
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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Popular amenities for Little Gasparilla Island rentals with a pool
House rentals with a pool

Brandnew Villa - pool & spa at canal south facing
absolutely stunning villa. pictures don't do it justice. lovely peaceful location. the pool is just amazing and the beautiful kitchen was just a pleasure to cook in. Marco was always responsive in anything we needed. we will most definitely be coming back. Thank you for a wonderful 2 weeks

The Harbor House
This vacation was truly amazing. The house was roomy enough for our large family and most importantly, it stayed cooled to our liking. It had everything we needed. There was always something for everyone to do....fishing, swimming, boating, kayaking. No one was ready to leave after our week long stay. I can't say enough great things about Ingrid. So responsive, helpful and accommodating. She truly cares about her guests. Everyone we met on the island was helpful and so friendly, giving us advice and recommendations. I hope that this place is available for many years to come because I will definitely come back. It was that perfect!

Waterfront Villa Shellflower with private pool
Our stay at this Airbnb was absolutely fantastic! The house itself was beautiful, clean, and perfectly located – we truly felt right at home from the moment we arrived. The house has everything you need. The host was super friendly and super communicative. We would happily stay here again in a heartbeat!

Beautiful Floridian Oasis
Tatyana’s place was amazing! Very very comfortable and very spacious. Pool and outdoor area was awesome! Just the overall layout of the house and how nice it was really made us feel comfortable.

Morning Glory - Walking Distance to Surfside Shops
The house was beautiful! Very peaceful and comfy. My family and I really enjoyed our stay.

Villa Sunset Serenade II
Loved our family vacation! Highly recommend staying here! The house was beautiful and the pool/hot tub was a favorite! The beds were also very comfortable! Loved how peaceful the canal was! We can’t wait to visit the area again!! Thank you Sebastian!!

Golden Pond Villa welcomes you!
This house is amazing! The furnishings are stunning, the patio and pool is super comfortable! The gourmet kitchen was well equipped with everything we needed for preparing family meals. Our favorite part was watching the lotus flowers bloom in the tranquil koi pond in the backyard! We can’t wait to return!

Modern Lakefront Villa, Great Pool, Near Beach!
Its amazing house with modern interior beautiful pool and lake view. Few gators in the lake. Venice has amazing beaches and restaurants. Im glad to open this city for our family.
Apartment rentals with a pool

Sunset Beach
We loved our stay at Edmund’s place. The perfect place to stay for beach access right out your front door.. it was so nice to be able to have a bathroom and food/snacks such a short walk from the beach!

One bedroom condo - overlooking harbor!
I came to town to sail, and I could see the sailboat right out the window. Perfect spot for me! Amy's condo had everything I needed and I felt right at home. It was very clean, cute, and cozy. Thank you, Amy!

Bayside Escape-Condo w/ Dock, Pool, and Near Beach
We rented this place to celebrate birthdays and it was perfect . We had everything we needed and just enough space for a family of four. This location is a short distance from a beach , shops , and restaurants. It is also a short drive to other beautiful beaches ! We spent lots of time in the pool that was the perfect temperature. Remote to TV in living room didn't work too well but we didn't spend much time inside as we were only there a few days so it wasn't a problem. Host was responsive and tried to get it fixed immediately. I would highly recommend this place to anyone .

Entire Beachside Condo! Don’t worry Beach Happy!
We stayed in this lovely place last year and will keep returning! It a perfect location if you love a quiet beach side stay. The renovations are beautiful and Nicholas was very responsive to communication. We couldn't have asked for a more perfect stay!

Gulf View 2/1 with Heated Pool, Kayaks and SUP
e had a fantastic stay at this condo on Midnight Pass! The location was absolutely perfect for kayaking, morning paddleboarding, and fishing—it doesn’t get better than this for outdoor lovers. The condo itself was spotless, peaceful, and had a relaxing vibe throughout. The neighbors were all friendly, and Suzanne was an incredible host—super responsive, kind, and helpful with any questions we had. Highly recommend staying here if you’re looking for a quiet, beachy getaway with easy access to the water!

Vintage Villa, Thirty-Five
This is our second year staying here. It was wonderfully peaceful this last weekend, just like last year. The beach is less than two minutes walk from the door. The kitchen had everything we needed in it. Plenty of beach items for use in the closet. The bathroom had more than enough towels and TP. We also used the pullout couch for our children, and they were very comfortable. we hope to book again soon, thank you!

Penthouse Suite in the heart of SW Cape Coral, FL
Fantastically beautiful accommodation. The apartment is furnished with style and love for detail. We would come back.

Stunning Views Penthouse-Waterview King Suite Golf
We loved our stay. The condo has great views and the building has lots to do with shops and restaurants within walking distance and live music (and dancing!) several nights. Regina was friendly and responsive and the kitchen was well-stocked with nearly every appliance/dish you could wish for. They provided plenty of beach chairs, towels, umbrellas and even cooler bags. There were also fishing poles but we didn't try that. The Sanibel beaches are about an hour's drive away which is longer than I had anticipated but not a big deal for us - just good to know. All-in-all a great stay in a beautiful property! I'd go back in a heartbeat!
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- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Public Beach
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Lido Key Beach
- Cortez Beach
- Coquina Beach
- Manasota Key Beach
- Barefoot beach Bonita Springs,FL
- Lovers Key Beach
- Myakka River State Park
- River Strand Golf and Country Club
- South Jetty Beach
- North Jetty Beach
- Marie Selby Botanical Gardens
- Englewood Beach
- Lakewood National Golf Club
- Tara Golf & Country Club
- Gasparilla Island State Park
- Stump Pass Beach State Park
- Boca Grande Pass