Family-friendly vacation rentals 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 modern kitchen features stainless steel appliances, bright white cabinets, and a clean countertop. In the background, large windows provide a view of the outdoor space. The cozy living area showcases a comfortable seating arrangement and tropical-themed decor, with light streaming through the glass doors.

4.94 out of 5 average rating, 193 reviews

5 miles to Disney- Private Pool - Arcade Games

Just 4 miles from Disney, our luxury townhome is your family’s perfect escape! With a private splash pool, brand-new 65” Smart TV, and family-friendly gear (stroller, pack n’ play, high chair), you’ll have everything needed for a carefree stay. Located across from Windsor Hills Resort’s clubhouse, enjoy resort perks like a pool, splash pad, fitness center, and theater! Sleeps 8 comfortably with 3 en-suite bedrooms, including a themed Disney beach kids’ room. Fun, comfort, and convenience await!

4.97 out of 5 average rating, 143 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!

4.98 out of 5 average rating, 120 reviews

A spacious themed room is depicted, featuring an imaginative design with a dark, cosmic ceiling. The room includes a large blue slide and a staircase, adjacent to cozy bean bag chairs for seating. Colorful space-themed murals enhance the playful atmosphere.

Villa in Kissimmee

4mi to Disney | Games | Private Pool

Get ready to make memories of a lifetime just over 3 miles to Disney when you stay at this newly renovated Star Wars and Lego-themed private pool villa. Located in Formosa Gardens Estates, a prestigious gated community, our home is professionally furnished with multigenerational families in mind and can comfortably sleep up to 15 guests. After a trip to the parks, enjoy a refreshing dip in the private pool and rest those tired feet in the spa (pool heat included in stays after 10 Dec 2025!).

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, 145 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

4.93 out of 5 average rating, 164 reviews

Family townhouse near Disney w/ pool

Welcome to your family-friendly Disney-area retreat, where easy mornings and playful evenings set the tone for your stay. This themed townhouse offers space to relax, resort perks, and a private splash pool just minutes from the parks. - Sleeps 7 | 3 bedrooms | 4 beds | 3 baths - Private heated splash pool (year-round) - Mickey-themed kids’ room w/ game console - Resort pool, waterslides, movie theater & gym - Full kitchen, washer & dryer, fast wifi - Crib, high chair & strollers included

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.

4.94 out of 5 average rating, 169 reviews

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

Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

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, 108 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 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, 241 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 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, 173 reviews

Mickey Pool • Frozen • Waterpark • Near Disney

✨ Step into the magic at our 3-bedroom Windsor Hills townhome — one of the closest gated resorts to the Disney Parks. Enjoy your private heated Mickey pool, an immersive Frozen-themed bedroom, and four Smart TVs for relaxing after park days. Take a break from the crowds with access to Windsor Hills’ resort pool, hot tubs, water park, movie theater, playgrounds, and more. A fun, comfortable home base for families and friends visiting Disney. ✨

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

4.97 out of 5 average rating, 121 reviews

3BD/3BA Themed House Near Disney

Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Popular amenities for Windsor Hills family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 204 reviews

Magic Stay at Windsor Hills! 2 bedroom apartment!

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

4.76 out of 5 average rating, 121 reviews

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

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, 216 reviews

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

5 out of 5 average rating, 68 reviews

3 Miles 2 Disney | DisneyThemed | Fully Renovated

5 out of 5 average rating, 11 reviews

Disney Pool Home / GameRoom / Free Water Park

The collage showcases various areas of the lakeside home. Highlights include a private patio dining set, a resort-style pool, a comfortable living space with a dining table, and vibrant bedrooms featuring bunk beds and colorful decor. The picturesque lake view complements the outdoor spaces.

4.99 out of 5 average rating, 138 reviews

Lake View - 5 Miles to Disney!

A children's suite hosts a whimsical treehouse-themed bunk bed with a slide, shaded by mural-painted trees. Soft green carpet covers the floor, and a plush gray sofa is positioned nearby. A stuffed Winnie the Pooh character adds a playful touch to the setting.

