
Holiday rentals with a pool in Estero Island
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Top-rated rentals with a pool in Estero Island
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Estero Island rentals with a pool
House rentals with a pool

Canal Waterfront house-Pool-Fishing and Game Room
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.

Resort-style living with an enclosed pool
I so enjoyed my coffee at the pool in the mornings. Quiet neighborhood and so close to restaurants and beaches. Easy access to Fort Meyers beach, Naples and an hour or so to Marco Island. Merry and Paul were right on it with any questions we had ❤️

Gorgeous 5 Star POOL/HOT TUB on a Canal
I had family coming into town for my wedding and we booked Jesse’s place. First of all, Jesse was absolutely amazing to work with. No matter the time of day, Jesse was so quick to respond to me when my family needed anything during our stay. The place was beautiful inside and out, the hot tub was an absolute must during this cold weather and heated so quickly. The place was perfectly clean and the home was so welcoming. I would absolutely book with Jesse again!

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.

Spacious Canal Oasis With Private Pool & BBQ Area
We had a great mini vacation with our dogs enjoying the water and pool/spa. The place was very spacious and close to everything we wanted to do. Phong was very responsive and helpful throughout our stay. We would definitely come back.

Clean house + pool + location
We booked another place first and it was disgusting and we reached out to Raiko and he let us check in early and was able to accommodate us in less than an hour. We love this place. it's open, beautiful and clean. can't wait to come back.
Condo rentals with a pool

Sunny Florida condo!
The listing was accurate. The unit was close to a busy road but still quiet. Plenty of food options within close driving distance There was plenty of space to relax when we were back at the condo.

Charming Townhouse close to Sanibel and FMB
The condo was super clean and had all the amenities that made it feel like a home away from home. The location was great for exploring the beach area of Fort Myers. Decor is nice and condo layout convenient. Parking spots are a bit difficult due to their location near the dumpster.

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

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
We love the area the condo is great kitchen needs a little updated pool area needs updated but we would stay there again.

2 King Bd~1st Fl, 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!

Perfectly located Old Naples condo
I truly feel that you cannot get a better physical location to stay in Naples Florida. It is hard to believe this place exists. The development is really cute, especially with the pool. Bill had everything you could possibly need in that place and then some. I never ran out of anything. Everyday was a new discovery as to what was in that condo. City water was great. Also, usually, I install my own shower head when I'm at an Airbnb, but there was no need to with this place which was really nice. Bill is a very nice, responsive, and flexible host.
Home rentals with a private pool

Luxury Waterfront Home with Pool
Loved this house! Would definitely stay again. It had everything we needed. The owner is friendly and very responsive. The location was great & the neighborhood was nice and quiet.

New Listing! Casadesisa
For 8-9 years now for a week in January we’ve been renting a house in the Cape Coral area and this was by far the best place we’ve had for the trip. The bedrooms were spacious and the 3rd bathroom really came in handy. The few questions that I had during our stay were answered in under an hour.

Blue Oasis - Saltwater Pool, Dock, Dog-Friendly
Excellent stay, pool was amazing. Internet was speedy fast

Awesome Location W/boat Dock, Pool, & Kayaks!
Stayed the month of February 2025. The house was beautiful & clean with everything we needed & more. Beautiful pool, screen porch & backyard. Host Josette was wonderful and responded immediately. We so appreciated having all the paper goods, soaps, detergent, trash bags & more provided. We would definitely love to stay at this house again!! 5 star and more.
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