House holiday rentals in Windsor Hills

Disney Pool Villa | Windsor Hills | Sleeps 8

BOOK EARLY! Rated top 1% & Guest Favorite. Our popular home fills up 3-4 months in advance. 3BR/3BA Private Pool Villa in Windsor Hills Resort, Kissimmee! Newly renovated, gated resort, 3 miles to Disney World. Modern beach-coastal design, updated kitchen, family-friendly layout. Free parking, Wi-Fi, full resort access (pool, splash park, gym, playground). Near Universal (20 min), SeaWorld (18 min), Legoland (40 min). Perfect location for vacations Disney trips, sports events, and conventions.

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

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.

Epic Arcade Disney Home w/ Pool | Sleeps 14

🏰 Epic Arcade Disney Home – 3 Miles to Parks Stay in this fully themed 6BR home that sleeps 14 and is designed for unforgettable family fun. Professionally cleaned and managed for a smooth, stress-free stay Highlights: 🎮 One of the most unique arcade rooms in Windsor Hills — a hit with kids and adults alike. (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 🛏️ Sleeps 14

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!

NEW 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!

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!

★Completely Renovated★ 3 mi to Disney+Free Resort!

Closest FREE resort to Disney Parks! Sandpiper Shores is a 6 bedroom 4 bathroom luxury villa that sleeps 14. BEST STAR RATING - OVER 200 REVIEWS! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting, & ROCK CLIMBING WALL! * Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW grill, & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

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

Welcome to The Colorful Cove, a vibrant family getaway near Disney and other top attractions. Enjoy an exceptional experience as you splash in a private pool, play fun games, enjoy outdoor dining and relax in rooms with updated furnitures and amazing themes. Plus, enjoy access to resort amenities including the waterpark, sports courts, fitness center and clubhouse Disney World-8 min drive Old Town-14 min drive Universal Studios-30 min drive Book For Unforgettable Memories In Kissimmee!

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.

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!

Themed Rooms • Private Pool • Family Dream Stay

Step into a fully themed, design-forward escape just minutes from Walt Disney World®, where every room tells a story and every detail is curated for unforgettable stays. Whether you're here for family fun or a magical getaway, this home blends comfort, style, and experience in one place. Unwind in your private pool and spa overlooking the tranquil Windsor Hills lake—where sunset swims and quiet mornings become part of the memory.