Vacation rentals with a pool in Windsor Hills

A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.

4.98 out of 5 average rating, 105 reviews

Mickey's Lakefront Villa at Sunset Lakes

Updated Pics Dec 2024. We have no gas burning appliances. We abide by the AirBnB enhanced cleaning protocol. We want our guests to be happy, healthy and safe in their home away from home. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

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.

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.

A serene backyard pool area is enclosed by a screened lanai, featuring two lounge chairs adorned with vibrant blue and green cushions. Lush greenery and trees are visible beyond the pool, enhancing the peaceful view. The clear water reflects the cloud-dotted sky.

4.96 out of 5 average rating, 169 reviews

4 bedroom, south facing pool 3 miles to Disney

Create family memories in our stunning pool home with Star Wars, Minnie and Mickie themed twin rooms. Elegant and comfortable king bed master bedroom with your own private bathroom and soaking tub! Delightful queen bedroom that also features its own private bathroom with shower. Enjoy a heated south facing pool (heating extra charge) with no rear neighbors. We are located in a guard gated community that features a large pool, clubhouse with a gym, arcade, movie room, and various sports courts.

A spacious pool area is featured, surrounded by palm trees and lounge chairs. The expansive waterpark includes vibrant waterslides, providing a lively atmosphere. A relaxing hot tub is also visible nearby, complemented by a well-maintained landscaping that enhances the resort's inviting ambiance.

4.98 out of 5 average rating, 172 reviews

Poolside 3Br~Windsor Hills~Waterpark~2mi to Disney

Your Windsor Hills Getaway starts here! This top-rated condo overlooks the resort pool & waterpark and is just minutes from Disney World! New appliances and updated furnishings, this 3rd floor condo sleeps 8, with plenty of parking. The screened-in balcony can’t be beat, overlooking the pool, hot tub, and waterpark with waterslides! The clubhouse is just steps away, with a store, food, drinks, game room, and fitness center. No resort, parking, or hidden fees. Full access to all amenities!

4.97 out of 5 average rating, 135 reviews

An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.

Villa in Kissimmee

*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!

4.96 out of 5 average rating, 145 reviews

A recreational game room is presented, featuring an air hockey table and a pool table centered in the space. Two gaming chairs are positioned near flat-screen monitors on the wall. Colorful LED lighting creates an engaging atmosphere in the room.

Villa in Kissimmee

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

4.96 out of 5 average rating, 167 reviews

A queen bed with white linens is centered in this room, complemented by matching nightstands and lamps. Behind the bed, a large mural depicts a castle under a starry sky. A mirror reflects the room's decor, adding to the bright and open atmosphere.

Townhouse in Kissimmee

Heated Mickey Pool, Frozen, Slides, Next 2 Disney

✨ Experience the magic as you step into our 3 bedroom townhome in the closest resort to the Disney Parks, Windsor Hills. Relax in your private, heated Mickey pool. Be transported to a land of ice and snow in a Frozen-themed bedroom. Watch your favorite movie on one of 4 smart TVs. Take a break from the parks by enjoying the resort pool, hot tubs, water park, movie theater, playgrounds, and more. Experience all the magic together with family and friends. Book today! ✨

A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.

5 out of 5 average rating, 236 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.

4.9 out of 5 average rating, 300 reviews

A bright living area features a light-colored sofa and a modern side table with a decorative lamp. Natural light floods through large windows, illuminating a dining space with a table and chairs, alongside a kitchen counter visible in the background.

Townhouse in Kissimmee

Disney fireworks new house - 5 minutes to Disney

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.

4.91 out of 5 average rating, 242 reviews

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

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

The aerial view showcases a spacious pool area surrounded by lush palm trees and lounge chairs. A bright water slide is visible in the background, leading to the pool. A serene lake serves as a picturesque backdrop, enhancing the resort's atmosphere.

4.86 out of 5 average rating, 192 reviews

One in a Minion condo your kids will love +450Mbps

Enjoy of sophisticated and modern accommodations on your next visit to Orlando. This One in a Minion themed two bedroom condo boasts 1082 SQ FT of living space and it's fully equipped for 6 guests. Conveniently located on the ground floor and a short stroll to the clubhouse, pool and dueling water slides. It features a smart lock, High-speed WIFI Internet +450Mbps, cable TV, telephone line, linens & towels and washer/dryer.

4.87 out of 5 average rating, 132 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.

Popular amenities for Windsor Hills rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A collage of images showcases the villa's vibrant interiors and amenities. The staircase features colorful beach-themed decor. The open living area contains comfortable seating and artistic wall murals. Bedrooms are themed with playful elements, and the outdoor area features a private pool and spa surrounded by greenery.

4.95 out of 5 average rating, 20 reviews

Paradise Cove at Windsor Hills Resorts

A clear view of a spacious outdoor pool area is presented, surrounded by a landscaped garden. Comfortable white lounge chairs are positioned around the pool, which features a water feature. Colorful umbrellas provide shade, enhancing the inviting atmosphere of the community.

