
Holiday rentals with a pool in Estero Island
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Top-rated rentals with a pool in Estero Island
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Popular amenities for Estero Island rentals with a pool
House rentals with a pool

Gorgeous 5 Star POOL/HOT TUB on a Canal
What a great place with a great host. The home was spotless and everything is new. Pool and hot tub were a great way to relax after a long day and they were both temperature/light controlled by a handy mobile app. Jesse was one of the most friendly and responsive hosts that I have ever encountered and even though I was very busy and a little overwhelmed with work this past week. Jesse’s beautiful home was so comfortable and made me feel so right at home that I didn’t mind the busy work schedule knowing I would be going back to such a clean and comfortable home. Stayed over 100 nights in Marriott last year and experienced like this are causing me to rethink how I think about work trip accommodations. Thanks so much Jesse for the excellent experience!

Private Heated Pool and Spa
the house was updated and very accommodating. we felt right at home. the outside amenities had the pool, jacuzzi, and an amazing area to sit outside and relax. beds were very comfortable. Alex had great communication and responded quickly. would not only recommend this house, but would stay here again.

Beautiful Home w/ Pool & Spa, Pet Friendly!
We very much enjoyed our stay at Dara's house. Communication with the host was easy and helpful. The house is in a quiet neighborhood not far from a major road that will lead you to all of the attractions in the Naples area. The house itself is spacious and well-laid out. The kitchen was perfect for those of us who like to cook. New appliances (everything worked) and lots of pots/pans and cooking utensils within easy reach. The bathrooms and bedrooms were a good size and there is an incredible amount of drawer and closet space. TVs everywhere, if you like that. But for us the hallmark was the heated pool and hot tub covered by a screen roof. So relaxing after a day of playing tourist. I hope I get the chance to return one day. This one's a real find!

Tropical House with Pool
My stay was amazing.. This was my first Air bnb and I definitely would recommend. The host was very easy going and proactive with communication. I have no complaints.

Whole cozy house for group of 5
Jose was a wonderful host, responded quickly and the house was beautiful, and clean. And the pool was warm, private and also clean. Just note that the “crib” is a pack and play not an actual crib. We were provided a bassinet on the second morning although our baby was too big for the bassinet.

Private Ultra Modern Home W pool
The home was absolutely beautiful nicest Airbnb I’ve stayed at Andy was a great host I’d recommend this place had a great trip everything about the house from the inside to the pool!

Spacious Canal Oasis with Pool, BBQ & Mini Golf
Beautiful place and spotless! The outdoor area was amazing. We didn't venture out very much because the property had everything we needed to relax. Publix was only 4 mins away to grab groceries. Sanibel was about a half hour as well as ft myers beach. Beds all very comfortable, our teenage son slept on the Murphy bed and said it was great. nice heated pool, fishing from the dock, quiet neighborhood. we took walks and felt very safe. could use a few more things in the kitchen like rubber scraper, pizza cutter, cooking pans for oven, pool towels and kitchen towels. We would definitely recommend this place and would stay here again!

Family Villa w/ private pool and hot tub!
We had an amazing vacation at Caleb’s property! The house was beautiful and we swam in the pool everyday for hours. Close proximity to several restaurants, stores, and the beach
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 !!

Charming Townhouse close to Sanibel and FMB
loved Lisa place! The location was perfect for all our activities, all within 35 minutes! The Villa was very clean and full of useful housewares so it was like being at home. Our dog loved the park 3 miles away and Fort Myers Beach allowed pets on leach. We will definitely use Lisa again, very nice lady!

Sanibel Harbour Resort - 216: Colorful condo
Everything was perfect, the place, the atmosphere, the spacious Apartment, very crean, perfect. I Would return

Beach condo on yachat marina
We loved seeing the dolphins throughout the day. Very clean !! The locals are very friendly. There was plenty of towels , and cleaning supplies. We love staying in that area!

Park Shore Resort Modern Top Floor 2 Bed 2 Bath
Lauren has done up the place very well and having beach towels and beach chairs really helped us. The place is clean and the view from the balcony overlooking the water body is gorgeous. Having a pull out sofa in the living area is an added bonus. The best part is that good eateries and a grocery store are walking distance from the apartment. Lauren is extremely responsive and helped us whenever we needed it. We would certainly like to stay here again if we visit Naples.

Amazing Condo-1 mile from Bonita Beach
Can not say enough about this condo! Everything was perfect and clean. The master bedroom was my favorite. The leather reclining furniture and mounted huge big screen TV was a plus also. The pool was very nice. Loved that everything is so close to get to. Beaches was beautiful. Susan was the best host with all the info and even let us know the place was ready and clean for whenever we wanted to check in. Will be staying here again for sure!! Thank you, Lisa West!

1st Floor, King Bds-Beach Gear, Walk Dining, Shops
This is a great apartment with large bedrooms and comfy beds, a very very well equipped kitchen and a garage full of surprises including a gas grill and beach stuff. Stacey was great from the beginning and was very helpful and immediate with any question. We’ll decently stay again when in the area. Thanks Stacey!

Stunning studio pool deck with balcony
We loved our time at in Fort Myers Beach and this space made it even more enjoyable. Ed was so helpful with everything we needed, highly recommend this spot!
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- Tigertail Beach
- Clam Pass Park
- Talis Park Golf Club
- Panther Run Golf Club
- Tarpon Bay Beach
- Englewood Beach
- Worthington Country Club
- Bonita National Golf & Country Club
- Seagate Beach Club
- Moorings Beach Private Park
- Delnor-Wiggins Pass State Park
- Barefoot beach Bonita Springs,FL
- Golf Club of the Everglades
- Esplanade Golf & Country Club of Naples
- Shadow Wood Country Club
- Del Tura Golf & Country Club
- Stonebridge Country Club
- Lovers Key Beach
- Naples Botanical Gardens
- Cypress Woods Golf & Country Club
- Keewaydin Island Beach
- Mediterra Golf Course
- Hunters Ridge Gold & Country Club
- Residents' Beach