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

Pool house near Hyatt Regency Coconut Point
The house was fabulous and better than the photos! We had family staying at the Hyatt Regency and this was the perfect location to meet up and be close. As a family, (ages 13-47) we spent the entire day at the house and everyone agreed, it was better than the Hyatt resort! There is a Publix grocery store and several many restaurants within an 8 minute drive. Also, I swoon for the hammock between two Pine trees. If we are lucky, we will come back for another stay!

Comfy Cape house 4 beds/2baths/heated pool/Jacuzzi
It felt like home! Beds were so comfortable! Pool was nice! Neighborhood was nice! It was close and convenient to everything.

Lovely pool house 5 minutes from the beach
Had a lovely stay here. Communication with Carmen was fantastic. Decorating in home was tasteful and lovely and we felt right at home.

Spacious Family Home/Heated Pool & Play Area
Miguel and Kleydis home was beautiful and clean and they were very responsive! I thought the house was a little closer to things to do and the beach which was my fault for not doing more research but all and all we had a wonderful week!

Private pool-spa home just blocks from the beach
Our recent stay at this home was simply the easiest and most beautiful vacation I've had. Ted answered our questions so quickly and made check in a breeze. The home is very well stocked for beach fun, a relaxing day be the pool in the backyard, or a restful nap in the quiet home. Just blocks from stores, beach, restaurants and a short drive to the Pier. The neighborhood is so quiet at night allowing us to peacefully relax outdoors. I really felt at home here and we will be using this home again upon our next visit. Thanks for making our vacation great.

Beautiful Home w/ Pool & Spa, Pet Friendly!
Beautiful home in peaceful neighborhood with great location! The home was very clean, had nice amenities, and we felt right at home. Loved the pool and private back yard. Dara was quick to respond to any questions and made the rental a 5 star experience.

Tropical House with Pool
We loved staying at Elle’s house!!! The pool and the park was ideal for my kids. The house was clean and had everything we needed. The area was so peaceful but yet only a few minutes drive to shops and restaurants. We had a fabulous stay and wished we would have stayed longer. Ele was very friendly and helpful. There was a plumbing issue in the bathroom and she came promptly to deal with it. The double beds were a little soft to our taste but other than that we had a great experience. Thank you Ele!

Spacious Canal Oasis with Pool, BBQ & Mini Golf
We had a fantastic week stay on kids Spring Break! Beautiful property, comfortable bedrooms and bathrooms, spacious well equipped kitchen. Amazing pool and hot tub, canal and yard. Mini golf, pool table, foosball table - added tons of fun to our stay. Thank you!
Condo rentals with a pool

Sunny Florida condo!
One of my favorite Airbnb rentals to date. The condo was clean, quiet and had everything we needed/wanted. On top of the space being great, Ken and Becky were amazing hosts. I usually stay in different places each time, but I'll be staying here anytime I'm in or near Fort Myers it's that good. 100% recommend booking with them !!

Condo With Heated Pool, Beaches Only Minutes Away
We were pleasantly surprised by Nicole’s apartment. It was extremely clean, lots of towels, linen, well appointed kitchen and everything else needed to make it like home. We didn’t need to buy or bring anything for the beach because we had beach chairs and an umbrella which were in really great shape. The apartment is within a short driving distance to beaches, stores, restaurants and shop. We had a great time and felt right at home. We highly recommend her place to anyone vacationing in the area.

Lovely 2 bedroom condo with pool & tennis courts
This condo was even cuter in person than it was in the photos. It was super clean, safe, spacious, had a gorgeous screened in balcony that looked out over the pool, and was centrally located really close to groceries, restaurants, multiple beaches, and more. We stayed here as a family of 4 and the kids had their own room and bathroom and we had a master with en suite. I saw another review that said there is a little noise from the busy road outside but you really only notice it if you're trying to sleep with the windows open. We originally booked a hotel that ended up being awful so I found this place last minute and they were able to get us in the very next morning. They let us check in early since we were kind of stranded, and walking in was like a breath of fresh air. Highly recommend this place for 2-4 people!

Siesta Village Short Walk to Beach w heated Pool
This place was fantastic with everything we needed. It was close to everything and a short drive to some of the other local activities. Short walk to multiple beach entrances and a cart, chairs, umbrella, etc. was all available to take to the beach. There’s a local shuttle that takes you all over the island for free and a market around the corner that’s fully stocked with everything you need to cook some meals there. We did the night time LED kayaking and then did the Mangrove Eco Tour with Kayaking SRQ, ask for Kaleb for the mangrove tour, the man knew everything about the area, its history, conservation, and gave some great restaurant and attraction recommendations in the area. Or… just hang out at the beach. We were there during tropical storm Debby and Kathryne communicated with us throughout. Absolute amazing stay… even with a tropical storm! We can’t wait to come back.

Peaceful retreat, pool, hot tub, near Siesta Key!
Absolutely beautiful home close to everything. Privacy was the key and home had everything and more! The most important was the communication and the host nailed it! I will definitely be back!

Siesta Key Beach Front Condo
We loved the condo! My favorite part was the screened in porch with very comfortable seating, view of the ocean, and a table for card games with grandkids. I would like to definitely rent again when we visit that beautiful area in the future.

Cozy Condo With Heated Pool
Perfect stay for my family! It had everything we needed and more. The beach chairs, mats & cooler made our beach days more enjoyable. Washer and dryer worked great and kitchen had everything we needed. We didn’t have time to use the paddleboard but it’s an awesome bonus. We would definitely stay again!

Amazing Condo-1 mile from Bonita Beach
Our family had a wonderful week long stay at Susan’s condo. She supplied everything we needed for great beach days and the pool was clean and warm! It is within walking distance to a bunch of restaurants and ice cream spots. Would definitely recommend to anyone looking for a quiet, yet fun place to stay in Bonita!
Home rentals with a private pool

Luxury Waterfront Home with Pool
Loved this house! Would definitely stay again. It had everything we needed. The owner is friendly and very responsive. The location was great & the neighborhood was nice and quiet.

Blue Oasis - Saltwater Pool, Dock, Dog-Friendly
This house was amazing. The description & pictures sold us but after seeing it in person, the pictures did not do it justice. Everything was very clean & organized. The house had pretty much anything you might need. The local host made sure we even had extra household items to start & was a quick response to any questions we had. We were traveling with our 2 pugs & felt very at home.

Awesome Location W/boat Dock, Pool, & Kayaks!
This was such an amazing stay. The house was fully equipped with absolutely everything you could need. All of the beds were comfy and the main suite was fantastic. The outside area was amazing, pool was large and heated to just the right temperature. The location was really relaxing and we enjoyed fishing. We couldn’t have asked for anything more, a fantastic stay.

New! Poolside Sunset Serenity In South Gulf Cove
Destinations to explore
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Seminole Vacation rentals
- Tampa Vacation rentals
- Central Florida Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Fort Lauderdale Vacation rentals
- Gold Coast Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Siesta Beach
- Captiva Island
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Yacht Club Public Beach
- Lido Key Beach
- Manasota Key Beach
- Clam Pass Park
- Myakka River State Park
- Englewood Beach
- The Club at The Strand
- Lovers Key Beach
- Tara Golf & Country Club
- Lakewood National Golf Club
- Seagate Beach Club
- Cypress Woods Golf & Country Club
- Talis Park Golf Club
- Worthington Country Club
- South Jetty Beach
- Van Wezel Performing Arts Hall
- The Quarry Golf Club Naples
- Esplanade Golf & Country Club of Naples
- Bonita National Golf & Country Club
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes