Vacation rentals with a pool in Winter Springs
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winter Springs
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 Springs 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.
Sep 4 – 11
Home in Oviedo
4.92 out of 5 average rating, 260 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
Apr 11 – 18
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
Apr 28 – May 5
Home in Altamonte Springs
4.82 out of 5 average rating, 110 reviewsQuiet Place, convenient to everything!
Mar 29 – Apr 5
Home in Orlando
4.94 out of 5 average rating, 124 reviewsThe Orlando Retreat.
Dec 1 – 8
Home in Deltona
4.94 out of 5 average rating, 110 reviewsExecutive Lake House w/Solar Heated Saltwater Pool
Jul 17 – 24
Home in Deltona
4.85 out of 5 average rating, 365 reviewsBeautiful lake view house
Oct 28 – Nov 4
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
Oct 7 – 14
Condo rentals with a pool
Condo in Orlando
4.82 out of 5 average rating, 107 reviewsDesigner Orlando Retreat near UCF & Outdoor Space
Jun 9 – 16
Condo in Kissimmee
4.98 out of 5 average rating, 290 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
Dec 15 – 22
Condo in Kissimmee
4.99 out of 5 average rating, 154 reviewsBright, Airy Home near Disney and Attractions
Nov 4 – 11
Condo in Kissimmee
4.92 out of 5 average rating, 264 reviewsBeautiful Beach Style Condo minutes from Disney
Nov 12 – 19
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, 150 reviewsHuge/Terrace Studio. Universal Studios Area.
Dec 27 – Jan 3
Condo in Kissimmee
4.96 out of 5 average rating, 155 reviewsWelcome to our Son Shine condo ....
Nov 4 – 11
Condo in Four Corners
4.86 out of 5 average rating, 107 reviews"Ocean's Gate" - 2BD/2BA condo near Disney
Jan 19 – 26
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
Apr 17 – 24
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Aug 16 – 23
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Nov 23 – 30
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
Oct 22 – 29
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
May 15 – 22
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
Apr 24 – May 1
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Oct 2 – 9
Quick stats about vacation rentals with a pool in Winter Springs
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.1K reviews
Nightly prices starting at
$20 before taxes and fees
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