Holiday rentals in Osteen

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Top-rated holiday rentals in Osteen

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Top guest favourite
A screened wrap-around porch offers views of the lake, with sunlight casting striped shadows on the floor. Two lounge chairs are positioned for relaxation, while a colorful playpen is set against the railing. Decorative surfboards are mounted on the walls, enhancing the space's charm.
Cottage in Sanford
4.98 out of 5 average rating, 242 reviews

Lakefront,Sanford airport, Boombah, Venue 1902,UCF

The lake front cottage is located on a private estate 1 mile south of Sanford airport, 4 miles to Sanford historic district, and 3 miles from Boombha Sports Complex. This cottage has a Fully equipped kitchen, light bright liv/din area, screened wrap around porch. Perfect spot for your next family vacation or weekend get away. While staying at the cottage you are welcome to enjoy our paddle boards and kayaks. Also catch and release fishing. No pets. Discounts for non-refundable cancellations.

Guest favourite
Guest house in Sanford
4.94 out of 5 average rating, 199 reviews

Little Hidden Cottage- Near Sanford Airport

Located in Sanford FL, our Hidden Little Cottage is a Private Studio Guest House with its own entrance, fence, features full kitchen & bath room, queen size bed, full size pull out couch & twin size travel bed, & provides flexible self check-in. We are located 7 minutes from the Sanford Airport and Boombah Sports Complex, 10 minutes to Downtown Sanford, I –4 & 4–17. We’re also central to many Central Florida attractions such as Natural Springs, Sandy Beaches, Theme Parks and Historic Districts

Guest favourite
Treehouse in Geneva
4.89 out of 5 average rating, 1,110 reviews

Treehouse at Danville

Private Getaway seen on Netflix' Most Amazing Vacation Rentals! Fulfill your dream of staying in a tree house! For safety reasons, this venue is for adults only. We do not allow children or pets. The Treehouse has a tree trunk elevator, private shower, air-conditioning, and real toilet inside so that you can bring your significant other(no compost toilet here). This 18 foot yurt has accent lighting to create the mood of living in the trees on a starry night. Danville is a glamping experience.

Top guest favourite
A charming houseboat with a teal exterior is shown moored at a marina, reflecting in calm waters. The upper deck is accessible by a ladder, and neighboring vessels and palm trees form a scenic background.
Houseboat in Sanford
4.96 out of 5 average rating, 126 reviews

Downtown Marina Floating Home Historic Sanford

You'll love this unique romantic escape located in historic downtown Sanford! This is a nearly new built top of the line Houseboat and you will be amazed at all the amenities fit on this 12x40 floating tiny home. Nicely suited for one couple. One step to get in and then all on one level other than the upper deck. (Ladder) Max occupancy at any time is 4. Walking distance to downtown restaurants, shops and so much more. Note that this is a very small space if you are used to a full size home.

Guest favourite
A charming exterior of a single-story home is shown, featuring a light blue façade and two large windows. A clear pathway leads to the front entrance, framed by lush green grass. A porch with two red chairs invites relaxation beneath the expansive oak trees overhead.
Flat in Sanford
4.92 out of 5 average rating, 114 reviews

The Bed & Brad

Kick back and relax in this calm, stylish space. Enjoy the splendors of Sanford’s historic district with its beautiful brick roads and magnificent oak lined streets dripping with southern Spanish Moss. Walk or ride to the downtown area where you can eat and drink till your hearts content. Enjoy a walk along the lake or stroll through the streets to look at glorious restored southern homes. The Bed & Brad offers you all the comforts of home where you can enjoy your stay at your own pace.

Guest favourite
A well-manicured pathway leads to the studio, surrounded by lush greenery and colorful plants. Visible are large windows framed by white curtains, providing a view of the scenic lake. A patio with a red umbrella and a picnic table is accessible for outdoor relaxation.
Guest house in Lake Mary
4.91 out of 5 average rating, 123 reviews

Nature Unique lake view Tiny Guest studio

Tiny Guest house studio with separate entrance for privacy and amazing Lake view. Unlimited rental of 2 Blue kayaks included during stay!! Walking distace from windixie supermarket, downtown lake Mary, restaurants, shopping centers, entertainment and dunking Donuts. Common areas outside studio are shared. Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl. 30 min to Daytona Beach. Near Wekiva springs. To go to Disney, easy access to I-4 and 4-17.

