Holiday rentals with a pool in Longwood
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Longwood
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 Longwood 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
17–24 Mar
Home in Altamonte Springs
4.82 out of 5 average rating, 110 reviewsQuiet Place, convenient to everything!
19–26 Nov
Home in Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
8–15 Aug
Home in Orlando
4.94 out of 5 average rating, 124 reviewsThe Orlando Retreat.
20–27 Apr
Home in Deltona
4.85 out of 5 average rating, 365 reviewsBeautiful lake view house
11–18 Oct
Home in Oviedo
4.92 out of 5 average rating, 283 reviews4 bedroom Modern pool home, close to UCF&Boombah
3–10 Aug
Home in Minneola
4.98 out of 5 average rating, 111 reviewsSpacious Home ~ Heated LED Pool & Ping Pong
13–20 Dec
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
16–23 Jun
Apartment rentals with a pool
Apartment in Orlando
4.91 out of 5 average rating, 150 reviewsHuge/Terrace Studio. Universal Studios Area.
27 Dec – 3 Jan
Apartment in Kissimmee
4.98 out of 5 average rating, 290 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
15–22 Dec
Apartment in Orlando
4.87 out of 5 average rating, 200 reviewsAirbnb's Choice- Best at Blue Heron- Stunning View
19–26 Jun
Apartment in Kissimmee
4.97 out of 5 average rating, 160 reviewsNew Lovely 3-bedroom Condo 5 minutes from Disney’s
23–30 Sep
Apartment in Kissimmee
4.94 out of 5 average rating, 186 reviewsLakeview Escape close to Disney&retail therapy
15–22 Jan
Apartment in Four Corners
4.99 out of 5 average rating, 148 reviewsOrlando Fun: Minutes to Disney and Margaritaville
23–30 Apr
Apartment in Davenport
4.84 out of 5 average rating, 141 reviewsFull Service Gated Resort, Close to Disney & MCO!
5–12 Dec
Apartment in Orlando
4.87 out of 5 average rating, 167 reviewsBeautiful Lakeview ★ 1 Mile to Disney ★ 1BDR/2BA
29 Jun – 6 Jul
Home rentals with a private pool
Townhouse in Kissimmee
4.82 out of 5 average rating, 192 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
17–24 Apr
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
13–20 Apr
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
22 Feb – 1 Mar
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
11–18 Sep
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
25 Jun – 2 Jul
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
3–10 Mar
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
1–8 Jan
Quick stats about holiday rentals with a pool in Longwood
Total rentals
10 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
530 reviews
Nightly prices starting at
$14 SGD before taxes and fees
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