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 Monday, all season long. It is the ideal location to watch every play, featuring wall-to-wall football action on a 25-foot Jumbotron. Multiple restaurants and bars are available, serving game-day favorites. Guests can enjoy game-day bites from various eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing. Whether cheering for a home team or tracking a fantasy lineup, The Big Chill is the ultimate NFL destination.
Create Starfish Characters Workshop
Watersound
Arts & Culture
An event invites participants to meet artist and author John Hollan at The Big Chill for a creative afternoon. Attendees can design their own unique starfish character from the Starfish Family, choosing outfits, colors, and accessories. The event also offers the opportunity to meet John Hollan and get a signed copy of his book. All necessary supplies are provided, and the activity is suitable for kids, families, and creative individuals. Fees apply, with each character costing $20.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Thursday throughout the season, offering a prime location to catch every play. The venue features a 25-foot Jumbotron, 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, whether they are cheering for their favorite team or managing a fantasy lineup.
Discover Watersound Weekend
Watersound
Outdoor Activities
The Watersound community is hosting an immersive experience from October 24–26, blending exploration, relaxation, and a sense of place. This weekend offers guided community tours, lifestyle events, and exclusive access to local amenities, designed to help guests determine if Watersound feels like home. A detailed schedule will be provided before the event, but a sample itinerary includes a beachfront bonfire at the Watersound Beach Club on Friday evening, where guests can mingle with ambassadors. Saturday morning features the RUN WATERSOUND 5K & 10K race, followed by guided tours of Watersound communities such as Watersound Origins, Watersound Camp Creek, Latitude Margaritaville Watersound, Watersound Club, and Watersound Fountains, showcasing available homes, club amenities, and natural beauty. The evening concludes with a poolside happy hour at the Camp Creek Inn. On Sunday, the Watersound Block Party at The Pavilion in Watersound Town Center will feature live music, local food trucks, fun activities, and the welcoming energy of the growing community.
DJ Dance Party
Watersound
Family Fun
The ultimate family dance party is an event not to be missed. Attendees can get ready to hit the stage and bust a move with DJ Dan Davis, who will be spinning all their favorite hits from 6–9:30 PM. The event is a night of high-energy fun, dancing, and family-friendly vibes, where the whole crew can light up the dance floor.
Discover Watersound Weekend
Watersound
Outdoor Activities
Attendees are invited to join an immersive experience from October 24–26, blending exploration, relaxation, and a true sense of place within the Watersound community. This weekend offers guided community tours, lifestyle events, and exclusive access to local amenities, serving as an ideal opportunity to discover if Watersound feels like home. A detailed schedule will be shared prior to the event, with a sample itinerary provided. Friday evening kicks off with a beachfront bonfire at the exclusive Watersound Beach Club, where guests can mingle with community ambassadors and other attendees. On Saturday, the morning begins with the RUN WATERSOUND 5K & 10K, a scenic race through the Watersound Origins community. Following this, guided tours of Watersound communities, including Watersound Origins, Watersound Camp Creek, Latitude Margaritaville Watersound, Watersound Club, and Watersound Fountains, will offer a closer look at available homes, club amenities, and the surrounding natural beauty. The evening concludes with a poolside happy hour at the stunning Camp Creek Inn. Sunday concludes the stay with the Watersound Block Party at The Pavilion in Watersound Town Center, featuring live music, local food trucks, fun activities, and the welcoming energy of the growing community.
RunWatersound 5K & 10K Race
Watersound
Outdoor Activities
At RunWatersound, participants of all skill levels engage in an annual 5k and 10k race. The event features a flat, scenic course that winds through the paths and streets of the Watersound Origins community, culminating in an awards ceremony and a time for camaraderie.
College Football on the Jumbotron
Watersound
Sports & Games
This establishment is hosting a College Football Watch Party every Saturday, all season long. Attendees can watch their favorite college football teams on a massive 25-ft Jumbotron, which is described as the biggest screen in town. The venue offers multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, ensuring all the big games are shown all day long. It's the ideal spot for fans to represent their alma mater or enjoy rivalries. Guests are encouraged to bring their friends, wear their team colors, and get loud for a proper College Football Saturday experience. The specific games featured on the Jumbotron will be posted weekly by Wednesday. Other games will be displayed on TVs under a covered pavilion, with several TVs available for requests on a first-come, first-served basis. Guests can ask a manager at the bars for any requests.
Discover Watersound Weekend
Watersound
Family Fun
Watersound invites guests to an immersive experience from October 24–26, blending exploration, relaxation, and a true sense of place. This weekend offers guided community tours, lifestyle events, and exclusive access to local amenities, making it ideal for those considering the Watersound community as a potential home. A detailed schedule will be shared prior to the event, with a sample itinerary provided. Friday evening kicks off with a beachfront bonfire at the exclusive Watersound Beach Club, where guests can mingle with community ambassadors and other attendees. Saturday morning begins with the RUN WATERSOUND 5K & 10K, a scenic race through the Watersound Origins community. Following the race, guided tours of various Watersound communities will be offered, including Watersound Origins, Watersound Camp Creek, Latitude Margaritaville Watersound, Watersound Club, and Watersound Fountains. These tours provide a closer look at available homes, club amenities, and the natural beauty of the surroundings. In the evening, a poolside happy hour will be held at the stunning Camp Creek Inn. Sunday concludes the stay with the Watersound Block Party at The Pavilion in Watersound Town Center. This event features live music, local food trucks, fun activities, and the welcoming atmosphere of the growing community.
