Vacation rentals in Windsor Hills

A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.

4.98 out of 5 average rating, 106 reviews

Mickey's Lakefront Villa at Sunset Lakes

Updated Pics Dec 2024. We have no gas burning appliances. We abide by the AirBnB enhanced cleaning protocol. We want our guests to be happy, healthy and safe in their home away from home. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

A playful bedroom features twin beds with a colorful 'Aloha' theme. The living area showcases a dining table for six and a comfortable seating arrangement. A screened patio displays a private pool. An entertainment room is equipped with game tables and superhero-themed decor.

5 out of 5 average rating, 13 reviews

Disney Family Fun Villa

Windsor Hills - NEW Fully Renovated 6Bed&4Bath Villa with FREE pool heat - Private South Facing Pool and Spa - Smart TVs in every room - Free WIFI - Fully renovated & equipped kitchen with granite countertops & new appliances - 1.5 Miles to Disney - Close to Universal Studios, Shopping,Restaurants,Waterparks - Gated Community - Free Clubhouse Access with New Waterpark, Basketball, Tennis & Volleyball Courts & Putting Green - Newly renovated Marketplace Bar & Grill, Games Room & Convenience Store

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, 139 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.

4.87 out of 5 average rating, 118 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!

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.

4.97 out of 5 average rating, 137 reviews

*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 recreational game room is presented, featuring an air hockey table and a pool table centered in the space. Two gaming chairs are positioned near flat-screen monitors on the wall. Colorful LED lighting creates an engaging atmosphere in the room.

4.96 out of 5 average rating, 147 reviews

Mr. Clean's Cozy Disney Home w/ Luxury Finishes

• 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

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, 237 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, 125 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.

5 out of 5 average rating, 65 reviews

3 Miles 2 Disney | Fully Renovated | DisneyThemed

✩Welcome to Belle's Villa in Windsor Hills✩ Calling all Disney enthusiasts! Located just 5 minutes from the enchantment of Disney and a mere 2 minutes from an array of restaurants, supermarkets, souvenir shops, and highways, this property is an ideal haven for families and kids. Immerse yourself in the magic with this beautifully renovated townhome that boasts a fully equipped kitchen, free parking, and access to the extensive amenities at Windsor Hills.

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.

5 out of 5 average rating, 15 reviews

Hibiscus Villa w/ themed rooms, game room and pool

Welcome to your luxurious single story 4-bedroom getaway in the heart of a gated resort just 2.6 miles from the magic of Disney World! This meticulously designed vacation home offers not only comfort and convenience but also an array of resort amenities that promise an unforgettable stay. Your dream vacation home is not just a place to stay; it's a gateway to a world of enchantment and relaxation. Book your stay now and let the magic begin!

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, 242 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

4.93 out of 5 average rating, 173 reviews

A modern keypad lock is installed on a door, featuring illuminated numbers for easy access. Blurred in the background, a vibrant green plant adds a touch of nature to the entryway, enhancing the welcoming ambiance of the space.

Guest suite in Kissimmee

It's too much like a elegant mini-hotel (7)

It's too much like a elegant mini hotel with rich artistic atmosphere！ All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

Popular amenities for Windsor Hills, Four Corners vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Windsor Hills, Four Corners home rentals

4.79 out of 5 average rating, 19 reviews

Themed Rooms with Private Pool in Kissimmee

The image showcases a colorful game room featuring themed decor, cozy lounging spots, and engaging game tables. A separate view displays a vibrant community water park with palm trees and pool areas. The combined images highlight the fun and relaxation available in the villa's surroundings.

4.9 out of 5 average rating, 50 reviews

ReDesigned | Windsor Hills | Location | Water Park

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

A spacious bedroom features a tufted bed with elegant linens, complemented by decorative pillows. A chandelier hangs above, casting a soft glow. Natural light streams through large windows, offering a view of the outdoors. A mirrored nightstand and a small desk are included in the design.

