
Vacation rentals with a pool in Gasparilla Island
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Top-rated rentals with a pool in Gasparilla Island
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Popular amenities for Gasparilla Island rentals with a pool
House rentals with a pool

3/2 Pool Home - Paradise Found!
We had the best time at Brandon’s place! It was one of the best vacations we’ve ever had! We love your home and we will definitely be back!!!

Canal home with heated pool, close to everything!
This is our fourth year in a row. We really like the location. Dave and Mary are responsive to issues that arise.

Brandnew Villa - pool & spa at canal south facing
Very happy with stay/house/amenities/pool/spa. Newer construction with tall ceilings, beautiful appointments, bathrooms, fixtures and appliances. Kitchen provided with every imaginable item needed to cook and entertain. Salt water pool and spa were wonderful and overlook canal intersection. Lovely step down from pool to wrap-around deck overlooking canal. Easily accommodated larger family gathering for dinner/swimming. Certainly one of the nicest homes we've visited in Florida. Highly recommended.

Waterfront Cape Coral Oasis+ Heated Pool | Kayaks
The house is a true gem! Beautiful comfortable and it has everything you need. Super family-friendly, everything has been thought to make you feel at home. The pool is beautiful and the summer kitchen is amazing. On top of that Romy goes above and beyond to make sure you have a good time and he’s super responsive. We are very happy we picked this house and we will come back!

Backyard Dream-Oasis! - Heated Pool
We had a wonderful time. Thank you!

Pelican Paradise - Villa Near SW Florida Beaches
Amazing place, felt super comfortable and spacey, loved the lights for the pool! Host was super responsive, and easy to talk to. The bath tub is great for a full soak bath and the window in the kitchen opens up to the pool to let in the cool breeze which was very relaxing when making breakfast in the morning. Overall the place was amazing and easy to get too, it was a super comfortable and relaxing experience.

Englewood Cottage with Pool, Hot Tub, and Fire Pit
As a Floridian who travels frequently and has been in a lot of rentals across the state, I was very impressed with Maria's place. The house was welcoming from the second you walk in. Maria has beautifully decorated every room, very unique Floridaesque pieces, down to the hand towels. Although it was just my daughter and me, I imagine this would be plenty of space for a bigger family. The backyard is amazing; I loved walking around and looking at the landscape. Even though there is a busy road nearby, it felt very secluded. Even though we ended up not bringing our dog, we enjoyed feeding our fish friends every day. There are several restaurants in the area to choose from, for breakfast/lunch/dinner. Nice central location, we took day trips to Sanibel and Boca Grande to ride our bikes, visited the Edison/Ford estate in Ft Myers. It was nice to relax in the pool/hot tub after returning "home" at the end of the day. I would definitely recommend this oasis to anyone looking for a rental.

Close to Cape Harbour western pool and dock, golf
We enjoyed our stay at Michael’s home. The space is clean, new and modern. The home was easy to find and the lock box was easy to use. Beds are comfortable, kitchen has all things needed to grill or cook in, closets have extra towels, pillows and bedding. There was also a variety of items if you have babies/toddlers. If you plan to take day trips to the beach, there are beach towels, beach chairs, beach umbrella and a small cooler. There are also bikes in the garage. Grocery stores and restaurants close by. The pool and outdoor space are so comfy, we loved eating outside and watching NBA and NHL playoffs on the patio TV. Oh, and the TVs all had Xfinity boxes to watch live TV! Also enjoyed having morning coffee on the back patio and taking in the serenity of the canal. I would recommend this home if you are planning a stay in Cape Coral!!
Condo rentals with a pool

Rare walkout condo on Sanibel beach-Fully Restored
This apartment was lovely and spotless. My family and I had a wonderful and relaxing time. The condo is very private and quiet. The beach is very close even though we got rough seas but weather was nice. Highly recommend this place.

