Our Tree House
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Our Tree House
Our Tree House by Oversee 30A | 2025 Diamond Winner-Best Rental Mgmt.
Modern style, coastal vibes, and just the right amount of “ahhh.” Our Tree House isn’t just a vacation home, it’s your group’s new 30A tradition. With five bedrooms, smart design, and serious comfort, this Watersound gem makes relaxing way too easy, including getting to the beach: It’s just a short bike ride or stroll away.
Highlights:
📍 Watersound
🏖️ Private deeded beach access!
🏡 5 bedrooms, 5.5 baths, including a carriage house
🚲 5 adult bikes for exploring 30A
💪🏼 Gated community with on-site security
😌 2 Living areas + 2 primary suites
☀️ Sunbathing deck and balcony
Inside, the main living area is open and bright, and made for lazy mornings and long evenings. The kitchen’s ready for a quick breakfast or cocktail shakers (your call), while the big dining table invites slow breakfasts, late dinners, and everything in between. Sink into the oversized sofa for movie night or an afternoon nap.
The first-floor primary suite? Soft lighting, sleek finishes, and a bathroom that could moonlight as a spa.
Just add bubbles. Upstairs, a second lounge opens to a sunlit balcony. Three additional bedrooms include another primary suite, a guest room, and a twin-over-queen bunk room, each with a flat-screen TV and en-suite bath.
Need even more space? The carriage house comes with its own queen bed, full bath, chill-out zone, and kitchenette. It’s basically a mini retreat for that friend who likes their coffee just so.
Outside, the private courtyard is the kind of place where time slows down. Fire up the grill, sip something cold on the porch, or stake your claim on the sun deck connecting the two houses. It’s peaceful, it’s pretty, and it pairs well with sandy feet.
Our Tree House is all the fun of a beach escape, with the polish of a designer stay. Kick off your shoes—and maybe keep them off all week.
Overview:
- .2 of a mile to the private beach access and community pool
-Parking: 2 designated spaces
-Beach Service: Includes 2 chairs and 1 umbrella (March–October)
-No Golf Carts: Rentals or personal golf carts are not permitted
-Community Guidelines: No weddings, parties, or gatherings exceeding guest limits
FIRST FLOOR
- Primary Bedroom: King bed, private bathroom, shower and soaking tub
SECOND FLOOR
- Primary Bedroom: King bed, private bathroom, shower
- Guest Bedroom: Queen bed, shared bathroom, shower/tub combo
- Bunk Room: Twin-over-queen bunk bed, private bath, shower
CARRIAGE HOUSE:
-Guest Room: Queen bed, private bathroom, shower
Check-in: 4:00 PM CST | Check-out: 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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11 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
Outdoor
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Balcony
Community Amenities
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Community pool
Indoor
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Wireless internet
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Fireplace
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
Kitchen
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Standard coffee maker
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Microwave
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Refrigerator
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Toaster
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Dishwasher
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Stove
Bed And Bathroom
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Hair dryer
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Iron & board
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Bathtub
Complimentary Items
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5 Oversee bikes
- Beach chairs
Bed and Baths
1st Floor
Primary Bedroom
1 King bed
full bathroom
half bathroom
2nd Floor
Primary Bedroom
1 King bed
bedroom
1 Queen bed
bedroom
1 Bunk bed
full bathroom
full bathroom
full bathroom
bedroom
1 Queen bed
full bathroom
Location
Upcoming Events
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday, all season long. It is considered 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 venue offers game-day bites from multiple eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing. Whether guests are cheering for their home team or tracking their fantasy lineup, this location is their 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 advised to ask for a manager at the bars for all requests.
NFL on the Jumbotron
Watersound
Live Music
The Big Chill hosts an NFL Watch Party every Monday throughout the season. It is described as the best location to view every play on their 25-foot Jumbotron, with multiple surrounding restaurants and bars offering game day food and drinks. The venue features game day bites from various eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing, making it an ideal destination for fans tracking their teams or fantasy lineups.
Family Movie Night
Watersound
Family Fun
The Big Chill hosts Family Movie Nights, inviting guests to gather for an evening under the stars. The event is perfect for all ages, featuring favorite family flicks on their Jumbotron. Guests simply need to arrive and enjoy the experience.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill is the ultimate destination for catching every play of the NFL season. The venue hosts an NFL Watch Party every Thursday, all season long, with wall-to-wall football action displayed on a 25-foot Jumbotron. The atmosphere is fan-friendly, featuring multiple restaurants and bars serving game-day favorites, including bites and full-service bars, as well as an outdoor viewing area. Fans can cheer for their home team or track their fantasy lineup at this premier NFL destination.
