House 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, 144 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 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, 123 reviews

Disney Escape at Windsor Hills

This is a fantastic family vacation townhouse located just four miles from Walt Disney World! Inside, you'll find a full kitchen with a breakfast bar, a dining table for six, and a living area with a TV for streaming all your favorite channels! Right outside, take a refreshing swim in your private pool. Guests will be able to enjoy a wide variety of resort-style amenities close by including a community clubhouse with a game room, Olympic-size pool, children's waterpark, putting green, and more!

A spacious living area features a comfortable dark gray sofa and a stylish coffee table, surrounded by neutral decor. A large flat-screen TV is positioned on a modern console against a bright wall, while natural light fills the space through multiple windows.

4.97 out of 5 average rating, 170 reviews

Cozy Disney Oasis Pool Home 10 Mins from Parks!

Our charming, pet-friendly home is located in the prime area of Kissimmee, Florida. Your family will be close to Disney parks, restaurants, Old Town, and Downtown Disney. Just bring your bag—we have everything you need! Settle into our fully equipped home, thoughtfully designed to create lasting memories with family and friends. Enjoy the Florida weather by cooling off in our open-air pool or grilling by the poolside lounges. Relax in our airy bedrooms, including Mickey and Minnie themed rooms!

A spacious living area is seen, featuring a large sectional sofa adorned with decorative pillows. Natural light enters through expansive glass doors, providing a view of the backyard and pool area. Elegant light fixtures hang from the ceiling, complementing the neutral color palette.

5 out of 5 average rating, 103 reviews

Cinderella's HolidayVilla-Minutes from Disney-NEW!

• Newest house in the #1 resort community in the Disney Area, Windsor Hills • ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. • 2 FUN children themed rooms (Star Wars & Frozen) • Onsite, driveway parking for 3 vehicles • FREE pool heat+BBQ with ALL rentals • Fully equipped+stocked kitchen; including Keurig machine • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1,000 Mbps! • Property is managed directly by owner FULLY REMODELED in Sept 2022!

An outdoor dining area features a large, custom-built farmhouse table surrounded by benches. Refreshments and fruit are displayed on the table, with a private pool visible in the background, enclosed by a screened lanai. Lush green grass complements the serene atmosphere.

4.95 out of 5 average rating, 216 reviews

★Completely Renovated★ 3 mi to Disney+Free Resort!

Closest FREE resort to Disney Parks! Sandpiper Shores is a 6 bedroom 4 bathroom luxury villa that sleeps 14. BEST STAR RATING - OVER 200 REVIEWS! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting, & ROCK CLIMBING WALL! * Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW grill, & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

4.98 out of 5 average rating, 180 reviews

*Modern Luxury Reunion Oasis | Pool, Spa & Cinema

Wow-factor luxury meets unforgettable family fun, just minutes to Disney, at this show-stopping home in the exclusive Reunion Resort. Step outside to a massive 2,400-sq-ft southwest-facing pool deck with outdoor kitchen, private pool, overflow spa, and no rear neighbors—perfect for all-day sun and sunset swims. Inside: private movie theater, billiards game room, and spectacular Star Wars & Frozen II theme bedrooms with tube slide, plus Xbox and PlayStation for nonstop entertainment.

The exterior of a two-story home is shown, featuring a well-maintained lawn and a paved driveway leading to a two-car garage. A circular entrance is highlighted by a decorative front door, with large windows allowing natural light to flow inside. The sky is partly cloudy.

4.97 out of 5 average rating, 116 reviews

Manor on Knottingham Near Disney

Welcome to "Manor on Knottingham," nestled in the heart of Four Corners. The rustic charm, adorned with vintage Disney-inspired decor, transports guests to a bygone era of beloved characters and timeless tales. Outside, enjoy the sparkling blue pool and warm summer weather. A great place for family and friends. "Manor on. Knottingham" promises an extraordinary stay, where the magic of Disney and the comfort of a home merge into an unforgettable experience.

A game room is presented with a red and neutral color scheme, featuring a billiard table with a set of colorful pool balls arranged on it. A television is mounted on the wall, and a dartboard is visible. The space is accented with vibrant wall art and seating areas.

4.9 out of 5 average rating, 133 reviews

No Airbnb Fee | Newly Renovated 4BR w/ Pool!

**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

The spacious living area features a light-filled environment with comfortable seating arrangements, including a sofa and armchair. A coffee table sits in the center, accompanied by a decorative bowl of sunflowers. A large television is positioned against a wall, complemented by neutral-toned decor.

4.89 out of 5 average rating, 104 reviews

4BD 2BA Kissimmee Pool House near Disney

This 4BD 2BA house is in a quiet part of Kissimmee less than 5 miles south of Disney! The master suite features a king bed and attached bath with double sinks and walk-in shower. The second room contains a queen bed and the last two rooms have two twins each. There is a fully equipped kitchen and two work spaces, each containing a desk, office chair and computer monitor. Shops, entertainment, and restaurants are just a few minutes away.

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, 153 reviews

Winter Special - 6 Mi to Disney - 4 Master Suites

📍 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!

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.

4.83 out of 5 average rating, 160 reviews

Orlando Home with Private Pool & Game Room !

