Family-friendly holiday rentals in Windsor Hills, Four Corners

Find and book unique family-friendly homes on Airbnb

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

Family-friendly home rentals with a hot tub

Guest favourite
Villa in Kissimmee
4.92 out of 5 average rating, 114 reviews

Just Renovated+Private Salt Pool/Spa+5mi to Disney

BarbaraRating, 5 stars3 days ago
Place was perfect for our needs. The communication was great. The house was lovely. There was plenty to keep the kids entertained. Thanks again and will definitely stay again.
Superhost
Townhouse in Kissimmee
4.77 out of 5 average rating, 313 reviews

Free Waterpark! Fantasy World - Fun at BnB

ArielRating, 5 stars2 weeks ago
We had a very nice time at this home. It was clean and well taken care of.
Guest favourite
Home in Kissimmee
4.89 out of 5 average rating, 130 reviews

Remy's Refuge: Stylish 4BR - 10 min to Disney!

MarthaRating, 5 stars1 month ago
We really enjoyed our stay! The house had plenty of room for all of us. The view was amazing outback. It was peaceful and quiet. Amanda and Trevor were very quick to answer any questions.
Guest favourite
Townhouse in Kissimmee
4.94 out of 5 average rating, 190 reviews

Beautiful family home near all attractions.

KatannaRating, 5 stars2 weeks ago
Super attentive and helpful. Very kind. Allowed a late checkout to help me accommodate my changed flight. Comfortable. Felt safe.
Superhost
Apartment in Davenport
4.83 out of 5 average rating, 121 reviews

Orlando Spacious 2-Suites & Resort-Style Pool

AnaRating, 5 stars1 week ago
I enjoyed my stay here so much. The apartment was so cute and cozy, super clean and spacious. It is in a gated property so itself safe and overall a great location. If and when I am back in town, I will definitely stay here again.
Superhost
Townhouse in Kissimmee
4.88 out of 5 average rating, 179 reviews

Elegant 4bdrs lakefront w/private pool

RebeccaRating, 5 stars1 month ago
We had a fantastic stay with friends at this Airbnb! The location was great—close to everything we needed. The rooms were spacious, clean, and beautifully presented. The pool was spotless and perfect for relaxing, and we really appreciated having access to the barbecue, which made our stay even more enjoyable. Simone was an excellent host—so easy to communicate with and provided clear, straightforward instructions for both check-in and check-out. Highly recommend and would definitely stay again!
Top guest favourite
Apartment in Kissimmee
4.94 out of 5 average rating, 353 reviews

Disney World Condo w/ Full Kitchen, Balcony & Pool

AnaRating, 5 stars1 week ago
Adam is a great host. We really appreciate the extra amenities that most airbnbs skimp out on like extra toilet paper rolls, my kids adored the extra Disney touches, and although having to wait for 3 toddlers to make it up to the 3rd floor was challenging for me they had no complaints! We very much enjoyed our stay and took advantage of what the resort had to offer! Thank you Adam for helping me find the airbnb when I accidentally put in the wrong directions. Your communication was greatly appreciated. Would stay again.
Guest favourite
Townhouse in Kissimmee
4.94 out of 5 average rating, 210 reviews

Relaxing Resort Stay Hot Tub Lake View Near Disney

MariaRating, 5 stars1 month ago
This was our second time staying at Nathalie’s place! We are just as happy as before. Thank you again and we will be back soon!

Family- and pet-friendly home rentals

Top guest favourite
Apartment in Champions Gate
4.85 out of 5 average rating, 278 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

RominaRating, 5 stars1 month ago
The apartment was super nice! The complex was good, we enjoyed the pool and the jacuzzi. Thanks very much we had an amazing stay.
Guest favourite
Townhouse in Kissimmee
4.87 out of 5 average rating, 137 reviews

Disney Vacation 8 miles to Disney World

DonovanRating, 5 stars2 weeks ago
Nice place clean and tidy.
Superhost
Townhouse in Kissimmee
4.7 out of 5 average rating, 166 reviews

Cozy Townhouse in Kissimmee, near Orlando!

