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.

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Top guest favourite

A two-story beach house features a bright blue exterior and large windows, surrounded by palm trees and lush greenery. A wooden staircase leads to the entrance, with a deck visible on the upper level. The sandy area offers a welcoming beach environment.

Home in Captiva

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

4.91 out of 5 average rating, 143 reviews

Guest favourite

Aerial view of a waterfront property featuring a modern single-story house with a red-tiled roof. Surrounding palm trees are visible, and the serene waterway reflects the sunset colors. Lush greenery is present nearby, enhancing the peaceful ambiance of the landscape.

Holiday home in Port Charlotte

Jaw-Dropping Waterfront Sunset Views and Gameroom!

Welcome to SUNSET MANOR! This waterfront property sits on a beautiful and spacious corner lot with all the amenities including a heated pool with a tranquil waterfall feature. The preserve across the way provides the ultimate private oasis. This is one of THE BEST views in all of Charlotte County! The house is located in a beautiful and quiet waterfront community - just a few miles from the beach, Boca Grande, Punta Gorda, Fort Myers, and more. World-class Florida living at your fingertips!

4.9 out of 5 average rating, 101 reviews

Guest favourite

A tranquil pool reflects a colorful sunset with hues of orange and pink in the sky, surrounded by lush greenery. The paved area features decorative stonework, enhancing the serene outdoor setting by the Gulf of Mexico.

Guest house in Englewood

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

4.91 out of 5 average rating, 309 reviews

Top guest favourite

Home in Placida

Seaside Boca (Pool + Sauna + Mini Golf + Spa)

As seen on TV fun for the whole family at this new Airbnb. With its Key West vibes you’ll be sure to have a great time here! Boca Grande is just minutes away, Publix and shopping center are a short bike ride and boats are welcome as the marina is right next door. House is located in the tranquil area of Cape Haze close to Golf courses where you can stroll or bike to you hearts content. We just added a Game Room, a Pool with jacuzzi, Sauna, plus a multi court and Mini Golf (pics jus refreshed)

4.95 out of 5 average rating, 37 reviews

Top guest favourite

The outdoor pool area features a screened enclosure, revealing lush greenery in the surrounding landscape. A comfortable seating area with lounge chairs is present. Colorful towels and glasses are arranged on the edge of the pool, with the still water reflecting the evening light.

Home in Rotonda

Vacation Paradise in Rotonda

This brand-new home with 3 bedrooms and 3 bathrooms is truly designed for comfort and relaxation. The spacious living room, huge kitchen, and big dining room are an open-layout living area. Our outdoor covered grilling area has outdoor furniture a hot tub, and a heated pool. Walking distance to Long Marsh Golf Club, a short drive to 3 more Gulf Clubs. A Playground for the kids and exercise paths are all here. Amazing 7 beaches to choose to visit with very good restaurants close to the area.

4.93 out of 5 average rating, 74 reviews

Top guest favourite

Home in Manasota Key

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Luxury beach house with pool in a charming old-FL beach town, one of FL’s best kept secrets! New kitchen, 2 covered balconies & a walled backyard oasis. Spend sunny days by turquoise waters of the Gulf & host a cookout on the covered patio & pool. Enjoy the sea breeze while sipping your favorite beverage on the covered balcony off the living area. Lounge in style in the patio or go for a swim in the 6’ deep heated pool. You're walking distance to restaurants/bars and 57 seconds to the beach!

4.99 out of 5 average rating, 73 reviews

Guest favourite

A scenic view showcases a private deck featuring a spa and circular seating area, positioned near lush greenery. The serene beach is visible in the background, leading to calm waters under a softly lit sky at sunset, creating a tranquil coastal atmosphere.

Home in Captiva

Beachfront North Captiva | Rooftop Deck | Hot Tub

Stella Maris: North Captiva Island, Florida Sleeps 6 · 3 bedrooms · 4 baths (all en-suite) Direct beachfront — steps from deck to white sand 360° rooftop deck — sunrise over the sound, sunset over the Gulf Private hot tub with ocean views 6-seater golf cart included on car-free island Safety Harbor Club included (pool, tennis); Island Club upgrade (pools, kayaks, bikes, pool bar) Fast Wi-Fi · Cathedral ceilings · Stone fireplace · Gourmet kitchen Met at the ferry with luggage and grocery help

4.96 out of 5 average rating, 49 reviews

Top guest favourite

An aerial view captures a two-story home nestled along a quiet waterway with lush greenery surrounding it. Nearby, other residences and a private dock are visible. The scenic backdrop showcases calm waters merging with a blue sky, highlighting the tranquil atmosphere of the location.

Home in Englewood

Lux Home on Gulf w/Private POOL & 50ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

5.0 out of 5 average rating, 66 reviews

Guest favourite

A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.

Home in Captiva

Beach Getaway + Golf Cart & Club Access

HOST PAYS AIRBNB FEE Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and proximity/ steps to the beach

4.94 out of 5 average rating, 156 reviews

Guest favourite

The charming villa is framed by lush palm trees and vibrant greenery, with a private dock visible at the water's edge. A boat is moored nearby, and the sky is bright with scattered clouds, while the three-story structure exhibits a classic coastal design.

Villa in Boca Grande

Luxury Retreats at Boca Grande - Boca Bay Watch

Watch the yachts cruise by en route to and from Miller's Dockside, while rocking on your private and serene breeze-filled balcony. Boca Bay Watch sleeps 8 and has 3 bedrooms and 3 bathrooms. This charming villa is a quick walk or golf cart ride downtown Boca Grande for shopping and dining. It is a most idyllic and exclusive community. Very walkable area allows for viewing of local palms and birds and exotic wildlife in addition to local attractions.

4.89 out of 5 average rating, 44 reviews

Top guest favourite

A beachfront property is depicted, featuring a two-story structure with a spacious porch. Surrounding landscape includes sand and lush greenery, leading to the waves of the Gulf of Mexico. Sunbathers are seen in the distance, enjoying the beach atmosphere.

Apartment in Englewood

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

4.91 out of 5 average rating, 235 reviews

Top guest favourite

Home in Englewood

Paradise on the Bay

Waterfront pool home just a short drive to Boca Grande with all the amenities that you would expect. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fantastic fishing from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 3 Kayaks and a canoe are available for your enjoyment.

4.99 out of 5 average rating, 127 reviews