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

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Kissimmee

4.9 out of 5 average rating, 130 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.

Superhost

Condo in Kissimmee

4.82 out of 5 average rating, 103 reviews

C2774-203-Windsor Hills Resort/3 Bedrm/Water Park

Experience the magic of Disney and create memories for a lifetime at your very own “Avengers Retreat" Conveniently situated less than 2 miles from the Walt Disney Resort, you can bring home the fantasy and adventure to this family-friendly condo in the highly sought-after resort of Windsor Hills. The floor plan boasts 3 Bedroom and 2 bathrooms and the entire design is inspired by your favorite Disney films FULL ACCESS to the resort Clubhouse (Pools/Water Park/Gym) NO resort fees; Free Parking

Guest favourite

Home in Kissimmee

4.99 out of 5 average rating, 110 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 favourite

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 favourite

Townhouse in Kissimmee

4.96 out of 5 average rating, 166 reviews

DISNEY R US! UNIVERSAL IS TOO!!!

This Is The Way!!! 🗡️ Our Magic is your Magic, only 3 Miles from the park and in a gated community with all the amenities needed to stay and rest a day if you want to. Head off to take a journey on the back of a banshee. Maybe try some grey stuff at Be Our Guest restaurant in Magic Kingdom. Travel only 15 minutes to wave a wand like Harry Potter in Universal Studios. Then come back and relax in the gated community pool/spa area for an night of rest. We want your trip to be Magical and Epic!

Guest favourite

Villa in Kissimmee

4.94 out of 5 average rating, 120 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 favourite

Home in Kissimmee

4.97 out of 5 average rating, 108 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

Superhost

Townhouse in Kissimmee

4.87 out of 5 average rating, 335 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 favourite

Condo in Kissimmee

4.94 out of 5 average rating, 133 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.

Guest favourite

Condo in Kissimmee

4.85 out of 5 average rating, 160 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

Guest favourite

Home in Kissimmee

5 out of 5 average rating, 192 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.

Superhost

Condo in Kissimmee

4.81 out of 5 average rating, 276 reviews

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

Clean and comfy with Disney SO close! Our Property Manager will see to any needs during your stay! The condo is beautifully renovated in Windsor Hills Resort with a new WATER PARK and tons of amenities. New carpet, 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!