Villas and Holiday homes in Winter Garden, FL

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Winter Garden, FL holiday homes
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30 Villa rentals in Winter Garden, FL

Handpicked Holiday Houses with a Swimming Pool in Winter Garden, FL

Enjoy a swim whenever you like, as these holiday homes in Winter Garden, FL feature excellent on-site pool facilities.

3-bedroom Villa In Enjoyable Orlando With Fitness Room, Ac, Wifi - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£346/nighttotal: £11418 (33 )

3-bedroom Villa In Enjoyable Orlando With Fitness Room, Ac, Wifi

1 2
house , Doctor Phillips
This three-bedroom, three-bathroom villa in Doctor Phillips, Orlando, offers convenient access to Arnold Palmer's Bay Hill Golf Club and Disney Springs.
Sleeping up to 12 guests, the property boasts a swimming pool, Jacuzzi, free WiFi, and a fitness room, alongside a microwave, dishwasher, and parking.
Family Friendly Villa Near Disney, Pool, Sleeps 5 - Winter Garden, FL
8.0 1 review
Winter Garden, FL
29/07 – 31/08
£94/nighttotal: £3102 (33 )

Family Friendly Villa Near Disney, Pool, Sleeps 5

2 2
house , Clermont
This two-bedroom, two-bathroom villa in Clermont's Vacation Village is situated less than 1.6km from Legends Golf & Country Club and Kings Ridge Driving Range, and under 3.2km from Lake Louisa State Park.
The property offers a fully equipped kitchen, including a fridge, microwave, and dishwasher, sleeps six guests, boasts a private swimming pool and hot tub, and is conveniently located near multiple golf courses and outdoor recreational opportunities.
Lilac Loft- Lake, Pool, Pickle Ball, Disney, Fun! - Winter Garden, FL
8.0 1 review
Winter Garden, FL
29/07 – 31/08
£216/nighttotal: £7128 (33 )

Lilac Loft- Lake, Pool, Pickle Ball, Disney, Fun!

2 2
house , Clermont
This holiday home in Castle Hill, Clermont, is approximately 27-32 kilometres from major Disney attractions including Magic Kingdom, Walt Disney World, and the Wizarding World of Harry Potter.
This 79-square-metre property offers 2 bedrooms, 2 bathrooms, a private swimming pool, a garden, tennis court, and parking, with complimentary WiFi and air conditioning.
Last Minute Disney Getaway! Private Patio & Themed Bedrooms. Book Now! #115909 - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£174/nighttotal: £5742 (33 )

Last Minute Disney Getaway! Private Patio & Themed Bedrooms. Book Now! #115909

3 2
house , Lake Butler
This Windermere holiday home, near Lake Butler, is situated 0.16 km from the Windermere Farmers' Market and 2.4 km from the Butler Chain of Lakes scenic boat tour.
The three-bedroom, two-bathroom property sleeps up to eleven guests and boasts a private patio, garden, swimming pool, spa, and home gym; an EV charger is also available.

Best family friendly Winter Garden, FL villas and holiday home

Among the 30 accommodations in Winter Garden, FL, here are the 4 best family friendly villas and holiday homes

88 M² House ∙ 2 Bedrooms ∙ 5 Guests - Winter Garden, FL
9.4 26 reviews
Winter Garden, FL
29/07 – 31/08
£112/nighttotal: £3696 (33 )

88 M² House ∙ 2 Bedrooms ∙ 5 Guests

2 2
house , Clermont
This three-bedroom A-frame house in Vacation Village, Clermont, Florida, is situated approximately 32 kilometres from Walt Disney World and other major theme parks, offering deeded lakefront access.
The 87-square-metre property features a fully equipped kitchen, two bathrooms, a private deck, swimming pool, spa and accommodates up to five guests, with access to community amenities including pickleball and shuffleboard courts.
Last Minute Disney Getaway! Luxury Villa With Private Pool. Book Now! #102051 - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£203/nighttotal: £6699 (33 )

Last Minute Disney Getaway! Luxury Villa With Private Pool. Book Now! #102051

3 2
house , Williamsburg
This Orlando property, situated within the Vista Cay Resort, offers convenient access to major theme parks; it's under 16km from Walt Disney World, and within 8km of Universal Studios and SeaWorld.
The three-bedroom, two-bathroom condo, sleeping up to six guests, boasts a fully equipped kitchen, private balcony, and access to resort amenities including a pool, fitness centre, and game room; complimentary Wi-Fi and parking are also provided.
Vista Cay 3br Townhome W/ Resort Access - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£209/nighttotal: £6897 (33 )

Vista Cay 3br Townhome W/ Resort Access

3 2
house , Williamsburg
This modern townhome is located in the Vista Cay Resort, Orlando, just 1 minute by car from Epic Universe and a short distance from Universal Studios and International Drive.
This family-friendly accommodation offers 4 bedrooms, 4 bathrooms, and a guest capacity of 9, with full access to resort amenities including pools and a fitness centre, and is managed by a local team providing 24/7 support.
Luxury 5br Villa Near Disney & Conv Center - Winter Garden, FL
10 2 reviews
Winter Garden, FL
29/07 – 31/08
£315/nighttotal: £10395 (33 )

Luxury 5br Villa Near Disney & Conv Center

5 2
house , Williamsburg
This non-smoking villa is located in Orlando's downtown district, 644 metres from the Orange County Convention Centre and 1.1 kilometres from The Orlando Eye, offering convenient access to major amusement parks.
This 178 square metre property accommodates up to 14 guests across 5 bedrooms and 5 bathrooms, featuring a communal swimming pool, garden, fitness centre, and a fully equipped kitchen with Wi-Fi and air conditioning.

