Out of Office
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Out of Office
Out of Office by Oversee 30A | 2025 Diamond Winner-Best Rental Mgmt.
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.
Highlights:
📍 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
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.
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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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10 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
Kitchen
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Dishwasher
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Stove
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Standard coffee maker
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Microwave
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Refrigerator
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Toaster
Indoor
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Wireless internet
Outdoor
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Garage
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Balcony
Complimentary Items
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4 Oversee bikes
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Golf cart
Community Amenities
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Community pool
Entertainment
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Cable
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Smart TV
Safety Features
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Carbon monoxide detector
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Fire extinguisher
Bed And Bathroom
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Hair dryer
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Iron & board
Bed and Baths
1st Floor
bedroom
1 Queen bed
Primary Bed Bedroom
1 King bed
full bathroom
full bathroom
2nd Floor
bedroom
1 King bed
bedroom
1 King bed
bedroom
1 Queen bed
full bathroom
full bathroom
Location
Upcoming Events
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday throughout the season. This venue is described as the ultimate NFL destination for catching every play, featuring wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites. Guests can enjoy game day bites, full-service bars, and a fan-friendly atmosphere with outdoor viewing. The specific games shown on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under the covered pavilion, with several TVs available for requests on a first-come basis by asking a manager at the bars.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday for the duration of the season. It is presented as the ideal location to catch every play, featuring wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars offering game-day favorites. The venue provides Game Day Bites from multiple eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing. Whether guests are supporting their home team or monitoring their fantasy lineup, the Big Chill is promoted as the ultimate NFL destination. The specific games shown on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis; guests are asked to request a manager at the bars for all requests.
NFL on the Jumbotron
Watersound
Sports & Games
An NFL Watch Party takes place every Monday throughout the season at The Big Chill. It is the ultimate destination for catching every play, featuring wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars. Guests can enjoy game day bites from various eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing. Whether attendees are cheering for their home team or tracking their fantasy lineup, this venue serves up all the game day favorites.
College Football on the Jumbotron
Watersound
Sports & Games
A College Football Watch Party is being held all season long. Attendees are invited to watch their favorite college football teams on a massive 25-ft Jumbotron, advertised as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, an electric atmosphere, and all the big games all day long. This is the place to be for those representing their alma mater or just enjoying the rivalries, encouraging them to bring their group, wear their colors, and get loud for College Football, done right. The specific games shown on the Jumbotron will be posted weekly by Wednesday. All other games will be shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Attendees are instructed to ask for a manager at the bars for all requests.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Thursday throughout the season, offering attendees the best place to catch every play. The venue provides wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game-day favorites. Guests can enjoy game-day bites from various eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing. This location serves as the ultimate NFL destination, whether guests are cheering for their home team or tracking their fantasy lineup.
College Football on the Jumbotron
Watersound
Sports & Games
An establishment is hosting a College Football Watch Party all season long. Attendees are invited to watch their favorite college football teams compete on a 25-ft Jumbotron, noted as the biggest screen in town. The venue offers multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere to enjoy all the big games. Guests are encouraged to bring their friends, wear their team colors, and participate in the excitement. The specific games shown on the Jumbotron will be posted weekly by Wednesday. All other games will be displayed on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Guests should ask a manager at the bars for all requests.
Karaoke Night
Watersound
Live Music
The public is invited to attend Karaoke Night, which is held every Friday at 7 PM.
