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

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

4.9 out of 5 average rating, 153 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.

Guest favorite

A themed room featuring bright yellow and black décor inspired by popular characters. A large TV is mounted on a wall with playful eye designs above it. A life-sized figure of a Minion stands beside a colorful, circular rug, creating a fun environment for guests.

Home in Kissimmee

4.88 out of 5 average rating, 8 reviews

10 Min to Disney |Themed | Sauna | Pool | Golf Sim

This 6BR dream villa is just minutes from Disney and fully redesigned for comfort and fun! 3 elegant bedrooms plus 3 themed rooms: Minions, Avatar, and Guardians of the Galaxy—plus a hidden Mario-themed speakeasy game room. A brand-new kitchen, bathrooms, and living spaces complete this magical escape. Recently completed down-to-the-studs renovation—every detail thoughtfully curated with luxury, comfort, and style in mind. Be among the first to experience it! Book now for an unforgettable stay!

Guest favorite

A townhouse exterior is shown beneath a gentle rainbow. Flanking palm trees provide a tropical setting, while the structure features multiple windows with white frames and dark shutters. A parked vehicle can be seen in front, enhancing the suburban feel.

Home in Kissimmee

4.88 out of 5 average rating, 112 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!

Superhost

Home in Kissimmee

4.85 out of 5 average rating, 124 reviews

Resort Home 3.5 miles to Disney with home theater

We welcome you to stay in our home located in the Windsor Hills community with a water park, slides, theatre and so much more! The house is just 3.5 miles from Disney’s Animal Kingdom. Our home has 6 large bedrooms including laundry in the home, an 8 seat home theatre, TVs in every room, a large swimming pool & spa with a large patio cover, plus a large kitchen fully equipped with everything you need for your stay. Please message us if you have any questions, we look forward to hosting you!

Guest favorite

An engaging game room showcases colorful murals and a variety of arcade games, including basketball and foosball. A vibrant Toy Story-themed bedroom features bunk beds and playful decor, while a view of the private heated pool is presented from the charming living area, surrounded by large windows.

Home in Kissimmee

4.88 out of 5 average rating, 24 reviews

Themed home 10min from Disney|Pool,Resort,Free BBQ

Welcome to The Colorful Cove—your vibrant family getaway near Disney! Kids will love the themed bedrooms with bunk beds and an exciting Mario themed game room packed with arcades and lots of fun games. Adults can enjoy sleek modern furnishings throughout and unwind in upgraded bathrooms. This spacious villa offers a private heated pool, movie nights, bbq grilling, and endless fun in a peaceful neighborhood. With colorful decor and attractions for all ages, it’s the ultimate Orlando retreat!

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, 294 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

A private outdoor space features a sparkling pool and a hot tub, both encased in a screened enclosure. A large dining table in vibrant turquoise seating is positioned beside the pool, surrounded by comfortable lounge chairs. Overhead lighting and decorative plants add to the ambiance.

Villa in Kissimmee

4.93 out of 5 average rating, 121 reviews

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

Closest FREE resort to Disney Parks! We've named it "Coral Cove" - a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in Dec 22! * Kitchen is loaded, & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! *Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! *New Roku smart TVs & NEST tech! *Every detail has been thought of!

Guest favorite

A playful bedroom features a wooden loft bed designed like a house, accompanied by a sturdy ladder. Soft bedding is arranged inside the loft. A colorful light fixture hangs from the ceiling, illuminating the room. A closet door can be seen in the background, beside a vibrant wall poster.

Home in Kissimmee

4.95 out of 5 average rating, 39 reviews

4 bed/ 4 bath Windsor Hills

Closest homes with pools to Disney 10-15 minutes drive. Walmart groceries, Starbucks 5 minutes very near. amenities liquor, pharmacies, smoke shops, restaurants, gas. Highway 192 close by.. 5 - 10 minutes in car. the full cancellation is meant for hurricanes, pandemics, etc. other exigencies. please don't book the house and tie up the calendar for many months only to cancel 10 days prior - it makes it harder to book last minute and cover mortgage and expenses on our side, etc.

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, 138 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, 230 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, 235 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

4.84 out of 5 average rating, 129 reviews

7754 - 6 Bedrooms w/ Pool & Water Park Included

🌟 Welcome to your ultimate vacation escape in the heart of Windsor Hills Resort! 🌟 This newly renovated 6-bedroom beauty is the perfect blend of luxury and fun, designed for families looking to unwind and create unforgettable memories. Just a stone’s throw from Disney World and surrounded by world-class dining, top-notch shopping, and Orlando’s hottest attractions, you’ll have everything you need for an amazing getaway.