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 house rentals in Winter Garden
House rentals with a pool
Home in Clermont
4.86 out of 5 average rating, 117 reviewsCozy Family Home near Disney
29 Jul – 5 Aug
Home in Davenport
4.87 out of 5 average rating, 135 reviewsInsta-worthy getaway near Disney w/ free parking!💎
27 Sep – 4 Oct
Home in Clermont
4.86 out of 5 average rating, 126 reviewsOur Poolhome by the Mouse house with Game Room.
15–22 Dec
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
22–29 Jul
Home in Clermont
4.9 out of 5 average rating, 117 reviewsStylish Villa Private Pool-SPA Near Parks Disney!
13–20 Oct
Home in Kissimmee
4.79 out of 5 average rating, 256 reviews3 bedroom Orlando Florida pool home
10–17 Dec
Home in Kissimmee
4.92 out of 5 average rating, 125 reviewsSouth Facing Pool Home! 5 Miles from Disney
10–17 May
Home in Davenport
4.95 out of 5 average rating, 161 reviewsDOLPHIN COVE NEAR DISNEY
20–27 Jan
Weekly house rentals
Home in Winter Park
4.9 out of 5 average rating, 133 reviewsGuest Suite in Winter Park/Orlando
27 Jun – 4 Jul
Home in Orlando
4.81 out of 5 average rating, 151 reviewsKing suite , Modern house perfect for vacation
6–13 Dec
Home in Winter Garden
4.9 out of 5 average rating, 20 reviewsPet Friendly Winter Garden Get-Away near Orlando
13–20 May
Home in Winter Garden
4.94 out of 5 average rating, 17 reviewsCozy home in Winter Garden
15–22 Jul
Home in Winter Garden
4.93 out of 5 average rating, 86 reviewsLuxury Home Winter Garden Near Disney & Universals
4–11 Jan
Home in Winter Garden
4.9 out of 5 average rating, 42 reviewsWinter Garden Experience
30 Mar – 6 Apr
Home in Minneola
5.0 out of 5 average rating, 59 reviewsCozy Studio Near Disney/Universal/Training center
21–28 May
Home in Clermont
5.0 out of 5 average rating, 18 reviewsLakefront home - country setting
30 Mar – 6 Apr
Private house rentals
Home in Orlando
4.98 out of 5 average rating, 41 reviews24/7 HomeCare Group
17–24 Oct
Home in Clermont
5.0 out of 5 average rating, 9 reviewsUnique 1 BR home/55+ Community
21–28 Oct
Home in Winter Garden
4.9 out of 5 average rating, 58 reviewsWATERFRONTWinterGdnHSE+VIEWS+Dock+Wildlife+Firepit
29 Sep – 6 Oct
Home in Clermont
5.0 out of 5 average rating, 12 reviews2BR 2BA Downtown Lake Townhouse
29 May – 5 Jun
Home in Clermont
5.0 out of 5 average rating, 27 reviewsThe Boho in the Boonies House
19–26 Jun
Home in Clermont
4.89 out of 5 average rating, 64 reviewsRelaxing Lakefront Home on Quiet Lake Glona
1–8 Jun
Home in Winter Garden
4.91 out of 5 average rating, 65 reviewsDisney Backyard Oasis
27 Mar – 3 Apr
Home in Howey-in-the-Hills
4.78 out of 5 average rating, 80 reviewsRustic 3-BR home w/spacious kitchen in Central FL
8–15 May
Quick stats about house rentals in Winter Garden
Total rentals
60 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2.3T reviews
Destinations to explore
- Orlando Holiday rentals
- Kissimmee Holiday rentals
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