College Football on the Jumbotron
Watersound
Sports & Games
A massive 25-ft Jumbotron—the biggest screen in town—will show a college football watch party all season long. Attendees can enjoy multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, with all the big games shown all day long. Whether people are supporting their alma mater or just attending for the rivalries, this is the place to watch college football. The specific games shown on the Jumbotron are posted weekly by Wednesday. All other games will be shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Attendees are asked to see a manager at the bars for all requests.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday for the entire season, offering a prime location to view every play. The venue features a 25-foot Jumbotron and is surrounded by multiple restaurants and bars serving game day favorites. Attendees can enjoy game day bites, full-service bars, and a fan-friendly atmosphere with outdoor viewing. It is presented as the ultimate NFL destination for fans cheering for their home team or tracking their fantasy lineup. The specific games shown on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under the covered pavilion, with several available for requests on a first-come basis by asking a manager at the bars.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill is the ultimate destination for catching every NFL game, hosting an NFL Watch Party every Sunday throughout the season. Visitors can watch the wall-to-wall football action on the 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites. The event features game day bites from various eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing options. Whether attendees are rooting for their favorite team or tracking their fantasy lineup, this location provides the ultimate NFL experience. The specific games displayed on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under a covered pavilion, and requests for specific games can be made to a manager at the bars on a first-come basis.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Monday throughout the season, offering the best place to catch every play. Attendees can enjoy wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites, including game day bites. The atmosphere is fan-friendly, with full-service bars and outdoor viewing options, making it the ultimate destination for cheering on a home team or tracking a fantasy lineup.
College Football on the Jumbotron
Watersound
Sports & Games
A college football watch party is being held all season long. Attendees are invited to watch their favorite college football teams compete on a massive 25-ft Jumbotron. Multiple restaurants and bars will be available, offering ice-cold drinks and an electric atmosphere with outdoor seating. All the big games will be shown all day long. This is the ideal spot for fans to represent their alma mater or enjoy the rivalries. Guests are encouraged to bring their friends, wear their team colors, and cheer loudly for a proper college football experience. The specific games shown on the Jumbotron will be posted weekly by Wednesday. All other games will be shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Guests should ask a manager at the bars for any requests.
NYE Celebration! College Football and Beach Ball Drop!
Watersound
Family Fun
The event organizers are hosting a family-friendly New Year's Eve Celebration to ring in 2026. The celebration will feature college football bowl games displayed on a Jumbotron, as well as an early New Year's Eve countdown and beach ball drop. The Beach Ball Drop will take place on stage with DJ Dan Davis during halftime of the game that begins at 6:30 p.m. The precise timing of the countdown and ball drop is dependent upon the progression of the game.
Sun, December 21
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday throughout the season. This venue is described as the ultimate NFL destination for catching every play, featuring wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites. Guests can enjoy game day bites, full-service bars, and a fan-friendly atmosphere with outdoor viewing. The specific games shown on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under the covered pavilion, with several TVs available for requests on a first-come basis by asking a manager at the bars.
Mon, December 22
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday for the duration of the season. It is presented as the ideal location to catch every play, featuring wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars offering game-day favorites. The venue provides Game Day Bites from multiple eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing. Whether guests are supporting their home team or monitoring their fantasy lineup, the Big Chill is promoted as the ultimate NFL destination. The specific games shown on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis; guests are asked to request a manager at the bars for all requests.
Mon, December 22
NFL on the Jumbotron
Watersound
Sports & Games
An NFL Watch Party takes place every Monday throughout the season at The Big Chill. It is the ultimate destination for catching every play, featuring wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars. Guests can enjoy game day bites from various eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing. Whether attendees are cheering for their home team or tracking their fantasy lineup, this venue serves up all the game day favorites.
Tue, December 23
College Football on the Jumbotron
Watersound
Sports & Games
A College Football Watch Party is being held all season long. Attendees are invited to watch their favorite college football teams on a massive 25-ft Jumbotron, advertised as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, an electric atmosphere, and all the big games all day long. This is the place to be for those representing their alma mater or just enjoying the rivalries, encouraging them to bring their group, wear their colors, and get loud for College Football, done right. The specific games shown on the Jumbotron will be posted weekly by Wednesday. All other games will be shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Attendees are instructed to ask for a manager at the bars for all requests.
Thu, December 25
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Thursday throughout the season, offering attendees the best place to catch every play. The venue provides wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game-day favorites. Guests can enjoy game-day bites from various eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing. This location serves as the ultimate NFL destination, whether guests are cheering for their home team or tracking their fantasy lineup.
