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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 stars4 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 stars1 month 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

SerkanRating, 5 stars3 months ago
Tüm ihtiyaçlar düşünülerek hazırlanmış çok konforlu ve geniş bir evdi. Talihsizliğimiz 48 sene sonra bölgeye kar yağması oldu ,sıcak havuzu kullanamadık maksimum seviyesi bile havuz ısıtmaya yetmedi. Bu arada beş kişilik rezervasyon için dolabı iki şişe su bırakmışlardı sanki o beş şişeye çıkarılabilir☺️
Guest favorite
A bathroom features a colorful shower curtain in vibrant hues of green, orange, and cream, complementing a sleek white vanity with a granite countertop. A cozy bath mat in green adds to the inviting atmosphere. Natural light is seen flowing through a nearby window.
Home in Lake Wales
4.93 out of 5 average rating, 121 reviews

*This must be THE PLACE FL*

MelissaRating, 5 stars1 week ago
The house is adorable & perfectly organized!! Every room was super clean with comfortable & cute furnishings. Appreciated all of the thoughtful touches - like the coffee station & games. Close to a cute brewery & the Bella Cosa wedding venue where we had a wedding to attend.
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 stars5 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 stars3 weeks 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, 120 reviews

3/2 Great Family Home Near Legoland

DianeRating, 5 stars3 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 stars3 weeks 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 stars2 weeks 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, 163 reviews

Child Friendly Apartment in Kissimmee Near Disney

KimberlyRating, 5 stars2 weeks 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
4.82 out of 5 average rating, 119 reviews

Comfortable Family Disney Orlando Universal

JoyRating, 5 stars1 week ago
Stay was amazing. Laura has great communication and went above and beyond to make our stay nice. My family and I will book again.
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 stars3 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 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, 269 reviews

Downtown Lakeland - 2 bed/1bath Luxury Apartment

AtiyahRating, 5 stars3 days ago
It was the perfect space and they communicated well!
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, 71 reviews

Apartment Close to Disney, Parks and Shopping

AstridRating, 5 stars1 week ago
Eine tolle, sehr gemütliche und perfekt ausgestattete Wohnung. Wir hatten eine schöne Zeit und haben uns sehr wohl gefühlt. Vielen Dank, auch für die sehr unkomplizierte Kommunikation.
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, 131 reviews

Quint & Cozy, Confidently Clean Apartment

LisaRating, 5 stars2 weeks 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.
Superhost
A modern two-story townhouse is displayed with a clean grey and orange exterior. Large windows provide ample natural light, while a paved pathway leads to the entrance. The surrounding grass is neatly maintained, contributing to the fresh ambiance of the entryway.
Apartment in Kissimmee
4.71 out of 5 average rating, 14 reviews

Apartment just 15 min to Disney

AnitaRating, 5 stars4 weeks ago
nos encantó la casa, con todo lo necesario para estar cómodos. La cocina esta muy bien equipada. Habia elementos de limpieza para lavavajillas, lavarropas y ducha generosamente. toallas extra. todo 10 puntos. ubicacion: muy cerca de los parques de Disney, no tan cerca de los parques de Universal. muchas gracias.

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, 132 reviews

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

JulieRating, 5 stars1 week ago
This was a great landing spot for our Disney adventure. We loved the fun Mickey & Minnie theme and appreciated the location which was close to WDW and Walmart for breakfast goods and sunscreen. Our host was proactive and responsive qoth communication, and flexible with checkout. We appreciated the easy checkbout process and great directions for checking in. We were excited by the resort amenities like the pool and exercise room when booking, but quickly realized after the first day at WDW that we wouldn't be able to use them. They would've been a nice break from the parks if we had a stay longer than 3 days. The value for the price was great with plenty of room for our family of 3.
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 week ago
Departamento tal cual las fotos, muy fácil acceso a los parques, muy buena comunicación del anfitrión, espacio muy cómodo que te hace sentir como en casa. Muy feliz con la elección y agradecido con el anfitrión por la bonita experiencia!!
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
4.93 out of 5 average rating, 134 reviews

Chic Condo + Star Wars Room | Pool & Near Disney

LynnRating, 5 stars2 weeks 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, 124 reviews

Cozy single story condo near Disney

CindyRating, 5 stars1 month ago
very nice place. clean and had everything we needed for our time there.
Superhost
An outdoor pool area is framed by palm trees, with clear water reflecting the blue sky. A spacious deck surrounds the pool, offering lounge spaces for relaxation. The view includes a serene lake in the background, enhancing the tranquil atmosphere.
Condo in Orlando
4.82 out of 5 average rating, 255 reviews

Orlando best location condo, one mile to Disney

Maximiliano JavierRating, 5 stars1 week ago
Impeccable stay! The apartment is very comfortable and has everything you need. Clean, very well located, beautiful view (lake and pool), free package delivery, and good parking (free). There are shops and restaurants within 100 meters. I definitely recommend it. Thanks, Ricardo!
Guest favorite
Condo in Kissimmee
4.89 out of 5 average rating, 226 reviews

Marvelous apartment near Disney first floor

PaulaRating, 5 stars3 days ago
Great for families or people that need more space and beds. Two bathrooms was a plus as well. Anderson is very communicative and makes sure that you are well taken care of.
Guest favorite
Condo in Kissimmee
4.86 out of 5 average rating, 174 reviews

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

JacobRating, 5 stars1 month 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, 228 reviews

DisneyWorld - 10min!Perfect 3brm Family Condo

A Melinda LeeRating, 5 stars3 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