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.
24–31 Aug
Home in Orlando
4.91 out of 5 average rating, 117 reviewsLakefront presidential suite / resort pool
14–21 May
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
9–16 Aug
Home in Deltona
4.96 out of 5 average rating, 149 reviewsSt. John’s Luxury Pool Lake House
8–15 Jun
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
25 Mar – 1 Apr
Home in Altamonte Springs
4.82 out of 5 average rating, 110 reviewsQuiet Place, convenient to everything!
12–19 Dec
Home in Oviedo
4.92 out of 5 average rating, 259 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
24–31 Mar
Home in Orlando
4.94 out of 5 average rating, 123 reviewsThe Orlando Retreat.
24–31 Jan
Condo rentals with a pool
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
4.94 out of 5 average rating, 109 reviewsCheery 2BR Condo w/zero entry pool near Disney
14–21 Oct
Condo in Kissimmee
4.98 out of 5 average rating, 289 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
3–10 Apr
Condo in Orlando
4.87 out of 5 average rating, 167 reviewsBeautiful Lakeview ★ 1 Mile to Disney ★ 1BDR/2BA
21–28 May
Condo in Kissimmee
4.94 out of 5 average rating, 186 reviewsLakeview Escape close to Disney&retail therapy
3–10 Oct
Condo in Orlando
4.91 out of 5 average rating, 149 reviewsHuge/Terrace Studio. Universal Studios Area.
15–22 Dec
Condo in Kissimmee
4.92 out of 5 average rating, 263 reviewsBeautiful Beach Style Condo minutes from Disney
14–21 Oct
Condo in Davenport
4.84 out of 5 average rating, 140 reviewsFull Service Gated Resort, Close to Disney & MCO!
8–15 Sep
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
9–16 Feb
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
16–23 Mar
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
28 Aug – 4 Sep
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
21–28 Jun
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
11–18 Sep
Quick stats about holiday rentals with a pool in Winter Springs
Total rentals
20 properties
Wi-Fi availability
20 properties include access to Wi-Fi
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
$34 NZD before taxes and fees
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- Rentals with pools United States
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