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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 24 Rentals in Osteen
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    Osteen
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Osteen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 15 kilometres of Osteen.
    Floating Cottage . . .afloat on the St. Johns River in Florida1 / 30
    (6)Excellent
    Sanford
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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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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    • 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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    Sanford, Central Florida 32771
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 13
    Beautiful Country Home, Vacation Destination1 / 44
    (1)Average
    Lake Helen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 May 2019
    The home in Lake Helen we rented for 3 nights was comfortable and spacious but needs a good deep cleaning. Windows, windowsills and baseboards were filthy. You had the...
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    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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    Lake Helen, Florida 32744
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Cozy Sanford Home near Orlando Resorts & Airport!1 / 24
    (2)Excellent
    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
    Reviewed 2 weeks ago
    Great place had a lot of room very comfortable and convenient to the 417 and plenty of parking and very private
    Reviewed 24 April 2019
    Great place and location Having a great time and has more than I expected. Clean and cozy wifi excellent TV very good. If the tournament next year is in Sanford we will be back.
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    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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    Sanford, Central Florida 32773
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Deltona Private Oasis Awaits! ONLY 30MIN T0 DAYTONA, 45MIN TO DISNEY & UNIVERSAL1 / 33
    (2)Excellent
    Deltona
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Patio
    • Grill
    • Washer
    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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    Deltona, Florida 32738
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    2BR BUNGALOW IN SANFORD HISTORIC DISTRICT1 / 16
    (1)Excellent
    Sanford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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
    Charming Lake Helen Home w/ Yard by Interstate 4!1 / 24
    (1)Excellent
    Lake Helen
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • 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
    Cozy Home - Mins to Disney, Daytona & New Smyrna!1 / 24
    (1)Excellent
    DeBary
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2019
    I stay in this cottage very long ago and visits again in January with my family very comfortable and friendly services they have for anyone that's the reason I like them and...
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    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
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • Hot Tub
    • Wi-Fi
    • Sauna
    • Shared Indoor Pool
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 5 bedroom / 4 bath lakefront estate home near the Orlando (Sanford) International Airport and the 417 Greenway for easy access to beaches and major attractions. The main living area of the home has several incredible gathering areas including a large kitchen, formal dining room, den, and...
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    Location Information
    Sanford, Central Florida 32773
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
    Sanford
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • 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
    The Historic Craftsman1 / 56
    (2)Excellent
    Sanford
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2019
    We needed a place for our family of 4 to stay for one night. Found this gem on Trip Advisor!! Quick and easy reservation, immediate response from owner who met us at the house...
    Reviewed 11 June 2019
    I recently attended a Bridal Shower in the Historic Craftsman house and it was AWESOME. The house has a great vibe and has plenty of room to entertain! The onsite caterer...
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    About this property
    Park Place Inn and Cottages is part of the Sanford Historic district and centrally located to downtown on one of the most scenic streets in town, Park Avenue. The property was built in the early 1930's in the Craftsman and Colonial style of the era. Park Place Inn is a vacation rental property that...
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    Location Information
    Sanford, Central Florida 32771
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Sanford
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Terrace
    • Shared Indoor Pool
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable 3 bedroom / 1 large bath loft which can accomodate 6 guests near the Orlando (Sanford) International Airport and the 417 Greenway for easy access to beaches and major attractions. The main living area of the loft has an open floor plan, including a large kitchen, dining area, TV...
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    Location Information
    Sanford, Central Florida 32773
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    The Ivy Cottage1 / 21
    (1)Excellent
    Sanford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2019
    The location is great! The Ivy Cottage is charming and has everything you could possible need. Conveniently close to the airport and great for a couple!
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    About this property
    Park Place Inn and Cottages is part of the Sanford Historic district and centrally located to downtown on one of the most scenic streets in town, Park Avenue. The property was built in the early 1930's in the Craftsman and Colonial style of the era. Park Place Inn is a vacation rental property that...
