Holiday rentals with a pool in Windsor Hills

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, 146 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.

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.

4.97 out of 5 average rating, 152 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!

A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.

4.86 out of 5 average rating, 138 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!

The exterior of the house is showcased, featuring a two-story design with light-colored walls and a prominent entrance. A spacious driveway accommodates up to four vehicles, bordered by well-maintained green lawns and trees. The property is set within a landscaped community.

4.97 out of 5 average rating, 155 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

The community pool area features a winding pool surrounded by palm trees and lounge chairs. A colorful water slide is visible, along with shaded cabanas. The well-maintained grounds include lush greenery and pathways leading to residential buildings in the background.

4.98 out of 5 average rating, 116 reviews

Family, Windsor Hills, Sleep In with 11AM Checkout

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.

4.97 out of 5 average rating, 78 reviews

Home mins to Disney, pool, arcade, waterslides

Welcome to Magic and Fun at Windsor Hills. Our enchanting Disney-themed 3-bedroom, 3-bathroom townhome offers all the comforts of home and features its own private plunge pool just steps away from the living room. Discover the ultimate getaway just moments away from the magic of Disney. Our entire home offers a sanctuary of comfort and convenience, meticulously designed to enhance your vacation experience. Newly renovated resort pool now OPEN!! Come and stay at Magic and Fun at Windsor.

A collage of vibrant images showcases the luxurious amenities available, featuring a spacious pool area, themed bedrooms, an arcade room, and outdoor seating. The photos capture a welcoming environment ideal for family gatherings and entertainment, beautifully arranged in a Mickey Mouse shape.

4.99 out of 5 average rating, 100 reviews

Cozy Themed Villa 6 BR | Close to Disney

🏖️☀️🏄‍♀️Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort — one of the closest communities to Disney World — you’ll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool — great for relaxing after a fun day at Disney.🌴👙🩳🥽🩴 ❤️❤️We'd love to welcome you here!

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, 244 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.

The image showcases a private pool surrounded by a screened lanai with colorful floatation devices resting on the water's surface. In the background, the open green space and Windsor Hills Resort amenities, including water slides and playgrounds, extend beyond the pool area, offering recreational opportunities.

4.96 out of 5 average rating, 49 reviews

Single-Level Pool Home, Resort Amenities, Disney

Welcome to this single-level fun house by FunStay Homes featuring unique themed rooms and a private pool/spa. - 24/7 gated community - Amazing Windsor Hills Resort amenities - No rear neighbors with open green space - Themed rooms: Harry Potter, Star Wars, Spiderman, Minions - 2 King Beds and 4 twin beds - Free Wifi and TV in every room - Pool/Spa heat available for an additional fee - Complimentary offerings include no resort fees

The game room features a foosball table and a pool table, offering ample space for entertainment. A large mural of an imaginative scene decorates one wall, while blue pendant lights illuminate the area. A utility unit is discreetly positioned in the corner.

4.8 out of 5 average rating, 25 reviews

Retreat w/ Game Room + Pool & BBQ | 8min Disney

Welcome to your dream vacation home in Orlando! Ideally located just minutes from Disney World, this 6-bedroom retreat is perfect for families and large groups. Relax in your private north-facing pool with BBQ grill, enjoy the fun themed bedrooms and game room, or unwind in the spacious living areas. With the clubhouse and resort-style amenities just a short 10-minute walk away, this home offers the perfect mix of comfort, fun, and convenience.

A private heated plunge pool is surrounded by a screened enclosure, ensuring safety and comfort. Colorful outdoor furniture invites relaxation, while a vibrant umbrella provides shade. The wall features a playful design, adding a touch of whimsy to the outdoor space.

4.94 out of 5 average rating, 52 reviews

*Magical Getaway* w/ Heated Pool! Close to Disney

Experience magic and adventure at our Disney-themed townhouse, ideal for families, friends, and Disney fans. Enjoy spacious rooms, vibrant Disney décor, and a private heated plunge pool. After a long day at the parks, unwind in cozy living spaces with modern amenities and movie nights. Located minutes from Disney World, it's the perfect base for a magical vacation. Create lasting memories in this enchanting, dream-like getaway!

4.83 out of 5 average rating, 214 reviews

A cozy living area is featured with comfortable seating, including a sleek sofa and stylish chairs. A contemporary fan hangs from the ceiling, while a wall-mounted TV is displayed above a dark cabinet. A dining area is set with a table and decorative plates, with views of the screened patio.

Townhouse in Kissimmee

Fun, Sun, Theme Parks and More

Build lasting vacation memories and sleep in style just minutes from Disney World. Your family will be at home in this spacious 3 bedroom townhouse with its own private heated pool (no extra charge) and full kitchen. And when you're not at Disney, it's just a 5 minute walk to the clubhouse and FREE heated pool and water park at the fabulous Windsor Hills resort.

