
Family-friendly holiday rentals in Estero Island
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Top-rated family-friendly rentals in Estero Island
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Estero Island family-friendly rentals
Family-friendly home rentals with a hot tub

Villa Oasis - Beautiful Pool/SPA Home on Canal
This house was absolutely incredible! From the moment we arrived, everything was spotless—even the baseboards and ceiling fans were immaculate. The home is super spacious, with room to spread out comfortably (even the garage was huge!). The kitchen was fully stocked with everything you could possibly need to cook indoors or grill outside, and there were multiple dining areas both inside and out. The pool and spa were beyond refreshing—clean, well-maintained, and surrounded by plenty of lounge chairs for everyone. We loved the outdoor eating area and the thoughtful extras like pool toys and bikes, which added a fun touch. My boys especially enjoyed exploring near the canal, which made for some great memories. The beds were super comfy, with plenty of extra linens and cozy throw blankets. The neighborhood was peaceful and quiet, and the house is in a perfect, central location. The hosts were amazing: extremely responsive and helpful.

Studio- Olde Naples, 2 blocks to beach Studio unit
Very close to 5th Ave and the beach. Plenty to do between the pool, shuffle board, corn hole, and board games. The bikes and beach chairs were in use daily. Responded to any questions or requests we had. Overall a great experience.

Fun! Boat Rental, Pool, Hot tub, Fish, Near Beach
Maggie's place was perfect for our family of 5 with 3 teenagers. We enjoyed fishing off the dock, swimming in the pool and loved all the birds and lizards in the back yard. There was an issue with the air conditioner and Maggie was responsive with the issue. The house was comfortable and in a great location to visit Sanibel Island and the Everglades. We would definitely stay at Maggie's place again.

Villa "Blue Diamond"
Beautiful villa with all amenities, the pool and the hot tub we will miss, hostess was available to us at all times. In the villa there were folders that were very well sorted with excursions, restaurants and shopping. Sven explained everything to us in the villa and gave us valuable tips. We had a great conversation as he knows the area we are from Germany. We can recommend the villa with a clear conscience and would come back any time. Thank you so much for the wonderful time. Best regards, Boba and Renato

8 Lakes Location 3/2 Gulf Access w/Pool + Hot Tub
This house is spectacular, great view, open floor.pla, great lanai, hot tub, pool. All amenities you need. Looking forward to visiting again

Amazing villa with great water view.
We had a fantastic stay! The house was incredibly well-equipped—there were plenty of essentials like paper towels, toilet paper, and all the little extras that make a stay comfortable and convenient. The pool and hot tub were both in perfect working order and made for a relaxing time day or night. The canal out back was a real highlight—great fishing with a wide variety of fish, including catfish, gar, and more. The house also came with five bicycles available for tenant use, which was a nice bonus, and there were TVs in every room—perfect for unwinding after a long day. The home felt truly luxurious, especially for the price. Jeff was a great host, and everything went smoothly. Highly recommend!

Patricia - with Kayaks, Bikes and Boat Dock
Great Villa! Everything was wonderful! Beautiful view from backyard on canal! Very clean and comfortable! Good location close to shopping! No complaints only good service! Very recommended!!! Thank you for all!!!

2nd Floor Beachfront Condo Sanibel Harbour
We had a fantastic stay at this condo! The place was clean, comfortable, and exactly as described. The location was perfect—close to everything but still quiet and relaxing. Check-in was super easy, and the host was friendly and responsive. We loved having coffee on the lanai each morning and looking for dolphins and manatees. We would definitely stay here again! Taylor family
Family- and pet-friendly home rentals

Sanibel Romantic Getaway
We had a wonderful week at Nancy’s place! It was just right for my husband, me, and our small dog. Location is great and it’s an easy walk to the beach! While small, the apartment has all the necessities. We particularly liked that there is a bike rack and the house is beside a bike path.

Villa Coral with boat dock & waterview- own pool
We spent the month of March at this home and enjoyed the experience. With only solar heat we were afraid we wouldn’t use the pool but it was great and enjoyed lots of floats. We thoroughly enjoyed the outdoor area and beautiful canal views. Everything looked like the pictures. We loved the quiet neighborhood too

Cottage Close to Vanderbilt Beach Heated Pool
The home was amazing with a heated pool, 5 minute drive and 20 minute walk to vanderbilt beach. The kitchen has everything you need and the bedrooms were great.

Best Value In Naples 4 Bdrm Pool Heat Walk Beach
This is our second year in a row staying at Bob’s home. We absolutely love the property. Close to the beach and lots of restaurants and many other things to do. The home is in great shape, very clean and all the amenities you need to enjoy the property! We will definitely book again.

Cozy Cottage Near Vanderbilt Beach
Great location! The place is very clean and the beds are super comfortable. The couch in the living room is very uncomfortable, but everything else was great.

