![](https://images.contentstack.io/v3/assets/blt00454ccee8f8fe6b/blt16c4083c315d71b6/618a126fc9714c667b4ff7c8/US_Gasparilla_Island_US_Header.jpg)
Holiday rentals with a pool in Gasparilla Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Gasparilla Island
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 Gasparilla Island rentals with a pool
House rentals with a pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-48982603/original/efd1c440-46be-4fa7-93b4-20ffb1ce1096.jpeg?im_w=720)
Home in Cape Coral
4.91 out of 5 average rating, 178 reviewsModern Oasis pool paradise
![](https://a0.muscache.com/im/pictures/miso/Hosting-37874488/original/122ee7f0-0977-4f2d-9671-1eb5bf1495f9.jpeg?im_w=720)
Home in Cape Coral
4.99 out of 5 average rating, 186 reviewsLUX Villa w/ Private Salt Water Pool, Lanai, Canal
![](https://a0.muscache.com/im/pictures/miso/Hosting-43775164/original/520225cd-06b7-496b-a34d-3020292797ac.jpeg?im_w=720)
Home in Rotonda West
4.93 out of 5 average rating, 106 reviewsWaterfront Villa Shellflower with private pool
![](https://a0.muscache.com/im/pictures/3e20152c-8819-401c-b894-63d110267330.jpg?im_w=720)
Home in Cape Coral
4.83 out of 5 average rating, 175 reviewsAmazing Modern Home with Pool and Hot Tub!
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MjAwNTU1OTU%3D/original/0628f5f8-c0b9-4a61-ba1f-9b31710261c9.jpeg?im_w=720)
Home in Cape Coral
4.88 out of 5 average rating, 193 reviewsRecently Renovated Home with Pool in SW Cape Coral
![](https://a0.muscache.com/im/pictures/f367bec6-f4da-4d2e-a6df-c9af1f3ec794.jpg?im_w=720)
Home in Cape Coral
4.98 out of 5 average rating, 122 reviewsVacation in Paradise
![](https://a0.muscache.com/im/pictures/hosting/Hosting-44305278/original/c5e692f0-da9e-4eb4-bcdd-fea4dd3328cb.jpeg?im_w=720)
Home in Port Charlotte
4.95 out of 5 average rating, 44 reviewsAmazing Peace River Views
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-51608443/original/ee74c8b5-f3e7-4103-9949-64f92d98959c.jpeg?im_w=720)
Home in Captiva
5 out of 5 average rating, 42 reviewsMy Sea Shack~ 1 minute to beach, SH Club, G-Cart
Apartment rentals with a pool
![](https://a0.muscache.com/im/pictures/9be30377-d6e7-49d1-a67d-ba13d3d34691.jpg?im_w=720)
Apartment in Englewood
4.95 out of 5 average rating, 104 reviewsSunset Beach
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MTk0NTI0Nw%3D%3D/original/41f2383b-9348-42f8-b253-77f2b805b440.jpeg?im_w=720)
Apartment in Sanibel
4.88 out of 5 average rating, 227 reviewsRare walkout condo on Sanibel beach-Fully Restored
![](https://a0.muscache.com/im/pictures/f0932aff-d256-4bd6-bded-4e0be61e3ee7.jpg?im_w=720)
Apartment in Siesta Key
4.94 out of 5 average rating, 185 reviewsSiesta key getaway!
![](https://a0.muscache.com/im/pictures/01093d81-c904-448b-ac30-17d273b086cc.jpg?im_w=720)
Apartment in Venice
4.82 out of 5 average rating, 233 reviewsUpdated beachy condo - ready for you!
![](https://a0.muscache.com/im/pictures/miso/Hosting-46855928/original/d22132d7-3f78-42cd-8072-52b23d64e4c9.jpeg?im_w=720)
Apartment in Longboat Key
4.97 out of 5 average rating, 157 reviewsDirect Oceanview Condo on Sunny Longboat!
![](https://a0.muscache.com/im/pictures/d45bf55f-b124-499c-a068-1ad07c453ef3.jpg?im_w=720)
Apartment in Siesta Key
4.96 out of 5 average rating, 287 reviewsOn the Beach; Siesta Key SunBum Studio
![](https://a0.muscache.com/im/pictures/miso/Hosting-49437189/original/7bce36cb-fe1c-48d5-9066-735532cad2e0.jpeg?im_w=720)
Apartment in Sarasota
4.96 out of 5 average rating, 131 reviewsLido-Key- Tiny Studio Holiday Cottage-A
![](https://a0.muscache.com/im/pictures/9fced2c3-66f6-41ad-bd01-af51936da532.jpg?im_w=720)
Apartment in Englewood
4.88 out of 5 average rating, 124 reviewsA Beautiful Sunset Awaits - Steps to Beach
Home rentals with a private pool
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-43566842/original/a80e8f77-d310-41ba-aaaf-5fed085e3d69.jpeg?im_w=720)
Home in Cape Coral
4.87 out of 5 average rating, 75 reviewsLuxury Waterfront Home with Pool
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-943012937930428126/original/1c0cd0be-c36c-42d5-bdb3-3906be36266c.png?im_w=720)
Home in Cape Coral
5 out of 5 average rating, 20 reviewsAwesome Location W/boat Dock, Pool, & Kayaks!
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-919412567561885756/original/37230adc-5656-4c55-a838-8da20768a0b2.jpeg?im_w=720)
Home in Cape Coral
5 out of 5 average rating, 6 reviewsBlue Oasis
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-1082477083535379513/original/03218c4d-7ed3-4db2-b809-96f03b29e1ec.jpeg?im_w=720)
Home in Port Charlotte
Serenity Haven: New Pool Home Near Englewood Beach
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-1102046871630869040/original/ec44a138-cfbb-49fe-9a64-edd909e73fd0.jpeg?im_w=720)
Villa in Placida
New Listing! Beach Villa Two Bedroom
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