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Kid-friendly vacation rentals in Winter Haven

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Winter Haven kid-friendly rentals

Kid-friendly house rentals

Guest favorite
A collection of board games is displayed on white shelves, featuring titles like 'Sequence' and 'Harry Potter.' A dartboard is mounted on the blue wall, adding a space for interactive entertainment. A closed door is visible in the background.
Home in Lakeland
4.93 out of 5 average rating, 91 reviews

Sleep and play near downtown

MariaRating, 5 stars2 weeks 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.
Top guest favorite
Home in Kissimmee
4.92 out of 5 average rating, 133 reviews

Disney Playhouse, Private Pool & Spa, Near Disney

AshleyRating, 5 stars3 weeks 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!
Superhost
A bright and airy living area features modern furniture in neutral tones. A sleek gray couch rests beside a contemporary coffee table. A spacious kitchen island with seating is visible, along with stylish lighting fixtures hanging from the ceiling.
Home in Davenport
4.8 out of 5 average rating, 15 reviews

Modern Legends, Near Disney, kings bed ste

MatthewRating, 5 stars1 month 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.
Superhost
The open-concept living area features high vaulted ceilings and is flooded with natural light. A comfortable couch and loveseat are arranged around a coffee table, while a large TV sits on a stand. A dining table with seating for six is visible in the background.
Home in Babson Park
4.9 out of 5 average rating, 31 reviews

Private Getaway | Enclosed Deck, Fenced Yard, Gym

AndiRating, 5 stars1 month ago
What a great house! Clean, comfortable and spacious. We had everything we needed. Brian was a great host! Definitely recommend!!!
Superhost
A cozy living area features a plush sofa adorned with decorative pillows. A vintage arcade game cabinet is positioned beside the seating, offering entertainment options. Natural light filters through a window adorned with patterned curtains, complementing the inviting atmosphere of the room.
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 favorite
A vibrant bunk room includes four bunk beds and a cozy seating area with a pink canopy. An arcade game machine offers entertainment options, while a pool area features loungers and colorful striped decor. The bathroom presents a bright shower curtain and inviting tub.
Home in Winter Haven
4.87 out of 5 average rating, 15 reviews

Family Fun: Pool, Arcade Games

ChristinaRating, 5 stars1 week ago
Our family of 6 absolutely LOVED our 3 nights we spent at Cory’s house. We were in Winter Haven to visit Legoland and this house had more than everything we could want/need during our time there. Cory had a stroller we could use in the park and even let us check in early. We LOVED the pool and all the Legos and video games. I will be recommending this listing to any family/friends who are visiting Legoland.
Guest favorite
A well-lit living room features a comfortable gray sofa and a light pink chair. A round coffee table is centered on a soft rug, while a contemporary TV stand holds a flat-screen television. Large windows provide natural light, and a door leads outside.
Home in Winter Haven
4.9 out of 5 average rating, 119 reviews

3/2 Great Family Home Near Legoland

DianeRating, 5 stars2 weeks ago
We absolutely loved staying at Laura‘s house! The house is just right in furnishings, amenities, and decor. Nice and open, everything super clean, a few decorative touches but no clutter. We loved having the yard for our dogs. Check in is easy and simple and Laura is extremely responsive when we had a question or two. We highly recommend this property.🧡
Superhost
An outdoor enclosed patio features a seating area with a cushioned couch and two matching chairs. A wooden coffee table sits in the center, complemented by a lantern. The backdrop includes large glass doors, providing a view into the interior.
Home in Winter Haven
4.85 out of 5 average rating, 144 reviews

Florida Getaway near Legoland& Orlando Attractions

Mary JaneRating, 5 stars1 week ago
Anne Marie was helpful when we were confused as to getting in (after an 12 hour car ride). The house was well equipped. Lovely patio television to watch final four playoffs. I would recommend to others and return myself.

