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 for the entire season. It is the premier location to view every game, featuring wall-to-wall football action on their 25-foot Jumbotron. The venue is surrounded by multiple restaurants and bars offering favorite game day bites and full-service bars. The atmosphere is fan-friendly and includes outdoor viewing options. Whether spectators are supporting their home team or monitoring a fantasy lineup, The Big Chill is the ultimate NFL destination. The specific games displayed 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, first-served basis. Guests should ask a manager at the bars for any requests.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday throughout the season. It is presented as the premier location to watch every play, featuring wall-to-wall football action on a 25-foot Jumbotron. Attendees are surrounded by multiple restaurants and bars serving game day favorites, including "Game Day Bites" from various eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing. For fans cheering on their team or tracking a fantasy lineup, this venue is described 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; patrons should ask 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. This location is promoted as the best place to catch every play, featuring wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites. The event offers game day bites from various eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing. It is presented as the ultimate NFL destination for fans cheering for their home team or tracking their fantasy lineup.
College Football on the Jumbotron
Watersound
Sports & Games
The venue is hosting an all-season College Football Watch Party, inviting attendees to experience game day by watching their favorite college football teams compete on a massive 25-ft Jumbotron, described as the biggest screen in town. They offer multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere to watch all the big games, all day long. This is the place for fans to represent their alma mater or enjoy the rivalries. Guests are encouraged to bring their friends, wear their team colors, and be loud for a great 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, first-served basis by asking a manager at the bars.
College Football on the Jumbotron
Watersound
Sports & Games
A college football watch party is scheduled to take place all season long. Attendees are invited to watch their favorite college football teams compete head-to-head on a massive 25-ft Jumbotron. Guests can enjoy multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, ensuring all the big games are shown all day long. This is presented as the ideal location for supporting one's alma mater or simply enjoying rivalries, encouraging attendees to bring their groups, wear their colors, and get loud. It is noted that 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, and guests should ask 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 for the entire season. It is presented as the best place to catch every play, offering wall-to-wall football action on a 25-foot Jumbotron, and it is surrounded by multiple restaurants and bars serving game-day favorites. The event includes game-day bites from multiple eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing. This event is considered the ultimate NFL destination for fans cheering for their home team or tracking their fantasy lineup.
The Big Chill Holiday Party – Pictures with Santa, Holiday Market, + More!
Watersound
Family Fun
The Big Chill's annual holiday party will take place on December 19th from 12-4 pm. The celebration under the Pavilion will feature pictures with Santa from 12-3 pm and live music with Mat Hall from 12-4 pm. The event will also host a Holiday Market on the Lawn, which is hosted by Anchored Market Ventures, along with other pop-ups and activities.
College Football on the Jumbotron
Watersound
Sports & Games
The venue hosts a College Football Watch Party all season long. Attendees can watch their favorite college football teams compete on a massive 25-ft Jumbotron, advertised as the biggest screen in town. The location offers multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, promising all the big games, all day long. Whether guests are supporting their alma mater or simply enjoying the rivalries, the venue is presented as the ideal location for college football viewing. Guests are encouraged to bring their friends, wear their team colors, and participate enthusiastically. It is noted that 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 can ask a manager at the bars for all requests.
Karaoke Night
Watersound
Live Music
A weekly Karaoke Night is held every Friday, beginning at 7 PM.
College Football on the Jumbotron
Watersound
Sports & Games
A college football watch party is being held all season long, inviting people to get ready for game day. Attendees can watch their favorite college football teams compete on a massive 25-ft Jumbotron, described as the biggest screen in town. The event offers multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere to watch all the big games, all day long. It is presented as the ideal location for both alumni and those interested in rivalries. Guests are encouraged to bring their friends, wear their team colors, and participate enthusiastically, emphasizing that this is "College Football, done right." 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 game requests on a first-come, first-served basis, and guests are advised to ask 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 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.
