House vacation rentals in Winter Garden
Find and book unique houses on Airbnb
Top-rated house rentals in Winter Garden
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation 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 Clermont
4.86 out of 5 average rating, 117 reviewsCozy Family Home near Disney
Oct 19 – 26
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
Jun 12 – 19
Home in Clermont
4.9 out of 5 average rating, 117 reviewsStylish Villa Private Pool-SPA Near Parks Disney!
Oct 24 – 31
Home in Clermont
4.89 out of 5 average rating, 108 reviewsHook's Cabin- Lake & Pool near Disney A-frame
Sep 4 – 11
Home in Clermont
4.88 out of 5 average rating, 132 reviewsDisney Pool Villa, Cranberry South,
Sep 17 – 24
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
Apr 21 – 28
Home in Davenport
4.87 out of 5 average rating, 135 reviewsInsta-worthy getaway near Disney w/ free parking!💎
Sep 27 – Oct 4
Home in Kissimmee
4.79 out of 5 average rating, 256 reviews3 bedroom Orlando Florida pool home
Jan 13 – 20
Weekly house rentals
Home in Orlando
4.9 out of 5 average rating, 178 reviewsDowntown Orlando-Harwood House-Lake Eola-Historic
Jan 2 – 9
Home in Orlando
4.93 out of 5 average rating, 120 reviewsHidden Gem in SODO! - MCO ~16min
Sep 28 – Oct 5
Home in Winter Park
4.9 out of 5 average rating, 135 reviewsGuest Suite in Winter Park/Orlando
Aug 5 – 12
Home in Altamonte Springs
4.97 out of 5 average rating, 276 reviewsEclectic Home Where Luxury Meets Affordability
Sep 11 – 18
Home in Winter Garden
4.9 out of 5 average rating, 20 reviewsPet Friendly Winter Garden Get-Away near Orlando
May 13 – 20
Home in Winter Garden
4.94 out of 5 average rating, 17 reviewsCozy home in Winter Garden
Sep 9 – 16
Home in Winter Garden
4.93 out of 5 average rating, 86 reviewsLuxury Home Winter Garden Near Disney & Universals
Jan 14 – 21
Home in Winter Garden
4.9 out of 5 average rating, 42 reviewsWinter Garden Experience
Sep 19 – 26
Private house rentals
Home in Clermont
4.88 out of 5 average rating, 8 reviewsClermont 2 Bedroom Bungalow
Sep 1 – 8
Home in Clermont
5.0 out of 5 average rating, 27 reviewsThe Boho in the Boonies House
May 7 – 14
Home in Clermont
5.0 out of 5 average rating, 12 reviews2BR 2BA Downtown Lake Townhouse
Sep 25 – Oct 2
Home in Winter Garden
4.9 out of 5 average rating, 58 reviewsWATERFRONTWinterGdnHSE+VIEWS+Dock+Wildlife+Firepit
Mar 26 – Apr 2
Home in Clermont
5.0 out of 5 average rating, 9 reviewsUnique 1 BR home/55+ Community
Aug 23 – 30
Home in Clermont
4.89 out of 5 average rating, 64 reviewsRelaxing Lakefront Home on Quiet Lake Glona
Jun 1 – 8
Home in Ocoee
4.93 out of 5 average rating, 71 reviewsWelcome to your perfect home away from home.
Oct 1 – 8
Home in Winter Garden
4.91 out of 5 average rating, 65 reviewsDisney Backyard Oasis
Oct 9 – 16
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
2.3K reviews
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