Holiday rentals with a pool in Winter Park
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winter Park
Guests agree: These homes with a pool 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 Park rentals with a pool
House rentals with a pool
Home in Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
24–31 Aug
Home in Orlando
4.91 out of 5 average rating, 117 reviewsLakefront presidential suite / resort pool
9–16 Jun
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
20–27 Dec
Home in Orlando
4.94 out of 5 average rating, 123 reviewsThe Orlando Retreat.
21–28 Aug
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 Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
16–23 Jun
Home in Edgewood
4.93 out of 5 average rating, 148 reviewsTropical Paradise in the heart of Orlando
20–27 Oct
Home in Sanford
4.86 out of 5 average rating, 214 reviewsPrivate Pool at Flamingo Cottage
22–29 Jan
Condo rentals with a pool
Condo in Orlando
4.91 out of 5 average rating, 149 reviewsHuge/Terrace Studio. Universal Studios Area.
15–22 Dec
Condo in Orlando
4.89 out of 5 average rating, 327 reviewsFantasticView, 1 BR/2BA, 1 MILE TO DISNEY-Sleeps 6
23–30 Nov
Condo in Kissimmee
4.96 out of 5 average rating, 136 reviews55B-DISNEY-STAR ISLAND, 1 BR DELUX-TENNIS/POOL/SPA
1–8 May
Condo in Kissimmee
4.98 out of 5 average rating, 289 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
30 Aug – 6 Sep
Condo in Orlando
4.91 out of 5 average rating, 183 reviewsDeluxe Studio:Lakeview, parking, pool
31 Aug – 7 Sep
Condo in Orlando
4.87 out of 5 average rating, 200 reviewsAirbnb's Choice- Best at Blue Heron- Stunning View
27 Jul – 3 Aug
Condo in Orlando
4.91 out of 5 average rating, 405 reviewsCozy Cay Condo Convn Ctr Vista Cay 2BR 2Ba 4 bds
24 Sep – 1 Oct
Condo in Orlando
4.81 out of 5 average rating, 342 reviewsLuxury Apt on I-Drive & view of Universal Orlando
17–24 Oct
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
22–29 Aug
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
3–10 Nov
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
22–29 Mar
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
26 Nov – 3 Dec
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
9–16 Dec
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
14–21 Nov
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
11–18 Dec
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
26 Oct – 2 Nov
Quick stats about holiday rentals with a pool in Winter Park
Total rentals
110 properties
Wi-Fi availability
110 properties include access to Wi-Fi
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.4K reviews
Destinations to explore
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- Rentals with pools United States
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