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
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Popular amenities for Gasparilla Island rentals with a pool
House rentals with a pool
Home in Cape Coral
4.99 out of 5 average rating, 174 reviewsLUX Villa w/ Private Salt Water Pool, Lanai, Canal
17–24 Oct
Home in Captiva
4.91 out of 5 average rating, 102 reviewsBlue Laguna - Vacation in paradise!
18–25 Apr
Home in Captiva
4.97 out of 5 average rating, 101 reviewsSteps To Private Beach Captiva Retreat Golfcart
2–9 Apr
Home in Englewood
4.99 out of 5 average rating, 102 reviewsParadise on the Bay
9–16 Dec
Home in Englewood
4.79 out of 5 average rating, 149 reviewsCustom Built Manasota Beach Home with Pool
31 Oct – 7 Nov
Home in Cape Coral
4.97 out of 5 average rating, 242 reviewsDolphin beach house
12–19 Sep
Home in Boca Grande
4.83 out of 5 average rating, 12 reviewsIsland Oasis- Boca Grande Club
16–23 Jan
Home in Englewood
5.0 out of 5 average rating, 15 reviewsVacation Condo- Beach Access!
11–18 Sep
Apartment rentals with a pool
Apartment in Venice
4.82 out of 5 average rating, 219 reviewsUpdated beachy condo - ready for you!
23–30 Jul
Apartment in Venice
4.86 out of 5 average rating, 140 reviewsThe Studio at the Beach 56
28 May – 4 Jun
Apartment in Siesta Key
4.96 out of 5 average rating, 275 reviewsOn the Beach; Siesta Key SunBum Studio
2–9 Dec
Apartment in Englewood
4.89 out of 5 average rating, 115 reviewsA Beautiful Sunset Awaits - Steps to Beach
27 Aug – 3 Sep
Apartment in Sarasota
4.96 out of 5 average rating, 120 reviewsLido-Key- Tiny Studio Holiday Cottage-A
11–18 Dec
Apartment in Sarasota
4.92 out of 5 average rating, 122 reviewsBeachside Siesta Key Cottage steps from the ocean
17–24 Jul
Apartment in Sarasota
4.89 out of 5 average rating, 127 reviewsGateway to Siesta Key 1/2 mile to the Beach!
22–29 Oct
Apartment in Placida
4.96 out of 5 average rating, 51 reviewsBeachfront Island Condo w/ Pool &Ferry Service Inc
18–25 Oct
Home rentals with a private pool
Home in Cape Coral
4.92 out of 5 average rating, 72 reviewsLuxury Waterfront Home with Pool
21–28 Dec
Home in Cape Coral
5.0 out of 5 average rating, 16 reviewsAwesome Location W/boat Dock, Pool, & Kayaks!
4–11 Oct
Home in Cape Coral
5.0 out of 5 average rating, 3 reviewsBlue Oasis
8–15 Nov
Home in Fort Myers Beach
147 Curlew St
3–10 May
Home in Port Charlotte
Serenity Haven: New Pool Home Near Englewood Beach
14–21 Jan
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