5 out of 5 average rating, 19 reviews

5 Min to Disney | 4 Suites | Hot tub & BBQ

5 out of 5 average rating, 18 reviews

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

The exterior of the home features a spacious driveway, paved in light-colored bricks, leading up to an attached garage with an ornate door. A well-maintained lawn with green grass and palm trees is visible, complemented by a clear blue sky filled with clouds.

4.8 out of 5 average rating, 111 reviews

View the Disney fireworks from your pool!

A spacious living area features a large sectional sofa, paired with a round coffee table. Natural light floods in through sliding glass doors that open to the pool area. Decorative accents include coastal-themed artwork and soft lighting fixtures, enhancing the inviting ambiance.

4.82 out of 5 average rating, 135 reviews

Park Place! 7 Min from Disney, Pool, Theater

4.93 out of 5 average rating, 29 reviews

Mario's Arcade Pool House

Windsor Hills, Four Corners condo rentals

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.

4.95 out of 5 average rating, 159 reviews

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

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, 213 reviews

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

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

4.97 out of 5 average rating, 402 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Condo in Orlando

Waterfront Resort Condo near Disney and Universal

An aerial view captures a resort-style pool surrounded by lounge chairs and umbrellas, centered within the community. Nearby, tennis courts and a basketball court are visible, bordered by lush greenery. Ample parking spaces are noted in the surrounding area.

4.97 out of 5 average rating, 129 reviews

Sol and Mar Resort Style Condo - NO RESORT FEES

4.83 out of 5 average rating, 300 reviews

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

A Star Wars themed bedroom features two twin beds with themed bedding. A decorative quilt with a pattern of star fighters is placed over one bed, while the other is dressed in a space-themed cover. A bedside table holds a lamp shaped like a lightsaber, with blue walls adorned with framed artwork.

4.92 out of 5 average rating, 176 reviews

Themed Resort Condo | Pool | Spa | Mins to Disney

A spacious pool area is surrounded by palm trees and tropical landscaping. Sun loungers line the pool deck, and a water park with slides is visible nearby. The multi-level condo buildings create a vibrant backdrop, ensuring a family-friendly environment.

4.79 out of 5 average rating, 144 reviews

Lovely vacation condo close to Disney & Universal!

Other great vacation rentals in Windsor Hills

5 out of 5 average rating, 8 reviews

Windsor Hills, Disney/Universal, Pool/SPA, 5BR5BA

A view of a spacious resort-style pool area featuring various sections including a water park with slides and a splash pad. Surrounding palm trees offer shade, while lounge chairs are positioned around the pool's edge, creating an inviting atmosphere for relaxation.

4.94 out of 5 average rating, 82 reviews

Poolside 3 Bed Vacation Retreat in Windsor Hills

4.94 out of 5 average rating, 33 reviews

Callaghan Cantina

A two-story villa is presented with a tiled roof and a welcoming front entrance. Lush greenery and flowering plants enhance the manicured lawn, while a spacious driveway leads to a two-car garage. Clear skies provide a bright backdrop to the home's inviting façade.

4.91 out of 5 average rating, 23 reviews

6BR/5BA DisneyVilla, Pool+Spa, GameRoom, Clubhouse

A vibrant pool area features floating toys around the water. The themed bedroom showcases a spacious bed with grey bedding against a colorful mural. A green water slide spirals down into a bright play area, while a character and colorful beds highlight fun for young guests. An arcade room displays classic games alongside modern consoles.

4.94 out of 5 average rating, 51 reviews

Themed Family Pool Home 10 Min to Disney Game Room

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, 57 reviews

Mickey Train Bed, Free Waterpark, 10 min 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, 34 reviews

Turkey, Touchdowns & 75” TV! Disney Magic 4mi

An outdoor dining area is displayed, featuring a white table surrounded by six grey chairs. A large TV is mounted on the wall, showcasing a performance. A stainless steel grill is positioned nearby, complemented by drinks and a platter of fresh strawberries on the table.