Vacation rentals with a pool in Maitland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Maitland
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 Maitland rentals with a pool
House rentals with a pool
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
4.94 out of 5 average rating, 125 reviewsThe Orlando Retreat.
Mar 19 – 26
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
Sep 22 – 29
Home in Altamonte Springs
4.8 out of 5 average rating, 111 reviewsQuiet Place, convenient to everything!
Sep 28 – Oct 5
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 Sanford
4.86 out of 5 average rating, 214 reviewsPrivate Pool at Flamingo Cottage
Aug 26 – Sep 2
Home in Orlando
4.87 out of 5 average rating, 166 reviews*Lakefront Pool Home *paddleboard*kayak*game room*
Jul 7 – 14
Home in Orlando
4.83 out of 5 average rating, 137 reviewsPrivate Luxury Pool / Swim up bar / Smart-home
Sep 13 – 20
Condo rentals with a pool
Condo in Orlando
4.82 out of 5 average rating, 108 reviewsDesigner Orlando Retreat near UCF & Outdoor Space
Sep 10 – 17
Condo in Orlando
4.89 out of 5 average rating, 152 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
4.87 out of 5 average rating, 200 reviewsAirbnb's Choice- Best at Blue Heron- Stunning View
Jun 9 – 16
Condo in Kissimmee
4.98 out of 5 average rating, 163 reviewsRemodeled, Stylish and Affordable Close to Disney
Aug 16 – 23
Condo in Orlando
4.91 out of 5 average rating, 184 reviewsDeluxe Studio:Lakeview, parking, pool
Jun 4 – 11
Condo in Orlando
4.81 out of 5 average rating, 343 reviewsLuxury Apt on I-Drive & view of Universal Orlando
Oct 25 – Nov 1
Condo in Orlando
4.87 out of 5 average rating, 167 reviewsBeautiful Lakeview ★ 1 Mile to Disney ★ 1BDR/2BA
Aug 16 – 23
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 Maitland
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 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
1.7K reviews
Destinations to explore
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