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Holiday Rentals in Winter Park

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    Travellers to Winter Park are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 27
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    8 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Balcony
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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... View all property information
    Location Information
    Winter Park, Central Florida 32789
    5 of 5 bubbles 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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    1 / 19
    5 of 5 bubbles (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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    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... View all property information
    Location Information
    Winter Park, Central Florida 32789
    5 of 5 bubbles 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 friendly.
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    1 / 37
    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,... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 28
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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,... View all property information
    Location Information
    Winter Park, Central Florida 34787
    1 / 18
    8 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    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 Summary If you are planning a big Orlando vacation with family and friends, this is perfect... View all property information
    Location Information
    Winter Park, Central Florida 33896
    1 / 22
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
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    • Patio
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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. Within a very close... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 18
    8 Bedrooms, 5 Bathrooms, Sleeps 17 | Quick View
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    • Internet Access
    • DVD Player
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    • Private Outdoor...
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    • Pet-friendly
    • Child-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 Summary Located just 15 minutes from Walt Disney World, this beautiful home offers the perfect... View all property information
    Location Information
    Winter Park, Central Florida 33896
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    1 / 35
    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.... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 27
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    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... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 40
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Waterfront
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    • x
    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... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Patio
    • Grill
    • Hot Tub
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    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... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Terrace
    • Central Heating
    • Grill
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Custom Home with Designer Appointments. Beautifully furnished with a mix of antique and modern furnishings. Beautiful Private back yard with a private pool, exotically landscaped with Oranges, Jasmine, Grapes, and Camelias Inside you can enjoy a Gourmet Kitchen, including a Keurig, and A French... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • DVD Player
    • Shared Garden
    • Shared Outdoor Pool...
    • Air Conditioning
    • Secure Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This property features The following: Spacious-748 sq ft 1 bed 1 bath Fully furnished-just move in! Great location-Full Sail University next block down, off 436, mins to shopping and schools. Community pool, tennis courts, and play ground. Small dogs ok . Available 01-Aug.2015. Close to all major... View all property information
    Location Information
    Winter Park, Central Florida 32792
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 10
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Winter Park, Central Florida 32803