Holiday rentals in Windsor Hills

4.93 out of 5 average rating, 176 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

4.97 out of 5 average rating, 174 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!

The exterior of the house is showcased, featuring a two-story design with light-colored walls and a prominent entrance. A spacious driveway accommodates up to four vehicles, bordered by well-maintained green lawns and trees. The property is set within a landscaped community.

4.95 out of 5 average rating, 172 reviews

Highest Rated Minutes to Disney! -Newly Renovated

• Newest house in the #1 community in the Disney Area, Windsor Hills • Only home with 7 bedrooms in the community (3 KING beds) • Extra privacy: only one side & no rear neighbors • 4 children themed bedrooms (Mickey, Star Wars, Toy Story, & Frozen) • Onsite, driveway parking for 4 vehicles • FREE pool heat + BBQ with all rentals • Fully equipped + stocked kitchen • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1000 Mbps • Property is managed directly by owner

4.94 out of 5 average rating, 110 reviews

Villa in Kissimmee

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"!

The living room features a playful Disney-themed design with a comfortable sectional sofa and an entertainment unit. A light-filled bedroom showcases a large bed with subtle Disney accents. The kitchen is equipped with modern appliances, and a dining area presents seating for multiple guests. A bird's-eye view reveals a sparkling pool area surrounded by lounge chairs.

4.97 out of 5 average rating, 109 reviews

Stunning Villa located 5-10 Min from Disney

Welcome to this BRAND-NEW dreamscape Vacation Villa with private views. Located at the desirable Summerville Resort offering a PRIME location, only 10 minutes from Disney World and 20 minutes from Universal Orlando, Sea World and Aquatica. Amazing entertainment and dining within minutes from your Villa, Disney Springs, Sunset Walk, City Walk, Disney’s Boardwalk, Walmart, Starbucks and more. This Villa is hypoallergenic and carefully cleaned and sanitized. The perfect getaway for your family!

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

Villa in Kissimmee

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!

Superhost

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, 119 reviews

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

A house perfect for families, located just minutes from Disney and other attractions in the Orlando area. This beautiful Windsor Hills pool home follows all federal, state, county, & CDC guidelines. All of our properties are properly cleaned for your safety. Maximum of 9 guests. This nearly 2,000 sq ft air-conditioned home has 4 bedrooms 4 bathrooms and a private pool. The house sleeps up to 9 people. Price includes taxes. House rules prohibit parties, pets, and smoking indoors.

5.0 out of 5 average rating, 6 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.