Holiday rentals in Windsor Hills

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.

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!

*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!

Themed Villa:10 min to Disney: Pool, Gameroom, BBQ

Welcome to Colorful Haven, 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 an amazing theme. 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—See Details Below!

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.

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.

Retreat w/ Game Room, Pool, Spa, BBQ | Near Disney

Welcome to your dream vacation home in Orlando! Ideally located just minutes from Disney World, this 6-bedroom retreat is perfect for families and large groups. Relax in your private north-facing pool with BBQ grill, enjoy the fun themed bedrooms and game room, or unwind in the spacious living areas. With the clubhouse and resort-style amenities just a short 10-minute walk away, this home offers the perfect mix of comfort, fun, and convenience.

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!

Modern Resort stay +Private Pool

Sleek, modern townhome in Windsor Hills Resort—just 2 miles from Disney! 3 bedrooms (fun kids' bunk room + luxe master), private plunge pool, and 5★ resort perks: water park, pool, spa, bar, kids club, mini golf, and more. Walkable, gated, family-friendly. Steps from Walmart & dining. Your dream Florida stay—without the all-inclusive price tag! Your vacation should feel effortless—and this townhome delivers just that!

Windsor Hills Single Level 4BR Home, Pool, GameRm

Welcome to this beautiful 4-bed, 4-bath Windsor Hills villa, just a few miles from Disney World! Perfect for families, this modern, spacious vacation home offers comfort, style, and access to resort amenities with no parking or resort fees. Relax, recharge, and create unforgettable memories in this family-friendly Orlando vacation rental, combining convenience, charm, and fun for an unforgettable Disney getaway.

Villa del Sole at Windsor Hills Resorts

Welcome to Villa Del Sole at Windsor Hills Resort! If you're planning a vacation to Florida, look no further than our luxurious 5-bedroom, 5-bathroom villa at Windsor Hills Resort. Designed to impress guests of all ages with its 2 kid-themed bedrooms and extensive amenities, Villa Del Sole promises a memorable stay. Make some memories at this unique and family-friendly place.

Fully Renovated w Heated pool, 3 miles from Disney

Located 3 miles from Disney, Infinity Blue Villa is a fully renovated 5BD/5BR rental property located at Windsor Hills Resort, a secure gated and quiet community The villa sleeps 10 guests. All 5 bedrooms have ensuite bathrooms. The game room is equipped with an air hockey table, a foosball table, a dual shot basketball game, an arcade and a PS5 console.