Kid-friendly holiday rentals in Windsor Hills, Four Corners

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Top-rated family-friendly rentals in Windsor Hills, Four Corners

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Home in Kissimmee

4.94 out of 5 average rating, 171 reviews

Tito's Beachy Townhouse, 1.5 miles from Disney

One of the closest and newest communities to Walt Disney World! Located just 5 minutes from Disney, our freshly updated townhouse is the perfect location for your next Florida adventure. A fully equipped kitchen, super-fast Wifi, community pool, and a brand new Walmart just down the street are only a few of the many amenities you will find with this incredible rental. Our 1600 sq. ft. home is bright, fresh, and waiting to welcome our next guests. Absolutely the best unit in the entire community!

20–27 Jul

£137 per night

Guest favourite

Apartment in Kissimmee

4.87 out of 5 average rating, 150 reviews

Luxurious Mickey's Dream Home!

Wonderful Mickey-themed 2 bed 2 bath condo in the Windsor Hills Resort located 2 miles from Disney World Entrance! Our Condo is a modern, clean & upgraded condo, that offers the comforts & convenience of home. Features: Granite counter-topped well-stocked kitchen, comfortable beds with clean linens, Smart TVs in all rooms, cable TV, free WiFi. Washer & dryer in unit, Valet trash pickup, with 2 elevators in the building. Free Parking, Free access to resort pool, waterpark & lots more (see below)

7–14 Oct

£133 per night

Guest favourite

Apartment in Kissimmee

4.82 out of 5 average rating, 149 reviews

Heated Waterpark 10 mins to Disney in Windsor Hill

Welcome to Windsor Hills' Gated Vacation Community! Perfect for an adventurous family vacation or a relaxing getaway in the sun. I am excited to host your stay. Your unit is located on the 3rd floor. Get a quick exercise and hike up (39 stairs) to the front door or catch a break and use the elevator located on the ground level. Once inside, enjoy the newly remodeled 2Bdr, 2Bth condo, fully equipped to accommodate your stay. We are a PET and SMOKE-FREE property. Additional cleaning fee applied.

20–27 Jan

£145 per night

Guest favourite

Home in Kissimmee

4.93 out of 5 average rating, 131 reviews

NEW! Star Wars Room, Frozen Room, close to Disney

This fantastic 4 bedroom, 4 bathroom house is located a few miles from Disney World in the highly coveted (and gated) Windsor Hills Resort. You will have access to all that Windsor Hills has to offer including A NEW WATER PARK, double Olympic sized pool, play grounds, clubhouse, gym, video arcade, marketplace and grill, tennis courts, and more! This home features two amazing themed bedrooms with a Twin/Full bunk bed for your little ones to enjoy and to help get into the spirit of the magic!

16–23 Sept

£321 per night

Guest favourite

Apartment in Kissimmee

4.89 out of 5 average rating, 152 reviews

Disney's Doorstep, 3 Bed 2 Bath, Waterslides!

Welcome to your dream vacation! This 3 bedroom, 2 bath, is right on Disney's doorstep, this amazing vacation rental has all the amenities you'd put on your dream list. Two water slides, a kids splash park, walk in pool, movie theater with wheelchair access, game room, fitness center, putting green, playground, shop for snacks, and more! This condo also comes fully furnished with a washer/dryer, WiFi, elevator for wheelchair access, and more. This is sure to be your relaxation destination.

7–14 Aug

£163 per night

Guest favourite

Apartment in Kissimmee

4.94 out of 5 average rating, 133 reviews

Minutes from the Magic - Windsor Hills 3br 2ba

**PLEASE NOTE** Pool will be closed for maintenance 9/5/2024 to 10/5/2024 Beautiful condo with incredible amenities just minutes from Walt Disney World. Plenty of room for the entire family with three bedrooms and two full baths. Windsor Hills is a gated resort community with all of the amenities you can imagine! Beautiful, zero-entry pool, splash pad, and water slides will help you beat the heat. A fitness center, arcade, shop, cafe, sports courts, and movie theater are on site!

30 Mar – 6 Apr

£142 per night

Superhost

Townhouse in Kissimmee

4.86 out of 5 average rating, 317 reviews

Splendid house 5 min from Disney

Crestwynd Bay condominium is only 1,5 miles to Disney Parks entrance. Walmart is 0,3 miles,very near. Beautiful and complete townhouse with 3 bedrooms, 3 bathrooms, kitchen equipped, laundry room, free WIFI, exterior area . Self check-in. This condo has community pool and children playground. Parking for car in front of the house. Is five minutes from target ,pharmacies , restaurants and fast foods. Ten minutes of outlets and 15 min from Universal and Island Parks. Great location!

18–25 Mar

£125 per night

Guest favourite

Apartment in Kissimmee

4.96 out of 5 average rating, 112 reviews

Windsor Hills Resort - Disney Pool View Condo

Location, location, location! Windsor Hills pool view condo and only 2 miles to Disney World! This newly updated 3 bedroom pool view condo is in the beautiful Windsor Hills Resort gated community. The single level condo is located in the closest building to the pool, water park, clubhouse, hot tub, movie theater, and arcade. The condo has one of the best balcony views in the entire resort. Located on the third floor, the balcony looks directly over the resort pool and lake.

20–27 Nov

£178 per night

Guest favourite

Apartment in Kissimmee

4.85 out of 5 average rating, 132 reviews

WH Condo. Pool/Waterpark and close to Disney!

Take an elevator to unit 302 and witness beautifully decorated Disney themed rooms. Directly outside is a lovely pool and kid-friendly waterpark. Other amenities include: game room, theater, exercise room, tennis courts, play grounds, sand volleyball, putting green, basketball court and a marketplace and grill. Located 15 minutes to all 4 Disney parks and Sea World! Looking for more space? Check out our townhome also located in Windsor Hills at 7668 Fitzclarence

27 Apr – 4 May

£155 per night

Guest favourite

Home in Kissimmee

5.0 out of 5 average rating, 175 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

14–21 May

£315 per night

Guest favourite

Apartment in Kissimmee

4.98 out of 5 average rating, 100 reviews

Disney Oasis

Enjoy Disney Oasis, our 3-bedroom, 2-bath condo, ideal for families! Nestled in a gated community with 24/7 security, we're just 3 miles from Walt Disney World® and close to other theme parks. Indulge in our resort-style amenities: a double Olympic-sized pool, thrilling waterslides, and a fun splash pad. Enjoy the convenience of nearby shopping, dining, and entertainment. Our condo is not just a place to stay, but a gateway to an unforgettable vacation!

5–12 Jan

£165 per night

Guest favourite

Townhouse in Kissimmee

4.92 out of 5 average rating, 227 reviews

Beautiful Farm House Decor near Disney, Sleeps 6

Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

18–23 Sept

£120 per night