Kid-friendly apartment rentals

Top guest favorite
An entryway features a clean, white wall with a small shelf displaying a decorative wooden elephant and a red jar. A white door with a black handle is visible, providing access to the apartment.
Apartment in Lakeland
4.96 out of 5 average rating, 112 reviews

Hidden Ruby-Apartment with Kitchen and Laundry

EmoryRating, 5 stars6 days ago
The Ruby Gem on Yaricel listing was great l. I really enjoyed my stay. I enjoyed it so much I decided to extend my stay for a couple more days. Yaricel was a great host. She made everything about my stay comfortable, from accommodating my early checkin, to her helpful attentiveness, quick response time and her willingness to assist in helping me properly extend my stay when I was unsure of the process. Overall I had a 5 star stay and I highly recommend Yaricel's listing when looking for a quality place to stay while visiting Lakeland. I look forward to staying again.
Guest favorite
A vibrant pool area features a large water fixture resembling a mushroom, with water cascading from its top. Lush palm trees surround the pool, and sun loungers are positioned around the tranquil blue water, enhancing the outdoor relaxation space.
Apartment in Kissimmee
4.88 out of 5 average rating, 162 reviews

Child Friendly Apartment in Kissimmee Near Disney

KimberlyRating, 5 stars1 week ago
Great place and super nice host, will be booking again in the future!
Guest favorite
An outdoor basketball court features a vibrant blue surface and a metal hoop surrounded by a chain-link fence. In the background, a parking area is visible alongside a multi-story building surrounded by greenery.
Apartment in Kissimmee
4.81 out of 5 average rating, 118 reviews

Comfortable Family Disney Orlando Universal

ChristopherRating, 5 stars1 week ago
Our family had such a great vacation thanks to this amazingly affordable and comfortable condo. Thanks to Laura and her family for letting us stay!
Guest favorite
A well-lit bedroom features a spacious bed with a white quilted cover and decorative pillows. A round mirror is mounted above a side table, complemented by wall art. The room is connected to another area visible through an open door.
Apartment in Kissimmee
4.93 out of 5 average rating, 183 reviews

Lovely one bedroom apartment.

KaylaRating, 5 stars2 weeks ago
Cute and quiet stay. Perfect place for two people. Very peaceful with a beautiful little lake behind property. About 25 minutes to Universal and to Disney World. We will definitely be booking this place again
Superhost
A light-colored sofa is positioned in a cozy living room, complemented by a glass coffee table featuring a mirrored surface. Decorative gold accents are displayed on the table, reflecting the soft lighting and enhancing the modern design of the space.
Apartment in Kissimmee
4.91 out of 5 average rating, 101 reviews

Fabulous Apt 4BD/3BA at Storey Lake (SL47513)

NataliaRating, 5 stars1 month ago
The accommodation made the trip a unique experience, it is comfortable, the cleanliness 10/10 and close to all the places of interest. Adriana is a super host, helpful at all times and attentive to any questions !!!! If you're traveling with family or friends, don't hesitate to stay here. 10/10 in everything
Superhost
A modern living area features a comfortable teal sofa adorned with textured throw pillows in soft hues. A cozy blanket drapes over the sofa, while a stylish tripod lamp stands nearby. Wall art adds a touch of color and personality to the space.
Apartment in Lakeland
4.9 out of 5 average rating, 267 reviews

Downtown Lakeland - 2 bed/1bath Luxury Apartment

SamanthaRating, 5 stars1 week ago
I had a very nice stay. I'm very particular about things and I really don't have complaints. There were a thing or two I brought to Mariana attention and she was very grateful and responsive. Just minor improvement areas . I would definitely stay again. The upstairs people did make a lot of noise all threw the night so if your not a parent and that gets to you might not be a place you can love but we did. I'm 100% Mariana would address it if it was bothering us.
Guest favorite
A clear swimming pool reflects the blue sky, surrounded by a sunny patio area. Lounge chairs, arranged neatly, offer a space for relaxation. Nearby, palm trees and well-maintained landscaping enhance the tranquil setting of the apartment complex.
Apartment in Kissimmee
4.94 out of 5 average rating, 70 reviews

Apartment Close to Disney, Parks and Shopping

MichelleRating, 5 stars5 days ago
Hello! We stayed here as part of our Disney trip, and the apartment was just as described. The couch is comfortable to sleep in. Definitely recommend!
Guest favorite
A serene garden space features a picnic table under a wooden pergola, surrounded by lush greenery and vibrant flowers. A paved path leads through the area, with a soft lawn and climbing plants along the white fence in the background.
Apartment in Winter Haven
4.92 out of 5 average rating, 130 reviews

Quint & Cozy, Confidently Clean Apartment

LisaRating, 5 stars1 week ago
I’ve been to a lot of Airbnb’s and the decor in this one was one of my favorites. Very comfortable bed. Lots of towels, toilet paper and soaps. The location was perfect for me because it’s right by my friend’s house so I was visiting. I went to a couple of different lakes and watch the sunrise. Had a couple of nice meals in Winterhaven would definitely definitely stay here again.

