Vacation 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.
Vacation 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 Altamonte Springs
4.8 out of 5 average rating, 111 reviewsQuiet Place, convenient to everything!
Sep 28 – Oct 5
Home in Orlando
4.94 out of 5 average rating, 125 reviewsThe Orlando Retreat.
Mar 19 – 26
Home in Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
Jul 27 – Aug 3
Home in Oviedo
4.92 out of 5 average rating, 283 reviews4 bedroom Modern pool home, close to UCF&Boombah
Oct 21 – 28
Home in Deltona
4.85 out of 5 average rating, 365 reviewsBeautiful lake view house
Oct 9 – 16
Home in Orlando
4.95 out of 5 average rating, 314 reviews*HALF HOME* (read desc) Pool/Disney/Universal
Aug 29 – Sep 5
Home in Orlando
4.87 out of 5 average rating, 166 reviews*Lakefront Pool Home *paddleboard*kayak*game room*
Jul 7 – 14
Home in Apopka
4.88 out of 5 average rating, 162 reviews* Luxury Pool * Hot Tub * 86 Inch TV *
Mar 19 – 26
Condo rentals with a pool
Condo in Orlando
4.9 out of 5 average rating, 151 reviewsHuge/Terrace Studio. Universal Studios Area.
Dec 27 – Jan 3
Condo in Kissimmee
4.98 out of 5 average rating, 291 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
Jan 28 – Feb 4
Condo in Orlando
4.82 out of 5 average rating, 108 reviewsDesigner Orlando Retreat near UCF & Outdoor Space
Sep 10 – 17
Condo in Four Corners
4.99 out of 5 average rating, 148 reviewsOrlando Fun: Minutes to Disney and Margaritaville
Apr 13 – 20
Condo in Orlando
4.87 out of 5 average rating, 200 reviewsAirbnb's Choice- Best at Blue Heron- Stunning View
Jun 9 – 16
Condo in Kissimmee
4.94 out of 5 average rating, 186 reviewsLakeview Escape close to Disney&retail therapy
Apr 24 – May 1
Condo in Kissimmee
4.98 out of 5 average rating, 163 reviewsRemodeled, Stylish and Affordable Close to Disney
Aug 16 – 23
Condo in Davenport
4.84 out of 5 average rating, 141 reviewsFull Service Gated Resort, Close to Disney & MCO!
Jan 3 – 10
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
Sep 10 – 17
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
Sep 16 – 23
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Aug 5 – 12
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Apr 21 – 28
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
Dec 10 – 17
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
Feb 7 – 14
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Jul 11 – 18
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Jan 8 – 15
Quick stats about vacation 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
$10 before taxes and fees
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