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Holiday Rentals with Pools in Winter Garden

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    Travellers to Winter Garden are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    34 Matching Rentals in the Winter Garden AreaView all 45 rentals
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    Winter Garden
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Winter Garden
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Property Description: Palisades Vacations offers Vacation Suites at the well-known Palisades Resort located near the West Gate of Walt Disney World. The area is in a natural and peaceful setting but close to all of the local attractions and seven world class golf courses. This condo property is...
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    Winter Garden, Central Florida 34787
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Winter Garden
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Property Description: Palisades Vacations offers Vacation Suites at the well-known Palisades Resort located near the West Gate of Walt Disney World. The area is in a natural and peaceful setting but close to all of the local attractions and seven world class golf courses. This condo property is...
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    Winter Garden, Central Florida 34787
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Buckeye Butterfly Villa1 / 18
    (1)Excellent
    Winter Garden
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Parking
    • Outdoor Dining Area
    • Balcony
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    I have just returned from staying with my 3 children (age 5, 9 and 11) and my parents from this villa for 3 weeks and we loved it. The villa is spotless, spacious, modern and...
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    About this property
    Stay only 5 miles from Disney World gates. High quality and modern furnishings greet you at Buckeye Butterfly Villa with a touch of elegance and panache. You will not be disappointed in our recently refurbished 3 bedroom/2 bath home. With one of 3 community pools located just a few steps away...
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    Winter Garden, Central Florida 34787
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    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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    • 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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    Location Information
    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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    • 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...
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    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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    • 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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    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...
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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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    • 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...
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    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 20 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
    4 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Children's Pool
    • Parking
    • 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
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    Windermere
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Parking
    • 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 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
    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
    Live like a king and stay close to the amazing theme parks of Orlando, courtesy of our spacious suite! As our guest, you’ll enjoy access to a convenient theme park shuttle that will take you directly to Walt Disney World, SeaWorld, and Universal Studios. We can’t wait to be your...
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    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Windermere
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Parking
    • 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 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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    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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    Windermere
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
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    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in our spacious suite, and you'll only be minutes away from amazing theme parks! As our guest, you’ll enjoy access to a convenient theme park shuttle that will take you directly to Walt Disney World, SeaWorld, and Universal Studios. We can’t wait to be your home-away-from-home! Our cozy suite...
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    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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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
    Our elegant and spacious 1 bedroom retreat is the perfect home base for your Orlando vacation! We think you'll love to be centrally located near Universal Boulevard, with excellent restaurants, shopping and entertainment just out your door! Orlando's theme parks are just minutes away, including...
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    Location Information
    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    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
    Dreaming of a vacation where you’re only minutes away from world-class theme parks? Turn your dream into reality, by staying in our spacious suite. As our guest, you’ll enjoy access to a convenient theme park shuttle that will take you directly to Walt Disney World, SeaWorld, and Universal Studios....
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    Location Information
    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    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 Wizarding World of Harry Potter and Universal Orlando are only a short drive away when you stay in our spacious suite. Our shuttle service can take you to SeaWorld, Universal Orlando, ICON Orlando, and the Disney parks. When your kids aren’t busy making friends with Mickey Mouse or learning...
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    Windermere, Central Florida 32819
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    On your next family vacation, stay close to the theme parks by booking a stay in our 1 bedroom suite. The shuttle service on-site can take you to SeaWorld, Universal Orlando, ICON Orlando, and the Disney parks. When your kids aren’t busy making friends with Mickey Mouse or learning about Hollywood...
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    Windermere, Central Florida 32819
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Windermere
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    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
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Children's Pool
    • Wi-Fi
    • Sauna
    • DVD Player
    • Housekeeping Included
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beautiful lakefront Resort & Spa is a tropical paradise that lies just 1.5 miles from SeaWorld® Orlando, 2 miles from Universal Orlando Resort™ and 6 miles from Walt Disney World®‎ Resort, as well as just 2.6 miles from the ICON Orlando 360™, Madame Tussauds Orlando and SEA LIFE Orlando...
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    Location Information
    Windermere, Central Florida 32819
    Condo/Apartment - 3 Bedrooms, 3 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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    Location Information
    Windermere, Central Florida 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Location Information
    Windermere, Central Florida 34786
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    • Internet Access
    Suitability
    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 4 bedrooms 3 bathrooms Sleeps 8 Covered porch Access to resort amenitiesBedrooms...
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    Windermere, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
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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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    Location Information
    Windermere, Central Florida 34786
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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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    Location Information
    Ocoee, Central Florida 34761
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Orlo Vista
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Wi-Fi
    • Washer
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Suitable for both family getaways or business trips, this cozy 1-bedroom, 1-bathroom vacation rental apartment offers an ideal location in western Orlando! Up to 4 travelers will be able to enjoy access to the community pool, hot tub, and fitness center for on-site entertainment. Theme parks galore...
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    Location Information
    Orlo Vista, Florida 32835
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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