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    Sanford, Central Florida 32771
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    The Coastal Cottage1 / 21
    (1)Excellent
    Sanford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Terrace
    • Parking
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2019
    The Coastal Cottage is GREAT! The actual living space is beautiful and clean, and the balcony outside is a totally awesome added bonus. The whole location is nice and calming...
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    About this property
    Park Place Inn and Cottages is part of the Sanford Historic district and centrally located to downtown on one of the most scenic streets in town, Park Avenue. The property was built in the early 1930's in the Craftsman and Colonial style of the era. Park Place Inn is a vacation rental property that...
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    Location Information
    Sanford, Central Florida 32771
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    DeBary
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked away in a deed restricted neighborhood, this beautiful executive home is truly a great place to unwind. You are literally 5 minutes from access to interstate 4. You can easily reach all central Florida attractions. The Kennedy Space Center is a must see location as well as the worlds most...
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    DeBary, Florida 32713
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    The Chef's Suite1 / 26
    (1)Excellent
    Sanford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2019
    This is an awesome space, especially for someone who likes to cook! The living space is beautiful and the kitchen is very spacious. Would definitely recommend for a small family...
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    About this property
    Park Place Inn and Cottages is part of the Sanford Historic district and centrally located to downtown on one of the most scenic streets in town, Park Avenue. The property was built in the early 1930's in the Craftsman and Colonial style of the era. Park Place Inn is a vacation rental property that...
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    Location Information
    Sanford, Central Florida 32771
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    The Charming & Chic Suite1 / 19
    (2)Excellent
    Sanford
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 November 2019
    This was my first stay at this Sanford Inn and I loved it! The property was well maintained and full of the individualistic charm that makes visiting Sanford a delightful...
    Reviewed 11 June 2019
    Has everything you could possibly need for your home away from home! Super clean and surprisingly spacious for a studio space! It has a nice sized kitchen and a great bathroom...
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    About this property
    Park Place Inn and Cottages is part of the Sanford Historic district and centrally located to downtown on one of the most scenic streets in town, Park Avenue. The property was built in the early 1930's in the Craftsman and Colonial style of the era. Park Place Inn is a vacation rental property that...
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    Location Information
    Sanford, Central Florida 32771
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Debary Florida Cozy Getaway1 / 7
    (1)Excellent
    DeBary
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Patio
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Clean, bright, and spacious remodeled spilt plan house on a small lake. Sanford Int Airport only 13 miles away. Easy access to the Sunrail/highways. We are half way between Disney and Daytona Beach. Discover the Natural side of Florida. We have gorgeous Springs (Blue, Gemini, Wekiva, and Deleon),...
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    DeBary, Florida 32713
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sanford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is located in a small private gated community just 2 minutes away from 2 major highways, I-4 & 417. The best of both worlds! Located just outside the high tourists areas, but close enough to enjoy all the fun Central Florida has to offer! You can easily access I-4 West where it's about 30...
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    Location Information
    Sanford, Central Florida 32771
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Deltona
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Garden
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is located in Deltona, FL, close to many natural parks and amazing natural springs. Only a 35 minutes drive to New Smyrna beach, Deltona Hills Golf club, outlets and grocery shops, and 60 min. drive to Daytona beach and Orlando area. It is a beautiful and spacious pool house in a quiet...
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    Deltona, Florida 32725
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Deltona
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of the Sunshine State from this ideally located 2-bedroom, 1-bathroom vacation rental house in Deltona. The home has the capacity to accommodate 4 guests and boasts a private, fenced yard and screened-in patio. Enjoy nearby attractions such as the Central Florida Zoo & Botanical...
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    Deltona, Florida 32725
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Pleasant Point River Retreat1 / 5
    (8)Very good
    Geneva
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Outdoor Dining Area
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 January 2019
    Perfect get away location on the river, with a front row seat in nature. Privacy, quiet and serene hiding place for a couple and/or a fisherman and her husband! We loved it.
    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...
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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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