
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
Get the amount of space that is right for you.
Popular amenities for Little Gasparilla Island rentals with a pool
House rentals with a pool

Spacious 2 Bedroom Home | Near Beach | Heated Pool

Morning Side

Waterfront Key West Style Home, Heated Pool

Family Fun-Relaxing Home w/heated Pool & Game Room

Newer 4bd/2ba Canal Pool House, Hot Tub & Game Rm!

*New Listing* ☀️TheAquaOasis🌴Pool-6 miles to beach

Tropical Bliss | Lush Garden Poolside Retreat

Bali Bliss Villa • Pool • 6 Min Drive to Beach
Condo rentals with a pool

Sunset Beach

One bedroom condo - overlooking harbor!

Bay Breeze @ManasotaKeyCondos

Entire Beachside Condo! Don’t worry Beach Happy!

Vintage Villa, Thirty-Five

Spacious 2BR 2BA Beach Condo for Perfect Vacation

Studio, pool, private beach, boat dock shark teeth

Private Beach, Fishing Dock & Heated Pool Paradise
Other vacation rentals with a pool

Suite Sun

Heated Pool, Cozy 2 Bed-2 Bath House

Boaters Dream, full refund*, heated pool, sleeps 6

Brand new and immaculate!

Luxury Beach Retreat w/ Heated Pool

Luxury Corner

Vacation Home by golf course with Private Pool

Fun in the Sun
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