Holiday rentals with a pool in Windsor Hills, Four Corners

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Popular amenities for Windsor Hills, Four Corners rentals with a pool

House rentals with a pool

Top guest favourite
Home in Kissimmee
4.96 out of 5 average rating, 159 reviews

4 bedroom, south facing pool 3 miles to Disney

MarioRating, 5 stars2 days ago
My family had an awesome weekend. The home beautiful inside & out, felt just like you're at home. I'll definitely book with Alex in the future..
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.
Top guest favourite
Home in Kissimmee
4.95 out of 5 average rating, 56 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

SarahRating, 5 stars6 days ago
We had a fantastic stay at this property! The place was spotless, comfortable, and had a very welcoming vibe. The location was ideal—close to restaurants, shops, and easy access to all things Orlando! One of the highlights was the pool area—it was beautiful, clean, and well-maintained, with plenty of lounge chairs and shaded spots to relax. I really appreciated the clear communication from the host and how easy the check-in process was. I would absolutely stay here again and highly recommend it to anyone looking for a relaxing and convenient place to stay!
Superhost
Home in Kissimmee
4.67 out of 5 average rating, 3 reviews

Windsor Hills Home w/Arcade Game Room|Near Disney

SuzanneRating, 5 stars3 months ago
Very reasonable price for a four bedroom home with a very cool game room. The Harry Potter themed room was over the top fun. The neighborhood pool was enjoyed by all and the food we got at the pool was well done for a small café.
Guest favourite
Home in Kissimmee
4.94 out of 5 average rating, 52 reviews

*NEW*Theater, FREE Resort, 3 Kings, 2 mi WDW

MoniqueRating, 5 stars3 weeks ago
Laura was wonderful to deal with! Very responsive whenever I contacted her. I would stay here again. My daughter even asked for Laura's listing page so she could book her next stay in one of Laura's homes!
Guest favourite
Home in Kissimmee
4.9 out of 5 average rating, 148 reviews

Contemporary Lakefront Villa, Minutes from Disney

BekimRating, 5 stars3 weeks ago
We had an excellent time at Romina’s place. I highly recommend the house for bigger families that are visiting Disney or Universal. Location is close to everything and the resort is awesome too that’s included in the stay. Romina was very responsive and the home was very clean. We definitely will be back again.
Top guest favourite
Home in Kissimmee
4.97 out of 5 average rating, 67 reviews

Fantastic home just 3 miles from Disney World!

SamanthaRating, 5 stars2 months ago
Jennifer’s place was great!! Our group was two families, 4 adults and 3 kids total. The house was huge and had lots of space for everyone! Super clean, looks just like the photos. The house is stocked with everything you need for traveling with young children. The neighbourhood is beautiful, quiet and super family-friendly. You can walk to the resort in 5 mins, which was a lot of fun. Jennifer was very friendly and always quick to respond. We had no issues and I would absolutely recommend this place to any large group or family looking for a great place to stay!
Guest favourite
Home in Reunion
4.96 out of 5 average rating, 178 reviews

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

KaylaRating, 5 stars3 weeks ago
We had such a great time staying at Michael’s place! Our five teenagers were never bored with all of the fun amenities! The kids had a great time with the karaoke machine, arcade games and outdoor area! My husband and I love coffee, so we really appreciated the coffee bar and supplies that were provided. The house was beautiful and Michael was extremely responsive. We would stay again!

Apartment rentals with a pool

Guest favourite
Apartment in Kissimmee
4.95 out of 5 average rating, 139 reviews

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

BrookeRating, 5 stars1 week ago
Kurt and Elizabeth were very responsive and approachable and gave us plenty of local recommendations. Mickasita is a great value and spacious unit with a short walk to the pool. I especially liked that this resort allows Amazon and grocery deliveries to avoid the chaos of the store.
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!
Superhost
Apartment in Kissimmee
4.85 out of 5 average rating, 149 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

WendiRating, 5 stars4 days ago
We had a great stay here, but the place was not as clean as you would expect. The host was quick to respond about the lack of cleanliness and it was resolved the next day. Overall, we enjoyed our stay and would stay here again.
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 stars3 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 stars2 weeks 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
Guest favourite
Apartment in Kissimmee
4.8 out of 5 average rating, 109 reviews

