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Holiday Rentals with Pools in Winter Garden

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    Travellers to Winter Garden are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    28 Matching Rentals in the Winter Garden AreaView all 35 rentals
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    Orlando holiday home, 10 minutes from Disney, gated community with pools1 / 25
    (3)Excellent
    Winter Garden
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sun, Fun and Amusement Parks - $99/Night1 / 16
    (2)Excellent
    Winter Garden
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Buckeye Butterfly Villa1 / 18
    (1)Excellent
    Winter Garden
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winter Garden
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Children's Pool
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Important Notes: As of 1/1/18 - the resort fee here will increase from $17.00/nt + tax to $20.00/nt + tax. You will now have a $20.00 + tax per night resort fee and the refundable security deposit (Up To $100.00) due upon arrival. ***************************** Liki Tiki will now be handing out...
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    Winter Garden, Central Florida 34787
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Winter Garden
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Children's Pool
    • Washer
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming Villa just 4 miles from Disney and minutes from other area attractions. Fully furnished 3 bedroom (king, queen & full beds), 2 bathroom home in a gated community for your security. In addition to the lovely home you have access to 3 pools, 2 jacuzzi's, playground, tennis courts, shuffle...
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    Winter Garden, Central Florida 34787
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Winter Garden
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With a stay at Liki Tiki Village by Diamond Resorts in Winter Garden (Four Corners), you'll be convenient to Lake Davenport. This family-friendly hotel is within the vicinity of Highland Reserve Golf Club and Mighty Jungle Golf. Make yourself at home in this air-conditioned room featuring a kitchen...
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    Winter Garden, Central Florida 34787
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Winter Garden
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Children's Pool
    • Air Conditioning
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Winter Garden, Central Florida 34787
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    The following rentals are within 15 kilometres of Winter Garden.
    Apopka
    9 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Solara Resort Vacation Home Rentals close to Disney World, Orlando Florida. The ultimate vacation resort is now in development. Only 8 miles to Disney and within a short drive to Universal, Disney Springs, and many local beaches. This gated resort community is in the center of it all! An extensive...
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    Apopka, Florida 34747
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 18
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    Hiawassee
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the SINGLE FAMILY HOME of your dreams in Kissimmee!! This 5 bedroom and 5 bathroom rental home in 2 floors is located in the Storey Lake Resort Community. The 5 bedrooms and 2 living rooms, all together with 7 LED TVs, come in handy to sleep up to 1O guests (2 king beds 2 queen and 1 set...
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    Hiawassee, Florida 32810
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Apopka
    9 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Solara Resort Vacation Home Rentals close to Disney World, Orlando Florida. The ultimate vacation resort is now in development. Only 8 miles to Disney and within a short drive to Universal, Disney Springs, and many local beaches. This gated resort community is in the center of it all! An extensive...
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    Location Information
    Apopka, Florida 34747
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 18
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    Apopka
    9 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Solara Resort Vacation Home Rentals close to Disney World, Orlando Florida. The ultimate vacation resort is now in development. Only 8 miles to Disney and within a short drive to Universal, Disney Springs, and many local beaches. This gated resort community is in the center of it all! An extensive...
    View all property information
    Location Information
    Apopka, Florida 34747
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 18
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    Apopka
    9 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Solara Resort Vacation Home Rentals close to Disney World, Orlando Florida. The ultimate vacation resort is now in development. Only 8 miles to Disney and within a short drive to Universal, Disney Springs, and many local beaches. This gated resort community is in the center of it all! An extensive...
    View all property information
    Location Information
    Apopka, Florida 34747
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 18
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    Apopka
    9 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Solara Resort Vacation Home Rentals close to Disney World, Orlando Florida. The ultimate vacation resort is now in development. Only 8 miles to Disney and within a short drive to Universal, Disney Springs, and many local beaches. This gated resort community is in the center of it all! An extensive...
    View all property information
    Location Information
    Apopka, Florida 34747
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 18
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    Windermere
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this elegant 1 Bedroom, 1 Bath Vacation rental near Disney located inside the spectacular Enclave Resort. This home comes fully furnished. Located only 30 minutes from Orlando International Airport, 15 minutes from Universal Studios and SeaWorld and 16 minutes to Walt Disney World. The...
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    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Hiawassee
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the SINGLE FAMILY HOME of your dreams in Kissimmee!! This 5 bedroom and 5 bathroom rental home in 2 floors is located in the Storey Lake Resort Community. The 5 bedrooms and 2 living rooms, all together with 7 LED TVs, come in handy to sleep up to 1O guests (2 king beds 2 queen and 1 set...
    View all property information
    Location Information
    Hiawassee, Florida 34746
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Apopka
    9 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Solara Resort Vacation Home Rentals close to Disney World, Orlando Florida. The ultimate vacation resort is now in development. Only 8 miles to Disney and within a short drive to Universal, Disney Springs, and many local beaches. This gated resort community is in the center of it all! An extensive...
