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Longwood Vacation Rentals

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    Don't let other travelers get your favorite Longwood area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 31 Rentals in Longwood
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    Longwood
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Longwood
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Longwood
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Longwood
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • DVD Player
    • Patio
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** NOTE: Another vacation rental unit is attached to this unit, and there may be other travelers present during your stay as the pool deck and yard are shared** Treat your family to an unforgettable Florida retreat in Longwood at this fantastic 3-bedroom, 2-bathroom vacation rental home! After...
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    Longwood, Florida 32779
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Longwood
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** NOTE: Another vacation rental unit is attached to this unit, and there may be other travelers present during your stay as the pool deck and yard are shared ** The Sunshine State awaits you at this 1-bath Longwood vacation rental studio with a courtyard! Built in the 1970’s, this home maintains...
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    Longwood, Florida 32779
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    The following rentals are within 5 miles of Longwood.
    Fern Park
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Key features 8 bedrooms 7 bathrooms Sleeps 16 Private pool Spillover tub Access to resort...
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    Fern Park, Florida 34747
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    Altamonte Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    • Private Yard
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MONTHLY RATES For 4 weeks or longer $2200 - $2400. ASK Owner FOR QUOTE! You will love our 1950s home in the Beautiful Bear Lakes Area and we can't wait to welcome our Guests! We purchased this home in January 2012 and transformed it into a beautiful jewel. We put in all the modern conveniences...
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    Altamonte Springs, Central Florida 32703
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Maitland
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Key features 6 bedrooms 6 bathrooms Sleeps 12 Private pool Access to resort amenitiesBedrooms...
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    Maitland, Florida 34747
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Altamonte Springs
    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Private Yard
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Vista Verde II Dream House & Vacation Paradise in Central Florida’s location just minutes from all popular Orlando and Daytona Beach attractions! Exclusive 1-bedroom, 1-bath vacation rental studio apartment sleeps up to 7 guests and has a 18,000 gallons private swimming pool, Charcoal BBQ...
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    Altamonte Springs, Central Florida 32714
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 8
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    3 bed/2 both Lake Front home1 / 25
    (1)Very good
    Lake Mary
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
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    • Patio
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 2018
    Just 15 minutes from Sanford this provided us with a convenient central base from which to explore the Real Florida (that is, keeping away from all things with a theme park, as...
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    About this property
    Cozy 3 bedroom 2 bath home on little Lake Mary very quiet and relaxing home in a family oriented community. This 1584 sqft. home, has a magnificent waterfront view; guests will enjoy gazing at Little Lake Mary from multiple rooms of the home. The Open floor plan and entryway draws you into a...
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    Lake Mary, Florida 32746
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 BD Furnished Quaint Altamonte  / North Orlando1 / 8
    (2)Excellent
    Altamonte Springs
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Porch
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    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 2017
    We stayed in this house for about a week and it suited us just fine. It had only one bathroom but we also have only one bathroom and are accustomed to that. The bedrooms were...
    Reviewed June 12, 2016
    We had to make an unexpected visit to the area for a death in the family. Owner was great to deal with especially with such short notice. The house was great. Plenty of...
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    About this property
    Located in Altamonte Springs, near Maitland, Winter Park, just minutes North of Orlando. Giving an expansive selection of Shopping, Malls, Restuarants, and Theatres available within 2 miles. Close to many Golf courses. Just blocks from Interstate 4. 30 minutes to Sea World, Universal and Disney's...
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    Altamonte Springs, Central Florida 32750
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Fern Park
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Key features 5 bedrooms 5 bathrooms Sleeps 10 Private pool Access to resort...
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    Fern Park, Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Altamonte Springs
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Hot Tub
    • Wi-Fi
    • Patio
    • Private Yard
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Vacation Adventure Begins Here! Casa Vista Verde IV Orlando-Altamonte Springs Dream House & Vacation Paradise! Exclusive & cozy 4-bedroom, 2-bath vacation rental home w Jacuzzi, ping pong and pool tables with a real nice yard! Our communal pool is outstanding and just 3 minutes drive with...
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    Altamonte Springs, Central Florida 32714
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Altamonte Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    *** Amazing Location *** Montly/Seasonal/yearly available. Beautiful “Three bedroom/2 bath townhome,” first floor, one story, upscale community, gated., within walking distance to Altamonte Mall, Cranes Roost Park. Uptown Altamonte, fine dining, wine tasting within walking distance. Enjoy the...
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    Location Information
    Altamonte Springs, Central Florida 32701
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Maitland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This beautiful 3 bedroom, 2 full bathrooms home is located in a lovely and quiet community. Close to shops, restaurants, just minutes away from Winter Park. Great for Disney vacations, corporate housing, holidays, UCF, or just to relax in sunny Florida. While in Florida this is your lovely home to...
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    Maitland, Florida 32751
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Altamonte Springs
    5 Bedrooms, 2 Bathrooms, Sleeps 20 Quick View
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    • Patio
    • Parking
    • Air Conditioning
    • Grill
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    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Orlando Area 5BR/2BA Home w/ Pool! Casa Vista Verde I Orlando-Altamonte Springs Dream House & Vacation Paradise Maximum occupancy for 10 guests and bedrooms are opened based number of guests! Exclusive 5-bedroom, 2-bath vacation rental home that sleeps up to 10 guests and has a 20,000 + gallons...