LakmalRating, 5 stars2 months ago
We stayed for 7 days at this lovely townhouse and had a fantastic time. The location was ideal—just a short drive from Disney and other major attractions. The neighborhood felt safe and quiet, which was great for relaxing after busy days out. The townhouse was clean, spacious, and well-equipped. The kitchen had everything we needed to cook meals, and having a washer and dryer was super convenient. The Wi-Fi worked well, and the air conditioning kept the whole place cool and comfortable. The kids especially loved the community pool.
Top guest favourite
Villa in Kissimmee
4.86 out of 5 average rating, 411 reviews

OMG! Disney Area, Movie Theater, Game Room & Pool!

ShamayaRating, 5 stars1 week ago
We had a wonderful stay !! It was very roomy and exactly like the pictures! Definitely would recommend and stay again !
Superhost
Home in Kissimmee
4.81 out of 5 average rating, 198 reviews

Walking distance clubhouse - premium location

MelodyRating, 5 stars1 week ago
The place was clean and exactly as described, and in a very peaceful neighborhood. Items like dish soap and detergent, hand soap, and laundry detergent were available upon arriving. Instructions for how to maintain the house and carpeting were clear and simple, and made it easier to remind everyone to be respectful of the place (without having to be the bad guy- lol). The gate entry was simple once we were checked in, location was easy to get to from our local plans. All in all, if you want to keep your large family or group together and happy, this place is a great choice.
Guest favourite
Townhouse in Davenport
4.79 out of 5 average rating, 217 reviews

Family Home near Orlando amusement parks!

CynthiaRating, 5 stars10 months ago
Alison’s place was great! It was very clean and very comfortable. She accommodated early check in which was very helpful after our long travel. Very few cons that were simple work arounds, is we wish there were more towels and pool towels. We also would’ve liked extra blankets. Overall, it was a great place and we would book again.
Guest favourite
Apartment in Orlando
4.99 out of 5 average rating, 138 reviews

Serene Lakeview By DisneyWorld -Universal Stds 8mi

CarrieRating, 5 stars1 month ago
Adir's place was fantastic. There were many personal touches that made it feel more cozy, which I've found in Orlando can be a struggle. I loved how there were cozy blankets, bathrobes, and a few treats when we arrived. The location is awesome. Very close to anything you could need, Disney, Universal, and the airport. Dollar Tree, Starbucks, Dunkin, Chick-Fil-A, Walgreens, and many more places are all within walking distance. I loved how peaceful the condo and location felt, despite being surrounded by everything. The view was beautiful to wake up to and my kids enjoyed playing in the pool. We would definitely recommend and be happy to stay again!
Top guest favourite
Townhouse in Kissimmee
4.99 out of 5 average rating, 104 reviews

Family friendly/Pet friendly Orlando paradise

CatherineRating, 5 stars3 days ago
We spent two weeks at Disney parks and this place was an excellent choice for our family of 3. We were close enough to take breaks during the hottest parts of the day. Andrea's place was very clean and comfortable. We appreciated all the amenities provided and clear instructions for check in/out. We would not hesitate to stay here again. Excellent host!!

Family-friendly home rentals with a pool

Top guest favourite
Townhouse in Kissimmee
4.89 out of 5 average rating, 72 reviews

3BR/3BA Close to Theme Park Game Zone Heated Pool

AngieRating, 5 stars1 month ago
Great stay! We just left the property and loved it. The townhouse was clean, the host was very responsive, and the property management company was easy to work with (we had to contact them once because the back door wouldn’t lock, and they were there within 20 minutes to fix the problem - very friendly too). Extremely comfortable beds, lots of extra charging spots (so important with all the things that need to be plugged in!), fun theming, and a nice perk with the small gaming closet upstairs that my son absolutely loved. Everything was easy to find in the unit itself, and the check in and checkout procedures were a breeze. I would recommend this property to anyone.
Guest favourite
Villa in Kissimmee
4.9 out of 5 average rating, 58 reviews

Hakuna Ma'Cottage - Southern Pool, Privacy Fence!

