Family-friendly vacation 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.

Newly Renovated Condo! 1.5 miles from Disney World

Make your next trip to Florida one to remember when you stay at our NEWLY RENOVATED 3 bedroom, 2 bath condo located at the Gated Resort Community of Windsor Hills, Four Corners. Just miles from Walt Disney World, Universal studios, Downtown districts, Shopping, golfing and many Restaurants, Windsor Hills has many resort's amenities that are perfect for the family vacation. Our condo grants access to an array of amazing amenities – water park, large pool, arcade room, movie theater and more!!

Luxury Mickey Themed Townhome in Windsor Hills Res

3 bed and 3 bath LUXURY Mickey themed townhome located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Mickey themed townhome is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The townhome offers the a screened private pool with pool fence and pool alarm for safety. All guests also have access to resort amenities including new waterpark. Lots of entertainment for all. * Security Deposit Require

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!

Brand new flooring, mattresses, AC, water heater and more! Disney SO close! Our Property Manager will see to any needs during your stay, a rental registration is required. Beautiful, clean and comfy condo in Windsor Hills Resort with a new WATER PARK and tons of amenities. Stainless appliances and granite, free wifi/cable, desk/charging station and PS 3 with games, Pack N play, stroller, high chair, wash/dryer, a starter kit of supplies. No hidden fees, free parking. Perfect for families!

It's too much like a elegant mini-hotel (2)

It's too much like a elegant mini hotel with rich artistic atmosphere！ All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

Toy Story Retreat Near Disney

Immerse yourself in the magic of Disney and create lifelong memories at your very own Toy Story Retreat. - Newly remodeled 3-bedroom, 2-bathroom condo - Family-friendly atmosphere with Disney-inspired design - Access to Windsor Hills Clubhouse with pools and gym - Ground-floor unit with greenspace views - Fully equipped kitchen and in-unit washer/dryer - Free WiFi and parking - Kid-friendly amenities like high chair and stroller - No extra fees, including resort fees

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Mr. Clean's Cozy Disney Home w/ Luxury Finishes

• 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

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.

Retro Retreat Themed 3BR + Waterpark Access

🛑 Stop scrolling. You’ve found it. This Disney-themed 3BR townhome ranks in the Top 10% of homes for ratings, reviews & reliability. 🎠 Just 2 miles from the parks, featuring a private plunge pool 💦 and standout 1950s-inspired retro décor 🎶✨ that sets it apart from cookie-cutter rentals. 🛌 Cozy themed rooms, 🐾 pet-friendly stays, and 🩱 resort pool & waterslides steps away. These dates disappear fast—book now!

StarWars Theme + Free Waterpark | 10 min to Disney

Family-friendly Star Wars Retreat in Windsor Hills Resort — just 10 minutes from Walt Disney World! Enjoy a private screened splash pool, smart TVs in every room, fully equipped kitchen with fun themed touches, and FREE access to resort waterpark, lagoon pool, hot tub, arcade, playgrounds, and sports courts. Washer/Dryer in the home. Spacious, modern, and perfect for multigenerational stays or longer vacations.

Disney-Inspired Suites • Game Room • Summerville

Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out