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    Location Information
    Altamonte Springs, Central Florida 32714
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 20
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    Fern Park
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Key features 8 bedrooms 7 bathrooms Sleeps 16 Private pool Theater room Themed bedrooms...
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    Location Information
    Fern Park, Florida 34747
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    Maitland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Close to everything. Minutes off major highway I-4. 2 bedrooms, 2 baths. Large living area, fully stocked kitchen, laundry, dinning room, great private porch & pool area. Plus outdoor shower. 30-40 minutes to attractions. 60 minutes to the beaches. Our guests call our home a fun & relaxing...
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    Maitland, Florida 32751
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Wekiva Springs
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
    • Air Conditioning
    • Washer
    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Vacation Adventure Begins Here! Casa Vista Verde III Orlando-Altamonte Springs Dream House & Vacation Paradise Exclusive 5-bedroom, 2-bath vacation rental home w Jacuzzi, fuss-ball, ping pong and pool tables with a real nice yard! (Our communal pool is being totally remodeled will be...
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    Wekiva Springs, Florida 32714
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Altamonte Springs
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Key features 4 bedrooms 3 bathrooms Sleeps 8 Private pool Access to resort amenitiesBedrooms...
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    Altamonte Springs, Central Florida 32701
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Maitland
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you travelling with a group and needs a place so all of you can be together? Well this is the perfect place for you. This entire house is able to sleeps 14 guests yet have all the comforts any traveler will need, the style and layout of the space creates a comfortable home-like togetherness for...
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    Maitland, Florida 32751
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    Altamonte Springs
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the best of Orlando with the entire family at this 5-bedroom, 4.5-bath Longwood vacation rental. It offers all the essentials for an easy vacation, like a fully equipped kitchen, 2 dining rooms, and a first-floor bedroom & bath! Everyone will love the deluxe theater room for watching Disney...
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    Altamonte Springs, Central Florida 32750
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Winter Springs
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tranquil Executive Rental/ Lease. Daily, Weekly, Monthly, Short term lease available. One year lease available. Approximately 4,000 sq. ft., Spacious 5 Bedrooms with flat screen T.Vs., 3 ½ bathroom, Family room, Master Chef Kitchen with a dual wine refrigerator, Washer and Dryer, upstairs office...
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    Winter Springs, Florida 32708
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Lake Mary
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located close to Orlando, in the Lake Mary/Sanford area, less than 5 minutes from shopping malls, movie theaters and numerous restaurants, with rapid I-4 and SR-417 access. Ideal central location with beaches, amusement parks, springs, all nearby. Up to 6 guests can share a very special getaway in...
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    Lake Mary, Florida 32771
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Altamonte Springs
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan an unforgettable retreat to celebrate an anniversary or your loved one’s birthday and stay at this Altamonte Springs 1-bedroom, 1-bathroom vacation rental house nestled right on Lake Marion. Begin each morning sipping coffee together on the porch before going canoeing with the provided canoe....
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    Location Information
    Altamonte Springs, Central Florida 32701
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Winter Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Showcase home boasting 3 bedrooms, 2 bathrooms and a large playroom full of kids toys and a basketball hoop. Quick drive to both 417 and I4 allowing easy access to all areas of Central Florida. This beautiful home has been completely renovated with a new kitchen, bathrooms, flooring, fresh paint,...
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    Winter Springs, Florida 32708
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fern Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Start your Florida vacation out right at this 1-bedroom, 1-bathroom Fern Park vacation rental guesthome. Perfect for small families and couples, this unit sleeps 4 and sits within an easy drive of the highway - trips to downtown Orlando will be a breeze! New updates to this property include an...
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    Location Information
    Fern Park, Florida 32730
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lake Mary
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private full size bath & bedrooms, keyless, premium full-size bed, huge spacious closet + dresser, brand NEW black desk + nightstand, Cable TV, stand, DVR service (behind sliding white door), fast WiFi, Laundry. Air is 71°F, ceiling fans, chair, clocks, radio, bedding, towels, lamps, new flooring,...
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    Location Information
    Lake Mary, Florida 32746
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Fern Park
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunshine State recreation and theme park thrills await 5 guests at this 'Old Florida Style' vacation rental, located between the towns of Fern Park and Casselberry. Enjoy a private getaway along Lake Prairie and a tropical atmosphere both inside the 3-bedroom, 2-bath home and out in the lush...
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    Location Information
    Fern Park, Florida 32730
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Wekiva Springs
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    Clear the calendar for an easy-going getaway at this 2-bedroom, 2-bathroom vacation rental house in Apopka! With accommodations for 5 guests and amenities sure to make you feel right at home, this cozy abode promises an easy going getaway for friends, family, and any Disney fanatics. Enjoy days...
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    Location Information
    Wekiva Springs, Florida 32703
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Lake Mary
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
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    • Balcony
    • Patio
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Please note that the homeowner lives on site, in the attached unit with some shared outdoor amenities** Experience the best of Lake Mary when you stay at this vacation rental apartment for 5! The 2-bedroom, 1-bathroom home sits on a quiet, private piece of land but is close to great attractions...
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    Location Information
    Lake Mary, Florida 32746
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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