Holiday rentals with a pool in Estero Bay

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Popular amenities for Estero Bay rentals with a pool

House rentals with a pool

Top guest favourite
Home in Bonita Springs
5 out of 5 average rating, 25 reviews

Private Palm Oasis - Close to Beach

ColleenRating, 5 stars3 weeks ago
Fabulous property in quiet corner of the Bonita Springs neighborhood. Beautifully remodeled home with all the conveniences and attention to details providing lots of extras for your stay. Screen covered pool with jacuzzi and relaxing outdoor living space. We loved the reclining family room sofa! Easy bike or drive to beaches, shops and restaurants. One of the nicest properties we have rented. Does not disappoint.
Top guest favourite
Home in Cape Coral
5 out of 5 average rating, 20 reviews

Backyard Dream-Oasis! - Heated Pool

VivianRating, 5 stars2 weeks ago
We had a wonderful time. Thank you!
Top guest favourite
Home in Cape Coral
4.97 out of 5 average rating, 116 reviews

Boater’s Paradise-Stunning Sunsets! Games Room!

MichelleRating, 5 stars3 weeks ago
Meghan was always responsive from check in to check out. The house was everything we wanted and needed. It was our second time there so we knew what to expect. It was even better than the last visit! The house had everything we needed. All we did was get our groceries and relaxed for the entire week. We’ll definitely be back!
Guest favourite
Home in Naples
4.94 out of 5 average rating, 121 reviews

LUX Oasis~10 min Beach/5th Ave~Custom pool w/shelf

ShannonRating, 5 stars1 month ago
We had a great Mother's Day weekend at Amy's place. The photos are accurate and the home is clean. The pool / patio area has great seating and feels very private with beautiful landscaping. Checking in was easy and good communication. We would stay here again! Thank you for sharing your home!
Top guest favourite
Home in Bonita Springs
4.97 out of 5 average rating, 97 reviews

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

KristieRating, 5 stars2 weeks ago
We had such a wonderful experience at Lana’s beautiful home. The inside and outside was beautiful and clean. My family will definitely stay there again!
Top guest favourite
Home in Bonita Springs
5 out of 5 average rating, 30 reviews

Villa Bonita

ChristianRating, 5 stars4 days ago
My friend and I stayed here over the weekend for a guys golf trip. The house was very clean and had all the amenities needed for the weekend. The highlight being the outdoor area - pool, hot tub, television and grill. We enjoyed our time there and were able to relax over the week end. Stores, restaurants, courses and of course the beach are all nearby. Id recommend this property to others who want stay in the Bonita Springs Naples area.
Top guest favourite
Home in Cape Coral
4.94 out of 5 average rating, 31 reviews

DOG friendly vacation home/3BR/2.5BA/heated pool

PascalRating, 5 stars3 weeks ago
very nice house, great and quiet location. very clean and great amenities. the kids loved the pool and the deck, outside seating is very comfy. we would stay here again, hopefully we can come back soon.
Guest favourite
Home in Naples
4.96 out of 5 average rating, 108 reviews

The Beach Getaway Home only steps from the water!

CindyRating, 5 stars1 month ago
We really enjoyed the pool with the waterfall fountain. The pool temp was perfect. We especially appreciated the child-safe gate separating the house from the pool. The little sunroom with door was great for noisy little early risers. There were plenty of towels provided for the bathrooms and pool/beach. The house was super clean. The beds were very comfortable. It was so nice to have beach chairs and sand toys. The house is in a great location: 1/2 mile walk to the beach, nice and quiet neighborhood, convenient to Whole Foods, ice cream shops. Melissa was very responsive and communicative, a super host!

Apartment rentals with a pool

Guest favourite
Apartment in Bonita Springs
4.94 out of 5 average rating, 17 reviews

Sally’s Seaside Escape – Walk to Beach + Views

HannahRating, 5 stars2 weeks ago
We loved our stay at this beach condo. It was the perfect size, very clean and in a great location. Sally was awesome and the place had ALL the beach necessities, cooler, ice packs, chairs, umbrella and towels. The condo was also very clean.
Guest favourite
Apartment in Bonita Springs
4.92 out of 5 average rating, 25 reviews

Oceanview Oasis on Bonita Beach Bld3 Floor5

BlairRating, 5 stars4 days ago
We had a lovely weekend here. Spent a lot of time on the balcony that was shaded and screened and had an awesome view of the gulf. Plenty of food and shopping very close. Place was clean and comfortable and well-stocked with everything we needed to enjoy florida.
Guest favourite
Apartment in Fort Myers Beach
4.89 out of 5 average rating, 62 reviews

3BR BeachCondo | Gulfside Pool | Hot tub | Sleep 8

VivianaRating, 5 stars1 week ago
The place was perfect for what we needed. We went with my toddlers, a 9 month baby, and my grandmother, and this place was so ADA friendly, had all the items you needed for our baby, and felt safe for our toddlers. The building is still in facade improvements after the hurricane (we went end of May 2025), and the island overall is in reconstruction mode, but the beach was direct access, beautiful sunsets, and just what we needed so a small weekend break.
Guest favourite
Apartment in Sanibel
4.89 out of 5 average rating, 243 reviews

Rare walkout condo on Sanibel beach-Fully Restored

HanyRating, 5 stars1 week ago
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.
Superhost
Apartment in Bonita Springs
4.92 out of 5 average rating, 119 reviews

Bonita Beach and Tennis 1903

DianaRating, 5 stars3 months ago
Everything was as expected, especially concerning construction. The grounds were still greatly in disrepair, but that didn’t bother us. The location to the beach was outstanding, which was the main feature we were looking for. As we don’t rent a car, we had to Uber everywhere we wanted to go. The only walkable restaurants were Doc’s (across the street 👍) and Coconut Jack’s. It was okay. The condo was fully furnished with everything we could possibly need, save for a beach cart which would have been nice. We especially enjoyed the lanai; it has a wonderful view. Communication was excellent and very responsive.
Guest favourite
Apartment in Fort Myers Beach
4.9 out of 5 average rating, 79 reviews

Boutique condo on the bay, short walk to the beach

ChelseaRating, 5 stars3 days ago
It was a great quiet getaway for my friends and I. It is a little bit of a quiet town, but that was perfect for us! If you are looking for a simple, peaceful beach getaway then this is the place for you.
Guest favourite
Apartment in Fort Myers Beach
5 out of 5 average rating, 11 reviews

Waterfront Condo | Huge Pool & Across from Beach

AngelaRating, 5 stars1 month ago
Nice condo. Loved the pool. The beach is directly across the street. Plenty of beach and pool supplies available. Recommend that you rent a car to get to restaurants and grocery store.
Top guest favourite
Apartment in Bonita Springs
4.8 out of 5 average rating, 113 reviews

Oceanview unit. Completely remodeled Pool is open!

RitaRating, 5 stars3 weeks ago
We came for a family graduation so didn't spend a whole lot of time there but did spend all of Sunday relaxing and using the pool which was wonderful to swim or just sit and read a book!

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