    View all property information
    Location Information
    Apopka, Florida 34747
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 18
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    Lakefront Boating Ski Kayak Jet Ski Paddle Board Spa 38x18 Pool Dock1 / 9
    (3)Excellent
    Ocoee
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 2017
    Near all Orlando attractions but in private community on small lake. Want for nothing!!! 3/3, screened in pool, hot tub, grilling area, fire pit, dock with gazebo, ski boat...
    Reviewed 18 April 2017
    Great rental - couldn't ask for anything more! Home has great open layout, on a beautiful lake with dock, gazebo, screened in large pool and hot tub. A new grill, fire pit and...
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    About this property
    This home opens in the front with very large double doors from a front screened in porch to a back screened in pool with double sliders opening the house allowing a beautiful Breeze fireplace inside fire pit outside pool is 38 feet by 18 feet jacuzzi allows for 6 people option for a boat rental for...
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    Ocoee, Central Florida 34761
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Apopka
    9 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Solara Resort Vacation Home Rentals close to Disney World, Orlando Florida. The ultimate vacation resort is now in development. Only 8 miles to Disney and within a short drive to Universal, Disney Springs, and many local beaches. This gated resort community is in the center of it all! An extensive...
    View all property information
    Location Information
    Apopka, Florida 34747
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 18
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    Orlando Area Pool Home1 / 32
    (4)Very good
    Apopka
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    I have written a review before. I keep getting this message, Trip Advisor might want to look into their system as to why it did not get registered.Stay Mary's home in Apopka...
    Reviewed 25 April 2017
    Bring our son and his family from Washington state and our daughter and her family from South Carolina to visit Mom and Dad from Tennessee and how could we not have a great...
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    About this property
    This Beautiful 4 bed 3 bath pool home is located on a quiet cul-de-sac in the wonderful community of Rock Springs Ridge. The home can accommodate up to 10 guests comfortably. Home offers full size living room- dining room- kitchen 4 bedrooms- fully equipped laundry room- 3 full baths and a private...
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    Apopka, Florida 32712
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Minneola
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • DVD Player
    • Grill
    • Wi-Fi
    • Patio
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a quiet community, 40 miles northwest of Orlando International Airport, 30 minute drive to Disney/Universal/Sea-World/Busch-Gardens and all theme Parks, beaches, fresh-water springs, the National-Training-Center and Orlando nightlife. Great for couples, solo adventurers, athletes in...
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    Minneola, Lake County 34715
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Apopka
    4 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, airy, and peaceful, this solid pine-interior ranch house is a unique get-away! It's right next to the 429, where you can be to family-friendly activities such as Disney and Universal within 30 minutes. Wekiva Springs and Rock Springs state parks are both within five minutes' drive, and...
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    Apopka, Florida 32703
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 15
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    Windermere
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Sauna
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have hosted numerous celebrities in this house and it has an amazing atmosphere. From the travertine floor to the high ceiling chandeliers this place will make you feel like staying at a house from MTV cribs. This is a very nice luxury house with an outside fire pit, solid wood dining table,...
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    Windermere, Central Florida 34786
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    Windermere
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Parking
    • Internet Access
    • Grill
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Stay - One month. This is the ultimate vacation home! The owners have named it PARADISE and it is. If you are looking for a private residence with all the amenities of a 5 Star Resort - look no further. The moment the electric gate opens and you see the directional signs to PARADISE (the...
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    Windermere, Central Florida 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Windermere
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 2016, this is a modern up-to-date home. It is five minute drive to Disney, and every night you can relax and watch the fireworks from the house. Taking a day off from the parks? Spend it by the community pool with a splash pad for children only a short walk away. Grocery stores and local...
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    Location Information
    Windermere, Central Florida 34786
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ocoee
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take your next Florida getaway to new heights by staying at this exceptional 5-bedroom, 3-bathroom Ocoee home. Situated in a terrific area near local attractions, boasting exceptional decor and ample room for 10 guests, this darling abode has everything you need to create lasting memories! THE...
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    Ocoee, Central Florida 34761
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Windermere
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This inviting four-bedroom, 3-bath town home in West Lucaya Village Resort features two king master suites, Mickey-themed full bedroom and a Finding Dory-themed twin bedroom.  With over 1,600 square feet of living space, you’ll be able to really enjoy your vacation without being in a cramped...
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    Windermere, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Windermere
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our spacious two-bedroom/two-bath suite offers plenty of space to sleep up to 6 people with a queen size bed in the master bedroom and two twin size beds in the second bedroom. The living and dining area is complete with a sofa bed. The two bedroom suite offers a fully equipped kitchen. Your...
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    Location Information
    Windermere, Central Florida 32819
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ocoee
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    • DVD Player
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Featuring a private enclosed pool, 3,000 square feet of living space and an ideal location just 30 minutes or less from Walt Disney World, there's no better place to book your Florida getaway! This 5-bedroom, 4-bath Ocoee vacation rental house invites 10 guests to settle into their Orlando area...
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    Location Information
    Ocoee, Central Florida 34761
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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