Vacation 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, 142 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, 174 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.

4.97 out of 5 average rating, 142 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!

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, 144 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

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, 180 reviews

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

Your Windsor Hills Getaway starts here! This 5-star 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!

4.98 out of 5 average rating, 111 reviews

Family, Disney, Windsor Hills, 11 am 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.

A light-filled living area features a gray sectional sofa with accent pillows, arranged around a low coffee table. A patterned rug sits beneath, while a tall floor lamp adds warmth. Large sliding glass doors provide views of the outdoor patio, framed by sheer curtains.

4.96 out of 5 average rating, 107 reviews

Star Wars Bungalow | 4 Mi to Disney | Waterpark

Enjoy your stay at this gorgeous, freshly renovated home! MINUTES to Walt Disney World. • 🎢 WATER SLIDES • 🌟THEMED Star Wars Retreat •🍴 Entertainer's Kitchen • 🤱 BOB Jogger Stroller available • 🏖️ Private patio with HEATED POOL • ☕️ **Latte and Coffee Bar** • 📶 Fiber High Speed Wi-Fi Thoughtfully curated for your ultimate ENJOYMENT. Beautiful modern interior, ceramic tile floors, and high quality decor throughout. This impeccable 3 bedroom, 3 bath home sleeps up to 8.

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.

4.96 out of 5 average rating, 172 reviews

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, 240 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.

A two-story vacation home is showcased with a tiled roof and a well-maintained front yard. Flanking the house are two neighboring properties, while a paved driveway leads to a garage. Green grass surrounds the structure, and the sky features a mix of clouds and blue.

4.88 out of 5 average rating, 127 reviews

2584 - 6 Bedroom w/ Pool and Water Park Included

Welcome to Your Ultimate Vacation Escape at Windsor Hills Resort! This charming vacation home in Windsor Hills Resort offers six spacious bedrooms and is perfect for the entire family. Located in one of the finest gated communities in the area, Windsor Hills Resort features 24-hour security, ensuring only permitted guests have access to the neighborhood. We’re just a short distance from Disney parks, shopping, dining, and many of Orlando’s top attractions.

4.98 out of 5 average rating, 103 reviews

An overview of luxury amenities includes a vibrant water park with slides, a spacious pool surrounded by palm trees, and a modern game room featuring foosball and striking wall art. Nearby, a tranquil bedroom setup and an inviting private pool are also highlighted.

Villa in Kissimmee

Luxury Villa in Windsor Hills Resort, 2 miles / 5

4 bed and 4 bath LUXURY VILLA located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Villa is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The Villa offers the ultimate game room, outdoor dinning, and a screened private pool & spa. All guests also have access to resort amenities. Lots of entertainment for all. * Security Deposit Required with reservation

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.

4.91 out of 5 average rating, 243 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

Popular amenities for Windsor Hills rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 5 reviews

NEW!-Fun-Relaxing-Private-Beautiful Vacation Home

An outdoor living space features comfortable seating arranged around a fire pit, facing a large screen displaying animated characters. The screened-in area includes a private pool, while lush greenery surrounds the space, offering a serene atmosphere for relaxation and entertainment.

4.83 out of 5 average rating, 18 reviews

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

A private swimming pool is surrounded by a screened enclosure, featuring a poolside theatre with a large projector screen. Lush greenery is visible beyond the pool area, creating a serene environment. Lounge chairs are positioned nearby for relaxation.

4.9 out of 5 average rating, 112 reviews

8 mins. to Disney W/Poolside Theater & Game Room

A themed room designed with a sci-fi aesthetic features dark blue walls illuminated by ambient LED lighting. A comfortable gray couch and an ottoman are positioned near a large wall-mounted television, creating an inviting entertainment space.

4.97 out of 5 average rating, 147 reviews

Winter Special - 6 Mi to Disney - 4 Master Suites

4.8 out of 5 average rating, 10 reviews

Windsor Hills Home w/Arcade Game Room|Near Disney

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.

4.96 out of 5 average rating, 45 reviews

4 bed/ 4 bath Windsor Hills

Superhost

5 out of 5 average rating, 4 reviews

Epic Home-FREE Water Park/Disney/South Facing 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 Wheelchair Friendly Home,Pool,Disney

Condo rentals with a pool

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

4.86 out of 5 average rating, 125 reviews

Stylish Condo 20 mins to Disney/King Bed

Superhost

A light-filled living area is furnished with a sectional sofa and a wooden coffee table. Two framed artworks are mounted on the wall beside a lamp. Tall windows with dark curtains offer views of the outdoor landscape, while a small chair and television provide additional seating and entertainment options.

4.77 out of 5 average rating, 245 reviews

Dumbo House

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, 214 reviews

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

A vibrant outdoor water park is depicted, featuring two large water slides and a colorful kids' splash area. Surrounding palm trees provide shade, and a spacious pool area is visible in the background, inviting relaxation and fun.

4.9 out of 5 average rating, 215 reviews

Disney's Doorstep, 3 Bed 2 Bath, Waterslides!

A spacious living area features a large leather sofa and wall art, creating an inviting space. The open-concept layout connects to the kitchen and dining area, while large windows allow natural light to fill the room. A vibrant resort-style pool area and water slides are visible outside.

4.97 out of 5 average rating, 149 reviews

Disney Oasis

A large stone sign displays the name 'Windsor Palms' surrounded by lush greenery and colorful flowerbeds. Palm trees are seen flanking the sign, under a clear blue sky, indicating an inviting entrance to the gated resort community.

4.93 out of 5 average rating, 140 reviews

Resort condo minutes from Disney!!!

4.82 out of 5 average rating, 303 reviews

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

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, 180 reviews

Mickey's Imagination Condo at Windsor Hills Resort

Other vacation rentals with a pool

4.98 out of 5 average rating, 89 reviews

Luxury Disney Townhome, Mickey POOL, Water Slides,

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, 21 reviews

Paradise Cove at Windsor Hills Resorts

A cozy dormitory space features two bunk beds draped with red fabric. A wooden door leads to the room, where a starry ceiling complements golden light fixtures. A Victorian-style chair and a small trunk add charm, while natural light filters through a window with red curtains.

4.93 out of 5 average rating, 57 reviews

Fully Themed Harry Potter Magical Experience!

5 out of 5 average rating, 29 reviews

Once upon a galaxy: Star Wars/fairytale retreat

A tranquil pool area features a clear blue pool and adjacent spa, both enclosed within a screened-in area. Lush greenery is visible beyond the pool deck, with a serene lake view in the background under a bright, blue sky.

4.92 out of 5 average rating, 84 reviews

Windsor Hills 5 bed/5 bath Pool Home, Games Room

5 out of 5 average rating, 18 reviews

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

A private backyard oasis features a heated pool and hot tub, framed by a screened enclosure. Large sun loungers are placed on the pool deck, offering a relaxing space. The scenic view includes lush greenery with no rear neighbors, ensuring privacy for guests.