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Holiday Rentals with Pools in Winter Garden

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    ₹ 14,829 Average
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    Travellers to Winter Garden are booking November dates now. Secure your holiday home today, and have the perfect trip.
    29 Matching Rentals in the Winter Garden AreaView all 44 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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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This offer is only valid in 7 Night Intervals on a Sunday to Sunday schedule. All other offers cannot be accommodated. Explore our 64 acres of lush landscape, stroll around the Polynesian-themed complex, and absorb its tropical beauty. Join your children in a pirate adventure at Liki Tiki Lagoon...
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    Winter Garden, Central Florida 34787
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Only Minutes to Disney World - Fully Furnished1 / 12
    (1)Excellent
    Winter Garden
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Children's Pool
    • Wi-Fi
    • Washer
    • DVD Player
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2016
    This home is very clean, it was a quiet gated community, we thoroughly enjoyed our stay there. We had no problems with this property except possibly the Direct TV losing signal...
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    About this property
    This beautifully furnished home has been loaded with all new furniture and appliances throughout the entire home. Located only miles from Walt Disney World. A beautiful, quiet gated community with lots of amenities to be enjoyed. Lots for the young and the young at heart. 3 Bedroom (1 King, 2...
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    Winter Garden, Central Florida 34787
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    • 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...
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    Apopka, Florida 34747
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 18
    Windermere
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Parking
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the best theme parks in Orlando when you stay in our modest suite! Book with us and you’ll have access to a theme park shuttle that will take you to Walt Disney World, Universal Studios, and SeaWorld. If you still have energy to burn after a day in the park, go for a swim in the outdoor pool,...
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    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Windermere
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Parking
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book a stay in our cheerful suite and get ready to explore the best theme parks Orlando has to offer! Stay with us and you’ll have access to a theme park shuttle that will take you to Walt Disney World, Universal Studios, and SeaWorld. If you still have energy to burn after a day in the park, go...
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    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Windermere
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    • Air Conditioning
    • Hot Tub
    • Housekeeping Included
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get ready to explore the best theme parks Orlando has to offer, courtesy of our economical suite! Stay with us and you’ll have access to a theme park shuttle that will take you to Walt Disney World, Universal Studios, and SeaWorld. If you still have energy to burn after a day in the park, go for a...
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    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Windermere
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This inviting four-bedroom, 3-bath town home in Lucaya Village Resort Phase 2 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 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Windermere
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Parking
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our bright and modern 1 bedroom suite in Orlando! You will love to be steps from Universal Boulevard, offering the best restaurants and attractions, and only minutes from the most popular Theme Parks. Other features you'll love: • Luxury King bed in the spacious bedroom • Queen Sofa bed...
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    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Windermere
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Shared Indoor Pool
    • Hot Tub
    • Balcony
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The next time you want to see Mickey Mouse or explore the movie magic at Universal Orlando, book a stay in our budget-friendly suite! Ideally located in the heart of Orlando, our suite offers a shuttle service that can get you to Universal Orlando, SeaWorld, or any of the Disney parks. When you’re...
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    Windermere, Central Florida 32819
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Windermere
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Air Conditioning
    • Washer
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Shared Indoor Pool
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get ready for a theme park adventure, courtesy of our budget-friendly suite. Ideally located in the heart of Orlando, our suite offers a shuttle service that can get you to Universal Orlando, SeaWorld, or any of the Disney parks. When you’re not going on rides, splash around in the pools. We even...
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    Location Information
    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    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
    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 Rental: 28 Days 'Paradise' is the ultimate vacation home! 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 main house) and ALMOST PARADISE (the...
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    Windermere, Central Florida 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    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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    • Cable/satellite TV
    Suitability
    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
    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
    Windermere
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This inviting four-bedroom, 3-bath town home in Lucaya Village Resort Phase 2 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 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Windermere
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This inviting four-bedroom, 3-bath town home in Lucaya Village Resort Phase 2 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 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Windermere
    9 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This amazing new Park Square designed and built 9  Bedroom 7 Bathroom model , is ready to book right now on Solterra  Resort! Just 8 miles from Disney, and within easy reach of the fabulous restaurants and the Champions Gate area , this unique resort will provide a fabulous luxury clubhouse...
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    Location Information
    Windermere, Central Florida 33837
    Holiday Rental House - 9 Bedrooms, 7 Bathrooms, Sleeps 18
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    Orlo Vista
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a vacation of fun with your family at this spacious townhome that's located on the popular ChampionsGate Resort - just minutes from the Walt Disney World® Resort theme parks and all Orlando has to offer. This stylish 5 bedroom home is a great choice for your family vacation base. With 5...
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    Orlo Vista, Florida 34747
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Windermere
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This inviting four-bedroom, 3-bath home in Lucaya Village Resort features two master suites and 2 Twin bedrooms. With over 1,600 square feet of living space, you’ll be able to really enjoy your vacation without being in a cramped hotel.  All of the bedrooms offer a TV, dresser and closet.  We...
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    Windermere, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Windermere
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • DVD Player
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The History of Bay Hill It was in 1960 that ground was broken in a South Orange County wilderness that 50 years later would be known as the home of one of golf’s greatest legends, and one of the finest golf courses in the world. This is the place where tradition is paramount, hospitality flows...
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    Windermere, Central Florida 32819
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Ocoee
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • 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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    Ocoee, Central Florida 34761
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Windermere
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Queen bed: 02 | Full Kitchen | Community Pool Resort Style Located in the heart of Orlando our apartment are close to the major theme parks and other top attractions such as I-Drive 360, Universal STUDIOS, Fun Spot, International Drive, Orlando International Premium Outlets, The Mall at Millenia...
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    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Apopka
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Sauna
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully decorated and designed luxury home with salt water swimming pool and spa, game room, barbecue grill and many more amenities. Centrally located to shopping, groceries, pharmacy and all major highways to all of Orlando’s Theme parks, universal studios, a Disney, Seaworld, international...
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    Apopka, Florida 32712
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Windermere
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    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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    Windermere, Central Florida 34786
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Windermere
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Parking
    • Internet Access
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Features: Free Wi-Fi. This luxurious two-bedroom, two-and-a-half bath cottage accommodates up to six guests comfortably, with a king-sized bed in one bedroom, a queen-sized bed in the additional guest bedroom, along with a sofa sleeper in the living room. This cottage is part of our Beach House...
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    Windermere, Central Florida 34747
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Windermere
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Parking
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Features: Free Wi-Fi. Welcome to the Cayman Cottage. This luxurious four-bedroom, four and 1/2-bath cottage accommodates up to 10 guests comfortably, with a king-sized bed in two bedrooms, a queen-sized bed in the two additional bedrooms, along with a sofa sleeper in the living room. Relax and...
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    Windermere, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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