DJ Dance Party
Watersound
Live Music
An ultimate family dance party is taking place, featuring DJ Dan Davis spinning popular hits from 6:00 PM to 9:30 PM. Attendees are encouraged to bring their families for a night of high-energy entertainment and dancing.
Karaoke Night
Watersound
Live Music
Game Day is offered for adults every Thursday at the library from Noon until 4:00 pm. Community members are encouraged to bring in and share card table games. The meeting space is available for family-friendly games that individuals bring in for others to play or learn. For more information, interested parties should call the library at 850-267-2809.
Holiday Market: Children’s Business Fair
Watersound
Markets & Shopping
Sign-ups begin every Thursday at 6:00 PM, with the event hosted by Ren and Dan. Guests are encouraged to warm up their vocal cords and enjoy a fun evening at LJ Schooners.
College Football on the Jumbotron
Watersound
Sports & Games
An establishment is hosting a season-long College Football Watch Party. Patrons are invited to join and watch their favorite college football teams compete on a massive 25-ft Jumbotron, touted as the biggest screen in town. Attendees can enjoy multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere while catching all the big games. Whether attendees are representing their alma mater or simply enjoying the rivalries, this location is presented as the ideal spot. Guests are encouraged to bring their friends, wear their team colors, and participate enthusiastically. The specific games displayed on the Jumbotron are scheduled to be posted weekly by Wednesday. All other games will be available on TVs located under a covered pavilion, with requests for specific games handled 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 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.
Mon, December 8
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday, all season long. It is considered 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 venue offers game-day bites from multiple eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing. Whether guests are cheering for their home team or tracking their fantasy lineup, this location is their 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 advised to ask for a manager at the bars for all requests.
Mon, December 8
NFL on the Jumbotron
Watersound
Live Music
The Big Chill hosts an NFL Watch Party every Monday throughout the season. It is described as the best location to view every play on their 25-foot Jumbotron, with multiple surrounding restaurants and bars offering game day food and drinks. The venue features game day bites from various eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing, making it an ideal destination for fans tracking their teams or fantasy lineups.
Wed, December 10
Family Movie Night
Watersound
Family Fun
The Big Chill hosts Family Movie Nights, inviting guests to gather for an evening under the stars. The event is perfect for all ages, featuring favorite family flicks on their Jumbotron. Guests simply need to arrive and enjoy the experience.
Thu, December 11
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill is the ultimate destination for catching every play of the NFL season. The venue hosts an NFL Watch Party every Thursday, all season long, with wall-to-wall football action displayed on a 25-foot Jumbotron. The atmosphere is fan-friendly, featuring multiple restaurants and bars serving game-day favorites, including bites and full-service bars, as well as an outdoor viewing area. Fans can cheer for their home team or track their fantasy lineup at this premier NFL destination.
Fri, December 12
DJ Dance Party
Watersound
Live Music
An ultimate family dance party is taking place, featuring DJ Dan Davis spinning popular hits from 6:00 PM to 9:30 PM. Attendees are encouraged to bring their families for a night of high-energy entertainment and dancing.
Fri, December 12
Karaoke Night
Watersound
Live Music
Game Day is offered for adults every Thursday at the library from Noon until 4:00 pm. Community members are encouraged to bring in and share card table games. The meeting space is available for family-friendly games that individuals bring in for others to play or learn. For more information, interested parties should call the library at 850-267-2809.
Sat, December 13
Holiday Market: Children’s Business Fair
Watersound
Markets & Shopping
Sign-ups begin every Thursday at 6:00 PM, with the event hosted by Ren and Dan. Guests are encouraged to warm up their vocal cords and enjoy a fun evening at LJ Schooners.
Sat, December 13
College Football on the Jumbotron
Watersound
Sports & Games
An establishment is hosting a season-long College Football Watch Party. Patrons are invited to join and watch their favorite college football teams compete on a massive 25-ft Jumbotron, touted as the biggest screen in town. Attendees can enjoy multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere while catching all the big games. Whether attendees are representing their alma mater or simply enjoying the rivalries, this location is presented as the ideal spot. Guests are encouraged to bring their friends, wear their team colors, and participate enthusiastically. The specific games displayed on the Jumbotron are scheduled to be posted weekly by Wednesday. All other games will be available on TVs located under a covered pavilion, with requests for specific games handled on a first-come basis by asking a manager at the bars.
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.
Host Family
Diamond Office at Sunnyside
Office location:
Diamond Office at Sunnyside, Florida
Contact Diamond Office at Sunnyside
Our Tree House
Rosemary Beach - Sleeps 11
5 bedrooms - 5 beds - 5.5 baths