Family-friendly holiday 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, 194 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!

A colorful kids' retreat features vibrant, themed wall art depicting racing characters against a bright, rainbow backdrop. A flat-screen TV is mounted on the wall, and a multi-drawer storage unit is positioned nearby. The room is designed to inspire imagination and enjoyment.

4.94 out of 5 average rating, 113 reviews

*NEW*FREEwtrprk/5mins2disney/3Bdm/freebreakfast

Before exploring your vacation home- please click the heart and save us as a favorite!! This truly does help us be seen and is greatly appreciated. Plus, you can always find us when you are ready to book :) check out our website theprimrosewh and find us on IG MINUTES to DISNEY WORLD & US 192 with lots of restaurants/shops/walmart 1min. NEWLY renovated BRIGHT & VIBRANT 3 bed, 3 bath END UNIT townhome with private pool in the popular WINDSOR HILLS Closest townhome to the CLUBHOUSE steps away

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!

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, 147 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

4.98 out of 5 average rating, 112 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.

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, 170 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.

An aerial view showcases a resort-style pool surrounded by lounge chairs. A colorful water park with slides is located nearby, complemented by lush greenery and palm trees. Multiple buildings are visible in the background, offering a welcoming atmosphere for families.

4.85 out of 5 average rating, 185 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. All amenities included in cost: 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

4.93 out of 5 average rating, 165 reviews

Windsor Hills townhouse w/ pool & game room

Welcome to your Disney-area home base - perfect for families and fun-filled stays just minutes from the parks. Enjoy space to relax, play, and recharge in a resort setting designed for all ages: - Sleeps 7 | 3 bedrooms | 4 beds | 3 baths - Private heated splash pool - open all year - Mickey-themed kids’ room w/ Xbox Series X - Free resort access - pool, hot tub & movie theater - Fast wifi, kitchen & in-unit washer/dryer - Family-friendly w/ crib, high chair & strollers

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, 176 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

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

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, 204 reviews

Magic Stay at Windsor Hills! 2 bedroom apartment!

5 out of 5 average rating, 69 reviews

3 Miles 2 Disney | DisneyThemed | Fully Renovated

An engaging game room showcases colorful murals and a variety of arcade games, including basketball and foosball. A vibrant Toy Story-themed bedroom features bunk beds and playful decor, while a view of the private heated pool is presented from the charming living area, surrounded by large windows.

4.91 out of 5 average rating, 33 reviews

Themed villa wt Pvt Pool near Disney|Gameroom, BBQ

5 out of 5 average rating, 11 reviews

Disney Pool Home / GameRoom / Free Water Park

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

4.82 out of 5 average rating, 304 reviews

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

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, 106 reviews

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

4.86 out of 5 average rating, 429 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 !

Superhost

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

Superhost

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.

Apartment

4.85 out of 5 average rating, 119 reviews

Westgate Vacation Villas - 1 Bedroom

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.

4.9 out of 5 average rating, 307 reviews

Disney fireworks new house - 5 minutes to Disney

A cozy living area features a light-colored sofa adorned with textured cushions, alongside a warm-toned armchair. Wall art in neutral hues adds character, and a wooden coffee table is centrally positioned. The kitchen area boasts wooden cabinetry and modern pendant lighting above the breakfast bar.

4.92 out of 5 average rating, 104 reviews

Boho Bliss Escape• Poolside•Minutes from Adventure

The exterior of the house displays a light blue facade with white trim and multiple windows. A well-manicured garden with shrubs borders the entrance, while a concrete pathway leads to the front door. Tall trees provide shade in the front yard.

4.88 out of 5 average rating, 218 reviews

Disney Home Windsor Hills 3BED 3BATH Pool Parking

Family-friendly home rentals with a pool

A spacious living area features a large sectional sofa and a cozy armchair, set against a dark accent wall. Natural light streams through expansive glass doors that open to a private heated pool area. Decorative plants and a modern light fixture add a stylish touch.

4.95 out of 5 average rating, 38 reviews

free waterpark-2 king suites-minutes to parks

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!

4.8 out of 5 average rating, 10 reviews

Windsor Hills Home w/Arcade Game Room|Near Disney

A whimsical children's bedroom features a train-themed bunk bed with a vibrant yellow slide. The walls are decorated with a mural depicting a lush landscape, complemented by cartoon elements. A 50” Roku TV is mounted on the wall, while colorful bedding enhances the playful atmosphere.

4.91 out of 5 average rating, 58 reviews

Mickey Train Bed, Free Waterpark, 10 min to Disney

5 out of 5 average rating, 21 reviews

Your Sun, Fun and Everything Relaxation Retreat!

An aerial view of the Windsor Hills Resort pool area is showcased, featuring vibrant green and yellow water slides alongside a large blue pool. Lush palm trees surround the area, creating a relaxing atmosphere, while guests enjoy the amenities under the clear sky.

5 out of 5 average rating, 36 reviews

Lakeview 3Br Perfect for Disney/Universal Families

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.

4.98 out of 5 average rating, 41 reviews

Pvt Pool~2 King Suites~Disney 4mi~Free H2O Slides