Apartment holiday rentals in Windsor Hills

4.95 out of 5 average rating, 21 reviews

My Disney Grandview

One-of-a-Kind Corner Penthouse Overlooking the Pool The Crown Jewel of Windsor Hills -the only top-floor corner condo directly overlooking the resort . No long walks or loading the car - step outside and you’re there ★ Perfect for Disney Families Sleeps 8-3 Bed/2 Bath Free Resort Access, and parking Gated community 9 min to Disney World Pack n’ play, high chair, stroller, Add my listing to your wishlist by clicking the ❤ in the upper-right I want you! Tell me what I can do to be your host

A vibrant water park area features colorful slides and splash pads. Water sprays from various playful fixtures, and guests can be seen enjoying the amenities. The backdrop includes a multi-story building with palm trees surrounding the area, providing a fun and engaging environment.

4.95 out of 5 average rating, 122 reviews

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!!

Superhost

A well-lit bedroom features two spacious beds positioned side by side, each adorned with neutral-toned bedding. Decorative wall art with abstract designs enhances the ambiance. Natural light filters through the window, illuminating the minimalist decor and adding to the room's inviting atmosphere.

4.69 out of 5 average rating, 88 reviews

Modern Disney Condo

Welcome to our luxurious retreat in the sought-after gated community of Windsor Hills. Ultra sleek design, overstocked kitchen with air fryer, king size master bedroom, TV in all bedrooms, & a screened balcony right off the vibrant living room. But that's not all! The resortoffers a spectacular pool, loungers, a full waterpark with thrilling slides, an arcade room, a game room, and even an outdoor ping pong table. Your ultimate family getaway awaits! We provide all essentials! 9min to Disney.

5.0 out of 5 average rating, 11 reviews

3BD condo 10 min Disney, 3 min walk Walmart

Enjoy our peaceful 3 bedrooms, (the master bedroom is an ensuite) 2-bathroom condo in the heart of Kissimmee. The condo is in a private gated community, conveniently located near the entrance. Enjoy the heated pool, hot tub, splash pad, playground, gym, and tennis court. The condo is conveniently located 10 minutes from Disney parks, Disney Springs is 15 minutes away and Universal Studios is 25 minutes away! For even more convenience, Walmart and Starbucks are a 3-minute walk from the condo.

Aerial view of the pool area shows vibrant water slides winding through landscaped surroundings. Multiple swimming pools can be seen, complemented by palm trees and open spaces. Sun loungers are arranged around the pools, offering ample relaxation spots for guests.

4.89 out of 5 average rating, 103 reviews

Apartment in Four Corners

Escape to this stylish 2-bedroom, 2-bathroom condo, perfect for families or friends seeking a memorable getaway. Enjoy spacious living area, complete with a comfortable sofa bed, and a fully-equipped kitchen. Relax in luxury with a king-size bed and en-suite bathroom. Access at NO ADDITIONAL cost to world-class pools, a lazy river, and a fitness center . Enjoy complimentary Wi-Fi and parking Located in the heart of Champions Gate, Aprox. 15 mins to Disney Parks & 30mins to Universal

A vibrant water park, featuring various slides and attractions, is accompanied by a spacious heated pool and tropical landscaping. The inviting living area showcases comfortable seating and artistic decor, while the bedroom presents a cozy bed against a colorful wall. Natural light fills the spaces.

4.88 out of 5 average rating, 100 reviews

Family-Friendly Condo Near Disney

Experience the magic of Disney and create memories for a family vacation. - Spacious 3 bedroom, 2 bathroom condo with 2 king beds and 2 twin beds - Family-friendly atmosphere in Windsor Hills resort - Free access to clubhouse, pools, water park, gym, and more - Heated resort pool open year-round - Complimentary parking and no resort fees - Community amenities include tennis, basketball, and movie theater - Resort pool is heated during winter months

4.96 out of 5 average rating, 114 reviews

Windsor Disney Retreat- Water Park | No Resort Fee

Skip the resort fees, not the magic. ✨ Our Disney-themed 3BR/2BA at Windsor Hills sits just 2.5 miles from the Disney gates — a Guest-Favorite, 4.96★ Superhost home ranked in Airbnb's top 5%. Kids get their own Lion King, Encanto & Alice in Wonderland rooms; parents get a full kitchen, in-unit laundry, fast Wi-Fi, and a ground-floor unit steps from the resort's heated pool, lagoon water park & clubhouse. No resort fees. Free parking. Just magic.

A welcoming living area features a dark brown sofa adorned with decorative pillows in warm tones. Greenery decorates the wall behind the sofa, complemented by a modern lamp. A nearby circular table and chair set add to the inviting space, with natural light filtering through a window.

4.91 out of 5 average rating, 147 reviews

Lush Green Retreat 10 Min to Parks Pets Allowed

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Superhost

A whimsical room features two full-sized beds adorned with colorful bedding inspired by a popular animated theme. The walls are decorated with snowflake motifs and soft, twinkling lights, creating a playful atmosphere. A connecting ensuite bathroom is visible in the background.

4.76 out of 5 average rating, 131 reviews

Luxury 2BR-2BA Windsor Hills Condo - Direct Entry

Completely refurbished 2 bedroom 2 bath, 1st floor unit located in Windsor Hills. 7-15 minute drive to Disney Parks. Condo features: cable TV, secure high speed internet, fully equipped kitchen, washer, dryer, and shimmering FROZEN ROOM with special lighting. Ground Features: Olympic-sized heated lagoon pool, water slides, children’s playgrounds, fitness center, movie theater, game room, outdoor grills...all within 2 min walk from the unit.

Superhost

A cozy living area is furnished with a gray sectional and a patterned armchair, providing a relaxed environment. The space includes a coffee table and a media console housing a TV. Large glass doors offer views of the private pool and screened lanai.

4.92 out of 5 average rating, 13 reviews

Windsor Hills Resort 5 Bedroom Pool+Spa Home

* Windsor Hills Resort Private Pool Home Sleeps up to 10 * 5 bedrooms/ 5 bathrooms * Windsor Hills Resort Gated Community * 4 miles to Disney World property * Fully equipped Kitchen with dining for 8 at the dining room table * Additional seating for 6 at the breakfast table * Private pool with spa faces North in screened-in lanai. * Outdoor Dining Seats 6 * Avengers Themed Game Room * Sun Loungers * 5-minute walk to the Clubhouse

4.96 out of 5 average rating, 24 reviews

Condo in Kissimmee

✨Spacious Family Condo | Garden View | 2 Miles from Disney✨ Welcome to your perfect vacation escape! Nestled in the heart of the highly sought-after Windsor Hills Resort, this beautifully updated second-floor condo offers a blend of comfort, style, and convenience—with elevator access, brand-new furnishings, and all the comforts of home, just 2 miles from the magic of Disney.