Modern 4 bedroom villa w/ private heated pool
The house is beautiful. It is very clean and had everything we needed for the week. We really enjoyed spending time in the enclosed pool area.

Charming cottage bay area
Very good stay in the house, which was exactly as advertised. Complete, comfortable and clean. Totally recommended.

Modern Townhouse close to beaches
Dan’s place was exactly what we were looking for. Somewhere close to friends, beach, local attractions, and a great place for us to stay. The house was what was described, with plenty of room for the 4 of us… with room to spare.
Family-friendly home rentals with a pool

Sunny Mid Island Beautifully Remodeled Home
The house was beautiful and very clean. The pool was perfect. Even when it was cool and windy at the beach, the pool was warm and protected from the wind. The beds were moderately comfortable. The only issue we had was the shower in the back bedroom bathroom had very little water pressure. The location was great to be able to walk to the beach, and was made easy with the wagon and other beach items that were available. The grill came in very handy as restaurants were a little difficult to come by. It’s only 1.7 miles from Time Square, but sometimes that was an hour drive.

Rare walkout condo on Sanibel beach-Fully Restored
absolutely gorgeous condo with walkout to the beach. it was spacious and clean and he was accommodating in allowing us to get in a little earlier than normal check in. high recommend this place I will defiantly be booking here again!

Villa La Vida
Absolutely beautiful and perfect location sparkling clean they have everything you need fishing poles beach chairs ext I will always use them again and we will be back for sure 120% perfect the pool and views are absolutely breathtaking I recommend this host to everybody thank you

PARADISE SUNSET
A beautiful location, very quiet neighborhood, yet within 1.5 miles of a large supermarket and drugstores. Pictures are very accurate of the home. We loved the outdoor pool area/lanai. There was an issue with the pool filter causing the pool to become too cold for swimming during the last few days, which was unfortunate for us, but that was not the hosts' fault, and they were very responsive, within minutes. The home as a very comfortable layout with several large sitting areas inside, as well as a very large lanai area. Kitchen is well equipped with everything we could need. We did not use the grill, but there was one available. We had an issue with the smoke detectors and, again, a simple text to our hosts brought immediate response and remedy. Alexina and her husband are lovely and very responsive. I would recommend this beautiful spot and we would return on our next trip to Cape Coral.

3 Bed 2 Bath Heated Pool Home in Fantastic Area!
Loved the house was perfect for peaceful vacation and to relax. Very nice neighborhood. Will definitely stay there again for the next vacation.

SeaClusion Oasis
Laura and Michael are wonderful hosts. Communication was excellent! The house is in a great location and the price was on point for the area. It was as described and nicely updated, the pictures don't do it justice. The third bedroom is accessed through the garage or back exterior door so it is a bit separate from the rest of the house and bathroom but it worked well for us. They provide everything you need for a comfortable stay, items for the kitchen, pool, beach, washer-dryer, and a good night's rest. The pool was refreshing and the beach just steps away. The dock on the back bay is a great place to dolphin watch or fish. A short drive or trolley ride to Times Square, shops, grocery and restaurants too! Overall a great stay and would recommend. We all wished we didn't have leave 🙂

Bimini Breeze - saltwater pool, boat dock, canal
We had a fantastic time at this beautiful home! The house was spotless! The view out the back sliding glass door was amazing. Beautiful pool and great canal view. The kids loved the pool and swam for hours everyday. The men in our group enjoyed fishing off the dock. The neighborhood was very quiet but close to everything. There were lots of great tourist destinations within less than an hour drive. The host was quick to answer all questions. There were tons of towels and a nice washer and dryer, which was helpful with so many water activities in the area. The garage housed many beach items, which were so nice to have!

Sanibel Harbour Resort - 137: Stairs to Beach
We recently stayed at the Sanibel Harbor condo with our one year old daughter and her great grandma, and we had the most amazing time! Her uncle also joined us for a fun filled Saturday. We can’t say enough great things about this stay. The immediate access to the water via stairs was a huge plus and one of the main reasons we chose this property. It was absolutely beautiful, especially considering how hard the area was hit just two years ago by Hurricane Ian. The restoration and care put into the property truly show. We’re so grateful for the memories made here!
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- Naples Beach
- Captiva Island
- Lovers Key Beach
- Barefoot beach Bonita Springs,FL
- Clam Pass Park
- Tigertail Beach
- The Club at The Strand
- Worthington Country Club
- Seagate Beach Club
- Panther Run Golf Club
- Delnor-Wiggins Pass State Park
- Englewood Beach
- Bonita National Golf & Country Club
- Morgan Beach
- Heritage Bay Golf & Country Club
- Boca Grande Pass
- Gasparilla Island State Park
- Stump Pass Beach State Park
- LaPlaya Golf Club
- Cypress Woods Golf & Country Club
- The Quarry Golf Club Naples
- Talis Park Golf Club
- Blind Pass Beach
- Sanibel Island Northern Beach