KaylaRating, 5 stars1 month ago
Great place to stay! Was perfect for our families Disney/Universal vacation. Its close to all Disneyworld parks as well as Universal in a quiet neighborhood. Gerry was very understanding and helpful with any question and concerns. We would stay again for another trip if needed and would recommend the stay to anyway for their Disneyworld vacation.
Superhost
Apartment in Kissimmee
4.64 out of 5 average rating, 44 reviews

Resort Oasis! 3BR w Pool Access near Disney World

SierraRating, 5 stars2 months ago
Perfect trip for myself and the tribe. I had booked a week before our vacation saw a bunch of bookings, but this one stood out the most plus the price was super cheap for a week' stay near Orlando. Our condo was amazing, loved the screened in patio, the kitchen was amazing and plenty of appliances for whatever we needed. Loved the in-unit washer and dryer was able to do all my laundry before leaving. The pool was heated so night swimming was great. The restaurant on site has plant-based options which was perfect for me. I could sit right by the pool sip a drink and eat. Arcade and theater all located near the pool which was great. The basketball court was great for us to play a few rounds, nice little walk from our condo. Truly enjoyed this property and the scenery of the landscape. The beds were super comfy, plenty of room for everyone to relax and have space from each other. Truly perfect vacation.
Superhost
Home in Kissimmee
4.92 out of 5 average rating, 38 reviews

Magical Vacation Home | Pool + Spa | Game Room

AndreRating, 5 stars2 weeks ago
Was a great place, my family and I enjoyed the pool a lot
Superhost
Home in Championsgate Village
4.68 out of 5 average rating, 108 reviews

5 BD/ 4.5 BA Private Pool! Champions Gate (1416WW)

GabriellaRating, 5 stars2 weeks ago
Beautiful house in a beautiful area.. the game room was a huge hit with the kids and we loved all the attention to detail throughout the home such as the leds in each room.. my family and I had a blast in the home as well as the resort which was also a beautiful and relaxing environment.. host was very responsive and helpful.. we will definitely be back for another staycation :)
Superhost
Home in Kissimmee
4.84 out of 5 average rating, 69 reviews

Paradise Villa Vaycay 2.5 Miles from Disney

SabinaRating, 5 stars1 month ago
Home was exactly as described. At most 15 minutes to each of the parks, 30min to universal. Had a few communication issues with the host on day of check in for some reason my messages were not received. The management company was a little hard to get a hold of at first but was there as we were checking in and was very responsive from that point forward. In total there were 11 adults during our stay and between phones and kids tablets/iPads the wi-fi was a bit on the slower side, considering the tv ran solely on wifi (just something to keep in mind). Overall would recommend if you’re looking for something comfortable for large groups/close to the parks!
Guest favourite
Home in Kissimmee
4.92 out of 5 average rating, 83 reviews

Windsor Hills 5 bed/5 bath Pool Home, Games Room

MelissaRating, 5 stars3 months ago
This was one of the most beautiful places I Have stayed. Matthew was on point with everything and anything. Soooooo close to the parks which was great for our visit. If I messaged he was back to me right away. I highly highly recommend this home!!! We will be back!
Guest favourite
Home in Kissimmee
4.92 out of 5 average rating, 60 reviews

Luxury 4 Bedroom Home - Resort Access! Disney!

WayneRating, 5 stars1 month ago
A beautiful home on the unrivalled Reunion private resort and a great base to explore the parks from.

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

  • Total rentals

    610 properties

  • Nightly prices starting at

    ₹6,027 before taxes and fees

  • Total number of reviews

    12K reviews

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    600 properties have a pool

  • Rentals with dedicated workspaces

    350 properties have a dedicated workspace

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