Holiday rentals with a pool in Windsor Hills

Boho Bliss Escape• Poolside•Minutes from Adventure

🌿✨ Welcome to Boho Bliss Townhouse! ✨🌿 Your boho-chic retreat near Kissimmee ’s top attractions! 🏰 8 min Walt Disney World w/o traffic!!!! 🎢 25 min Universal ✈️ 25 min Orlando Airport 🐊 Gatorland 🛍️ Old Town Kissimmee 🎡 ICON Park features The Wheel, dining, and SEA LIFE Aquarium 🌊 Lake Tohopekaliga 🍖 Medieval Times offers dinner and a show. 🎢 Fun Spot America provides amusement park fun 🌿 Kissimmee Lakefront Park offers a relaxing lakeside experience 🌳 Shingle Creek Park is perfect for nature

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.

*Brand New!* 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!

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

Family, Disney, Windsor Hills, 11 am checkout.

Walk into your home away from home. Enjoy a relaxing stay. Located on 4th floor. Enjoy morning coffee on a screened-in balcony or a late snack. Pet-free home. Please NO Smoking. Children are always welcome. Come enjoy all of the accommodating facilities at Windsor Hills with a top-notched 24/7 gated security. FREE parking & leisure activities! Maximum of 3 cars allowed per reservation. This includes all guest that are visiting. All unregistered drivers will be denied access by HOA.

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.

Disney fireworks new house - 5 minutes to Disney

Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

DISNEY, WATER park, Private POOL, Comfort by A3G

Your dream getaway, starts In this 3beds 3 baths vacation home away from home! With private pool, Located in the amazing 5 stars resort at WINDSOR HILLS, only 3 miles away from all the wonders and magic of Disney. For Endless entertainment just walk to the Clubhouse and encounter the beautiful typhoon style pool, jacuzzi, brand new water park, arcade, fitness center, volleyball and basquetbol courts, kids playground and much more

Disney Dreamin'

Looking for a WARM family vacation? LOOK NO FURTHER for the perfect vacation rental in the highly sought out WINDSOR HILLS, the closest gated community to Disney World. Only 15 minutes away! =D This home was designed and decorated as a place that I would want my family and friends to stay in. I hope that you and your family will feel warm and welcomed and can enjoy the fruits of your labor. -christina

3BD/3BA Themed House Near Disney

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

7754 Windsor Hills 6B Luxury Pool Home Near Disney

Welcome to Your Ultimate Windsor Hills Vacation Escape! This newly renovated 6-bedroom beauty is the perfect blend of luxury and fun, designed for families looking to unwind and create unforgettable memories. Just a stone’s throw from Disney World and surrounded by world-class dining, top-notch shopping, and Orlando’s hottest attractions, you’ll have everything you need for an amazing getaway.

Mickey's Imagination Condo at Windsor Hills Resort

Newly renovated 3BR/2BA first-floor condo just minutes from Disney! Family-friendly with Disney-themed rooms: Mickey’s Clubhouse kids’ room with toys & costumes, Animal Kingdom guest room with nursery, and Classic Mickey master with vintage Disney décor. Enjoy a fully stocked kitchen, baby gear, and resort amenities—perfect for families ready to experience the magic!