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Osteen Holiday Rentals

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    Don't let other travellers get your favourite Osteen area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 22 Rentals in Osteen
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    SunShine Ranch1 / 139
    (3)Average
    Osteen
    8 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    Osteen
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 15 kilometres of Osteen.
    Luxury Florida Pool home 2 Bedroom 2 Bath1 / 21
    (2)Excellent
    Deltona
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pleasant Point River Retreat1 / 5
    (7)Very good
    Geneva
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Outdoor Dining Area
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 December 2016
    It was Charming even had nice Collectibles a handmade ship on the fireplace everything we needed we had. Perfect place to put the boat in nice and quiet. The only thing we...
    Reviewed 1 March 2016
    Great place for fishing or just to relax and escape the city life and enjoy a retreat with amazing wild life surrounding.
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    About this property
    Located on the scenic St. John's River in Geneva, Seminole County, Florida these 2 fully furnished 1 bedroom 2 bathroom non-smoking luxury cabins are overlooking the water for spectacular sunrises and fishing from the back deck. Safe, secure and private with a private boat ramp for launching....
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    Location Information
    Geneva, Florida 32732
    Cabin Holiday Rental - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Lake Helen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful country home in the historic, Lake Helen, FL. The 1600 sq ft home features a 3bd/2b, open-concept, floor plan that has plenty of room for entertainment or just some tranquility and peace away from home. During your stay you can enjoy the gorgeous view, through the living room windows,...
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    Location Information
    Lake Helen, Florida 32744
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Floating Cottage . . .afloat on the St. Johns River in Florida1 / 23
    (3)Excellent
    Sanford
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2018
    We stayed three nights and wish it could have been longer. The cottage has everything you need to rest, relax, and enjoy life on the water. If you are looking for a beautiful...
    Reviewed 7 May 2018
    The entire booking experience from start to finish was absolutely SUPERB!!Kim was very engaged and amiable from our first interaction. Her customer service is far beyond...
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    About this property
    Welcome to FLOATING COTTAGE . . . charming and unique houseboat vacation rental on the St. Johns River . Imagine relaxation, gently afloat in a quiet, clean-water designated marina in Sanford, Florida. Poised to delight, Floating Cottage provides a peaceful environment to relax, replenish and...
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    Location Information
    Sanford, Central Florida 32771
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ninovan on the Shore, A river retreat with history1 / 27
    (2)Excellent
    Sanford
    4 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Waterfront
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2018
    We rented this property for multifamily use with 3 generations as it was our son's wedding week/weekend and it was a wonderful choice! My daughter and I arrived early enough to...
    Reviewed 25 February 2016
    The most beautiful and relaxing mini-vacation I have ever taken with the family. The house was immaculate and well stocked. Annemarie is the best hostess ever! always...
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    About this property
    A quiet house with a large cabin feel, tucked away from the hustle and bustle of Orlando and Daytona Beach but is within short driving distances from some of Florida's amazing springs and nature walks! The house boast an amazing view of the Saint John's river, the Lake Monroe Conservation area, and...
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    Location Information
    Sanford, Central Florida 32771
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 13
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    Deltona Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is located on a quiet street with no front neighbors. Enjoy this newly decorated 3 bed, 2 bath pool home with private fenced in yard. As you enter this home you will notice how clean and clutter free it is. This home has been decorated and fitted to feel like a home away from home. Enjoy...
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    Deltona Pines, Florida 32725
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Deltona Private Oasis Awaits! ONLY 30MIN T0 DAYTONA, 45MIN TO DISNEY & UNIVERSAL1 / 31
    (2)Excellent
    Deltona
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Central Heating
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    This house was amazing, it looked like it was newly upgraded and it had lots of space! 4 bedrooms, 2 bathrooms, and lots of space for the kids to run around. There is a lake...
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    About this property
    Located in a safe and clean neighborhood. Our Home is on a cul de sac over-viewing a lake, so it feels like your own private oasis! It has a open concept floor-plan, you can be in the kitchen and still enjoy the views of the lake. It also has a spacious drive-way that can fit a trailer, multiple of...
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    Location Information
    Deltona, Florida 32738
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2BR BUNGALOW IN SANFORD HISTORIC DISTRICT1 / 16
    (1)Excellent
    Sanford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Balcony
    • Terrace
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 April 2016
    Absolutely loved our time spent in this adorable 2 BR Bungalow. Newly remodeled with high end kitchen and entertainment but still held on to the essence of the historic...
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    About this property
    COMPLETELY RENOVATED BUNGALO WITH QUEEN SIZE BEDS IN BOTH BEDROOMS. ALL NEW FURNITURE AND BEDDING. COMPLETELY NEW KITCHEN AND BATHROOM. WASHER AND DRYER IN LAUNDRY ROOM. LARGE BACK YARD. NICE FRONT PORCH WITH VIEWS OF CITY PARK. REAR DECK WITH GRILLE. FIRST TIME ON THE MARKET SINCE COMPLETE...
