Family-friendly holiday rentals in Windsor Hills, Four Corners

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

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 stars6 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
4.88 out of 5 average rating, 129 reviews

Orlando Disney new House at Resort with lake view!

LisaRating, 5 stars2 weeks ago
This property lived up to the poctures. It was well equipped, clean, comfortable. We have stayed at a number of places in Orlando amd other cities. This one is in the top 2 or 3. We would stay again.
Top Guest favourite
Townhouse in Reunion
4.94 out of 5 average rating, 124 reviews

Luxurious Reunion 3 bd Townhouse- Close to Disney

TracyRating, 5 stars1 week ago
We loved the house! Very homey and convenient. We didn’t have a car so we didn’t drive or walk the property much but pool was very close. The kids loved it. We took an uber daily to Disney. Nice it was a gated community, felt safe. Would definitely book again.
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
Villa in Kissimmee
4.9 out of 5 average rating, 212 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

ShakeriaRating, 5 stars2 weeks ago
My Daughter Spent Her 8th Birthday In Disney But The House Was The Icing On The Cake✨ My Family Enjoyed The Pool & The Heated Hot Tub, She Provided The Necessary Necessities & Overall The Place Was Beautiful, I Love The Master Shower That’s My Favorite Part Of The House, The House Is Spacious With Tons Of Restaurants & Stores Just A Few Miles Aways, Disney Was Super Close & Overall We Enjoyed Our Stay Here At Mad Men Magic Kingdom House. There Was A Misunderstanding With A Neighbor & When I Reached Out To Rebecca She Responded In A Timely Manner & I Appreciate That! I Would Definitely Recommend Mad Men Magic Kingdom House To Everyone I Know🤍 Thank You For This Experience
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 stars4 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
Townhouse in Kissimmee
4.88 out of 5 average rating, 321 reviews

Roomy 2br w/ jacuzzi close to Disney

JonishaRating, 5 stars2 weeks ago
Great location place was very nice and kept well enjoyed the hot tub and the resort this place was well equipped with all necessities for your stay it was very welcoming! Great place to stay would Love to visit again!
Superhost
Apartment 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- and pet-friendly home rentals

Guest favourite
Townhouse in Kissimmee
4.87 out of 5 average rating, 137 reviews

Disney Vacation 8 miles to Disney World

DonovanRating, 5 stars3 weeks ago
Nice place clean and tidy.
Superhost
Townhouse in Kissimmee
4.71 out of 5 average rating, 167 reviews

Cozy Townhouse in Kissimmee, near Orlando!

LynnRating, 5 stars2 months ago
Maria's place was super cozy. It had everything we needed and then some. the property is beautiful. Pools were nice. and the staff at the gates were very welcoming. No problems. very relaxing.
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 stars2 weeks ago
We had a wonderful stay !! It was very roomy and exactly like the pictures! Definitely would recommend and stay again !
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.
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
Condo in Orlando
4.99 out of 5 average rating, 139 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 stars6 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!!
Guest favourite
Home in Davenport
4.83 out of 5 average rating, 103 reviews

Highgate Palace-near Disney World. 20min Drive

AleishaRating, 5 stars1 month ago
Aaron is an amazing host that truly cares about what is happening with his guests. We had a little trouble with our travel and Aaron went above and beyond to accommodate us when things went out of our control. The home is very nice and exactly as described. It was clean and looked well kept. The beds are extremely comfortable and the home is spacious. I will definitely book with Aaron again if I am back in Orlando!

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
Home in Kissimmee
4.66 out of 5 average rating, 53 reviews

Free Water Park & Luxury Living!

Donna LorainneRating, 5 stars2 months ago
Stay was wonderful, close to Disney, and close to airport. Beautiful place to come home to after long hot day at Disney. Pool was great to relax in and home was big enough for 2 families with one child each and grandparents. Quiet bedrooms and fun games room which was a nice touch. Kitchen had all amenities you needed. Private location.
Superhost
Apartment in Kissimmee
4.55 out of 5 average rating, 31 reviews

W. Hills 2817 - 2/2 Completely Remodeled!

SaraRating, 5 stars2 months ago
This is our second stay at this location. It’s not far from Disney (13 min drive) and conveniently located near a Starbucks, gas station, and a Walmart for all your basic needs. The complex has a beautiful pool and waterpark that is walkable/ short distance from the unit. This is a first floor unit, which makes it great for guests with mobility issues. Ample parking is available, so no need to worry, parking close is easy and perfect for loading/unloading items. The unit is spacious and beds are very comfortable.
Superhost
Condo in Kissimmee
4.71 out of 5 average rating, 31 reviews

Disney Getaway

AngelRating, 5 stars1 month ago
It was a great stay for our family! Host responded quickly and we enjoyed the amenities.
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 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
4.94 out of 5 average rating, 70 reviews

5 Mins To Disney W/Poolside Theater & Games Room

MahalingamRating, 5 stars1 month ago
Good location in Orlando. Convenient to visit Disney parks. The community is clean, gated and the house was in good condition. Pretty close go good restaurants and department stores. We visited with 4 adults and 4 kids and the house was pretty spacious for our group.

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

  • Total rentals

    610 properties

  • Nightly prices starting at

    $117 NZD 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

Destinations to explore