Vacation rentals with a pool in Windsor Hills, Four Corners

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Top-rated rentals with a pool in Windsor Hills, Four Corners

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Guest favorite

Home in Kissimmee

4.99 out of 5 average rating, 109 reviews

Game & Theater Room, Castle Bunks, Pool & Spa

Vacation at Windsor’s Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.

Guest favorite

Condo in Kissimmee

4.83 out of 5 average rating, 167 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.

Guest favorite

Villa in Kissimmee

4.94 out of 5 average rating, 119 reviews

★Completely New★ 3 miles to Disney + Free Resort!

Closest FREE resort to Disney Parks! Plumeria Place is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in March 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 9' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

Guest favorite

Home in Kissimmee

4.93 out of 5 average rating, 138 reviews

NEW! Galaxies & Snowflakes! 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!

Guest favorite

Home in Kissimmee

4.97 out of 5 average rating, 106 reviews

Highest Rated Minutes to Disney! -Newly Renovated

• Newest house in the #1 community in the Disney Area, Windsor Hills • Only home with 7 bedrooms in the community (3 KING beds) • Extra privacy: only one side & no rear neighbors • 4 children themed bedrooms (Mickey, Star Wars, Toy Story, & Frozen) • Onsite, driveway parking for 4 vehicles • FREE pool heat + BBQ with all rentals • Fully equipped + stocked kitchen • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1000 Mbps • Property is managed directly by owner

Guest favorite

Condo in Kissimmee

4.9 out of 5 average rating, 174 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.

Superhost

Condo in Kissimmee

4.83 out of 5 average rating, 139 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

Welcome to our Star Wars themed rental in Kissimmee, FL, just 3 miles from Disney World! Experience the ultimate vacation in a galaxy far, far away. Located in Windsor Hills Resort with a heated community pool and two water slides. The kids bedroom has Star Wars decor, twin bunk beds, and an electronic pinball machine. The condo is decorated with Star Wars artwork and a half-sized Darth Vader figure. The kitchen is fully equipped. Don't miss this chance to live out your Star Wars fantasies.

Guest favorite

Condo in Windsor Hills

5 out of 5 average rating, 156 reviews

Mickey's Imagination Condo at Windsor Hills Resort

Please note: we are adhering to strict CDC cleaning guidelines to help protect our guests from covid-19. This newly renovated 3-bedroom, 2-bathroom first-floor unit condo is located just minutes from the gates of Disney World. Our condo is family-friendly (or "kids at heart") and creatively Disney-themed. We have a Mickey's clubhouse-themed kids' room, Animal Kingdom guest room with nursery and tastefully decorated film Mickey master bedroom. There is something for everyone in the family!

Superhost

Townhouse in Kissimmee

4.87 out of 5 average rating, 334 reviews

Splendid house 1, 5 miles to 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 parks and sea world. Great location!

Guest favorite

Townhouse in Kissimmee

4.89 out of 5 average rating, 141 reviews

*** Newly furnished 3 BDR/3Bath next to Disney ***

Newly furnished and decorated 3 BDR/3 bath townhome in a gated, secured community less than 2 miles from Disney area. This is a prime location for visitors. Walmart is less than a mile away, and lots of restaurants, shops and tourist attractions are available nearby on US-192. Disney and Universal Studios theme parks are only a short drive away. Otherwise relax in the living room sofa and enjoy Netflix and DISNEY+ on the 4K 60" TV, take a dip in the pool, or read a book on the patio !

Guest favorite

Home in Kissimmee

4.95 out of 5 average rating, 129 reviews

Jackies’s Jungle View Vacation Villa

ALL NEW fully remodeled and updated! 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.

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 130 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.