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Winter Park Holiday Rentals

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    Travellers to Winter Park are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    All 38 Rentals in Winter Park
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Winter Park, Central Florida 32792
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
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    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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    Winter Park, Central Florida 32804
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Reviewed 1 November 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 14 April 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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    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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    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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    • Satellite TV
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    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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    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
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    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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    Winter Park, Central Florida 32789
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2br - 1000ft2 - Winter Park House1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
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    Pet friendly
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    Reviewed 25 January 2017
    Orlando is very spread out and very sparse public transport. With the house located in winter park it was fairly central to where we needed to be. Quiet neighbourhood. Owners a...
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    About this property
    Furnished with original furniture from the 1950's era in a home built in 1955 with original wood floors, bathroom tile, plaster walls and kitchen cabinetry. Clean lines, simple and comfortable. FURNISHED Mid Century Modern Short/Long term rental located in Olde Winter Park. Two bedroom/ one and...
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    Winter Park, Central Florida 32789
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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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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    Winter Park, Central Florida 32789
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Secure Parking
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    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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    Botanical Gardens - Orlando / Winter Park1 / 22
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed 4 weeks ago
    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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    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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    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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    Winter Park, Central Florida 32789
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
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    Winter Park, Central Florida 32792
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
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    About this property
    Nestled between the cities of Winter Park and Orlando, Audubon Park is a gem that recently won the National Main Street Award for its uniqueness! This quiet little street is close to local parks, dining, nightlife, shopping, yoga and more! You’ll love the coziness, in-garden-feeling and locally...
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    Winter Park, Central Florida 32789
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Housekeeping Included
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    Winter Park, Central Florida 32789
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    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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    Winter Park, Central Florida 34787
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    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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    Winter Park, Central Florida 32804
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Winter Park, Central Florida 32789
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Winter Park, Central Florida 32789
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Winter Park, Central Florida 32789
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Winter Park, Central Florida 32792
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Winter Park, Central Florida 32789
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Winter Park, Central Florida 32792
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Central Florida 32792
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Winter Park, Central Florida 32789
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    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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    Winter Park, Central Florida 32789
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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