Holiday 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.

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Guest favourite

Home in Placida

5 out of 5 average rating, 28 reviews

Coconut Paradise POOL! Little Gasparilla Island

Hurricane Updates: house is 100% great perfect and ready for Rental!!! Beach is beautiful! Relax with the whole family at this peaceful place to stay on Little Gasparilla Island! Newer Pool Home! Fast STARLINK Internet!! Heated pool/Hot tub. Private beach access and dock access. Boat Access only. Take the private water taxi across the bay to a true island paradise. Or bring your own boat! Boats must be 24’ of less. Over 50 coconut palms. Pool table, kayaks, house fully stocked!!!

Superhost

Guest house in Englewood

4.91 out of 5 average rating, 249 reviews

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.

Guest favourite

Home in Captiva

4.97 out of 5 average rating, 114 reviews

The Pearl Beach House, North Captiva Island,FL

This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs

Guest favourite

Home in Placida

4.89 out of 5 average rating, 18 reviews

AMAZING Cape Haze Location -community kayak launch

Ready for warm sunshine, tropical breezes and lush landscaping? Spaniard's Retreat is the ideal location for your get away. This home is set in the charming Old Florida neighborhood of Cape Haze. Old banyan and pin-oak trees line the picturesque streets where homes are spaciously placed. Upon entering you will be greeted by the panoramic sliding doors overlooking the heated pool and spa. This truly feels like a private oasis. 3 bedrooms and 2.5 baths offer generous accommodations.

Guest favourite

Home in Placida

5 out of 5 average rating, 31 reviews

Canal home with heated pool, close to everything!

We survived Helene and Milton! We are ready for your stay. Salt Water Canal, pool, clean, serene!! Situated nicely near beaches, golf, bike paths, lovely kayaking, boating, restaurants. Come enjoy our home. Relax in our clean and comfortable home. Close to everything! Amenities pictured in the photos section are available at no extra charge, ask for availability. Pool has the option to be heated, but requires an additional charge per day. Our house is your house!

Guest favourite

Villa in Englewood

4.93 out of 5 average rating, 107 reviews

Casa Blu: Serene Pool Villa, Minutes to Beach

Welcome to Casa Blu, your cozy retreat in Florida's sun-kissed paradise. Close to restaurants, parks, and beaches, and Old Englewood. Just 7 miles to Englewood Beach. The stresses of daily life melts away with its single-floor layout, comfy bedrooms with private baths await. Enjoy fast WiFi, Smart TVs, and a fully equipped kitchen. Unwind on the screened lanai or take a dip in the private saltwater pool. Everything's covered, from beach gear to a pack 'n play.

Guest favourite

Home in Placida

4.96 out of 5 average rating, 112 reviews

My Little House with direct, quick access!

******2 King beds, 1 queen now. My Little house is fine, minus beautiful trees. I was unable to respond to inquiries during and after hurricane for almost a month. AirBnB penalized me for a poor response rate during that time. I've always had 100% evidently, I could've prevented the hurricane. It's 100% their fault, matter of fact, I made sure my guests were refunded before it hit. Questions? Feel free to ask. ***** I replaced the full size bed with a queen

Guest favourite

Home in Englewood

4.94 out of 5 average rating, 116 reviews

Island Home, Casita, Saltwater Heated Pool, Beach

With a short stroll to the warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

Guest favourite

Home in Rotonda West

4.94 out of 5 average rating, 108 reviews

Waterfront Villa Shellflower with private pool

Villa Shellflower is located in Rotonda West on a large and quiet property. Right next to the property is the Rontonda River, a wide freshwater canal. The 1564-square-foot house has been furnished with great attention to detail. The large saltwater pool, the southwest-facing sun deck, as well as the cozy dining area provide the perfect holiday feeling. The next dream beach is only 20 minutes away by car.

Guest favourite

Home in Englewood

4.86 out of 5 average rating, 102 reviews

Lemon Bay Luxury 6 BR Villa with Pool&Tennis Court

This beautiful house is located at the Lemon Bay and close to the Manasota Beach. The beach is just a 0.6 mile walk or 0.8 drive away. The property offers a 1/2 acre lot. This house offers, with a 34x12 feet swimming pool and own tennis court, a completely new rental experience. You will find the barbecue area outside of the pool area. The charging of EV is not allowed and an extra fee will be charged.

Guest favourite

Home in Englewood

4.99 out of 5 average rating, 108 reviews

Paradise on the Bay

Waterfront pool home with all the amenities. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fish from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 2 Kayaks and 1 pebble boat is available for your enjoyment.

Guest favourite

Rental unit in Englewood

4.94 out of 5 average rating, 412 reviews

BEACH FRONT Unit w/Pool Sandy Toes #3

With a heavy heart we ask you not to book this unit. We unfortunately lost it all during the hurricane Milton. If you already have a booking in place at Sandy Toes we are working on canceling your stays with a full refund. If you need immediate assistance for a refund please contact Airbnb directly. Thank you, Louise