Kid-friendly holiday rentals in Winter Haven

The entire house was incredible! The attention to detail was impeccable to the privacy fencing outside to the art on the walls. The more we explored the house the more we realized that the owners literally thought of everything when designing and furnishings the home. 10 out of 10 would recommend. Can't wait for my next visit

Our family loved staying the Cypress Gardens lake house. The location on lake Eloise was scenic and we loved looking out on the lake from the pool or patio. House was super clean and comfortable. Boat access was great with the multiple docking spots, and renting the pontoon was a great way to spend the day. Family all had fun and would like to come back someday. We also appreciated the history on Cypress Gardens and old florida before Disney changed things up.

Great experience, we visited legoland and the property was right down the street. Great location

The place is stunning, very well maintained, peaceful and yet fun. Love the view, overall loved it all. So much my husband and grandkids are already looking forward to a next trip. Wonderful hostess Andrew was very cordial and on top of anything we needed help with. Very welcoming , cozy and friendly experience. Hospitality beyond expectations. Thank you team Andrew for allowing us to stay at your lovely place!

I thought the place was great, the kids loved the pool in the backyard. This was drivable to Disney which we opted to do for a few days and Jennifer was always so responsive. There was some live music across at the community pool but I didn't think it was overkill and the kids slept right through it. I will rent again.. hopefully soon!

Terry was very accommodating. His property is beautiful and is close to all nearby Orlando attractions. My kid loved the pool and hot tub

Our family stayed here for our summer trip to Legoland. The house was perfect for our family of six with plenty of space! It was super clean and had a beautiful outdoor porch area that our family really enjoyed. The beds were extremely comfortable and we all felt right at home. We especially liked the sound machines in each room! The only “issue” was the driveway was small and with the neighbor’s broken fence leaning onto the property, it makes for a tight squeeze for your vehicle. However, the host was amazing at communicating and made us aware of the fence issue ahead of time, letting us know they have gone through the proper channels to hopefully get the neighbors to repair the fence. Overall, the stay was great and we would definitely stay here again!!

Great stay!!! Was perfect for what I needed. So CLEAN!

This was our 3rd stay since March of 2025. This is our go to place when visiting family in Lakeland. Nice apartment, clean, cozy, and quiet. Location is great as it's close to everything. Downtown Lakeland is one of my favorite places to shop local. Lakeside Village Mall (shops and eateries) is about a 10 minute drive, and Walmart is about 3 minutes away for groceries. We always make sure to eat at the 1916 Irish Pub at Cleveland Heights Golf Course. Fat Jacks (a local diner) on Flordia Ave is right down the road and was our go to place for breakfast. Yaricel is the perfect host.

The pictures just don’t do this amazing place justice! It is so comfy and home like! The hosts are super nice and even when I over slept because I got in late and was so comfortable , they still were super hospitable. I can’t wait to come back . And the coffee was amazing too!

Came here with my partner to visit legoland and the location of the air bnb is perfect and the host is very kind and helpful.

Cai Ling and John’s place was great. It was just as described. It was clean and had what we needed for our short stay. As they stated they only provide limited supplies so if you need additional supplies please bring them. I would definitely stay there again.

My son and I thoroughly enjoyed staying at Jared's place! It looked exactly like the photos, very clean, and included all the basics needs (shampoo, conditioner, body wash, hand soap, laundry detergent, and dishwasher pods). The location was ideal, as our main goal was Legoland but we wanted to explore Orlando's attractions as well. It's also the perfect location for Disney travelers, though we didn't go there on this trip. Jared was an excellent host! Proactive and prompt in communication and appreciative of feedback. When asking my son what I should include he shared, "I had a huge, comfy bed all to myself!" (Referencing the sofa bed.) I would absolutely stay here again and will recommend it to anyone who asks!

Great stay! Lizandra was kind and responsive. We needed more bedding and she brought us exactly what we needed at night in the rain! Really appreciated her thoughtfulness!

I had an amazing time staying here. It had everything as described. Area was quiet and the house was beautiful. The host greeted me upon check in and was super friendly and helpful with all my questions. I definitely would stay here again.

Great home! Felt very private inside. Awesome water pressure.

Brittany went above and beyond and was an amazing host. All of the information we needed was clearly laid out and she was warm and responsive to all questions. The Airbnb itself was also immaculate with everything our family needed. I wish I could give more than five stars.

Hello, I stated here with my husband and three children we loved this apartment from the moment we walked in super clean very modern we just loved it very much, Rafaela was also very responsive and answered all questions! Would stay here again!

The condo was immaculate, clean, large, and very comfortable. Had everything we needed and much more. Place is well taken care of, and I’d definitely recommend and stay again. Definitely 5 stars!

They place was cute and close to get restaurant and entertainment host is responsive

I enjoyed my stay here so much. The apartment was so cute and cozy, super clean and spacious. It is in a gated property so itself safe and overall a great location. If and when I am back in town, I will definitely stay here again.

This was one of my best Airbnb stays in a while. The resort location, amenities, and clubhouse staff were very convenient. The host had very clear instructions and was very communicative. The apartment itself was very spacious. Much larger than I expected. Thanks!

Great location, comfortable and clean - perfect spot to visit Orlando and all it has to offer!! This condo was clean, modern, comfy beds & furniture, efficiently equipped kitchen, etc. We liked this being in a quiet, private community and really enjoyed the pool & clubhouse! Nothing negative to share! This is a great choice!

Surroundings are beautiful and peaceful ! Beds and comfortable !