Fri, December 26
College Football on the Jumbotron
Watersound
Sports & Games
An establishment is hosting a College Football Watch Party all season long. Attendees are invited to watch their favorite college football teams compete on a 25-ft Jumbotron, noted as the biggest screen in town. The venue offers multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere to enjoy all the big games. Guests are encouraged to bring their friends, wear their team colors, and participate in the excitement. The specific games shown on the Jumbotron will be posted weekly by Wednesday. All other games will be displayed on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Guests should ask a manager at the bars for all requests.
Fri, December 26
Karaoke Night
Watersound
Live Music
The public is invited to attend Karaoke Night, which is held every Friday at 7 PM.
Sat, December 27
College Football on the Jumbotron
Watersound
Sports & Games
A massive 25-ft Jumbotron—the biggest screen in town—will show a college football watch party all season long. Attendees can enjoy multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, with all the big games shown all day long. Whether people are supporting their alma mater or just attending for the rivalries, this is the place to watch college football. The specific games shown on the Jumbotron are posted weekly by Wednesday. All other games will be shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Attendees are asked to see a manager at the bars for all requests.
Sun, December 28
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday for the entire season, offering a prime location to view every play. The venue features a 25-foot Jumbotron and is surrounded by multiple restaurants and bars serving game day favorites. Attendees can enjoy game day bites, full-service bars, and a fan-friendly atmosphere with outdoor viewing. It is presented as the ultimate NFL destination for fans cheering for their home team or tracking their fantasy lineup. The specific games shown on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under the covered pavilion, with several available for requests on a first-come basis by asking a manager at the bars.
Mon, December 29
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill is the ultimate destination for catching every NFL game, hosting an NFL Watch Party every Sunday throughout the season. Visitors can watch the wall-to-wall football action on the 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites.
The event features game day bites from various eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing options. Whether attendees are rooting for their favorite team or tracking their fantasy lineup, this location provides the ultimate NFL experience.
The specific games displayed on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under a covered pavilion, and requests for specific games can be made to a manager at the bars on a first-come basis.
Mon, December 29
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Monday throughout the season, offering the best place to catch every play. Attendees can enjoy wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites, including game day bites. The atmosphere is fan-friendly, with full-service bars and outdoor viewing options, making it the ultimate destination for cheering on a home team or tracking a fantasy lineup.
Tue, December 30
College Football on the Jumbotron
Watersound
Sports & Games
A college football watch party is being held all season long. Attendees are invited to watch their favorite college football teams compete on a massive 25-ft Jumbotron. Multiple restaurants and bars will be available, offering ice-cold drinks and an electric atmosphere with outdoor seating. All the big games will be shown all day long. This is the ideal spot for fans to represent their alma mater or enjoy the rivalries. Guests are encouraged to bring their friends, wear their team colors, and cheer loudly for a proper college football experience. The specific games shown on the Jumbotron will be posted weekly by Wednesday. All other games will be shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Guests should ask a manager at the bars for any requests.
Wed, December 31
NYE Celebration! College Football and Beach Ball Drop!
Watersound
Family Fun
The event organizers are hosting a family-friendly New Year’s Eve Celebration to ring in 2026. The celebration will feature college football bowl games displayed on a Jumbotron, as well as an early New Year’s Eve countdown and beach ball drop. The Beach Ball Drop will take place on stage with DJ Dan Davis during halftime of the game that begins at 6:30 p.m. The precise timing of the countdown and ball drop is dependent upon the progression of the game.
Reviews - 5
Google
We take multiple trips to Santa Rosa every year and this is hands down our favorite place we’ve ever stayed in!!!
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!!
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
Airbnb
Airbnb
Host Family
Diamond Office at Sunnyside
Office location:
Diamond Office at Sunnyside, Florida
Contact Diamond Office at Sunnyside
Out of Office
Santa Rosa Beach - Sleeps 10
5 bedrooms - 5 beds - 4 baths