Holiday rentals in Windsor Hills

4.93 out of 5 average rating, 177 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 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!

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.

4.86 out of 5 average rating, 146 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, 175 reviews

*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!

4.94 out of 5 average rating, 110 reviews

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

Welcome To The Manatee Manor - A 5 bedroom, 5 bath home located in Windsor Hills, right in the heart of Kissimmee's tourist area, and mere minutes to the gates of Disney! With a feel of 'Better than home', you'll never want to leave. Outfitted with all the standards that you come to expect (Pool, Hot Tub, plenty of space, and serene décor), in addition to themed rooms, big screen smart TVs, and complimentary pool/hot tub heat - life doesn't get any better than when you stay at "The Manor"!

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.

4.99 out of 5 average rating, 111 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!

4.87 out of 5 average rating, 402 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, 255 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.

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.