Vacation rentals with a pool in Gasparilla Island

Find and book unique homes with a pool on Airbnb

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Popular amenities for Gasparilla Island rentals with a pool

House rentals with a pool

Guest favorite
Home in Bonita Springs
4.93 out of 5 average rating, 141 reviews

Pool house near Hyatt Regency Coconut Point

CarrieRating, 5 stars1 week ago
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!
Guest favorite
Home in Cape Coral
4.85 out of 5 average rating, 92 reviews

Comfy Cape house 4 beds/2baths/heated pool/Jacuzzi

HeatherRating, 5 stars3 weeks ago
It felt like home! Beds were so comfortable! Pool was nice! Neighborhood was nice! It was close and convenient to everything.
Superhost
Home in Venice
4.56 out of 5 average rating, 16 reviews

Lovely pool house 5 minutes from the beach

LindaRating, 5 stars12 months ago
Had a lovely stay here. Communication with Carmen was fantastic. Decorating in home was tasteful and lovely and we felt right at home.
Top guest favorite
Home in Cape Coral
5 out of 5 average rating, 10 reviews

Spacious Family Home/Heated Pool & Play Area

AprilRating, 5 stars3 weeks ago
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!
Top guest favorite
Home in Naples
4.99 out of 5 average rating, 84 reviews

Private pool-spa home just blocks from the beach

AnnaRating, 5 stars1 week ago
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.
Top guest favorite
Home in Naples
4.97 out of 5 average rating, 37 reviews

Beautiful Home w/ Pool & Spa, Pet Friendly!

DianeRating, 5 stars2 weeks ago
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.
Superhost
Home in Cape Coral
4.85 out of 5 average rating, 33 reviews

Tropical House with Pool

LaetitiaRating, 5 stars2 weeks ago
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!
Guest favorite
Home in Cape Coral
4.92 out of 5 average rating, 49 reviews

Spacious Canal Oasis with Pool, BBQ & Mini Golf

EugeniyRating, 5 stars1 week ago
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

Guest favorite
Condo in Fort Myers
4.76 out of 5 average rating, 84 reviews

Sunny Florida condo!

JesseRating, 5 stars2 weeks ago
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 !!
Superhost
Condo in Englewood
4.87 out of 5 average rating, 47 reviews

Condo With Heated Pool, Beaches Only Minutes Away

DanRating, 5 stars3 weeks ago
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.
Guest favorite
Condo in Osprey
4.92 out of 5 average rating, 12 reviews

Lovely 2 bedroom condo with pool & tennis courts

CariRating, 5 stars1 month ago
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!
Guest favorite
Condo in Siesta Key
4.87 out of 5 average rating, 101 reviews

Siesta Village Short Walk to Beach w heated Pool

CoryRating, 5 stars8 months ago
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.
Guest favorite
Condo in Sarasota
4.97 out of 5 average rating, 65 reviews

Peaceful retreat, pool, hot tub, near Siesta Key!

EmmaRating, 5 stars1 week ago
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!
Guest favorite
Condo in Siesta Key
4.94 out of 5 average rating, 105 reviews

Siesta Key Beach Front Condo

LindaRating, 5 stars2 weeks ago
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.
Superhost
Condo in Englewood
4.78 out of 5 average rating, 46 reviews

Cozy Condo With Heated Pool

NatalieRating, 5 stars1 month ago
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!
Guest favorite
Condo in Bonita Springs
4.93 out of 5 average rating, 117 reviews

Amazing Condo-1 mile from Bonita Beach

MarianneRating, 5 stars1 week ago
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

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