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Vacation rentals with a pool in Little Gasparilla Island

Find and book unique homes with a pool on Airbnb

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Popular amenities for Little Gasparilla Island rentals with a pool

House rentals with a pool

Guest favorite

Home in Punta Gorda

4.95 out of 5 average rating, 152 reviews

Seasonal vacation rental with Heated pool

CynthiaRating, 5 stars4 days ago
Great place and a lovely stay. Thank you!
Guest favorite

Home in North Port

5 out of 5 average rating, 26 reviews

Charming Saltwater Heated Pool House (North Port)

AnnRating, 5 stars5 months ago
This is a great place to stay! It’s very private and relaxing. It’s perfect for 4 adults (2 couples). The other rooms are perfect for children. The kitchen was fun to prepare meals in for our family. The pool and hot tub were fun for us to relax in after a hot day exploring Florida.
Guest favorite

Home in North Port

5 out of 5 average rating, 30 reviews

New 4-bedroom house with saltwater pool and spa!

OlenkaRating, 5 stars4 weeks ago
I will definitely be staying here again! Beautiful house! Very clean!
Guest favorite

Home in North Port

5 out of 5 average rating, 12 reviews

3bd 2th Solar Heat Pool Large home W/ big yard

JenniferRating, 5 stars3 weeks ago
Great Place to stay. If ever in the area would stay again.
Guest favorite

Home in Cape Coral

5 out of 5 average rating, 13 reviews

Canal Waterfront house-Pool-Fishing and Game Room

NataliRating, 5 stars2 months ago
Perfect the house to spend wonderful days with your family,excellent place,the house we loved,clean,comfortable and with all the necessary things,the hostess left all instructions, we would definitely come back again.
Guest favorite

Home in Rotonda West

4.94 out of 5 average rating, 68 reviews

Luxury Pool & Spa Villa with 2 Master Suites

SandraRating, 5 stars4 months ago
Another wonderful stay at Diane’s villa.Everything anybody can want on a vacation ,lovely villa ,very peaceful location,driving distance to beaches and large choice of restaurants.We had our flight home to UK cancelled due to hurricane Helene but Diane checked in on us all the time and allowed us to rearrange our departure which was such a relief.Not an experience we wish to repeat but look forward to a return visit next spring.
Superhost

Home in Cape Coral

4.69 out of 5 average rating, 102 reviews

The Getaway Place - 6 Bdrm 4 full 2 half 4035 sf

TannerRating, 5 stars6 months ago
We loved this home! It worked well for our family vacation this year. The space was very accommodating and we had everything we needed. Thankful to be able to stay here. We did want to mention that the 6th bedroom did not have a door which was kind of sad for our family who had to sleep there but overall, it worked well for us.
Guest favorite

Home in Cape Coral

4.9 out of 5 average rating, 81 reviews

Tropical Retreat: Pool, Hot Tub, Patio Bliss

MeganRating, 5 stars3 days ago
We really enjoyed our stay here! The kitchen was fully stocked with the essentials. The home was perfect for traveling with a baby and a toddler because it is clutter free and baby-proofed. There are also amenities for a baby such as a pack n play and high chair. The pool had the perfect area for the babies to play. Very private and comfortable home. The hosts are very kind. Highly recommend!

Condo rentals with a pool

Guest favorite

Condo in Englewood

4.95 out of 5 average rating, 109 reviews

Sunset Beach

MichelleRating, 5 stars2 months ago
The location has a perfect beachfront view to enjoy coffee outside in the morning. The area was still recovering from the hurricane but walking on the beach was still enjoyable. All of the amenities and items available for use in the condo left very little to be needed.
Superhost

Condo in Englewood

4.87 out of 5 average rating, 45 reviews

Condo With Heated Pool, Beaches Only Minutes Away

KarenRating, 5 stars7 months ago
I thoroughly enjoyed the ARBNB . It was very clean and I felt like I was right at home . The kitchen was well stocked and the appliances worked perfectly . I loved the washer and dryer! It was close to restaurants and beaches . The location was quiet and close to beaches . Would highly recommend property to anyone traveling. Plus the pool was clean and close to unit !
Superhost

Condo in Englewood

4.78 out of 5 average rating, 111 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

DebbieRating, 5 stars4 months ago
My sister and I stayed for a week and had a wonderful time. The beach was just steps away, and the pool was conveniently located across the road. The condo provided everything we needed for the beach. It was very nice, although the door lock and code could benefit from improved security. Additionally, the ice maker was not clean and had a slimy residue inside. It may need cleaning after each check out other than that it was a great place to stay and would stay again Thanks Debbie & Katie
Superhost

Condo in Osprey

4.89 out of 5 average rating, 9 reviews

Lovely 2 bedroom condo with pool & tennis courts

MarlynRating, 5 stars11 months ago
This is our second year staying in this complex. There are many walking trails that are a short drive, close to several beaches, restaurants and grocery stores.
Guest favorite

Condo in Venice

4.96 out of 5 average rating, 101 reviews

Vintage Villa, Thirty-Five

MarleneRating, 5 stars5 months ago
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!
Guest favorite

Condo in Punta Gorda

4.93 out of 5 average rating, 14 reviews

Fabulous Burnt Store Marina

JillRating, 5 stars2 months ago
If you’re looking for a super quiet, well-appointed place with a top-notch pool area (and friendly building residents to chat with while sunning), this is the place for you. A bit far from the shops, so you’ll need a car to run errands. But if you’re just down for relaxing, this is it!
Guest favorite

Condo in Englewood

5 out of 5 average rating, 8 reviews

Sunset Rendezvous Beach Condo Upper Unit

BeatrizRating, 5 stars6 months ago
The condominium was very nice and the location was great! Pool, beach, boat dock and restaurants all accessible and easy to get to. Place was very clean and peaceful at night. Teens had fun using local trolley to get around key, shops and restaurants. I would definitely stay here again. Michael was a great host!
Guest favorite

Condo in Port Charlotte

4.93 out of 5 average rating, 14 reviews

River View/Screen Lanai/Heated Pool/Fishing Pier

AnnetteRating, 5 stars2 days ago
Beautiful condo with amazing view. The screened in lanai is the perfect spot to relax. The place is beautifully decorated and was very clean. Kitchen and bathrooms are gorgeous. Well equipped kitchen which made cooking easy. Pool looks beautiful and clubhouse has pool table, ping pong, and small workout room. Just be aware that the TV only works with streaming services (no cable, no channels) and if you are not from the USA you can’t sign up for anything. Everyone was super friendly in the complex and it was very quiet. Would not hesitate to stay again.

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