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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 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
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
Home in Babson Park
4.91 out of 5 average rating, 32 reviews

Private Getaway | Enclosed Deck, Fenced Yard, Gym

AmberRating, 5 starstoday
Great place! Would stay again. Beds were comfortable!
Guest favourite
Home in Lake Wales
4.93 out of 5 average rating, 121 reviews

*This must be THE PLACE FL*

MelissaRating, 5 stars3 days 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
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 favourite
Home in Winter Haven
4.87 out of 5 average rating, 15 reviews

Family Fun: Pool, Arcade Games

ChristinaRating, 5 stars2 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 favourite
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
Home in Winter Haven
4.85 out of 5 average rating, 144 reviews

Florida Getaway near Legoland& Orlando Attractions

Mary JaneRating, 5 stars2 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.

Family-friendly apartment rentals

Top guest favourite
Flat in Lakeland
4.96 out of 5 average rating, 112 reviews

Hidden Ruby-Apartment with Kitchen and Laundry

EmoryRating, 5 stars1 week 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 favourite
Flat
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 favourite
Flat in Kissimmee
4.82 out of 5 average rating, 119 reviews

Comfortable Family Disney Orlando Universal

JoyRating, 5 stars2 days 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 favourite
Flat 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
Guest favourite
Flat 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 place made the trip a unique experience, it's comfortable, cleaning 10/10 and close to all the places of interest. Adriana is a super host, attentive at all times and pending any questions !!!! If you are traveling with family or friends do not hesitate to stay here. 10/10 in all
Superhost
Flat in Lakeland
4.9 out of 5 average rating, 268 reviews

Downtown Lakeland - 2 bed/1bath Luxury Apartment

TonikkaRating, 5 stars1 week ago
If I EVERRRR come back to Lakeland, this would be where I stay! Staying here felt like home & the host was very sweet. The home is just what I needed to relax! Thank you 💕
Guest favourite
Flat in Kissimmee
4.94 out of 5 average rating, 71 reviews

Apartment Close to Disney, Parks and Shopping

MichelleRating, 5 stars1 week 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 favourite
Flat 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.

Family-friendly apartment rentals

Guest favourite
Apartment in Kissimmee
4.95 out of 5 average rating, 131 reviews

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

JulieRating, 5 stars3 days 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 favourite
Apartment in Kissimmee
4.88 out of 5 average rating, 125 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

GiancarloRating, 5 stars6 days ago
Apartment just like the photos, very easy access to the parks, very good communication from the host, very comfortable space that makes you feel at home. Very happy with the choice and grateful to the host for the nice experience!!
Guest favourite
Apartment 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 favourite
Apartment in Kissimmee
4.92 out of 5 average rating, 133 reviews

Chic Condo + Star Wars Room | Pool & Near Disney

LynnRating, 5 stars1 week 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 favourite
Apartment in Kissimmee
4.93 out of 5 average rating, 123 reviews

Cozy single story condo near Disney

AmyRating, 5 stars1 month ago
Highly recommend. Very clean and quiet area. Easy drive to Disney Parks
Guest favourite
Apartment in Kissimmee
4.9 out of 5 average rating, 223 reviews

Marvelous apartment near Disney first floor

JanelleRating, 5 stars3 days ago
The place felt very clean and comfortable. Very responsive and clear instructions. We enjoyed our stay!
Guest favourite
Apartment in Kissimmee
4.86 out of 5 average rating, 173 reviews

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

JacobRating, 5 stars4 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 favourite
Apartment 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 holiday rentals that are kid-friendly in Winter Haven

  • Total rentals

    100 properties

  • Nightly prices starting at

    £30 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