5 out of 5 average rating, 40 reviews

Holidays, Hoops, & Hunny @ the Pooh-L! Disney 4 mi

Family- and pet-friendly home rentals

A private pool area is showcased, featuring a spacious pool with an integrated spa. The space is illuminated with soft purple lighting, enhancing the tranquil atmosphere. The screened enclosure provides protection while allowing views of the surrounding greenery.

4.87 out of 5 average rating, 105 reviews

Cinderella’s, 4 miles Disney, Pool • Spa • Games

4.86 out of 5 average rating, 427 reviews

A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.

Villa in Kissimmee

OMG! Disney Area, Movie Theater, Game Room & Pool!

An engaging Star Wars-themed game room features a foosball table, arcade machines, and a spacious seating area. Murals depict scenes from the franchise, with screens displaying games. The room is designed for fun and entertainment, offering a vibrant environment for guests.

4.82 out of 5 average rating, 154 reviews

Orlando Home with Private Pool & Game Room !

A spacious living area features a large sectional sofa with an oversized ottoman, inviting comfort. Colorful wall decals of Mickey and Minnie Mouse add a fun theme, while framed pictures decorate the walls. Natural light enters through the vertical blinds of the sliding glass door.

4.91 out of 5 average rating, 251 reviews

Disney R US! Universal Escape! 3BDR 3Bath

A playful bedroom features a bunk bed framed by vibrant dinosaur murals and soft green lighting. The room combines adventure and comfort with a cozy seating area and themed decor, creating an engaging space for families.

4.72 out of 5 average rating, 116 reviews

Fantasy World Jurassic Park Villa, Free Water Park

A spacious living area features a blend of modern and mid-century design elements. A large wooden dining table is accompanied by comfortable seating, while a green feature wall and decorative plants add a touch of nature. Light filters through the windows, illuminating the inviting space.

4.91 out of 5 average rating, 141 reviews

Disney Themed Townhome- 5 miles to Disney Property

The exterior of the home displays a welcoming front porch, accompanied by a bright red door. Lush greenery lines the pathway, with neat shrubs creating a private ambiance. The light beige facade is complemented by a well-maintained lawn leading up to the entrance.

4.82 out of 5 average rating, 239 reviews

Disney’s Home Away From Home (5 miles from Disney)

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.

4.85 out of 5 average rating, 119 reviews

Westgate Vacation Villas - 1 Bedroom

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 37 reviews

free waterpark-2 king suites-minutes to parks

A private screened-in pool area features a clear blue pool surrounded by a spacious deck. Two lounge chairs are set alongside the pool, providing a space for relaxation. The backdrop includes a green lawn and trees, creating a serene outdoor environment.

4.94 out of 5 average rating, 31 reviews

Luxury 6 Bedroom Pool Home in Windsor Hills

An expansive lagoon-style pool is surrounded by lush palm trees and comfortable seating areas, inviting relaxation. Below, a dining table is set with white plates, bowls, and cutlery, arranged on a decorative placemat, showcasing a cozy dining atmosphere.

4.96 out of 5 average rating, 82 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

5 out of 5 average rating, 15 reviews

4 minutes to Disney - Sleeps 14, Arcade, Pool

4.8 out of 5 average rating, 10 reviews

Windsor Hills Home w/Arcade Game Room|Near Disney

A private heated pool area is surrounded by a screened enclosure, featuring lounge chairs and outdoor dining options. The pool is complemented by multi-colored lights, creating an inviting space. The image also includes three themed kids' bedrooms, showcasing vibrant decor and comfortable sleeping arrangements.

4.9 out of 5 average rating, 69 reviews

Themed Windsor Hills 6BR Private Pool Gameroom

5 out of 5 average rating, 32 reviews

Once upon a galaxy: Star Wars/fairytale retreat

A spacious poolside dining area is featured, with a large table set for meals. Elegant place settings include green plates and silverware. A large screen is visible, showcasing outdoor entertainment, with colorful sunset hues reflecting through the screened enclosure.