
Kid-friendly holiday rentals in Winter Haven
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Top-rated family-friendly rentals in Winter Haven
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
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Popular amenities for Winter Haven family-friendly rentals
Kid-friendly house rentals

Sleep and play near downtown
Amazing stay! Booked this for my daughter’s cheer competition and had an amazing stay! It was only 4 minutes from the convention center. So close to lake Morton where we saw the swans and ducks and Lake Mirror to walk peacefully around. Alex’s place had lots of extras that the kids enjoyed: darts, foosball, games, a big open backyard, and was just a stroll down from lake Hunter where we enjoyed morning coffee. The neighborhood is super cute on a cobblestone road, and the neighbors were very friendly. It’s also only a mile or so from Bonnet Springs Park, which is a must do if you have kids: nature play grounds, water play, tree houses, a children’s museum and more. All in all, a wonderful place.

Family house w/free WiFi, near Disney & Champion G
The stay was fantastic. We would rent again. Nice neighborhood.

Luxury ,Game Room, Private Pool & Spa, Near Disney
We had a great spring break trip here! My boys loved the pool and game room! Well worth the money! Location was great close to food, shopping and Disney! Highly recommend this place for families! The hosts are super helpful and friendly!

Modern Legends, Near Disney, kings bed ste
The home was super clean upon arrival and the space was as advertised. The owner was responsive to any questions we had. I would stay here again.

Private Getaway with Game Room, Gym, and Deck
Thanks to Brian. His place was very accommodating for our family's needs. Would definitely recommend him to anyone staying in the Babson Park area.

Brand New Home By Legoland– Perfect for Families!
We stayed here for a weekend to be close to a music festival. The stay was perfect and house was just as described. I found it relaxing to stay in a house that was so kid friendly. I would recommend the house to anyone traveling with kids. Jadé was a great host!

Disney Pool Villa, Cranberry South,
This house was absolutely amazing and had everything we needed! Our kids had a blast with the heated pool and all the games—it was nonstop fun. The house was spotless and looked exactly like the pictures. We highly recommend it! all the instructions to enter were a breeze. Martin was very responsive and checked in on us. LOVED LOVED LOVED.

3/2 Great Family Home Near Legoland
Home was clean and comfortable. Master bedroom bed was just right. Master bathroom is spacious and clean. A great value and would definitely recommend. I was on a business trip but could imagine this working well for a family visiting local attractions.
Family-friendly apartment rentals

Hidden Ruby-Apartment with Kitchen and Laundry
I really enjoyed my stay. The place was beautiful and perfect. I will definitely book this place again

Child Friendly Apartment in Kissimmee Near Disney
The house is very nice bigger than what you see in the images, it is comfortable spacious it is close to everything, the neighborhood is quiet nice the Super is next door, it is a perfect place, close to the parks, the house is very well equipped, it was really a hit and she was very attentive to answer my concerns. The best place I could have chosen!

Comfortable Family Disney Orlando Universal
It was very close to Disney and was clean. It was comfortable and we enjoyed it

Lovely one bedroom apartment.
Seamless check in and check out Fast responder Definitely would recommend

Downtown Lakeland - 2 bed/1bath Luxury Apartment
Clean, comfortable apartment as described. Host communicated regularly to ensure our stay was going well. Responded immediately when we had some trouble getting in. Nice location. Walkable to lake, coffee shop, and restaurants. Not far from downtown. Would consider booking again.

Apartment Close to Disney, Parks and Shopping
Amazing stay! Amenities were great!! Location was perfect!

Quint & Cozy, Confidently Clean Apartment
As always. my stay was perfect. This was not 1st, 2nd 3rd, or 4th, stay. Loved it.

Apartment just 15 min to Disney
Place was exactly like pictures. Everything is new. There’s no blackout in the bedrooms, if you like a dark place to sleep, this is not it. It bothered me a little in the morning. The host is very responsive and overall we have a great experience.
Family-friendly apartment rentals

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun
Kurt and Elizabeth’s place was exactly how it stated it would be! And it was so close to Disney! Such an easy drive and the water slides/pool area was icing on the cake!

Near Disney/Universal Lovely 2bedroom/2bath Condo
Very easy check-in, easy to find, spacious apartment, clean with all the necessary amenities. Overall, very clean and comfortable beds. I recommend and would stay again.

Condo near Disney Orlando 3 Bdr
Great place, super close to Disney and other amenities! Highly recommend!

Caribe Condo- Near Disney & FREE Resort Amenities
Condo was so pretty, clean and easy to find! Kayla was super responsive, nice and receptive! Looked just like advertised! Will definitely come back here next time i visit the area!

Lovely 3BR 2BA condo, great amenities and location
Great place to stay clean and very welcoming

Marvelous apartment near Disney first floor
My parents, husband, and I stayed at Anderson’s place for a spring break vacation. We were happy the condo was on the first floor and right next to the handicap parking spots since my parents have difficulty walking for a variety of reasons. The unit itself was very nice and we really liked the layout. The beds were not as comfortable as we would have liked, but if we had been walking around at the Disney parks all day like we had when we were all younger, we surely would have been too tired to notice any discomfort from beds. We checked out both pools and the one near the clubhouse was very nice! However, we did not swim in it due to time. Overall, I feel like the place was worth the money spent to stay there.

One in a Minion condo your kids will love +450Mbps
Great place for my family to stay! There were no issues, the pool and water park were right at the back of the condo, which was a plus. The host was very friendly and responded quickly to our questions. I recommend it to everyone.

Perfect place for your Disney escape
Thanks to Maria and Andy for hosting a great 4-week vacation. Everything was as described and everything worked. It was clean. The location is great. The bed was comfortable. It was well stocked for all consumables. Legacy Dunes is a private, well maintained and quiet resort with great facilities. Lots of trees and ample room to walk. Close to everything. Communication was prompt, helpful and friendly. We would definitely stay here again.
Quick stats about holiday rentals that are kid-friendly in Winter Haven
Total rentals
90 properties
Nightly prices starting at
£31 before taxes and fees
Total number of reviews
6.3K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
30 properties have a pool
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- Universal Studios Florida
- Orange County Convention Center
- Old Town Kissimmee
- Universal's Volcano Bay
- Reunion Resort Golf Courses - Palmer & Watson
- Disney's Animal Kingdom Theme Park
- Discovery Cove
- Disney Springs
- SeaWorld Orlando
- Busch Gardens Tampa Bay
- ESPN Wide World of Sports
- Amalie Arena
- Reunion West
- Raymond James Stadium
- Amway Center
- ChampionsGate Golf Club
- Universal Orlando Resort
- Kissimmee Lakefront Park
- Universal's Islands of Adventure
- Epcot
- Ventura Country Club
- Disney's Hollywood Studios
- Curtis Hixon Waterfront Park
- Tampa Theatre