4.93 out of 5 average rating, 150 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

A modern kitchen area features a large island with three sleek bar stools. Stainless steel appliances, including a gas stove and microwave, complement the white cabinetry. A dining table is visible in the background, surrounded by comfortable chairs and illuminated by natural light.

5 out of 5 average rating, 34 reviews

Fantastic 4 Suites Villa 5 min to Disney

5 out of 5 average rating, 10 reviews

4 minutes to Disney - Sleeps 14, Arcade, Pool

The image showcases a dynamic Star Wars-themed laser arena featuring vibrant space-themed decor and accessible game elements. The private heated pool area is surrounded by a screened enclosure, providing extra comfort. Adjacent, two twin beds are positioned in an accessible suite, equipped with assistive devices.

4.95 out of 5 average rating, 22 reviews

Windsor Hills Handicap-Accessible Home,Pool,Disney

5 out of 5 average rating, 18 reviews

Fun+Game Room+Outdoor Theater+Themed BRs+Pool/Spa

A private splash pool is enclosed within a screened patio, featuring a stone surface for easy movement. Two red lounge chairs are positioned alongside the pool, with greenery visible in the background, creating a sense of openness and tranquility.

4.8 out of 5 average rating, 10 reviews

Perfect Townhome Near Disney!

4.96 out of 5 average rating, 192 reviews

A private pool area featuring a clear blue pool with spa and surrounding palm trees. A giant outdoor chess set is visible nearby, along with a colorful tube slide leading to a vibrant bunk bed room. A game table with billiards is also showcased in the movie theater room.

Home in Four Corners

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

Condo rentals with a pool

A spacious living area features two light blue sofas with orange accent pillows, positioned around a wooden coffee table. A decorative wall clock and art pieces add character, while a glimpse of the kitchen is visible in the background, showcasing modern appliances and an inviting atmosphere.

4.9 out of 5 average rating, 321 reviews

Beautiful Beach Style Condo minutes from Disney

4.95 out of 5 average rating, 185 reviews

3161-305 Resort Lake View Disney Universal Orlando

Superhost

A comfortable living room features a spacious sectional sofa adorned with decorative cushions. A large TV is mounted on the wall, displaying a serene landscape. Light enters through sliding glass doors, leading to a balcony, enhancing the room's bright ambiance.

4.8 out of 5 average rating, 202 reviews

Magic Stay at Windsor Hills! 2 bedroom apartment!

A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.

4.97 out of 5 average rating, 193 reviews

303_To Infinity & the Ocean Breeze Apartment

The living room features a comfortable sofa with colorful accent pillows, a coffee table, and a flat-screen TV mounted on the wall. A round dining table with chairs is visible in the background, along with artwork and decor that add a touch of elegance.

4.86 out of 5 average rating, 212 reviews

@Look@ ~ 3bed/2bath/1st floor! ~ Sleeps 7!

An aerial view of the community water park features vibrant water slides and a children's water play area. Lounge chairs are arranged around the expansive pool, surrounded by lush greenery. Additional seating is provided near the water slides, creating an inviting space for relaxation and fun.

4.85 out of 5 average rating, 195 reviews

Heated Waterpark 10 mins to Disney in Windsor Hill

Superhost

A spacious bedroom is adorned with a blue accent wall featuring a starry pattern. A large, plush bed covered in a soft blue throw and white linens is centrally placed. A framed picture is mounted above the bed, and a small plant adds a touch of greenery.

4.9 out of 5 average rating, 244 reviews

Disney Oasis by the lake

Condo in View Park-Windsor Hills

A vibrant children's room features a twin-over-full bunk bed with colorful bedding. The walls are painted in cheerful red and yellow tones, adorned with whimsical cloud and star decorations. A toy storage area holds stuffed animals and games, and a cozy seating area enhances the playful atmosphere.

5 out of 5 average rating, 177 reviews

Mickey's Imagination Condo at Windsor Hills Resort

Home rentals with a private pool

An open living space features a comfortable beige sectional sofa with colorful accent pillows. A dining table is visible beside a modern kitchen with stainless steel appliances. Large sliding glass doors provide a view of the pool area, enhancing the connection to the outdoors.

Villa in Championsgate Village

Wr001or (1stfororlando)

A spacious living area is highlighted by a large wall-mounted TV above a modern electric fireplace. The white sectional sofa, accented with colorful pillows, faces a sleek coffee table on a patterned rug. Natural light floods in through large windows draped with light curtains.

4.14 out of 5 average rating, 7 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

The exterior of the home features a two-story structure with a light beige facade and a tiled roof. Lush landscaping, including palm trees and shrubs, enhances the entrance, while a spacious driveway leads to a two-car garage.

Beautiful 9 Br Pool Home In the Solterra Resort!

4.95 out of 5 average rating, 116 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Villa in Kissimmee

4.78 out of 5 average rating, 255 reviews

Visit Disney World from a Sunny Home with a Pool

The image displays four distinct areas of the villa. A games room features a foosball table and a billiard table with a laundry area in the background. A cozy bedroom showcases a queen bed with nightstands. A private screened pool invites relaxation. A kitchen area includes modern appliances and seating at the bar.