Family-friendly 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).

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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, 119 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!

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4.95 out of 5 average rating, 214 reviews

Townhouse in Kissimmee

Themed room Walk to amenities 5 miles to Disney

Just 4 miles from Disney, our luxury townhome is your family’s perfect escape! With a private splash pool, brand-new 65” Smart TV, and family-friendly gear (stroller, pack n’ play, high chair), you’ll have everything needed for a carefree stay. Located across from Windsor Hills Resort’s clubhouse, enjoy resort perks like a pool, splash pad, fitness center, and theater! Sleeps 8 comfortably with 3 en-suite bedrooms, including a themed Disney beach kids’ room. Fun, comfort, and convenience await!

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4.99 out of 5 average rating, 159 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.

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4.97 out of 5 average rating, 173 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!

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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, 157 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!

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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"!

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4.89 out of 5 average rating, 103 reviews

A landscaped resort area is showcased, featuring a large swimming pool that reflects the evening sky. Surrounding palm trees and well-maintained greenery create a serene environment. The elegant clubhouse is visible in the background, inviting guests to explore the amenities.

Villa in Kissimmee

Relaxing Vacation Resort Villa

Enjoy this beautiful vacation villa in the 24-hour guard-gated Windsor Hills Resort with one of the BEST LOCATIONS IN THE RESORT, just steps away from the Resort-Style Pool & Waterpark and Poolside Cafe. RELAX and enjoy the convenience of being only 2 miles from Walt Disney World and less than 15 mins from other major theme parks. You can visit the parks in the morning, come back to have lunch at the pool, and be back in the parks for dinner and fireworks with ease. Have a Great Vacation!

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4.91 out of 5 average rating, 242 reviews

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.

Apartment in Kissimmee

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

Welcome to your dream vacation! This 3 bedroom, 2 bath, is right on Disney's doorstep, this amazing vacation rental has all the amenities you'd put on your dream list. Two water slides, a kids splash park, walk in pool, movie theater with wheelchair access, game room, fitness center, putting green, playground, shop for snacks, and more! This condo also comes fully furnished with a washer/dryer, WiFi, elevator for wheelchair access, and more. This is sure to be your relaxation destination.

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4.87 out of 5 average rating, 401 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!

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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.

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