Vacation 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.
Vacation rentals for every style
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Popular amenities for Gasparilla Island rentals with a pool
House rentals with a pool
Home in Captiva
4.97 out of 5 average rating, 101 reviewsSteps To Private Beach Captiva Retreat Golfcart
Nov 27 – Dec 4
Home in Cape Coral
4.99 out of 5 average rating, 175 reviewsLUX Villa w/ Private Salt Water Pool, Lanai, Canal
Sep 9 – 16
Home in Cape Coral
4.91 out of 5 average rating, 159 reviewsModern Oasis pool paradise
Sep 12 – 19
Home in Cape Coral
4.83 out of 5 average rating, 168 reviewsAmazing Modern Home with Pool and Hot Tub!
Oct 29 – Nov 5
Home in Captiva
4.91 out of 5 average rating, 102 reviewsBlue Laguna - Vacation in paradise!
Mar 4 – 11
Home in Englewood
4.99 out of 5 average rating, 102 reviewsParadise on the Bay
Dec 9 – 16
Home in Cape Coral
4.97 out of 5 average rating, 242 reviewsDolphin beach house
Sep 12 – 19
Home in Venice
4.85 out of 5 average rating, 136 reviewsGetaway Relax Home/Beaches 5-10minutes/Heated Pool
Jul 5 – 12
Condo rentals with a pool
Condo in Englewood
4.89 out of 5 average rating, 115 reviewsA Beautiful Sunset Awaits - Steps to Beach
Nov 18 – 25
Condo in Siesta Key
4.87 out of 5 average rating, 209 reviewsSiesta Key Beach Community!
Jun 11 – 18
Condo in Venice
4.82 out of 5 average rating, 219 reviewsUpdated beachy condo - ready for you!
Dec 12 – 19
Condo in Sarasota
4.8 out of 5 average rating, 199 reviewsNear beach. Pool view. King bed. Daily rentals
Jan 9 – 16
Condo in Venice
4.86 out of 5 average rating, 140 reviewsThe Studio at the Beach 56
Jan 3 – 10
Condo in Siesta Key
4.96 out of 5 average rating, 275 reviewsOn the Beach; Siesta Key SunBum Studio
Mar 9 – 16
Condo in Sarasota
4.96 out of 5 average rating, 120 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Dec 11 – 18
Condo in Sarasota
4.92 out of 5 average rating, 122 reviewsBeachside Siesta Key Cottage steps from the ocean
Jul 16 – 23
Home rentals with a private pool
Home in Cape Coral
4.92 out of 5 average rating, 72 reviewsLuxury Waterfront Home with Pool
Dec 21 – 28
Home in Cape Coral
5.0 out of 5 average rating, 16 reviewsAwesome Location W/boat Dock, Pool, & Kayaks!
Nov 29 – Dec 6
Home in Cape Coral
5.0 out of 5 average rating, 3 reviewsBlue Oasis
Jan 14 – 21
Home in Fort Myers Beach
147 Curlew St
May 15 – 22
Home in Bonita Springs
New place to stayCoastal Waterfront Home W/pool-Tiki-Dock
Oct 1 – 8
Home in Port Charlotte
Serenity Haven: New Pool Home Near Englewood Beach
Jan 15 – 22
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