Kid-friendly holiday rentals in Windsor Hills, Four Corners

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Windsor Hills, Four Corners family-friendly rentals

Kid-friendly house rentals

Superhost
Home in Kissimmee
4.96 out of 5 average rating, 158 reviews

4 bedroom, south facing pool 3 miles to Disney

JohannRating, 5 stars5 days ago
We spent two great weeks at Alex's place, a family of six. The house was very nice and clean, the kitchen was well equipped and the beds were really comfortable. We used the porch and the pool a lot as we loved to be outside in the warmth. Communication with Alex was smooth and he responded quickly. We highly recommend and would love to stay there again.
Superhost
Home in Kissimmee
5 out of 5 average rating, 19 reviews

A Galaxy’s Edge Experience Awaits! 5 Min to Disney

StephenRating, 5 stars1 month ago
Great stay - thank you!!! Super close to the parks and the house was in great shape, very clean and everyone enjoyed the theming! Would definitely look to book here again and recommend =)
Superhost
Home in Kissimmee
4.97 out of 5 average rating, 128 reviews

Mins to Disney NO Airbnb Fees- Close to everything

StephanieRating, 5 stars2 weeks ago
We had such a great time staying at Randy’s place for a short family vacation to Disney! We had 4 adults and 2 toddlers and the space was PERFECT. Each of our girls had their own room and there were 2 pack-n-plays available for use. There were plenty of towels for using the plunge pool out back (which was pretty warm!) as well as showering. The kitchen had all of the things we needed to make dinner for 1 night and breakfasts on the go. Best of all, Disney was a pretty quick drive, as well as Publix and other stores we needed during our trip. GREAT value for the money for a small group! Randy was super nice and provided very helpful information. We would definitely stay again!
Superhost
Home in Kissimmee
5 out of 5 average rating, 18 reviews

Luxury 6 Bedroom Pool Home in Windsor Hills

ElizabethRating, 5 stars2 weeks ago
As an ex owner of a rental property in Florida I am fussy about where I stay. We travelled as a party of 13 and Steven’s place was superb for us. The house is clean, plenty of space, ideally suited for restaurants, things to do etc. We had two minor issues which we dealt with efficiently. I highly recommend Steven’s place.
Superhost
Home in Kissimmee
4.93 out of 5 average rating, 75 reviews

Ultimate Adventure Villa Top Rated 5 Star Disney m

JoeyRating, 5 stars6 days ago
My family and I had an amazing time staying here. Everything was just as the pictures show. I had a minor concern that I just wanted to bring attention to the hosts (nothing that needed immediate repair) as squirrels has made holes in several spots on the back patio lanai and were making their way in and within a day or 2 there was a repair guy at the house to replace the damaged screens. That was unexpected and great job being proactive to repair the screen for not only us, but for future guests to enjoy that awesome pool/patio area in the future. My kids LOVED the arcade, and the movie theater, but most importantly they loved the pool. Eddy was always super quick to respond and very helpful. I would definitely stay here again. We loved our stay.
Superhost
Home in Kissimmee
4.88 out of 5 average rating, 105 reviews

Disney Escape at Windsor Hills

DorisRating, 5 stars2 weeks ago
Thank you so much for an amazing stay! The place was super clean, cozy, and just like the photos. We especially loved the pool — it was perfect for relaxing and enjoying the peaceful atmosphere. Everything was calm and beautiful, and the communication with the host was great. We had a fantastic time and would definitely love to come back!
Superhost
Home in Kissimmee
4.96 out of 5 average rating, 56 reviews

Home mins to Disney, pool, arcade, waterslides

GhislaineRating, 5 stars1 week ago
Tim and Angie, Airbnb was wonderful and very comforting. The kids and I had a great time! My daughter absolutely loved the Stitch-themed room, and both kids really enjoyed the mini water area. We definitely plan to come back. Tim and Angie were very responsive and accommodating. You absolutely deserve a five-star rating!
Superhost
Home in Kissimmee
4.85 out of 5 average rating, 13 reviews

Themed Luxury 6BR Getaway with Resort Amenities Pr

StephanieRating, 5 stars2 months ago
It was a beautiful experience! The place was the perfect spot for a weekend get away. The only complaint was the bed for some of the rooms were a bit uncomfortable. I believe because they were air mattress. But other than that! This place is exactly how it shows on the pictures.

