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Kid-friendly holiday rentals in Winter Haven

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Winter Haven family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Lakeland
4.99 out of 5 average rating, 89 reviews

Sleep and play near downtown

MariaRating, 5 stars4 days ago
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.
Home in Davenport
4.5 out of 5 average rating, 12 reviews

Family house w/free WiFi, near Disney & Champion G

JustinRating, 5 stars13 months ago
The stay was fantastic. We would rent again. Nice neighborhood.
Top guest favourite
Home in Kissimmee
4.92 out of 5 average rating, 133 reviews

Luxury ,Game Room, Private Pool & Spa, Near Disney

AshleyRating, 5 stars1 week ago
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!
Guest favourite
Home in Davenport
4.86 out of 5 average rating, 14 reviews

Modern Legends, Near Disney, kings bed ste

MatthewRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Babson Park
4.93 out of 5 average rating, 29 reviews

Private Getaway with Game Room, Gym, and Deck

WilliamRating, 5 stars1 month ago
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.
Top guest favourite
Home in Lake Wales
5 out of 5 average rating, 8 reviews

Brand New Home By Legoland– Perfect for Families!

KelliRating, 5 stars3 months ago
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!
Superhost
Home in Clermont
4.87 out of 5 average rating, 149 reviews

Disney Pool Villa, Cranberry South,

CharleyRating, 5 stars4 months ago
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.
Guest favourite
Home in Winter Haven
4.9 out of 5 average rating, 118 reviews

3/2 Great Family Home Near Legoland

MatthewRating, 5 stars2 weeks ago
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

Top guest favourite
Flat in Lakeland
4.95 out of 5 average rating, 109 reviews

Hidden Ruby-Apartment with Kitchen and Laundry

DoraRating, 5 stars1 week ago
I really enjoyed my stay. The place was beautiful and perfect. I will definitely book this place again
Guest favourite
Flat
4.88 out of 5 average rating, 160 reviews

Child Friendly Apartment in Kissimmee Near Disney

StephanieRating, 5 stars3 weeks ago
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!
Superhost
Flat in Kissimmee
4.81 out of 5 average rating, 115 reviews

Comfortable Family Disney Orlando Universal

MelissaRating, 5 stars1 week ago
It was very close to Disney and was clean. It was comfortable and we enjoyed it
Guest favourite
Flat in Kissimmee
4.93 out of 5 average rating, 182 reviews

Lovely one bedroom apartment.

NydiaRating, 5 stars1 week ago
Seamless check in and check out Fast responder Definitely would recommend
Guest favourite
Flat in Lakeland
4.91 out of 5 average rating, 264 reviews

Downtown Lakeland - 2 bed/1bath Luxury Apartment

RuthRating, 5 stars2 weeks ago
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.
Guest favourite
Flat in Kissimmee
4.94 out of 5 average rating, 69 reviews

Apartment Close to Disney, Parks and Shopping

GabriellaRating, 5 stars3 days ago
Amazing stay! Amenities were great!! Location was perfect!
Guest favourite
Flat in Winter Haven
4.92 out of 5 average rating, 129 reviews

Quint & Cozy, Confidently Clean Apartment

KieshaRating, 5 stars1 week ago
As always. my stay was perfect. This was not 1st, 2nd 3rd, or 4th, stay. Loved it.
Superhost
Flat in Kissimmee
4.67 out of 5 average rating, 12 reviews

Apartment just 15 min to Disney

EduardaRating, 5 stars2 weeks ago
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

Guest favourite
Apartment in Kissimmee
4.95 out of 5 average rating, 130 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

TessRating, 5 stars1 week ago
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!
Guest favourite
Apartment in Kissimmee
4.89 out of 5 average rating, 122 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

KennyRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Kissimmee
4.79 out of 5 average rating, 202 reviews

Condo near Disney Orlando 3 Bdr

CourtneyRating, 5 stars2 months ago
Great place, super close to Disney and other amenities! Highly recommend!
Guest favourite
Apartment in Kissimmee
4.92 out of 5 average rating, 131 reviews

Caribe Condo- Near Disney & FREE Resort Amenities

HeavenRating, 5 stars3 days ago
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!
Superhost
Apartment in Kissimmee
4.81 out of 5 average rating, 128 reviews

Lovely 3BR 2BA condo, great amenities and location

TakirraRating, 5 stars1 month ago
Great place to stay clean and very welcoming
Guest favourite
Apartment in Kissimmee
4.89 out of 5 average rating, 218 reviews

Marvelous apartment near Disney first floor

ErikaRating, 5 stars1 week ago
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.
Superhost
Apartment in Kissimmee
4.85 out of 5 average rating, 172 reviews

One in a Minion condo your kids will love +450Mbps

MairowinRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Kissimmee
4.92 out of 5 average rating, 209 reviews

Perfect place for your Disney escape

GregoryRating, 5 stars1 month ago
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

Destinations to explore