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 Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
22–29 Dec
Home in Deltona
4.96 out of 5 average rating, 150 reviewsSt. John’s Luxury Pool Lake House
17–24 Mar
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
4–11 Apr
Home in Altamonte Springs
4.82 out of 5 average rating, 110 reviewsQuiet Place, convenient to everything!
7–14 Sep
Home in Oviedo
4.92 out of 5 average rating, 260 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
10–17 Apr
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
22–29 Jun
Home in Orlando
4.94 out of 5 average rating, 124 reviewsThe Orlando Retreat.
20–27 Apr
Home in Deltona
4.94 out of 5 average rating, 110 reviewsExecutive Lake House w/Solar Heated Saltwater Pool
16–23 Jul
Apartment rentals with a pool
Apartment in Orlando
4.82 out of 5 average rating, 107 reviewsDesigner Orlando Retreat near UCF & Outdoor Space
9–16 Jun
Apartment in Kissimmee
4.98 out of 5 average rating, 290 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
21–28 Nov
Apartment in Orlando
4.91 out of 5 average rating, 407 reviewsCozy Cay Condo Convn Ctr Vista Cay 2BR 2Ba 4 bds
19–26 Oct
Apartment in Orlando
4.91 out of 5 average rating, 150 reviewsHuge/Terrace Studio. Universal Studios Area.
15–22 Dec
Apartment in Davenport
4.85 out of 5 average rating, 268 reviewsNear Disney w POOL 3BR/2BA Tuscany-style -Sleeps 8
6–13 Sep
Apartment in Kissimmee
4.91 out of 5 average rating, 111 reviewsModern Storey Lake Resort Disney Orlando 3171-206
16–23 Sep
Apartment in Kissimmee
4.92 out of 5 average rating, 264 reviewsBeautiful Beach Style Condo minutes from Disney
21–28 Oct
Apartment in Kissimmee
4.94 out of 5 average rating, 159 reviewsAffordable condo 3 miles from Disney and Golf!
7–14 Jan
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
4–11 Sep
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
30 Jan – 6 Feb
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
24–31 Aug
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
11–18 Jan
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
4–11 Oct
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
3–10 Dec
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
25 Jun – 2 Jul
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
6–13 Dec
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
1.1K reviews
Nightly prices starting at
$27 SGD before taxes and fees
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- Rentals with pools United States
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