Family-friendly apartment rentals

Superhost
Flat in Kissimmee
4.82 out of 5 average rating, 115 reviews

1-105 Pool Side, Minutes from Disney, gated Resort

VivianRating, 5 stars1 month ago
Everything was great and beautiful. We enjoyed our stay and can’t wait to book again. ;)
Superhost
Flat in Kissimmee
4.64 out of 5 average rating, 111 reviews

Cozy Condo - 2 Miles from Disney portal

CamilleRating, 5 stars8 months ago
This stay was great! We had trouble with the internet and they fixed it right away. The only downside was that the splash pad area wasn’t working and we were told that it would be but we are aware that isn’t the Airbnb’s fault. That is out of their control.
Guest favourite
Flat in Kissimmee
4.89 out of 5 average rating, 45 reviews

Beautiful Condo near Disney

RachelRating, 5 stars2 months ago
This was the perfect place to stay for our first time in Florida. Clean cozy, lots of amenities and definitely worth the price! Centrally located so it wasn't too far away from food and shopping!!
Top guest favourite
Flat in Kissimmee
4.95 out of 5 average rating, 57 reviews

Luxury Lake View Condo Near Disney

EugeneRating, 5 stars3 weeks ago
It’s a perfect place to stay during the Disney visit. 10 - 15 min drive to Disney parks. Large 3 bedroom property in a modern complex. Very clean. The host was very responsive. Kids enjoyed the pool and water park.
Top guest favourite
Flat in Kissimmee
4.95 out of 5 average rating, 107 reviews

Oceanic Oasis Near Disney

IsobelRating, 5 stars3 days ago
We really enjoyed our stay. Fantastic place and location! Jared was really helpful and a great host😊
Guest favourite
Flat in Kissimmee
4.89 out of 5 average rating, 368 reviews

Superb Townhouse Newly Renovated 1 mile to Disney

HunterRating, 5 stars1 week ago
Great and safe place to stay! Only 12-16 minutes from every park and Disney Springs!
Guest favourite
Flat in Kissimmee
4.77 out of 5 average rating, 219 reviews

King Bed First Floor Family Condo Disney Universal

MariahRating, 5 stars1 week ago
The accommodations are exactly as pictured and was in a perfect location with so many places around. Also, you couldn't ask for a more considerate, friendly and informative host. The recommendations and instructions given were extremely helpful.
Superhost
Flat in Kissimmee
4.75 out of 5 average rating, 316 reviews

2BR Nice/Convenient Resort Condo 3 Miles to Disney

ShamirahRating, 5 stars1 month ago
Beautiful condo just like the photos! Great host! Easy check in. Very close to Disney World, plenty of shops and restaurants just as described. Will stay again.

Family-friendly apartment rentals

Guest favourite
Apartment in Kissimmee
4.95 out of 5 average rating, 138 reviews

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

CamilaRating, 5 stars2 weeks ago
We had an amazing time! The home was spotless, comfortable, and felt very safe—which made it easy to relax and enjoy our stay. The kids had an absolute blast at the water park and could have stayed there all day. The location is perfect—just a short drive to supermarkets, restaurants, and other local attractions, which made everything so convenient. The neighborhood was peaceful and quiet at night, which we really appreciated. The check-in process was smooth and the host was very responsive and helpful. We definitely plan to come back again and would highly recommend this place to anyone looking for a fun, family-friendly getaway!
Superhost
Apartment in Kissimmee
4.8 out of 5 average rating, 198 reviews

Magic Stay at Windsor Hills! 2 bedroom apartment!

