Holiday 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.
Holiday 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 Deltona
4.96 out of 5 average rating, 150 reviewsSt. John’s Luxury Pool Lake House
15–22 Jan
Home in Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
31 Oct – 7 Nov
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
15–22 Sep
Home in Altamonte Springs
4.82 out of 5 average rating, 110 reviewsQuiet Place, convenient to everything!
23–30 Aug
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
10–17 Jun
Home in Oviedo
4.92 out of 5 average rating, 259 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
4–11 Apr
Home in Deltona
4.94 out of 5 average rating, 110 reviewsExecutive Lake House w/Solar Heated Saltwater Pool
15–22 Jul
Home in Orlando
4.94 out of 5 average rating, 123 reviewsThe Orlando Retreat.
23 Feb – 2 Mar
Apartment rentals with a pool
Apartment in Kissimmee
4.98 out of 5 average rating, 289 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
30 Aug – 6 Sep
Apartment in Kissimmee
4.95 out of 5 average rating, 110 reviewsCheery 2BR Condo w/zero entry pool near Disney
11–18 Oct
Apartment in Orlando
4.89 out of 5 average rating, 327 reviewsFantasticView, 1 BR/2BA, 1 MILE TO DISNEY-Sleeps 6
9–16 Nov
Apartment in Orlando
4.87 out of 5 average rating, 167 reviewsBeautiful Lakeview ★ 1 Mile to Disney ★ 1BDR/2BA
21–28 May
Apartment in Orlando
4.91 out of 5 average rating, 149 reviewsHuge/Terrace Studio. Universal Studios Area.
15–22 Dec
Apartment in Kissimmee
4.9 out of 5 average rating, 180 reviewsPerfect Condo | Pool & Tiki Bar | 15 min. Disney
14–21 May
Apartment in Kissimmee
4.96 out of 5 average rating, 155 reviewsWelcome to our Son Shine condo ....
25 Mar – 1 Apr
Apartment in Orlando
4.97 out of 5 average rating, 296 reviewsLuxurious Waterfront Resort near Disney &Universal
24 Sep – 1 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
5–12 Sep
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
19–26 Jun
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!
23–30 Nov
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
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
20–27 May
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
14–21 Mar
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
1–8 Aug
Quick stats about holiday 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
1.1T reviews
Nightly prices starting at
₹1,669 before taxes and fees
Destinations to explore
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- Rentals with pools United States
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