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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Superhost

The outdoor pool area is enclosed with a screen, providing a view of the surrounding landscape. A blue pool features a partially submerged step and is bordered by a brick patio. A beach ball floats in the water, while lounge chairs are positioned nearby for relaxation.

Home in Kissimmee

4.89 out of 5 average rating, 158 reviews

Contemporary Lakefront Villa, Minutes from Disney

Welcome to our fabulous home! Our newly remodeled, lake front home is centrally located 5 minutes from Disney and minutes away from Walmart, stores, restaurants. Our home features 6 bedrooms, 4 bathrooms and a movie room. Our large open concept kitchen makes it easy for families to enjoy while cooking, eating or relaxing. After a long day at the parks you can relax in our newly renovated pool. Our home is in the beautiful Windsor Hills neighborhood, and is a 3 minute walk to the main clubhouse.

Top guest favorite

The spacious living area features comfortable seating arrangements, large windows, and a decorative area rug. The view leads to the private screened-in pool, providing a seamless indoor-outdoor experience. The room is illuminated by natural light and complemented by a modern ceiling fan.

Home in Kissimmee

4.99 out of 5 average rating, 137 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

Home in Kissimmee

4.87 out of 5 average rating, 114 reviews

Disney Escape at Windsor Hills

This is a fantastic family vacation townhouse located just four miles from Walt Disney World! Inside, you'll find a full kitchen with a breakfast bar, a dining table for six, and a living area with a TV for streaming all your favorite channels! Right outside, take a refreshing swim in your private pool. Guests will be able to enjoy a wide variety of resort-style amenities close by including a community clubhouse with a game room, Olympic-size pool, children's waterpark, putting green, and more!

Top guest favorite

Townhouse in Kissimmee

4.94 out of 5 average rating, 186 reviews

5 miles to Disney- Private Pool - Arcade Games

Just 4 miles from Disney, our luxury townhome is your family’s perfect escape! With a private splash pool, brand-new 65” Smart TV, and family-friendly gear (stroller, pack n’ play, high chair), you’ll have everything needed for a carefree stay. Located across from Windsor Hills Resort’s clubhouse, enjoy resort perks like a pool, splash pad, fitness center, and theater! Sleeps 8 comfortably with 3 en-suite bedrooms, including a themed Disney beach kids’ room. Fun, comfort, and convenience await!

Top guest favorite

Villa in Kissimmee

4.97 out of 5 average rating, 132 reviews

*Brand New!* Minutes to Disney + Free Resort!

Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 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 & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

Top guest favorite

The resort's expansive pool area is surrounded by lush palm trees and manicured landscaping. A vibrant water park feature is visible in the background, inviting guests to enjoy refreshing water activities. Clear blue skies and fluffy clouds create a delightful atmosphere.

Condo in Kissimmee

4.82 out of 5 average rating, 297 reviews

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!

Brand new flooring, mattresses, AC, water heater and more! Disney SO close! Our Property Manager will see to any needs during your stay, a rental registration is required. Beautiful, clean and comfy condo in Windsor Hills Resort with a new WATER PARK and tons of amenities. Stainless appliances and granite, free wifi/cable, desk/charging station and PS 3 with games, Pack N play, stroller, high chair, wash/dryer, a starter kit of supplies. No hidden fees, free parking. Perfect for families!

Top guest favorite

Condo in Kissimmee

4.98 out of 5 average rating, 107 reviews

Disney, Universal Windsor Hills, Family friendly.

Walk into your home away from home. Enjoy a relaxing stay. Located on 4th floor. Enjoy morning coffee on a screened-in balcony or a late snack. Pet-free home. Please NO Smoking. Children are always welcome. Come enjoy all of the accommodating facilities at Windsor Hills with a top-notched 24/7 gated security. FREE parking & leisure activities! Maximum of 3 cars allowed per reservation. This includes all guest that are visiting. All unregistered drivers will be denied access by HOA.

Top guest favorite

An aerial view of the resort pool area, showcasing a large, winding swimming pool surrounded by palm trees and lounge chairs. A smaller hot tub is located nearby. In the background, a colorful water park can be seen, inviting guests for aquatic fun.

Condo in Kissimmee

4.95 out of 5 average rating, 152 reviews

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

Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

Top guest favorite

A screened-in patio presents a private pool area with crystal-clear water. The pool features a shallow edge and curves gently, surrounded by light-colored pavers. Ample outdoor seating is visible in a shaded corner, providing a relaxed space for enjoyment.

Villa in Kissimmee

4.96 out of 5 average rating, 141 reviews

Mr. Clean's Cozy Disney Home w/ Luxury Finishes

• Newest house in the #1 resort community in the Disney Area, Windsor Hills • ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. • 2 FUN children themed rooms (Star Wars, & Frozen) • Onsite, driveway parking for 3 vehicles • FREE pool heat + BBQ with ALL rentals • Fully equipped + stocked kitchen; including Keurig machine • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1,000 Mbps!! • Property is managed directly by owner

Top guest favorite

Home in Kissimmee

5 out of 5 average rating, 234 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.

Guest favorite

A private pool area is enclosed by a protective screen, providing a serene oasis. The pool is surrounded by tiled flooring, with a table and chairs nearby for relaxation. Bright curtains frame the entrance to the living space, enhancing the overall inviting atmosphere.

Townhouse in Kissimmee

4.91 out of 5 average rating, 242 reviews

DISNEY, WATER park, Private POOL, Comfort by A3G

Your dream getaway, starts In this 3beds 3 baths vacation home away from home! With private pool, Located in the amazing 5 stars resort at WINDSOR HILLS, only 3 miles away from all the wonders and magic of Disney. For Endless entertainment just walk to the Clubhouse and encounter the beautiful typhoon style pool, jacuzzi, brand new water park, arcade, fitness center, volleyball and basquetbol courts, kids playground and much more

Guest favorite

A spacious living room is showcased, featuring a modern sectional sofa and a large flat-screen TV mounted on a light-colored wall. Natural light filters through sheer curtains, enhancing the airy feel. A dining area with a contemporary table is visible, complementing the overall decor.

Home in Kissimmee

4.85 out of 5 average rating, 131 reviews

7754 Windsor Hills 6B Luxury Pool Home Near Disney

🌟 Welcome to Your Ultimate Windsor Hills Vacation Escape! 🌟 Discover the perfect blend of luxury, comfort, and fun in this newly renovated 6-bedroom, 4-bathroom villa at Windsor Hills Resort Orlando, located just 5 miles from Walt Disney World. With a private pool, game room, and access to world-class resort amenities, this home is designed for families and groups who want an unforgettable Orlando vacation.