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Holiday rentals in Osteen

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Top-rated holiday rentals in Osteen

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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, 117 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.

Top guest favourite
A studio-style living space features a spacious bed with neutral bedding, complemented by decorative pillows. A round mirror hangs over a wooden nightstand. The kitchenette area includes a small microwave and cabinetry, while an area rug adds warmth to the wooden floor.
Guest suite in Sanford
4.98 out of 5 average rating, 239 reviews

The Secret Sanctuary in Sanford, 5min from Airport

Welcome to your quiet, spacious, and private sanctuary. Enjoy all new appliances in the full size kitchen, a 50” flat screen TV, and a shaded outdoor area surrounded by greenery. It is located only minutes from the Orlando Sanford International Airport, Historic Downtown Sanford’s restaurants and shops, Lake Monroe’s scenic waterfront, and is centrally located between Florida’s beaches and the amusement parks. **Space is cleaned with EPA approved cleaners, including high touch surfaces**

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
4.95 out of 5 average rating, 101 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.

Guest favourite
Guest house in Sanford
4.94 out of 5 average rating, 174 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, 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
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
4.95 out of 5 average rating, 108 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
A cozy lounge area features a gray sofa and a small dining table with two wooden chairs. A wall with natural wood accents complements a colorful beach-themed art piece. Light streams through a nearby window, enhancing the inviting atmosphere.
Guest suite in Orange City
4.94 out of 5 average rating, 126 reviews

The Hillside Haven Oasis

Enjoy a warm and inviting stay in our beautiful Sanctuary in your own private guest quarters, sweetly dubbed, "The Hillside Haven Oasis" This is an extension of our home, similar to a Mother In Law Suite. Only shared space would be the outdoors and we leave that for your private enjoyment. We created this Oasis with a desire is for our guests to feel calm, comfort and tranquility while being showered with Florida Sun. It would be our privilege to serve you as our guests here. :)

Top guest favourite
Home in Orange City
4.98 out of 5 average rating, 120 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

Guest favourite
A cozy bedroom features a black platform bed dressed in a navy and white patterned duvet. A wooden dresser stands adjacent to the bed, and a small desk is positioned nearby. Natural light illuminates the space, highlighting the serene beach artwork on the wall.
Guest suite in Eatonville
4.97 out of 5 average rating, 193 reviews

Private entrance/bathroom 10 min from DT Orlando

Welcome to your home away from home! Our cozy room with a attached bathroom is the perfect retreat for your visit to Orlando. Located just 10min from downtown Orlando, 30min from MCO and Disney, and 20 min from Universal, you'll have the best of both worlds - convenience and comfort. Whether you're here for business or pleasure, our room is the perfect place to call your temporary home. Book your stay with us today and experience the best of our city.

Top guest favourite
A welcoming entrance features a bright red door beneath a yellow awning. A pathway made of pavers leads to several outdoor seating arrangements, with black metal tables and chairs. Lush green grass and trees are visible in the background, offering a serene atmosphere.
Guest suite in Geneva
4.95 out of 5 average rating, 239 reviews

The Weathered Inn at Cedar Knoll Flying Ranch

Fly in with your personal airplane to our private airport or cruise the Saint John’s river and tie up to our dock or hop in your car in and enjoy 130 acres of pristine Florida living ! We have a $20 maintenance fee for use of a golf cart to enjoy trails, head to the water to fish or visit our Scottish Highland cows and their babies! Go kayaking, fishing or canoeing on the St. John’s River or just enjoy the Florida sunshine!

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, 476 reviews

Mira Bella South

Tiny Home (one of two guest houses) on a private 13 acres in a small equestrian town. Away from the main house, so it is private, but not isolated. Ideal for 2 guests, but there is a pull-out sofa which could be comfortable for one more adult or a couple younger kids. (Some have mentioned it's not that comfy for grown-ups. Very firm.) (If dates you want are unavailable, search for Tiny Home in Lake Helen - Mira Bella North.)

Top guest favourite
A serene lake scene is captured at sunset, reflecting hues of orange and blue across the water's surface. A wooden dock extends into the lake, surrounded by lush greenery, providing a tranquil atmosphere.
Guest suite in Chuluota
4.99 out of 5 average rating, 633 reviews

Enjoy Our Beautiful Sunsets and Peaceful Sunrises

Our Studio is nestled in Chuluota near Oviedo, UCF, Geneva on historically beautiful Lake Catherine. Our lake is land locked and feels very private where you can relax and enjoy the view. Coffee on the lake in the mornings or a glass of wine at sunset is what we live for and you can enjoy that same view from our paradise that we call our Key West Studio.

Top guest favourite
The living area contains a comfortable seating arrangement with a spacious couch and two armchairs. Natural light floods in through multiple windows, and a light rug sits under a small coffee table. A fan is positioned above for airflow, enhancing the inviting ambiance.
Guest house in Lake Helen
4.95 out of 5 average rating, 100 reviews

Lake Helen Getaway

Keep it simple at this peaceful and centrally-located studio less than a mile off of I4 in a quiet equestrian, golf cart community. Close to shopping/restaurants, Stetson University, historic downtown Deland, Blue Springs, DeLeon Springs, Cassadaga spiritualist community, Daytona Beach, New Smyrna Beach, and only 48mi from Disney/38mi Universal Studios.

Popular amenities for Osteen holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Volusia County
  5. Osteen