Elegant 4/2 home with forest views, appointed space comfortably accommodates up to 11 guests, making it ideal for families and large groups. Professionally decorated with modern furniture and designer decor, the home has a fully equipped kitchen and a welcoming living area. Enjoy outdoor dining and take a dip in the heated pool, or unwind in the thrilling Star Wars theme Game Room. “10 Minutes to all the Disney Parks”

4.94 out of 5 average rating, 114 reviews

Enchanted Home Near Disney w/ Arcade Room

Welcome to our enchanting 3-bedroom, 3-bathroom haven, meticulously designed to embrace your family's comfort and imagination! Step into themed suites straight out of your favorite stories, including Toy Story and Mickey Mouse. With a spacious capacity for up to 10 guests, your Disney adventure begins right here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Popular amenities for house rentals in Windsor Hills

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A swimming pool is situated in front of a club house, surrounded by palm trees and lounge chairs. The pool is clear and reflects the sky, while the club house features large windows and a rounded roof design. Sunlight illuminates the area.

4.94 out of 5 average rating, 68 reviews

Designer House <Next to Disney> Gated Resort

5 out of 5 average rating, 5 reviews

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

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, 35 reviews

Themed villa wt Pvt Pool near Disney|Gameroom, BBQ

5 out of 5 average rating, 12 reviews

Disney Pool Home / GameRoom / Free Water Park

A private screened patio features a dining set with a glass table and wicker chairs, overlooking a serene lake. The clear blue sky is reflected in the water, while a pool glistens nearby, creating a peaceful outdoor space.

4.96 out of 5 average rating, 50 reviews

Serene 6BR Retreat | Pool, Lake View, Near Disney

A spacious living area features two gray sofas facing a television mounted on the wall. A circular ottoman and a round coffee table are placed on a patterned area rug. Natural light enters through vertical blinds, and a potted plant adds a touch of greenery.

4.92 out of 5 average rating, 74 reviews

3 Bedroom / 2.5 Bath Townhome (Mins to Disney)

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, 14 reviews

Elegant Disney Retreat | Pool, Hot Tub & Game Room

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.

4.93 out of 5 average rating, 75 reviews

8 Mins To Disney W/Poolside Theater & Games Room

Weekly house rentals

5 out of 5 average rating, 15 reviews

Magic Stay near Disney

4.97 out of 5 average rating, 39 reviews

4 Miles to Disney! Private pool -5 Bedroom Home

5 out of 5 average rating, 4 reviews

Your Cozy 3 BD Home w/ Private Hot Tub & BBQ Gril

5 out of 5 average rating, 3 reviews

Home Luxury 03 Beds/ Close Disney At Magic Village

The exterior of a light blue house features a welcoming entrance with a dark blue door and decorative molding. Large windows allow natural light to illuminate the interior, surrounded by well-maintained green shrubs. The pathway leads up to the entrance, enhancing accessibility.

4.73 out of 5 average rating, 30 reviews

Windsor Hills Town Home

4.97 out of 5 average rating, 75 reviews

Home mins to Disney, pool, arcade, waterslides

A screened-in pool area is visible, featuring a clear blue pool bordered by a smooth concrete deck. Two chairs are positioned beside the pool, with a palm tree and colorful decorations enhancing the surroundings. The backdrop includes a white privacy fence and greenery.

4.91 out of 5 average rating, 66 reviews

Cozy Home close to Disney with a Heated pool!

5 out of 5 average rating, 9 reviews

Disney Southfield Getaway!

Private house rentals

A cozy living area features a large sectional sofa with decorative pillows, positioned near a wall-mounted flat-screen television. A light-colored coffee table and a woven basket are present. Natural light fills the room through the large window, adorned with white blinds, creating a welcoming ambiance.

4.91 out of 5 average rating, 97 reviews

Resort 2 bedroom Townhome near Disney World

A collage showcases a vibrant water park with colorful slides, a game room featuring a pool table and retro arcade games, a spacious villa exterior with palm landscaping, and a sunlit pool area enclosed by a screened lanai, inviting relaxation.

4.8 out of 5 average rating, 41 reviews

Luxurious home 2 miles from Disney - Windsor Hill

4.8 out of 5 average rating, 5 reviews

Fun & Relaxing Oasis | Near Parks + Private Pool

A spacious screened-in pool area features a clear blue pool with colorful floats resting on its surface. Lounge chairs and a small table provide seating options, surrounded by palm trees and tropical landscaping, contributing to a private outdoor retreat.

4.94 out of 5 average rating, 62 reviews

3 BR Private Pool Home 5 miles from Disney

4.94 out of 5 average rating, 99 reviews

Lakeside Paradise, 15 min Disney + Saltwater Pool

4.94 out of 5 average rating, 32 reviews

Magical 3bd Townhome near Disney

A private outdoor area features a heated pool with integrated spa and water fountain, surrounded by lounge chairs under a blue sky. A shaded dining area is visible alongside a summer kitchen, complemented by greenery and a basketball hoop in the background.

5 out of 5 average rating, 21 reviews

Modern Luxury 5BR Pool Movie+Game Rm @Encore 7770