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Winter Park Holiday Rentals

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    Travellers to Winter Park are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 17 Rentals in Winter Park
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    2br - 1000ft2 - Winter Park House1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Botanical Gardens - Orlando / Winter Park1 / 22
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 July 2017
    This Small Condo is in Winter Parks and around the corner from a Botanical Garden. It is on a quiet street with nice trees and plants around. We really felt at home here within...
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    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Air Conditioning
    • Parking
    • Grill
    • Private Garden
    • 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
    Holiday Rental House - 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
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    • Washer
    • Private Garden
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    • Wi-Fi
    • Air Conditioning
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    • Grill
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    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Waterfront
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect spot to enjoy the sunset over our lake, sit by the outdoor fireplace, use the putting green & relax. Or walk to Baldwin Park shops & restaurants (0.8 miles)! Only 10 min drive to Park Ave/Rollins. 35 Min to Disney, 25 to Universal. Enjoy! This adorable mother-in-law cottage/suite has lots...
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    Location Information
    Winter Park, Central Florida 32789
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    8 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • 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
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 18
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
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    • Private Garden
    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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our brand New home is Perfect for anyone, or any family or group with plenty of rooms. Its spotless clean, and have 5 star reviews across all platforms. Walk into our front patio area, into the main stairwell, and living room to the right. Just across is the new modern kitchen, equipped with all...
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    Winter Park, Central Florida 32803
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    8 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • 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 8 bedrooms 5 bathrooms Sleeps 18 Private pool Game room Home theater Access to...
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    Location Information
    Winter Park, Central Florida 33896
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 18
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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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    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
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Garden
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
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    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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