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Winter Park Vacation Rentals

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    Travelers to Winter Park are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    All 15 Rentals in Winter Park
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    Botanical Gardens - Orlando / Winter Park1 / 22
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2br - 1000ft2 - Winter Park House1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park-College Park-Orlando-11 / 27
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • DVD Player
    • Balcony
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 1, 2016
    Rental for an entire apartment. Full kitchen livingroom and bedroom. Owners are wonderful to work with. We will rent from again. Thanks for your kindnesses.
    Reviewed April 14, 2016
    While planning to attend a family wedding, my husband and I wanted to find a nice place that was less expensive and more spacious than the hotels that were recommended to us...
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    About this property
    Comfortable 1bd/1bath home with convenient location midway between historic Winter Park and Downtown Orlando. Just a hop away from I-4. Within close distance you will find a unique selection of specialty shops, parks, and restaurants for every taste on Edgewater Dr.. Historic Dubdread golf...
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    Location Information
    Winter Park, Central Florida 32789
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • Washer
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close to Downtown Orlando or the main interstate to get you anywhere quickly. Beautiful Mead Gardens is a block down the road and is no cost to park and walk the gardens or picnic. It is close to nightlife,...
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    Location Information
    Winter Park, Central Florida 32789
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautifully appointed 3 bedroom cottage on 400 acre Lake Fairview. We are central to College Park, Winter Park, and Altamonte Springs giving you the most comprehensive selection of shopping, eateries, and theater selections available in Orlando. Just minutes from from Interstate 4 and the down...
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    Location Information
    Winter Park, Central Florida 32804
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    • Private Yard
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your own private unit includes 1 master bedroom with Queen bed Full Kitchen with stove, refrigerator, microwave, coffee maker 32' flat screen tv. Access to Washer/dryer Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close to Downtown Orlando or the...
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    Location Information
    Winter Park, Central Florida 32789
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the tropical splendor that is Liki Tiki Village Resort Orlando, Florida. Relax in spacious condominiums and accommodations that includes a variety of amenities, including a water park, for the whole family. Liki Tiki Village is located only seven miles from Walt Disney World, SeaWorld,...
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    Location Information
    Winter Park, Central Florida 34787
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakeside, on the shores of Lake Killarney, is in the exclusive village town of Winter Park (32789). You are 7 min to downtown Orlando, 20 min to Universal/ Disney. A 5,700 sq. ft family estate home with 285 ft of shoreline situated in an eco-sanctuary of rare birds & teeming aquatic life....
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    Winter Park, Central Florida 32789
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Winter Park-College Park-Orlando -21 / 19
    (2)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Parking
    • Grill
    • Patio
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 3, 2017
    We had a duplex that was very clean. Near to shopping and highway, so we never got lost. In 2018 if duplex is available we will call. Dan & Shirley were so helpfully and...
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    About this property
    This is a great little neighborhood chock full of local businesses, great people, nice neighbors and just a nice homey feeling. I can't get enough of the Main Street (Edgewater Dr.) running through, you have everything from some pretty great restaurants, plenty of yoga studios (YAY), to great...
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    Location Information
    Winter Park, Central Florida 32789
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The first thing you notice when you walk into this tiny house is how spacious it is. A beautiful view of the lake is is framed by a picture window. The couch is inset into a 'window-box' where you can let your troubles melt away. Relax outside on your teak chairs only steps from the lake. Lots of...
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    Location Information
    Winter Park, Central Florida 32804
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    8 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    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 5 bathrooms Sleeps 18 Private pool Game room Access to resort...
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    Location Information
    Winter Park, Central Florida 33896
    Rental Home - 8 Bedrooms, 5 Bathrooms, Sleeps 18
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    6 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is situated in the prestigious new Champions Gate development, close to Disney and Reunion and just off Highway 27 and Highway 192. A quick drive to Disney (12 miles), and only a few minutes from Interstate 4 to get to Universal, this is the ideal base for a great Orlando vacation....
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    Location Information
    Winter Park, Central Florida 33896
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just because it's a tiny house doesn't mean you have to skimp on style! With an open floor plan and high ceilings, this tiny home is filled with light and air. The Ritz has high-end finishes, including a full-size, stainless steel fridge, glass stove cooktop and Italian tile throughout. With 3...
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    Location Information
    Winter Park, Central Florida 32804
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy our guest house in our back yard with your private entrance. We are in Winter Park where you are minutes away from the Park Ave strip and Winter Park Village with a car. Make this your home away from home while in town. The studio was fully furnished in late 2015. We added a kitchen with 2...
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    Location Information
    Winter Park, Central Florida 32789
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Winter Park Flight and Weather Info
    Airports nearby (1)
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    Orlando Intl Airport
    12.6 miles from Winter Park
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