Frequently asked questions about villa rentals in Winter Garden, FL

Destinations nearby

Best Winter Garden, FL villas and holiday homes with parking

Dog-friendly Condo With A Kitchenette, Ac, Pools, Hot Tubs, Tennis, & Gym - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£113/nighttotal: £3729 (33 )

Dog-friendly Condo With A Kitchenette, Ac, Pools, Hot Tubs, Tennis, & Gym

2 2
house , Orlando
This dog-friendly apartment is located in Orlando, within 2 kilometres of The Wheel At Icon Park, Universal Studios' Islands of Adventure and Universal Studios Orlando.
This 54 square metre accommodation offers 2 bedrooms, 2 bathrooms, a kitchenette with a dishwasher and oven, and can sleep up to 7 guests, with on-site amenities including swimming pools, hot tubs, tennis courts and a gym.
Home With Large Deck & Privacy Fenced In Backyard - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£276/nighttotal: £9108 (33 )

Home With Large Deck & Privacy Fenced In Backyard

3 2
house , Ocoee
This Ocoee dwelling is conveniently located approximately 16 kilometres from Universal Studios’ Islands of Adventure and Universal Studios Orlando, 16 kilometres from the Holy Land Experience, 14 kilometres from the Kia Centre, and 14 kilometres from Camping World Stadium.
This holiday home accommodates up to 13 guests with 3 bathrooms, a fully equipped kitchen, air conditioning, WiFi, and private parking, plus a fenced garden and spacious deck for outdoor enjoyment.
Best Place For Vacation Or Business Comfort, Safety - Winter Garden, FL
9.7 318 reviews
Winter Garden, FL
29/07 – 31/08
£228/nighttotal: £7524 (33 )

Best Place For Vacation Or Business Comfort, Safety

3 2
apartment , Williamsburg
This family-friendly holiday home is situated just 2 kilometres from Shingle Creek Golf Course and The Wheel at ICON Park™, and within 3 kilometres of the Orange County Convention Center and Aquatica, offering easy access to a range of attractions. The property has excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
This spacious property features 3 bedrooms and 4 bathrooms, providing ample space for families or groups. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, spa, fitness centre, tennis court, and parking.
25 Mi To Disney Home With Shared Pool In Orlando - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£118/nighttotal: £3894 (33 )

25 Mi To Disney Home With Shared Pool In Orlando

3 2
house , Pine Hills
This Pine Hills holiday home is situated approximately 16-19 kilometres from Orlando attractions including Camping World Stadium, the Amway Center, and Universal Studios Florida, offering easy access to theme parks and city amenities.
This three-bedroom property boasts 113 square metres of floor space, accommodating up to six guests and featuring a fully equipped kitchen, air conditioning, a terrace, parking, and free Wi-Fi.

Best Winter Garden, FL villas and holiday homes with a garden

Hope House- Vacation Village 1 Bedroom With Loft - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£154/nighttotal: £5082 (33 )

Hope House- Vacation Village 1 Bedroom With Loft

1 2
house , Clermont
Hope House, a one-bedroom property in Clermont, Florida, is conveniently located 27-35 km from Walt Disney World Resort.
This 88 square metre house, featuring a loft bedroom and two bathrooms, comfortably sleeps five guests and includes a fully equipped kitchen, air conditioning, and a garden.
Last Minute Disney Getaway! Modern Condo With Amazing Views. Book Now! #147473 - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£140/nighttotal: £4620 (33 )

Last Minute Disney Getaway! Modern Condo With Amazing Views. Book Now! #147473

2 2
house , Orlando
This two-bedroom apartment, sleeping four, is situated in Orlando's International Drive district, 8km from Walt Disney World Resort, 26km from Universal Studios Florida, and 40km from Orlando International Airport.
The 1230 square metre property boasts a fully equipped kitchen, private balcony, swimming pool access, and resort amenities including a fitness centre and children's splash park; making it ideal for families visiting Orlando's theme parks.
Charming Villa Near Disney, Pool, 4 Beds, Sleeps 5 - Winter Garden, FL
8.0 3 reviews
Winter Garden, FL
29/07 – 31/08
£102/nighttotal: £3366 (33 )

Charming Villa Near Disney, Pool, 4 Beds, Sleeps 5

2 2
house , Clermont
This lakefront villa in Clermont's Vacation Village neighbourhood is situated within a gated community, offering a 48 kilometre drive to major theme parks such as Magic Kingdom® Park and Walt Disney World® Resort, and is adjacent to Lake Louisa State Park.
This family-friendly holiday home accommodates six guests, featuring two bedrooms, one bathroom, air conditioning, a swimming pool, a jacuzzi, and a kitchen equipped with a fridge, microwave oven, and dishwasher, with community amenities including shuffleboard, tennis, and basketball courts.
Last Minute Disney Getaway! Luxury Villa With Private Patio. Book Now! #115911 - Winter Garden, FL
Winter Garden, FL
29/07 – 31/08
£196/nighttotal: £6468 (33 )

Last Minute Disney Getaway! Luxury Villa With Private Patio. Book Now! #115911

5 2
house , Windermere
This Windermere holiday home is situated in southwest Orange County, Florida, 4km from Lake Butler, 0.16km from the Windermere Farmers' Market, and within 4.6km of several golf courses including the Isleworth Golf & Country Club.
The five-bedroom, four-bathroom property sleeps up to 11 guests, offering a fully equipped kitchen, alfresco dining, indoor games (shuffleboard, foosball), a fireplace, covered patio, private patio with table tennis, and a balcony terrace; plus a mid-stay clean for bookings over 28 days and pet-friendly accommodation (fees apply, pets must be approved).
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