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Winter Park Holiday Rentals

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    Travellers to Winter Park are booking November dates now. Secure your holiday rental today, and have the perfect trip.
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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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    Winter Park-College Park-Orlando -21 / 19
    (2)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    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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    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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    • Satellite TV
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    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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    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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    8 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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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 Key features 8 bedrooms 5 bathrooms Sleeps 18 Private pool Game room Access to resort...
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    Winter Park, Central Florida 33896
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 18
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
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    • Grill
    • Porch
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    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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    Winter Park, Central Florida 32804
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Hot Tub
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    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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    Winter Park, Central Florida 34787
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    8 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
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    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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    2br - 1000ft2 - Winter Park House1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Patio
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Delightful Lakefront Condo, Pet Friendly and Short Walk to Shops and Dining1 / 20
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Winter Park, Central Florida 32789
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Paris - Pool Home In The Heart Of Winter Park !! Elegant Modern Paris Decor1 / 24
    (20)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
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    Pet friendly
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    Winter Park, Central Florida 32792
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Walk to Park Ave Shops, Restaurants, LiveTheater, Farmers Mrkt, & Lakefront walk1 / 23
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    Winter Park, Central Florida 32789
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    A beautiful pool side apartment in a wonderful old Winter Park neighborhood.1 / 23
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Housekeeping Included
    • Patio
    • Washer
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    Pet friendly
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    Smoking allowed
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    Winter Park, Central Florida 32789
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Winter Park, Central Florida 32789
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Beautiful home in Winter Park, Steps from Park Ave., Shops Restaurants1 / 23
    (1)Excellent
    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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    Chill Out at This Family-Friendly Heated Pool Home In Winter Park, Florida1 / 24
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
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    Pet friendly
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    Location Information
    Winter Park, Central Florida 32789
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Steps to Park Ave, Shops, Restaurants, Rollins college.1 / 19
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Winter Park, Central Florida 32789
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • DVD Player
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    Location Information
    Winter Park, Central Florida 32789
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Casa Justine - Upscale Winter Park Home \ Elegant Living Room, Great Pool1 / 24
    (40)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Location Information
    Winter Park, Central Florida 32792
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Hidden Historic Jewel In Downtown Location!1 / 9
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Winter Park, Central Florida 32789
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bright & Airy Modern Cottage in Heart of Town, Walk everywhere, pet friendly1 / 24
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
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    Winter Park, Central Florida 32789
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beautiful 3/3 Pool Home Centrally Located In  Exclusive Winter Park, Florida1 / 18
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Winter Park, Central Florida 32789
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ideal Location, Charming Home, Spacious with a Full Lap Pool!1 / 18
    (22)Excellent
    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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    Charming Clean Home1 / 15
    (3)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Satellite TV
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    Winter Park, Central Florida 32789
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Cute Guest House In Our Backyard Winter Park Mins1 / 20
    (5)Very good
    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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    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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    Winter Park Home With Hints Of Florida Keys And Lovely Pool Oasis1 / 6
    (19)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Private Outdoor Pool (Unheated)
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    Winter Park, Central Florida 32789
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Casa Aloma - Elegant Winter Park House with Great Pool and Huge Backyard!!1 / 24
    (28)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Winter Park, Central Florida 32792
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Lakefront Home With Pool In Charming Olde Winter Park1 / 24
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    Winter Park, Central Florida 32789
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Just Like Home... With A Pool!1 / 23
    (25)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Winter Park, Central Florida 32792
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    Winter Park, Central Florida 32792
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    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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    Location Information
    Winter Park, Central Florida 32789
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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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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