Mon, October 20
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Monday, all season long. It is the ideal location to watch every play, featuring wall-to-wall football action on a 25-foot Jumbotron. Multiple restaurants and bars are available, serving game-day favorites. Guests can enjoy game-day bites from various eateries, full-service bars, a fan-friendly atmosphere, and outdoor viewing. Whether cheering for a home team or tracking a fantasy lineup, The Big Chill is the ultimate NFL destination.
Tue, October 21
Create Starfish Characters Workshop
Watersound
Arts & Culture
An event invites participants to meet artist and author John Hollan at The Big Chill for a creative afternoon. Attendees can design their own unique starfish character from the Starfish Family, choosing outfits, colors, and accessories. The event also offers the opportunity to meet John Hollan and get a signed copy of his book. All necessary supplies are provided, and the activity is suitable for kids, families, and creative individuals. Fees apply, with each character costing $20.
Thu, October 23
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Thursday throughout the season, offering a prime location to catch every play. The venue features a 25-foot Jumbotron, 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, whether they are cheering for their favorite team or managing a fantasy lineup.
Fri, October 24
Discover Watersound Weekend
Watersound
Outdoor Activities
The Watersound community is hosting an immersive experience from October 24–26, blending exploration, relaxation, and a sense of place. This weekend offers guided community tours, lifestyle events, and exclusive access to local amenities, designed to help guests determine if Watersound feels like home. A detailed schedule will be provided before the event, but a sample itinerary includes a beachfront bonfire at the Watersound Beach Club on Friday evening, where guests can mingle with ambassadors. Saturday morning features the RUN WATERSOUND 5K & 10K race, followed by guided tours of Watersound communities such as Watersound Origins, Watersound Camp Creek, Latitude Margaritaville Watersound, Watersound Club, and Watersound Fountains, showcasing available homes, club amenities, and natural beauty. The evening concludes with a poolside happy hour at the Camp Creek Inn. On Sunday, the Watersound Block Party at The Pavilion in Watersound Town Center will feature live music, local food trucks, fun activities, and the welcoming energy of the growing community.
Fri, October 24
DJ Dance Party
Watersound
Family Fun
The ultimate family dance party is an event not to be missed. Attendees can get ready to hit the stage and bust a move with DJ Dan Davis, who will be spinning all their favorite hits from 6–9:30 PM. The event is a night of high-energy fun, dancing, and family-friendly vibes, where the whole crew can light up the dance floor.
Sat, October 25
Discover Watersound Weekend
Watersound
Outdoor Activities
Attendees are invited to join an immersive experience from October 24–26, blending exploration, relaxation, and a true sense of place within the Watersound community. This weekend offers guided community tours, lifestyle events, and exclusive access to local amenities, serving as an ideal opportunity to discover if Watersound feels like home. A detailed schedule will be shared prior to the event, with a sample itinerary provided. Friday evening kicks off with a beachfront bonfire at the exclusive Watersound Beach Club, where guests can mingle with community ambassadors and other attendees. On Saturday, the morning begins with the RUN WATERSOUND 5K & 10K, a scenic race through the Watersound Origins community. Following this, guided tours of Watersound communities, including Watersound Origins, Watersound Camp Creek, Latitude Margaritaville Watersound, Watersound Club, and Watersound Fountains, will offer a closer look at available homes, club amenities, and the surrounding natural beauty. The evening concludes with a poolside happy hour at the stunning Camp Creek Inn. Sunday concludes the stay with the Watersound Block Party at The Pavilion in Watersound Town Center, featuring live music, local food trucks, fun activities, and the welcoming energy of the growing community.
Sat, October 25
RunWatersound 5K & 10K Race
Watersound
Outdoor Activities
At RunWatersound, participants of all skill levels engage in an annual 5k and 10k race. The event features a flat, scenic course that winds through the paths and streets of the Watersound Origins community, culminating in an awards ceremony and a time for camaraderie.
Sat, October 25
College Football on the Jumbotron
Watersound
Sports & Games
This establishment is hosting a College Football Watch Party every Saturday, all season long. Attendees can watch their favorite college football teams on a massive 25-ft Jumbotron, which is described as the biggest screen in town. The venue offers multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, ensuring all the big games are shown all day long. It’s the ideal spot for fans to represent their alma mater or enjoy rivalries. Guests are encouraged to bring their friends, wear their team colors, and get loud for a proper College Football Saturday experience. The specific games featured on the Jumbotron will be posted weekly by Wednesday. Other games will be displayed on TVs under a covered pavilion, with several TVs available for requests on a first-come, first-served basis. Guests can ask a manager at the bars for any requests.
Sun, October 26
Discover Watersound Weekend
Watersound
Family Fun
Watersound invites guests to an immersive experience from October 24–26, blending exploration, relaxation, and a true sense of place. This weekend offers guided community tours, lifestyle events, and exclusive access to local amenities, making it ideal for those considering the Watersound community as a potential home. A detailed schedule will be shared prior to the event, with a sample itinerary provided.
Friday evening kicks off with a beachfront bonfire at the exclusive Watersound Beach Club, where guests can mingle with community ambassadors and other attendees.
Saturday morning begins with the RUN WATERSOUND 5K & 10K, a scenic race through the Watersound Origins community. Following the race, guided tours of various Watersound communities will be offered, including Watersound Origins, Watersound Camp Creek, Latitude Margaritaville Watersound, Watersound Club, and Watersound Fountains. These tours provide a closer look at available homes, club amenities, and the natural beauty of the surroundings. In the evening, a poolside happy hour will be held at the stunning Camp Creek Inn.
Sunday concludes the stay with the Watersound Block Party at The Pavilion in Watersound Town Center. This event features live music, local food trucks, fun activities, and the welcoming atmosphere of the growing community.
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