Holiday rentals in Windsor Hills

4.93 out of 5 average rating, 178 reviews

Apartment in Kissimmee

New Luxury Condo near Disney

Steps from the swimming pool and water park. Covid-19 safe. 500 megabytes of Wi-Fi! The apartment has a privileged location: it is in the gated community of Windsor Hills, the closest to the parks. 10 minutes from Animal Kingdom, Epcot, Hollywood Studios and Magic Kingdom and 25 minutes from Universal parks. In addition, it has easy access to the airport (US 192, FL 417 and I-4), Downtown Orlando, Miami and all the attractions of the Central Florida region (Daytona Beach, Clearwater, St. Petersburg).

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.

5.0 out of 5 average rating, 28 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 - BBQ Grill- 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 & Putting Green - Newly renovated Marketplace Bar&Grill, Games Room, Convenience Store

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.

5.0 out of 5 average rating, 120 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!

4.99 out of 5 average rating, 161 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.

4.97 out of 5 average rating, 175 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

*Hibiscus Hideaway* 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.

4.85 out of 5 average rating, 158 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!

5.0 out of 5 average rating, 7 reviews

Townhouse in Kissimmee

Disney Inspired 3 Bedroom Townhome w/Private Pool!

Our Mickey themed townhome is 15-20 minutes away from the Disney World parks giving YOU the best of both worlds. With 1 bedroom downstairs and two bedrooms upstairs, each with their own bathroom and shower, you'll have the perfect place to stay that gives a Disney Magic VIBE without the chaos of staying inside Disney World resort areas. Our townhome is located in the gated, guarded Windsor Hills Resort Club and is a 60 second walk from amenities like fitness center, pools and game room.

4.87 out of 5 average rating, 403 reviews

A bright bedroom features a spacious bed adorned with colorful bedding and a throw pillow. Two bedside lamps are positioned on dark nightstands. Natural light flows through large windows, and an ensuite bathroom is visible in the background.

Townhouse in Kissimmee

Splendid house 1, 5 miles to Disney

Crestwynd Bay condominium is only 1,5 miles to Disney Parks entrance. Walmart is 0,3 miles,very near. Beautiful and complete townhouse with 3 bedrooms, 3 bathrooms, kitchen equipped, laundry room, free WIFI, exterior area . Self check-in. This condo has community pool and children playground. Parking for car in front of the house. Is five minutes from target ,pharmacies , restaurants and fast foods. Ten minutes of outlets and 15 min from Universal parks and sea world. Great location!

5.0 out of 5 average rating, 8 reviews

Magic and Marvel Manor 15 Min to Disney

Welcome to Heroes & Princesses Hideaway! Just 15 minutes from Disney, this magical retreat features immersive Marvel, Disney, Moana, and Frozen-themed rooms the whole family will love. After a day at the parks, relax in spacious living areas, enjoy family fun, and create unforgettable memories. Perfect for families seeking comfort, adventure, and a little Disney magic close to all the attractions!Bring the whole family to this great place with lots of room for fun.

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, 256 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.

4.98 out of 5 average rating, 129 reviews

An overview of luxury amenities includes a vibrant water park with slides, a spacious pool surrounded by palm trees, and a modern game room featuring foosball and striking wall art. Nearby, a tranquil bedroom setup and an inviting private pool are also highlighted.

Villa in Kissimmee

Luxury Villa Windsor Hills Resort 2 miles / Disney

4 bed and 4 bath LUXURY VILLA located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Villa is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The Villa offers the ultimate game room, outdoor dinning, and a screened private pool & spa. All guests also have access to resort amenities. Lots of entertainment for all. * Security Deposit Required with reservation

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.