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    Location Information
    Sanford, Central Florida 32771
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    NEW! Charming Lake Helen Home w/ Yard1 / 24
    (1)Excellent
    Lake Helen
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 September 2018
    From the minute you pull into the driveway to entering this home you will feel the magic of the small town and this fully equipped bungalow . While residing there a month, I was...
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    About this property
    Located in the quaint and historic town of Lake Helen, this vacation rental house is the perfect home base for your group of up to 5 friends or family. Offering 3 bedrooms and 2 full baths, your group is sure to settle right in among all the comforts of home. Enjoy easy access to numerous...
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    Location Information
    Lake Helen, Florida 32744
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    DeBary
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This listing is for one private bedroom. Our home is a split level with the upstairs reserved for guests. We reside in the other side of the home downstairs. The upstairs has it's own kitchen with a microwave, toaster, coffee maker, and a fridge. There is also a small living room upstairs for our...
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    Location Information
    DeBary, Florida 32713
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sanford
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Patio
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy all the lively attractions and scenic beauty of this quaint Florida town from this 2-bedroom, 1-bathroom vacation rental apartment, which comfortably sleeps 6 in Sanford. This 2nd-story unit offers a beautiful, residential location, a handsome garden, patio and deck, and 750 square feet of...
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    Sanford, Central Florida 32771
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sanford
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take the family on a trip to an Orlando oasis when you stay at this 3-bedroom, 3-bathroom vacation rental home that sleeps 8 in Sanford. Sitting just outside of the city, this home offers all the comforts of home paired with an ideal location to reach the excitement of Orlando nearby. Whether...
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    Location Information
    Sanford, Central Florida 32773
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sanford
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gather your loved ones for a relaxing getaway to this 2-bedroom, 1-bathroom vacation rental apartment in Sanford, Florida. You’ll love staying at this quaint property that features large windows, high ceilings, and beautiful french doors that open to a great balcony sitting under a giant oak tree....
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    Location Information
    Sanford, Central Florida 32771
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Sanford
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Up to 2 guests can experience the beauty of Florida from this 1-bathroom vacation rental studio in the heart of Sanford. This luxurious space is perfect for a secluded getaway and features elegantly stocked cupboards, plush furniture, and a complete kitchenette. Moments away are the attractions and...
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    Location Information
    Sanford, Central Florida 32771
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Beaches and attractions. Free coffee and light breakfast1 / 12
    (3)Excellent
    DeBary
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Patio
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2018
    This is a clean, comfortable room. Also, there is a very nice pool to rest and relax after a busy day. Shari is a friendly and helpful hostess. I'll stay here every time I visit...
    Reviewed 3 September 2018
    Great hosts, charming home with independent amenities, free snacks, we felt like home, they’re friendly and respectful. 100% recomended, they make my trip
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    About this property
    This is a shared residence.The upstairs is reserved for guests and private. We live downstairs with our dog Some areas are common areas such as the dining room, kitchen, and back patio. We have hosted other families and will give you as much or as little interaction as possible. Perfect for...
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    Location Information
    DeBary, Florida 32713
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Sanford
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elevate your next trip to central Florida by staying at this pristine 3-bedroom, 2-bathroom vacation rental townhouse in Sanford. This 1,920-square-foot unit sleeps 7 travelers and offers access to the community pool. Eat with the locals in downtown after a visit to the Zoo & Botanical Gardens near...
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    Location Information
    Sanford, Central Florida 32771
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Sanford
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit the historic town of Sanford from this vintage 3-bedroom, 3.5-bathroom vacation rental house with 1,400 square-feet of living space and sleeping accommodations for 6. Located just a few minutes from Main Street, enjoy quick access to a plethora of restaurants, antique shops, farmers markets,...
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    Location Information
    Sanford, Central Florida 32771
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    DeBary
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Patio
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This rental is a single room in our home. It is located upstairs and is private. Our home is located in central Florida and has many activities close by. The attraction area begins about 40- 45 minutes south on Interstate 4 (our home is about 5 minutes from the exit). The beaches start about 35-40...
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    Location Information
    DeBary, Florida 32713
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    DeBary
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • DVD Player
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please inquire w/ Evolve about 10% Military Discount ** Nestled between Daytona Beach and Orlando, this 3-bedroom, 2-bath Debary vacation rental house provides up to 9 guests with a prime location! From this newly renovated home, enjoy easy access to several white sandy beaches while also...
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    Location Information
    DeBary, Florida 32713
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Sanford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled under a 100-years-old live oak tree, 'Chef's Suite at Live Oak,' an executive 1-bed vacation rental apartment, offers comfort, intimacy, and upscale living for 2 guests in Sanford, FL. Enjoy a peaceful resort-like experience at this quiet, end-unit, with all the modern essentials for an...
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    Location Information
    Sanford, Central Florida 32771
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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