Vacation rentals in Windsor Hills

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, 24 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, 151 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 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, 110 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 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, 158 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 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.

4.87 out of 5 average rating, 144 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!

4.98 out of 5 average rating, 122 reviews

11 am checkout, Windsor Hills, Family, Disney.

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.

4.99 out of 5 average rating, 104 reviews

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.

4.99 out of 5 average rating, 249 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 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.

4.97 out of 5 average rating, 37 reviews

Epic Arcade Disney Home w/ Pool | Sleeps 14

🏰 Epic Arcade Disney Home – 3 Miles to Parks Stay in this fully themed 6BR home designed for unforgettable family fun - just minutes from the parks Highlights: 🎮 One of the most unique arcade rooms in Windsor Hills (air hockey, basketball, racing + more) 👑 Princess room and 🐉 dragon-themed room kids love 🏊 Private pool and spa 📍 3 miles to Disney 🌴 Windsor Hills Resort amenities (water park, slides, gym & more) 🛏️ Sleeps 14 comfortably

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.

4.96 out of 5 average rating, 25 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!

4.85 out of 5 average rating, 13 reviews

A modern living area features a spacious grey sofa facing a large flat-screen TV mounted on the wall. Natural light fills the room through expansive glass doors, which open to a private plunge pool area surrounded by tropical plants.

Townhouse in Kissimmee

Modern Resort stay +Private Pool

Sleek, modern townhome in Windsor Hills Resort—just 2 miles from Disney! 3 bedrooms (fun kids' bunk room + luxe master), private plunge pool, and 5★ resort perks: water park, pool, spa, bar, kids club, mini golf, and more. Walkable, gated, family-friendly. Steps from Walmart & dining. Your dream Florida stay—without the all-inclusive price tag! Your vacation should feel effortless—and this townhome delivers just that!

5 out of 5 average rating, 76 reviews

Townhouse in Kissimmee

Windsor Hills | Pool | 2.5mi to Disney | Themed

Welcome to Belle’s Villa — your family’s ideal home base just minutes from Disney. Skip the cramped hotel room and enjoy your own private pool, thoughtfully designed spaces, and a home where both kids and parents can truly relax. Located in the highly sought-after Windsor Hills Resort, you’ll be close to the parks while enjoying a quiet, comfortable retreat at the end of each day.

Popular amenities for Windsor Hills, Four Corners vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Windsor Hills, Four Corners home rentals

4.94 out of 5 average rating, 64 reviews

Livin' the Dream, 3Kings, Closest FREE Resort WDW

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.

4.93 out of 5 average rating, 44 reviews

Themed villa: Pvt Pool: Near Disney: Gameroom, BBQ

5 out of 5 average rating, 23 reviews

15 minutes to Disney - Sleeps 14, Arcade, Pool

5 out of 5 average rating, 48 reviews

Once upon a galaxy: Star Wars/fairytale retreat

4.91 out of 5 average rating, 11 reviews

Villa 2655, Heated Pool/Grill, Game Rm, & PS5

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, 69 reviews

ReDesigned | Windsor Hills | Location | Water Park

An inviting private pool area is shown within a screened enclosure, featuring clear blue water and a rounded pool shape. Comfortable outdoor seating is placed beside the pool, with lush greenery decoratively lining the wall, enhancing the tranquil space.

4.97 out of 5 average rating, 33 reviews

Home, Private Pool, 10 min to Disney, 3 BR/2 Baths

Superhost

4.91 out of 5 average rating, 11 reviews

EPIC! Themed-Arcade-Theatre-Pool Table-3mi>Disney

Windsor Hills, Four Corners condo rentals

Superhost

A large condominium structure stands under a clear blue sky. Several palm trees frame the entrance, and well-maintained landscaping lies around the building. Vehicles are parked in designated spaces in front, with a visible path leading to the entrance.

4.72 out of 5 average rating, 127 reviews

Minutes to Disney best of Home, with a Resort feel

The living area features a comfortable sofa facing a large smart TV mounted on the wall. Natural light enters through windows, enhancing the space. A round coffee table sits in the center, surrounded by potted plants, with a dining area and a modern kitchen visible in the background.

4.93 out of 5 average rating, 215 reviews

Magical Stay Near Disney & ESPN

A bright living area features a comfortable brown sofa and loveseat, accented with decorative pillows. A modern coffee table is centered on tiles that enhance the spaciousness. Natural light filters through large windows, while a flat-screen TV is mounted on the wall, framed by stylish light curtains.

4.86 out of 5 average rating, 161 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

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.

4.91 out of 5 average rating, 231 reviews

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

4.94 out of 5 average rating, 238 reviews

Andy's Toy Chest at Resort Minutes from Disney!

A spacious living area features a large leather sofa and wall art, creating an inviting space. The open-concept layout connects to the kitchen and dining area, while large windows allow natural light to fill the room. A vibrant resort-style pool area and water slides are visible outside.

4.96 out of 5 average rating, 160 reviews

Disney Oasis

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.

4.8 out of 5 average rating, 157 reviews

Lovely vacation condo close to Disney & Universal!

4.87 out of 5 average rating, 434 reviews

Westgate Vacation Villas - 1 Bedroom

Other great vacation rentals in Windsor Hills

A movie room designed for family entertainment features comfortable seating arranged in rows facing a large screen displaying animated characters. The walls are dark, enhancing the cinematic experience, while a framed movie poster adds a touch of décor to the space.

4.8 out of 5 average rating, 115 reviews

*Windsor Hills Ohana Oasis* 4/4 Disney Pool Home

5 out of 5 average rating, 23 reviews

Townhouse in Kissimmee

Parkside Windsor Retreat 15 Min Disney!

An outdoor dining area is presented under a screened enclosure, featuring a wooden table with seating for eight. A movie screen displays a scene from Disney Moana. The surrounding pool area includes lounge chairs, with vibrant colors reflecting in the evening sky.

5 out of 5 average rating, 27 reviews

Luxe Windsor Hills w/Poolside Theatre & GameRoom

4.81 out of 5 average rating, 16 reviews

Windsor Hills Home w/Arcade Game Room|Near Disney

5 out of 5 average rating, 4 reviews

Windsor Hills Lakeview •Walk to Waterpark •2mi WDW

4.94 out of 5 average rating, 102 reviews

The Manatee Manor | 5 BR•Windsor Hills•Game Room

A comfortable living area features leather seating arranged around a decorative coffee table. A large television is mounted on the wall, displaying a serene outdoor scene. Sliding glass doors provide a view of the private patio and pool area, enhancing natural light within the space.