Vacation 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.
Vacation 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.
Dec 22 – 29
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
Apr 4 – 11
Home in Orlando
4.94 out of 5 average rating, 124 reviewsThe Orlando Retreat.
Apr 20 – 27
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 Orlando
4.91 out of 5 average rating, 117 reviewsLakefront presidential suite / resort pool
Jun 21 – 28
Home in Oviedo
4.92 out of 5 average rating, 283 reviews4 bedroom Modern pool home, close to UCF&Boombah
Apr 7 – 14
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
Apr 21 – 28
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
Jun 12 – 19
Condo rentals with a pool
Condo in Orlando
4.91 out of 5 average rating, 150 reviewsHuge/Terrace Studio. Universal Studios Area.
Dec 15 – 22
Condo in Orlando
4.82 out of 5 average rating, 397 reviewsModern Studio with Private Terrace near Universal
Aug 4 – 11
Condo in Kissimmee
4.98 out of 5 average rating, 290 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
Nov 21 – 28
Condo in Orlando
4.91 out of 5 average rating, 407 reviewsCozy Cay Condo Convn Ctr Vista Cay 2BR 2Ba 4 bds
Oct 19 – 26
Condo in Orlando
4.87 out of 5 average rating, 200 reviewsAirbnb's Choice- Best at Blue Heron- Stunning View
Sep 21 – 28
Condo in Orlando
4.91 out of 5 average rating, 184 reviewsDeluxe Studio:Lakeview, parking, pool
Aug 31 – Sep 7
Condo in Orlando
4.94 out of 5 average rating, 109 reviewsVCR1-204 Deluxe Condo - Convention Center
Sep 24 – Oct 1
Condo in Orlando
4.82 out of 5 average rating, 107 reviewsDesigner Orlando Retreat near UCF & Outdoor Space
Jun 9 – 16
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 Park
Total rentals
110 properties
Wifi availability
110 properties include access to wifi
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
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