aprons and gloves for use during the activity. There is a fee of $25 per shirt.

Thu, July 16

Sounds Like Summer: Christmas in July

Watersound

Family Fun

The Pavilion hosts a signature summer series from June through August 2026, featuring a variety of community entertainment. Attendees can enjoy monthly children's plays, live music from 30A Songwriters Festival artists, and family nights with inclusive activities. Additionally, the series includes neighborhood races organized with Fleet Feet to encourage community engagement and friendly competition.

Fri, July 17

Noah’s Magic and Comedy Show!

Watersound

Family Fun

Noah's Magic and Comedy Show brings a captivating performance to The Big Chill this summer, featuring Noah Wells and his daughter, London. This family-friendly event offers 45 minutes of illusions, comedy, mind-reading, and interactive audience participation suitable for all ages. As a three-time Merlin Award winner recognized by the International Magicians Society, Noah Wells holds the record for the longest-running magic show in Florida and has performed for over one million guests along the Emerald Coast.

Fri, July 17

Craft & Canvas Art Class hosted by Uniquely Clever *Must Pre-register

Watersound

Workshops & Classes

Uniquely Clever hosts the Craft and Canvas art class on Fridays from 5:00 PM to 6:00 PM. The class is held in the screened-in area located to the left of the Jumbotron. Participants are required to pre-register to attend.

Fri, July 17

Face Paint with Uniquely Clever Art

Watersound

Arts & Culture

Katlyn of Uniquely Clever will be available for face painting. Fees apply for this activity, and no prior sign-ups are necessary.

Fri, July 17

DJ Dance Party w/ DJ Dan

Watersound

Family Fun

Sat, July 18

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of hair styling services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, and mermaid-style hair with beachy waves and bold accents. Additionally, attendees can receive custom braids tailored to their personal style. While fees apply for these services, the event provides a creative opportunity for participants to express themselves through unique hair designs.

Sat, July 18

FIFA World Cup on Jumbotron

Watersound

Sports & Games

The venue features FIFA World Cup matches on the Jumbotron until the nightly programmed entertainment begins. Afterwards, the games remain available for viewing on the televisions located in the Pavilion.

Reviews - 9

Charlotte, NC

May 2026

Google

Oversee did an excellent job managing my vacation home rental in 30A. Their team was professional, responsive, and made the entire process stress-free. Communication was clear, and they took great care of both the property and questions I had. I highly recommend them to anyone looking for reliable vacation rental management services.

john

Memphis, TN

Nov 2025

Google

We take multiple trips to Santa Rosa every year and this is hands down our favorite place we’ve ever stayed in!!!

kathy

Sep 2025

Vrbo

jodi

Aug 2025

Airbnb

Darling beach home in a gated community. Sea Grove beach was amazing and perfect and not too populated! Ocean water was clear, blue teal, and of course, gorgeous sand. We stayed at the end of August and it got a lot busier towards Labor Day weekend. The golf cart was an added bonus always fun to get a house with one, made coffee and donut runs to Turbo in morning easy and fun! The Big Chill is right up the road, easy drive in golf cart but we took the Tahoe, amazing ice cream spot in the evening. Alys Beach is one beach over. Ate dinners on Alys beach, it‚’s one of the dreamiest spots in Florida to walk the streets. It feels like Greece. Amazing trip!

kelly

Mccomb, MS

Jul 2025

Google

Loved “Out of Office”
Can’t say enough about this home and experience! The home was immaculate, tastefully decorated, full of personal touches to make you feel at home, and convenient to town and beaches! Excellent responses from management, extras you won’t get anywhere else, like beach chairs, umbrellas and a wagon. And it comes with a beautiful golf cart and 4 bikes! Games are available, they make sure you’re comfortable with a beautifully functioning kitchen, extra supplies like laundry pods, and toiletries, a welcome package, and Oversee quick response for any questions!
In a neighborhood, but the beauty of this is- you can get out of the rat race, and still get to fun things easily. Private neighborhood pool and access to a private beach!
We loved this place and will be back! It was perfect for our family to be able to spend quality time together!!! Win win!!

julie

Bulverde, TX

Jul 2025

Google

Absolutely beautiful home! Super clean and with all the amenities that we could ask for. We will definitely be back and we will definitely recommend

sarah

Jun 2025

Airbnb

This was our 2nd year staying at this beautiful home. We love everything about the home. The neighborhood is quiet and peaceful. Very well maintained. The management company was responsive to us and kept in touch. They fixed any issues very quickly. We would definitely come back again!

julie