House holiday rentals in Winter Garden
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Top-rated house rentals in Winter Garden
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Garden house rentals
House rentals with a pool
Home in Kissimmee
4.91 out of 5 average rating, 44 reviewsLuxury Poolside Escape: 3BR, 2BA w/ Large Driveway
Home in Davenport
4.91 out of 5 average rating, 122 reviewsThe Shire -Private Pool & Hot Tub, Close to parks!
Home in Orlando
4.87 out of 5 average rating, 181 reviewsPool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
Home in Davenport
4.89 out of 5 average rating, 9 reviewsSplash & Play ~ Poolside Bliss ~ 15 Mins to Disney
Home in Davenport
4.83 out of 5 average rating, 18 reviewsBeautiful stylish Home with hot tub pool
Home in Kissimmee
4.91 out of 5 average rating, 35 reviewsEntire house 3BR/2BA Private SaltWaterPool
Home in Clermont
4.91 out of 5 average rating, 138 reviewsStylish Villa Private Pool-SPA Near Parks Disney!
Home in Apopka
4.88 out of 5 average rating, 120 reviewsCountry Pool home on 2 acres-30 minutes to Disney
Weekly house rentals
Home in Davenport
4.77 out of 5 average rating, 44 reviews969T-Single Storey House 20 min from Disney 4 bed
Home in Kissimmee
4.78 out of 5 average rating, 9 reviewsSUPER VILLA - 7BDR|5.5BAs POOL & THEME ROOMs!
Home in Kissimmee
4.95 out of 5 average rating, 20 reviews9001-WW 5 Bedroom ALL Suites Pool Home
Home in Clermont
4.97 out of 5 average rating, 173 reviewsCaribe Villa Brisa- Disney is only 6 miles away!
Home in Kissimmee
4.9 out of 5 average rating, 120 reviews5BD Windsor Westside Private Pool (WW 9025)
Home in Kissimmee
4.76 out of 5 average rating, 127 reviewsWonderful Family Home 3/2 w/pool, Gorgeous Sunsets
Home in Kissimmee
4.88 out of 5 average rating, 130 reviews6BR Disney Vacation Home w\2 Suites Pool + Hot Tub
Home in Davenport
5 out of 5 average rating, 5 reviewsBRAND NEW 2024 10Bedrms/Sleeps22 At Windsor Island
Private house rentals
Home in Auburndale
4.94 out of 5 average rating, 152 reviewsLake Whistler Beach House with lakefront pool
Home in Orlando
4.87 out of 5 average rating, 38 reviewsPrivate luxury home w additional Suite on 0.6 acre
Home in Davenport
4.89 out of 5 average rating, 141 reviewsPrivate Haven: Free Pool Heat & BBQ/5Bedroom/4.5Ba
Home in Kissimmee
5 out of 5 average rating, 4 reviewsWow House PLUS Apartment*Pool*Near Disney*GolfView
Home in Apopka
4.94 out of 5 average rating, 151 reviewsQuiet Home Near Wekiva and Rock Springs
Home in Davenport
4.82 out of 5 average rating, 144 reviewsBeautiful cozy home with pool and spa
Home in Casselberry
4.94 out of 5 average rating, 97 reviewsVilla with Pool-Patio
Home in Davenport
4.6 out of 5 average rating, 43 reviewsEntire House Davenport My Dream House
Quick stats about house rentals in Winter Garden
Total rentals
60 properties
Total number of reviews
2.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- St Petersburg Holiday rentals
- Daytona Beach Holiday rentals
- Anna Maria Island Holiday rentals
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- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- Kissimmee Holiday rentals
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- Rentals with pools Winter Garden
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- Rentals with outdoor seating Winter Garden
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