DaniellaRating, 5 stars1 month ago
We had a great stay at Thiago's place, which has a fun Disney themed children's room that the kids loved. We also loved that the kids had their own little table in the living room, which they used allot. Convenient that there are two bathrooms and a kitchen. The resort is nice and very close to the Disney parks, which is perfect if you are visiting the parks. It's also close by to Walmart and gas station. Overall a great stay in a great apartment, very suitable for a family of 4 to 5 people. Would recommend!
Top guest favourite
Apartment in Four Corners
4.99 out of 5 average rating, 120 reviews

The Mouse Pad: Luxury Condo near Walt Disney World

FatimaRating, 5 stars5 days ago
From the moment my family arrived, everything about Brittany's place exceeded everyone's expectations. The space was spotless, beautifully decorated, and thoughtfully stocked with everything we needed for a comfortable stay. It truly felt like a home away from home. The host was incredibly kind, responsive, and made check-in and check-out seamless. The location was ideal—quiet and peaceful, yet close to great restaurants, shops, and attractions. Every detail, from the cozy linens to the well-equipped kitchen, was just right. We would absolutely stay here again and recommend it to anyone looking for a relaxing, high-quality Airbnb experience. Thank you for such a memorable stay!
Superhost
Apartment in Kissimmee
4.84 out of 5 average rating, 148 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

JamesRating, 5 stars2 months ago
Excellent location within community and is an easy walk to the pool. Kids loved the Star Wars room and the bunk beds were very sturdy.
Top guest favourite
Apartment in View Park-Windsor Hills
5 out of 5 average rating, 170 reviews

Mickey's Imagination Condo at Windsor Hills Resort

HeidiRating, 5 stars2 weeks ago
Booked a last min stay for my family of 6 including 5 yr daughter and 2 yr old son as well as my in laws. The place was overall perfect for us! It was clean, spacious and comfortable; we felt right at home with how well appointed and stocked everything was (probably the most stocked for any place I’ve ever rented). The hosts truly thought of every need a family traveling with children may have! The hosts were kind, friendly and accommodating with allowing us to extend our stay an extra day and also offered a flexible check out so we could enjoy the awesome amenities before heading out. We loved the pool/water park; it was so convenient to be able to order yummy food and drinks for lunch at the pool. The condo was located 15-20 min from Magic Kingdom which easily allowed us to head back from the park each day for a midday nap - perfect timing given the 90+ temps. We were only 20 min from Disney Springs. The Walmart was super close too! Def recommend and will be back for future stays!
Guest favourite
Apartment in Kissimmee
4.82 out of 5 average rating, 289 reviews

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!

SharondaRating, 5 stars1 week ago
Great!!! Vacation home had all the amenities a woman like me love. Plenty of everything from dishes to sheets very clean and comfortable. To say the least just right in the day far as neighborhood activities and quite peaceful and serene at night. Everything imaginable is located right around the corner a big bonus . It Felt like home away from home. Mrs.Mary place was sunshine after the rain Thanks for saving my vacation I will be recommending you to another who wants a fabulous place to stay while on vacation
Top guest favourite
Apartment in Kissimmee
4.98 out of 5 average rating, 155 reviews

Poolside! 3BR Condo in Windsor Hills-2mi to Disney

JordanRating, 5 stars5 days ago
We had a great time at this condo. We stayed for 9 days and had everything we needed. My four year old loved the toys, games, and books that were available. We appreciated all of the pool toys, noodles, and float as well. The kitchen had everything we needed and so much more. We loved being so close to the pool. You also cant get closer to Disney without staying on Disney property. We would stay here again as well as recommend it to friends.
Guest favourite
Apartment in Kissimmee
4.85 out of 5 average rating, 178 reviews

WH Condo. Pool/Waterpark and close to Disney!

EmileeRating, 5 stars2 weeks ago
Perfect place if you have infants and/or toddlers! Tons of baby and kid friendly items (walker, small stroller, step stools, tons more). These items made it so much easier to pack light. The splash pad/water park area is also great for little kids. Definitely recommend staying here!

Quick stats about holiday rentals that are kid-friendly in Windsor Hills, Four Corners

  • Total rentals

    260 properties

  • Nightly prices starting at

    $128 SGD before taxes and fees

  • Total number of reviews

    6.7K reviews

  • Family-friendly rentals

    240 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    260 properties have a pool

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