Top guest favourite
A light-filled living space features a gray sofa positioned across from an open doorway leading to a porch. A round white coffee table displays a decorative tray, while a wall clock and nature-themed artwork add subtle touches to the room.
Tiny home in Lake Helen
4.99 out of 5 average rating, 503 reviews

Mira Bella South

Tiny Home with full kitchen on a peaceful 13 acres in a small town. Owner lives on site, but the tiny home is away from the main house so it is private. Ideal for 2 guests, but there is a pull-out sofa which could be comfortable for one more adult or a couple kids. Room for more than one car or a trailer. (Not suitable for 4-legged travelers due to free ranging ducks, peacocks and close proximity to horses and miniature donkeys) (If your dates are unavailable, search Mira Bella North)

Guest favourite
The inviting living room features a light-colored sofa flanked by two dark gray armchairs. A round coffee table is centrally placed, surrounded by a textured area rug. Natural light is provided by large windows, enhancing the room's spacious feel.
Home in Deltona
4.94 out of 5 average rating, 121 reviews

Stunning home with screened patio & fenced yard

Renovated family home in a quiet residential neighborhood. 45 minutes away from Daytona Beach and New Smyrna Beaches, and an hour away from Disney, Universal Studios, Animal kingdom, Epcot, and all Orlando attractions. Deltona is know for its many lakes and Springs. Family friendly and centrally located between Daytona Beach and Orlando parks. Daytona Speedway is only 36 minutes drive. Visiting with an infant, for your convenience, we provide a Playpen, a bouncing seat, and a tub.

Top guest favourite
Home in Orange City
4.99 out of 5 average rating, 145 reviews

The Lemon Cottage -NO EXTRA FEES

Our cottage is nestled in Orange City RV Park. It is your home away from home! Our kitchen is equipped with all pots, pans, and dishes you will need. Our living room has a queen pull out sofa. Our bathroom provides towels, shampoo & conditioner, and a hair dryer. The bedroom has a queen size bed. We are pet friendly; we allow up to two pets. - 20m Daytona Speedway - 26m Daytona Beach - 35m Universal Studios - 41m Disney World - 66m Kennedy Space Center - 73m Legoland

Top guest favourite
An enclosed patio features a large dining table surrounded by six chairs, providing a relaxed space for meals. Comfortable seating is arranged nearby. The expansive glass walls offer clear views of the St. Johns River and the lush landscape outside, inviting natural light into the space.
Home in Osteen
4.97 out of 5 average rating, 36 reviews

Gorgeous St. Johns River home 3bdrm/2 bth

Welcome to La Casita on Lemon Bluff retreat located directly along the St. Johns River, where modern elegance meets natural serenity. Enjoy an open kitchen, chic bedrooms, and spa-like bathrooms. As the day winds down, sip cocktails on the dock or unwind in the enclosed patio while barbecuing. La Casita seamlessly blends comfort and sophistication, offering a tranquil escape where the river extends your living space. Book now for a serene riverside retreat.

Guest favourite
The studio features a well-organized layout with a spacious area containing two beds, one with a dark throw and accent pillows. A desk with a chair is positioned nearby, while soft lighting from bedside lamps creates a cozy ambiance. A scenic wall art piece complements the decor.
Guest suite in Deltona
4.9 out of 5 average rating, 63 reviews

Relaxing Studio Suite – Big Bath + Private Entry

Stay in a prime location between Daytona Beach and Orlando! This private studio offers a queen bed and queen sofa bed, perfect for couples, families, or solo travelers. Relax in a spacious bathroom with a walk-in shower and bathtub for ultimate comfort. Just a short drive to top attractions: • 30 min to Daytona Beach ☀️🏖️ • 40 min to Orlando’s theme parks 🎢✨ • 15 min to Blue Spring State Park 🌿💦 Enjoy a peaceful retreat with easy access to adventure!

Top guest favourite
A welcoming living area features comfortable seating arrangements around a central ottoman. A large television is placed on a stylish console, with decorative plants and artwork enhancing the space. Natural light streams through windows, contributing to a bright, inviting environment.
Home in Sanford
4.98 out of 5 average rating, 167 reviews

The Cypress House

This beautiful 2 bedroom, 1 bathroom Ranch Style home is conveniently located 3.5 miles from the Sanford International Airport and Boombah Sports Complex. The inviting landscape and backyard where you can cool off in the rustic style stock tank pool or grill out and relax on the patio. The open floor plan creates a spacious feel and every finish was selected with care. For a glamping experience check out our other listing: https://abnb.me/z3XrgOSPNFb

Popular amenities for Osteen holiday rentals

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