Vacation rentals with a pool in Little Gasparilla Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Little 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 Little Gasparilla Island rentals with a pool
House rentals with a pool
Home in Englewood
5.0 out of 5 average rating, 19 reviewsCape Haze Cottage
Dec 3 – 10
Home in Englewood
5.0 out of 5 average rating, 15 reviewsVacation Condo- Beach Access!
Dec 8 – 15
Home in Englewood
5.0 out of 5 average rating, 3 reviewsPet Friendly Pool Home with Large Private Yard
Sep 2 – 9
Home in Rotonda West
5.0 out of 5 average rating, 12 reviewsFairways and Beaches with a Heated Pool
Nov 19 – 26
Home in Rotonda West
4.93 out of 5 average rating, 96 reviewsWaterfront Villa Shellflower with private pool
Sep 27 – Oct 4
Home in Port Charlotte
4.95 out of 5 average rating, 19 reviewsPrivate Pool Lounge & Game Room, 3bedroom/2bath
Oct 25 – Nov 1
Home in North Port
4.94 out of 5 average rating, 17 reviewsEntire Home. 2/bd & 2/bath. Heated Pool.
Jul 23 – 30
Home in Englewood
5.0 out of 5 average rating, 20 reviewsManasota Tree House - steps from the beach & bay
May 8 – 15
Condo rentals with a pool
Condo in Englewood
4.89 out of 5 average rating, 117 reviewsA Beautiful Sunset Awaits - Steps to Beach
Aug 30 – Sep 6
Condo in Venice
4.87 out of 5 average rating, 141 reviewsThe Studio at the Beach 56
Oct 13 – 20
Condo in Siesta Key
4.93 out of 5 average rating, 181 reviewsSiesta key getaway!
Jul 7 – 14
Condo in Venice
4.82 out of 5 average rating, 219 reviewsUpdated beachy condo - ready for you!
Dec 12 – 19
Condo in Siesta Key
4.96 out of 5 average rating, 276 reviewsOn the Beach; Siesta Key SunBum Studio
Mar 4 – 11
Condo in Sarasota
4.96 out of 5 average rating, 121 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Dec 1 – 8
Condo in Sarasota
4.95 out of 5 average rating, 124 reviewsCozy Beach Side 1BD/2BA, Walk to Beach & Pool
Sep 13 – 20
Condo in Siesta Key
4.96 out of 5 average rating, 105 reviewsSiesta Key Condo. Checkout our great rates!
Oct 14 – 21
Home rentals with a private pool
Home in Cape Coral
4.92 out of 5 average rating, 72 reviewsLuxury Waterfront Home with Pool
Oct 5 – 12
Home in Cape Coral
5.0 out of 5 average rating, 16 reviewsAwesome Location W/boat Dock, Pool, & Kayaks!
Dec 25 – Jan 1
Home in Cape Coral
5.0 out of 5 average rating, 4 reviewsBlue Oasis
Aug 11 – 18
Home in Port Charlotte
Serenity Haven: New Pool Home Near Englewood Beach
Jun 4 – 11
Home in Fort Myers Beach
147 Curlew St
May 16 – 23
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