Sun, December 14
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday for the entire season. It is the premier location to view every game, featuring wall-to-wall football action on their 25-foot Jumbotron. The venue is surrounded by multiple restaurants and bars offering favorite game day bites and full-service bars. The atmosphere is fan-friendly and includes outdoor viewing options. Whether spectators are supporting their home team or monitoring a fantasy lineup, The Big Chill is the ultimate NFL destination. The specific games displayed 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, first-served basis. Guests should ask a manager at the bars for any requests.
Mon, December 15
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday throughout the season. It is presented as the premier location to watch every play, featuring wall-to-wall football action on a 25-foot Jumbotron. Attendees are surrounded by multiple restaurants and bars serving game day favorites, including “Game Day Bites” from various eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing. For fans cheering on their team or tracking a fantasy lineup, this venue is described 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; patrons should ask a manager at the bars for all requests.
Mon, December 15
NFL on the Jumbotron
Watersound
Sports & Games
An NFL Watch Party takes place every Monday throughout the season at The Big Chill. This location is promoted as the best place to catch every play, featuring wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites. The event offers game day bites from various eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing. It is presented as the ultimate NFL destination for fans cheering for their home team or tracking their fantasy lineup.
Tue, December 16
College Football on the Jumbotron
Watersound
Sports & Games
The venue is hosting an all-season College Football Watch Party, inviting attendees to experience game day by watching their favorite college football teams compete on a massive 25-ft Jumbotron, described as the biggest screen in town. They offer multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere to watch all the big games, all day long. This is the place for fans to represent their alma mater or enjoy the rivalries. Guests are encouraged to bring their friends, wear their team colors, and be loud for a great 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, first-served basis by asking a manager at the bars.
Wed, December 17
College Football on the Jumbotron
Watersound
Sports & Games
A college football watch party is scheduled to take place all season long. Attendees are invited to watch their favorite college football teams compete head-to-head on a massive 25-ft Jumbotron. Guests can enjoy multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, ensuring all the big games are shown all day long. This is presented as the ideal location for supporting one’s alma mater or simply enjoying rivalries, encouraging attendees to bring their groups, wear their colors, and get loud. It is noted that 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, and guests should ask a manager at the bars for all requests.
Thu, December 18
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Thursday for the entire season. It is presented as the best place to catch every play, offering wall-to-wall football action on a 25-foot Jumbotron, and it is surrounded by multiple restaurants and bars serving game-day favorites. The event includes game-day bites from multiple eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing. This event is considered the ultimate NFL destination for fans cheering for their home team or tracking their fantasy lineup.
Fri, December 19
The Big Chill Holiday Party – Pictures with Santa, Holiday Market, + More!
Watersound
Family Fun
The Big Chill’s annual holiday party will take place on December 19th from 12-4 pm. The celebration under the Pavilion will feature pictures with Santa from 12-3 pm and live music with Mat Hall from 12-4 pm. The event will also host a Holiday Market on the Lawn, which is hosted by Anchored Market Ventures, along with other pop-ups and activities.
Fri, December 19
College Football on the Jumbotron
Watersound
Sports & Games
The venue hosts a College Football Watch Party all season long. Attendees can watch their favorite college football teams compete on a massive 25-ft Jumbotron, advertised as the biggest screen in town.
The location offers multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, promising all the big games, all day long.
Whether guests are supporting their alma mater or simply enjoying the rivalries, the venue is presented as the ideal location for college football viewing. Guests are encouraged to bring their friends, wear their team colors, and participate enthusiastically.
It is noted that 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 can ask a manager at the bars for all requests.
Fri, December 19
Karaoke Night
Watersound
Live Music
A weekly Karaoke Night is held every Friday, beginning at 7 PM.
Sat, December 20
College Football on the Jumbotron
Watersound
Sports & Games
A college football watch party is being held all season long, inviting people to get ready for game day. Attendees can watch their favorite college football teams compete on a massive 25-ft Jumbotron, described as the biggest screen in town. The event offers multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere to watch all the big games, all day long. It is presented as the ideal location for both alumni and those interested in rivalries. Guests are encouraged to bring their friends, wear their team colors, and participate enthusiastically, emphasizing that this is “College Football, done right.” 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 game requests on a first-come, first-served basis, and guests are advised to ask a manager at the bars for all requests.
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.
Reviews - 4
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