Entire Beachside Condo! Don’t worry Beach Happy!
This is the third time we’ve stayed at this location and it does not disappoint! The place has been renovated and looks great! The host is clear and we had no issues getting into the condo. I used the laundry room and that was straight forward. The location is so close to the beach. We enjoyed our time and plan to come back!

South Seas Resort Beach Villa 🌴 On The Beach !
We had an amazing stay at this condo for our honeymoon. It was the perfect place to relax together and just enjoy the beach! The condo was extremely nice and it was great to have an umbrella and chairs available to use! Elizabeth was very helpful and had so much information for us and recommendations which was so helpful as first time visitors! The area was beautiful and the pool was also very nice! We cannot wait to come back to Sanibel/Captiva!

EBT 206C Exceptional Panoramic Gulf Views +2 Bikes
Caihlin was a fantastic host. Very responsive to our questions/concerns. The place was just as beautiful as the pictures showed and we enjoyed everything about it. There were plenty of beach items to use, so we didn't need to purchase anything to enjoy the beach. There were plenty of games to play, books to read and even a drawer full of extra batteries for the TV remote if needed. We even had access to their 2 bikes and took an enjoyable morning bike ride into Fort Myers beach. You will not be disappointed at all with your stay.

On the Beach; Siesta Key SunBum Studio
This is our 5th time staying here, and the place and location speak for itself. The one thing that takes this place over the top in our opinion is the amazing and friendly hosts, Honestly they have treated us like family and made sure our stay has been amazing and safe. We were there for hurricane Helene and they made sure we were taken care of the whole time. I can’t thank them enough, including Vince who is always on top of everything. Thank you from the bottom of my heart.

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!

2nd Floor Beachfront Condo Sanibel Harbour
The place was exactly as described—clean, comfortable, and well-equipped with everything we needed. The check-in process was smooth. The location was peaceful, perfect for relaxing. We especially enjoyed being right on the water for the beautiful sunsets.

Anchor house +6 min. from Siesta Beach+heated pool
If you are looking for a place in Sarasota with everything you need closed to you like restaurants, dinner, food shopping etc at just minutes from siesta key then this is the place. Very clean and definitely what you see in pictures is what you getting. I stay here with m wife and two kids, we are very happy with pick this place, will definitely book again.
Home rentals with a private pool

New! Beautiful Pool Home Near Siesta Key Beach
It was a short stay for us, but it was exactly what we needed! The house was fully stocked with necessities. Instructions were very clear, not overwhelming. The neighborhood is nice, very close to supermarkets, shopping, restaurants, coffe shops, beach, and local areas whether you want a casual night out or a party night out! Great location😉

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!
As described. Paradise found. The location was perfect. Very close and easy access to the Caloosahatchee River. We rented a pontoon boat for a couple days from the Patriot boat rentals company in Cape Coral. Jim was extremely helpful and got use a great deal. The home was beautiful with plenty of room for 5 adults. The swimming pool was perfect to relax in after a day on the water. If you like to bbq there was a gas grill and a smoker to use. The best beaches in the area were near by. The neighborhood was safe and quiet. We stayed 5 days at this little bit of paradise and would highly recommend this location to friends. Perfect is how I would describe it.

New! Poolside Sunset Serenity In South Gulf Cove

Comfy Home W/ Heated Pool Near Siesta Key Beach
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- Siesta Beach
- Captiva Island
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Lido Key Beach
- Manasota Key Beach
- Clam Pass Park
- Lovers Key Beach
- Barefoot beach Bonita Springs,FL
- Myakka River State Park
- Worthington Country Club
- The Club at The Strand
- South Jetty Beach
- Seagate Beach Club
- Marie Selby Botanical Gardens
- North Jetty Beach
- Delnor-Wiggins Pass State Park
- The Quarry Golf Club Naples
- Bonita National Golf & Country Club
- Van Wezel Performing Arts Hall
- LaPlaya Golf Club
- Cypress Woods Golf & Country Club
- Talis Park Golf Club