1.5 Miles Away from Disney, 2 Bedrooms Unit

XavierRating, 5 stars2 weeks ago
We had a truly wonderful stay at this property in Orlando! The location was absolutely perfect—close to everything we needed to enjoy our vacation to the fullest. The home was spotless, well-equipped, and had all the essentials to make us feel comfortable and at ease. Lynn was incredibly responsive and always available if we needed anything, which was greatly appreciated. I highly recommend this property and would like to sincerely thank Lynn for making our stay so enjoyable!
Superhost
Apartment in Kissimmee
4.85 out of 5 average rating, 111 reviews

Westgate Vaction Villas - 1 Bedroom

JoseRating, 5 stars3 months ago
This was my 2nd time staying at one of Eddies places. As always he did not disappoint! 10/10!!
Guest favourite
Apartment in Kissimmee
4.85 out of 5 average rating, 178 reviews

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

DeannaRating, 5 stars3 weeks ago
One In A Minion was perfect and exactly what we were looking for. Ground floor, a very short walk to the pool. The decor went excellent with the theme and brought joy for the children. The gated entrance gave an extra peace of mind. A perfect place for a family to unwind and relax.

Home rentals with a private pool

Villa in Championsgate Village

Disney's Championsgate: Private Pool & Arcade Fun!

AurianaRating, 5 stars6 months ago
This property was very nice and matched the photos to a T. The house was spotless & very spacious. The renovated design was modern and the themed rooms were perfectly executed. The only downside was the check-in process at the gate, but after a quick phone call, the issue was resolved. I absolutely loved the space. 10/10.
Villa in Kissimmee

Disney Dreams Luxury Home Private Water Park

CorlesaRating, 5 stars47 months ago
The home was very nice. It accommodated our family extremely well. The post was accurate and it definitely felt like a Home away from Home! We were also able to get responses from the Host in a timely manner. I would stay at this property again!
Superhost
Home in Davenport
4.95 out of 5 average rating, 115 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

RachelRating, 5 stars1 month ago
Had a great stay at Phil's place. The home was perfect for mother's day weekend. My daughter loved the pool. The home was clean! 10/10 recommend.
Villa in Kissimmee
4.79 out of 5 average rating, 251 reviews

Visit Disney World from a Sunny Home with a Pool

ClaudiaRating, 5 stars3 weeks ago
I can’t say enough good things about this Airbnb – it was absolutely incredible from start to finish. The space was spotless, nicely decorated and had every amenity we could have possibly needed (and then some!). It truly felt like a home away from home, with thoughtful touches throughout that made our stay extra special. The host was communicative welcoming and very helpful!
Guest favourite
Villa in Kissimmee
4.92 out of 5 average rating, 49 reviews

Family Retreat Near Disney with Pool & Hot Tub!

KimRating, 5 stars1 week ago
I really love this place. If I had to change one thing it would have been to be sure that it’s listed as only one bathtub, which wasn’t a big deal cause I’m grandma, but it could be a hassle for others.
Home in Championsgate Village
4.83 out of 5 average rating, 48 reviews

Sleeps 16! Pool + Arcade | Orlando Resort Retreat

MindyRating, 5 stars2 weeks ago
Pictures shown is exactly how the place looks. Felt secure in the neighborhood. Plenty of amenities. Pool and hot tub was a plus. Game room was also a plus for the little ones.
Villa in Davenport
4.67 out of 5 average rating, 6 reviews

Amazing Dream Solterra Villa -Disney/club/pool/spa

CraigRating, 5 stars48 months ago
They house is exactly like described and had a lot of room. The cleaning could be a bit better, but they apparently had a very short turn-around. Be prepared to have parties going on around you. They do not enforce the noise ordinance at midnight like they should. We were not their to party, so this did have an affect on some of our guests. Overall, it was a pleasant stay. Edward is a super host for a reason. He always returned my emails and texts. When we needed something he was sure to get it to us. He made us feel comfortable about this purchase from the very beginning.
Home in Kissimmee
4.38 out of 5 average rating, 8 reviews

Vacation Resort Home Right Outside of Disney World

VictoriaRating, 5 stars8 months ago
We evacuated our coastal home ahead of a hurricane and found this pet-friendly rental to be exactly what we needed. The house was fun, which helped lift our spirits during a difficult time. However, the real highlight was the hosts, who were incredibly accommodating and gracious, making an extremely stressful situation much easier to manage.

Quick stats about holiday rentals with a pool in Windsor Hills, Four Corners

  • Total rentals

    670 properties

  • Nightly prices starting at

    ₹4,317 before taxes and fees

  • Total number of reviews

    12K reviews

  • Family-friendly rentals

    600 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    370 properties have a dedicated workspace

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