Popular amenities for Windsor Hills rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 179 reviews

4 bedroom, south facing pool 3 miles to Disney

5 out of 5 average rating, 4 reviews

Fully themed, free arcade, south facing pool & spa

A state-of-the-art game room features plush recliner seats arranged in front of a large projection screen. The walls are adorned with vibrant Star Wars themes and artwork. Soft lighting highlights the ceiling's design, creating an engaging atmosphere for entertainment.

4.91 out of 5 average rating, 75 reviews

Jedi Training Camp Top Rated 5 Star Villa

4.76 out of 5 average rating, 133 reviews

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291

4.75 out of 5 average rating, 4 reviews

Lakeside Magic 5BR Disney Villa w/ Pool & Lakeview

A welcoming entryway is highlighted by a wooden staircase with white railing and a decorative mural on the wall. A green velvet bench sits beside a woven basket. A vibrant neon sign reads 'The happiest place on earth,' adding a cheerful touch to the space.

5 out of 5 average rating, 15 reviews

Magical Disney Themes | Pool, Hot Tub & Game Room

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.

4.88 out of 5 average rating, 124 reviews

Disney Escape at Windsor Hills

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.

4.82 out of 5 average rating, 17 reviews

Perfect Townhome Near Disney!

Condo rentals with a pool

An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.

4.93 out of 5 average rating, 180 reviews

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

The living area features a comfortable sofa facing a large smart TV mounted on the wall. Natural light enters through windows, enhancing the space. A round coffee table sits in the center, surrounded by potted plants, with a dining area and a modern kitchen visible in the background.

4.93 out of 5 average rating, 214 reviews

Magical Stay Near Disney & ESPN

4.83 out of 5 average rating, 164 reviews

A modern bedroom features a spacious bed adorned with red and gray textiles. A large circular light installation highlights the textured wall behind. Two floor lamps provide soft illumination, while a desk with a chair is situated nearby. Floor-to-ceiling curtains frame the window.

Condo in Davenport

Intense Space-Themed Condo Near Disney

4.82 out of 5 average rating, 310 reviews

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

A spacious pool area is surrounded by palm trees and tropical landscaping. Sun loungers line the pool deck, and a water park with slides is visible nearby. The multi-level condo buildings create a vibrant backdrop, ensuring a family-friendly environment.

4.79 out of 5 average rating, 151 reviews

Lovely vacation condo close to Disney & Universal!

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, 188 reviews

Poolside 3Br Windsor Hills, Waterpark, Disney 2mi

The exterior of the Westgate Vacation Villas showcases an elegantly designed building with multiple levels. Soft lighting from street lamps illuminates the entrance. Rows of golf carts are parked in front, surrounded by manicured landscaping and palm trees under a clear blue sky.

4.86 out of 5 average rating, 263 reviews

Westgate Vacation Villas - 1 Bedroom

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.

4.85 out of 5 average rating, 203 reviews

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

Other holiday rentals with a pool

5 out of 5 average rating, 3 reviews

Apartment in Kissimmee

°o° Modern 3B/2B Condo in Windsor Hills by Disney

4.88 out of 5 average rating, 51 reviews

A living area features a comfortable sofa adorned with colorful cushions, complemented by a blue armchair with a yellow accent pillow. A wooden coffee table sits centrally, while a flat-screen TV is positioned on a dark wood console. Natural light enters through sliding glass doors, leading to a private balcony.

Apartment in Kissimmee

Beautiful Condo near Disney

5 out of 5 average rating, 74 reviews

Townhouse in Kissimmee

3 Miles 2 Disney | DisneyThemed | Fully Renovated

A two-story villa is presented with a tiled roof and a welcoming front entrance. Lush greenery and flowering plants enhance the manicured lawn, while a spacious driveway leads to a two-car garage. Clear skies provide a bright backdrop to the home's inviting façade.

4.89 out of 5 average rating, 28 reviews

6BR/5BA DisneyVilla, Pool+Spa, GameRoom, Clubhouse

The image captures a vibrant outdoor resort area featuring a lagoon-style pool and waterslides in shades of blue and green. Sun loungers are arranged around the pool, surrounded by palm trees and open green spaces. A two-story condo building stands in the background.

4.95 out of 5 average rating, 38 reviews

Sunny Condo Retreat~Less-Stress|Organized|Clean

The image showcases four views, including a modern kitchen with granite countertops, a vibrant water park with slides, a spacious pool area with sun loungers, and a cozy bedroom featuring a comfortable bed and natural light from large windows.

4.88 out of 5 average rating, 26 reviews

Windsor Hills Condo Near Disney

5 out of 5 average rating, 14 reviews

Condo in Orlando

3BR Presidential-Bonnet Creek-On Disney Grounds!