Vacation rentals with a pool in Winter Garden
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winter Garden
Guests agree: these homes with a pool 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 rentals with a pool
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 Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
Jun 22 – 29
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
Condo rentals with a pool
Condo in Kissimmee
4.94 out of 5 average rating, 160 reviewsLike Home Family Getaway
Dec 5 – 12
Condo in Four Corners
4.86 out of 5 average rating, 107 reviews"Ocean's Gate" - 2BD/2BA condo near Disney
Dec 4 – 11
Condo in Kissimmee
4.92 out of 5 average rating, 264 reviewsBeautiful Beach Style Condo minutes from Disney
Oct 21 – 28
Condo in Kissimmee
4.94 out of 5 average rating, 159 reviewsAffordable condo 3 miles from Disney and Golf!
Jan 7 – 14
Condo in Kissimmee
4.79 out of 5 average rating, 153 reviewsMickey's Retreat
Jul 11 – 18
Condo in Orlando
4.97 out of 5 average rating, 297 reviewsLuxurious Waterfront Resort near Disney &Universal
Aug 29 – Sep 5
Condo in Kissimmee
4.97 out of 5 average rating, 160 reviewsNew Lovely 3-bedroom Condo 5 minutes from Disney’s
Apr 11 – 18
Condo in Four Corners
4.99 out of 5 average rating, 148 reviewsOrlando Fun: Minutes to Disney and Margaritaville
Oct 29 – Nov 5
Home rentals with a private pool
Townhouse in Kissimmee
4.83 out of 5 average rating, 191 reviewsBeach House with Private Pool and Clubhouse near Disney
Sep 4 – 11
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
Jan 30 – Feb 6
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Aug 24 – 31
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Jan 11 – 18
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
Oct 4 – 11
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
Dec 3 – 10
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Jun 25 – Jul 2
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Dec 6 – 13
Quick stats about vacation rentals with a pool in Winter Garden
Total rentals
20 properties
Local attractions
Winter Garden Downtown Pavilion and Farmers Market, Best Buy, and Miller's Ale House - Winter Garden
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
180 reviews
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