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, 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.

4.94 out of 5 average rating, 104 reviews

A vibrant water park area features colorful slides and splash pads. Water sprays from various playful fixtures, and guests can be seen enjoying the amenities. The backdrop includes a multi-story building with palm trees surrounding the area, providing a fun and engaging environment.

Flat in Kissimmee

Newly Renovated Condo! 1.5 miles from Disney World

Make your next trip to Florida one to remember when you stay at our NEWLY RENOVATED 3 bedroom, 2 bath condo located at the Gated Resort Community of Windsor Hills, Four Corners. Just miles from Walt Disney World, Universal studios, Downtown districts, Shopping, golfing and many Restaurants, Windsor Hills has many resort's amenities that are perfect for the family vacation. Our condo grants access to an array of amazing amenities – water park, large pool, arcade room, movie theater and more!!

4.97 out of 5 average rating, 152 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!

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

4.99 out of 5 average rating, 100 reviews

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.

Villa in Kissimmee

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.

A screened-in private splash pool is surrounded by comfortable seating, featuring playful Minion characters on the walls of the adjoining rooms. The layout includes vibrant décor and modern furnishings, creating a family-friendly space with direct access to outdoor relaxation.

4.82 out of 5 average rating, 161 reviews

Themed Pool Home 2 Miles to Disney

Welcome to your dream vacation home! - Newly remodeled 3 bedroom, 3 bathroom townhome with themed rooms - Private splash pool, fully screened-in - Prestigious Windsor Hills Resort with no resort fee - Access to a new kids water park, clubhouse, gym, and more - Free Wifi and fast internet for your Zoom meetings - 24 hour security and gated access - Have a pet? $250 pet fee on 1st; $125 each additional pet - Check out our 5 Star Reviews!

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.

4.96 out of 5 average rating, 158 reviews

Spring Discounts - 6 Mi. to Disney - Plunge Pool

📍 Amazing Location Near Disney • 6 miles to Walt Disney World • 15 miles to Universal Orlando Resort • 13 miles to SeaWorld Orlando • 30 miles to LEGOLAND Florida • 25 miles to Orlando International Airport • 1 mile to Walmart, Target, Publix & dining 🏡 4 bedrooms, each with a private bath. Smart TVs in every room. Private free heated plunge pool, plus resort pool access and free parking. One of the closest communities to 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, 246 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

A collage showcases various areas of Mickey's Star Wars Retreat. A spacious bedroom features a king-sized bed with blue accents. In another scene, a bright water park is viewed from above. An open kitchen with modern stools, a child's room with themed decor, and a cozy living area with a sectional sofa complete the visual narrative.

4.98 out of 5 average rating, 109 reviews

StarWars Theme + Free Waterpark | 10 min to Disney

Family-friendly Star Wars Retreat in Windsor Hills Resort — just 10 minutes from Walt Disney World! Enjoy a private screened splash pool, smart TVs in every room, fully equipped kitchen with fun themed touches, and FREE access to resort waterpark, lagoon pool, hot tub, arcade, playgrounds, and sports courts. Washer/Dryer in the home. Spacious, modern, and perfect for multigenerational stays or longer vacations.

4.95 out of 5 average rating, 139 reviews

Disney-Inspired Suites • Game Room • Summerville

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

5 out of 5 average rating, 4 reviews

Fully themed, free arcade, south facing pool & spa

5 out of 5 average rating, 74 reviews

3 Miles 2 Disney | DisneyThemed | Fully Renovated

5 out of 5 average rating, 59 reviews

An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.

Home in Four Corners

Gorgeous 5BR @ Encore Next to Disney - 305

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.

4.94 out of 5 average rating, 47 reviews

free waterpark-2 king suites-minutes to parks

4.93 out of 5 average rating, 59 reviews

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.

Apartment in Kissimmee

Fully Themed Harry Potter Magical Experience!

A vibrant gaming room features a blend of classic arcade machines and modern gaming consoles. Two large screens display colorful graphics, while two Daytona USA racing machines and various arcade units provide entertainment. A sleek red and black couch offers comfortable seating in this lively space.

4.95 out of 5 average rating, 91 reviews

Ultimate Adventure Villa Top Rated 5 Star Disney m

4.9 out of 5 average rating, 72 reviews

Themed Windsor Hills 6BR Private Pool Gameroom

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

Elegant Disney Themes | Pool, Hot Tub & Game Room

Family- and pet-friendly home rentals

A charming two-story cottage is featured, exhibiting a cheerful yellow exterior. A small balcony is visible above the entrance, flanked by white railings. Lush palm trees and landscaped foliage surround the property, enhancing the inviting open space in a sunny environment.

5 out of 5 average rating, 147 reviews

Margaritaville Cottage 10 Minutes to DisneyWorld!

4.95 out of 5 average rating, 107 reviews

Modern 3BR, Resort + Heated Pool, 10 Min Disney

4.99 out of 5 average rating, 145 reviews

A private pool area is illuminated in a soft green hue, surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, with a table set under an umbrella. String lights create a warm ambiance as the evening sky darkens.

Villa in Davenport

Magical Disney House-Pool & Hot Tub,Free Waterpark

4.89 out of 5 average rating, 102 reviews

A private pool and spa area is enclosed by a screen, offering views of a serene sunset through palm trees. The pool features a textured surface and a safety railing, with vibrant water reflecting the evening sky. A lush green lawn surrounds the space, contributing to the tranquil environment.

Villa in Davenport

25%off/Close to Disney/Hot Tub/Private Pool/Fenced

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

4.86 out of 5 average rating, 265 reviews

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

Westgate Vacation Villas - 1 Bedroom

4.92 out of 5 average rating, 103 reviews

A vibrant game room is showcased with neon accents and colorful lighting. Three black gaming chairs are positioned in front of a large screen, while a foosball table and a multi-game table are placed nearby. A netted structure adds a unique element to the playful environment.

Home in Davenport

Disney-Themed Home w/ Game Room & Private Hot Tub!

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.

4.89 out of 5 average rating, 314 reviews

Disney fireworks new house - 5 minutes to Disney

Family-friendly home rentals with a pool

4.79 out of 5 average rating, 14 reviews

Getaway Cove Villa

A spacious living area features a contemporary design with a large flat-screen TV mounted on the wall, surrounded by comfortable seating. A stylish coffee table is centered on a soft area rug, and decorative plants add a touch of greenery. The bright space is complemented by warm lighting.

4.95 out of 5 average rating, 22 reviews

Hibiscus Villa w/ themed rooms, game room and pool

A spacious two-story villa is surrounded by a manicured lawn and tropical landscaping. A paved driveway leads up to the entrance, framed by palm trees and vibrant greenery. The exterior features a light-colored stucco finish and a welcoming front porch.

4.89 out of 5 average rating, 18 reviews

5BD Formosa Gardens Near Disney (FG 7939)

A screened-in outdoor area features a private pool surrounded by a patio. Lounge chairs are positioned beside the pool, offering a relaxed space for sunbathing. Lush greenery is visible beyond the enclosure, creating a tranquil setting for outdoor enjoyment.

4.92 out of 5 average rating, 65 reviews

5BR Home w/Pool near Disney Animal Kingdom

5 out of 5 average rating, 3 reviews

NEW Stuning 09 Bedroom/LED At Pool/ Solara Resort

4.95 out of 5 average rating, 43 reviews

Free Waterpark, 2 Miles to Disney, Windsor Hills

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

A vibrant game room features themed decor with neon accents. The room includes an air hockey table, a dual basketball hoop game, and arcade machines. A large TV is mounted on the wall, and colorful lighting creates an engaging atmosphere for entertainment.