Kid-friendly condo rentals

Guest favorite
A vibrant arcade area features several gaming machines, including a claw machine filled with plush toys, a colorful racing game, and a basketball shooting game. The space is well-lit, inviting guests to enjoy a fun experience.
Condo in Kissimmee
4.95 out of 5 average rating, 130 reviews

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

TessRating, 5 stars3 weeks 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 favorite
A playground area is displayed featuring a colorful play structure with a slide and swings. The sandy surface is surrounded by benches and picnic tables. In the background, green residential buildings are visible, contributing to a family-friendly atmosphere.
Condo in Kissimmee
4.88 out of 5 average rating, 125 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

GiancarloRating, 5 stars1 day ago
The apartment is just as shown in the photos, very easy access to the parks, very good communication from the host, very comfortable space that makes you feel right at home. Very happy with the choice and grateful to the host for the nice experience!!
Guest favorite
A two-story condo building is depicted, featuring a vibrant blue exterior and arched windows. Lush palm trees are visible in front, and a designated accessible parking space is positioned nearby. The scene is set under a partly cloudy sky, contributing to a bright atmosphere.
Condo in Kissimmee
4.79 out of 5 average rating, 202 reviews

Condo near Disney Orlando 3 Bdr

CourtneyRating, 5 stars3 months ago
Great place, super close to Disney and other amenities! Highly recommend!
Guest favorite
A welcoming hallway features stylish wall art with the phrase 'Be Our Guest' illuminated by soft lighting. The entrance leads to a cozy dining area with modern furnishings, creating an inviting atmosphere for guests.
Condo in Kissimmee
4.92 out of 5 average rating, 133 reviews

Chic Condo + Star Wars Room | Pool & Near Disney

LynnRating, 5 stars4 days ago
We had a fantastic stay here and will return! The unit was beautifully decorated, very clean, and the Disney paintings throughout were the perfect touch. While we didn’t find all of the hidden Mickey’s and Minnie’s, we had a lot of fun searching for them! Thank you for sharing this beautiful home with us!
Guest favorite
A beach volleyball court is set in a grassy area, surrounded by palm trees and lush greenery. The court features a sandy playing surface and a blue net, offering an opportunity for outdoor recreation in a tranquil setting.
Condo in Kissimmee
4.93 out of 5 average rating, 123 reviews

Cozy single story condo near Disney

AmyRating, 5 stars4 weeks ago
Highly recommend. Very clean and quiet area. Easy drive to Disney Parks
Guest favorite
Condo in Kissimmee
4.9 out of 5 average rating, 222 reviews

Marvelous apartment near Disney first floor

FrankRating, 5 stars3 days ago
Great stay ! Very beautiful inside clean and the beds were tidy I will definitely visit again
Guest favorite
Condo in Kissimmee
4.86 out of 5 average rating, 173 reviews

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

JacobRating, 5 stars3 weeks ago
Alfonso was an excellent host. He was super responsive and proactive with his communication. The unit was perfect, located very close to all the Disney/Universal attractions. The Clubhouse, Pool and Slides are located 100 yards from the unit was a hit. Right outside of gate neighborhood was everything you needed, Walmart, Starbucks and all the food and shopping you needed. Excellent host and unit
Guest favorite
A spacious living area features a large sectional sofa and armchairs, bathed in natural light from expansive windows. A coffee table stands at the center, complemented by neutral-toned decor. Soft curtains frame the windows, and a calming artwork is displayed on the wall.
Condo in Kissimmee
4.93 out of 5 average rating, 227 reviews

DisneyWorld - 10min!Perfect 3brm Family Condo

A Melinda LeeRating, 5 stars2 months ago
John was extremely helpful host. There were lots of extras that made our stay even better. I would recommend to friends and would stay again.

Quick stats about vacation rentals that are kid-friendly in Winter Haven

  • Total rentals

    100 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    6.6K reviews

  • Family-friendly rentals

    80 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