Apartment holiday rentals in Windsor Hills

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Top-rated apartment rentals in Windsor Hills

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Guest favourite
Apartment in Kissimmee
4.92 out of 5 average rating, 12 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

Top Guest favourite
A large lagoon-style pool is illuminated under a colorful sunset, surrounded by palm trees and lounge chairs. The well-lit area features gentle slopes leading into the water, enhancing the inviting appeal of the recreational space.
Apartment in Kissimmee
4.92 out of 5 average rating, 63 reviews

Whiskey Bent Disney Townhouse 3 bedroom 3 bath

Come relax at our townhouse with private pool in Windsor Hills Resort. A 24/7 gated resort offering a clubhouse, with a lagoon style Swimming Pool that is heated for use year round and has a Water Park,fitness center, Tennis court,Putting Green, Basketball court,Sand Volleyball, Ping Pong,playground, game room,DVD rental and ATM You will be located just a couple of miles from the Walt Disney World entrances and also close to Universal, golfing, shopping and many other attractions. No resort fee

Top Guest favourite
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.
Apartment in Kissimmee
4.95 out of 5 average rating, 114 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!!

Top Guest favourite
Apartment in Kissimmee
4.96 out of 5 average rating, 101 reviews

Disney Family Vacation Deal! Windsor Hills+Pool

Perfect for families traveling to Disney, our spacious 3 bedroom condo at Windsor Hills offers resort-style pools, waterpark access, and fun Disney-themed bedrooms just minutes from Disney World. What Makes It Special: - Walk to the resort’s pool & waterpark - all included! - Complimentary fast Wi-Fi + free parking - No hidden resort fees - Family & kid-friendly rooms with Disney themes - Fully equipped kitchen Superhost (nearly 100 reviews!) , Guest Favorite, Excellent customer service!

Guest favourite
A spacious dining area features a large wooden table set for multiple guests with white dinnerware. Soft lighting hangs above, and a modern artwork piece adorns the wall. In the background, a well-lit living area with a large screen TV and a balcony can be seen.
Apartment in Kissimmee
4.87 out of 5 average rating, 119 reviews

3175-205 Resort 3BR Apt by Disney World Orlando

Just minutes from DISNEY, Stylish BRAND NEW fully renovated 3bed/2bath fully equipped apartment for up to 8 guests, located in the family friendly Secret Lake Resort. Master suite has a KING bed & 55" TV. Second bedroom has 2 QUEEN beds & 65" TV. Third Bedroom has 2 FULL beds & 65" TV. The open floor plan blends Kitchen, Dining & Living room w/ a 65" TV. Close to Disney Parks, Margarita Ville Water Park, Outlet malls & Retail stores. Amenities: Wi-Fi, Pool, BBQ & Gym. NO RESORT FEES

Top Guest favourite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 147 reviews

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!

Top Guest favourite
A private balcony is showcased with a round table and two woven chairs, providing a serene view of the lake and surrounding landscape. Soft morning light reflects on the water, while a small potted plant adds a touch of greenery to the setting.
Apartment in Orlando
4.97 out of 5 average rating, 104 reviews

2-Bedroom Renovated Lakeside Condo Near Disney

This large lakeside renovated (July 2023) condo is located minutes from all theme parks and is within walking distance to many restaurants and an outlet mall. Enjoy our two main pools (with tiki bar and hot tub) and poolside recliners. Condo includes: large private balcony; laundry; two full bathrooms; master king bed/ensuite; second bedroom with XL twin beds and a bunk bed nook for kids; 55-inch Samsung smart TV in living area and Amazon Fire TVs in each bedroom.

Top Guest favourite
The living room features a sectional sofa adorned with colorful pillows, paired with a coffee table centered on an area rug. A wall-mounted TV is visible, along with a floor lamp and decorative wall hangings. Natural light enters through a window, creating a bright and open atmosphere.
Apartment in Bay Lake
4.96 out of 5 average rating, 109 reviews

Vibrant Haven 10 Min to Parks Pet-Friendly

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.
Apartment in Kissimmee
4.75 out of 5 average rating, 130 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.

Top Guest favourite
Apartment in Kissimmee
4.93 out of 5 average rating, 15 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.

Top Guest favourite
A colorful water slide complex features multiple slides in vibrant green and blue. The area includes a splash pad with various water activities and ample space for relaxation. Lush palm trees surround the site, complementing the bright blue sky overhead.
Apartment in Four Corners
5 out of 5 average rating, 22 reviews

Enchanted Poolside Retreat

Relax in a luxurious poolside condo with breathtaking views in the heart of Windsor Hills. Just minutes from Disney, our space offers a serene retreat with resort-style amenities, a private balcony, and a beautiful view of the pool. Perfect for families or couples seeking comfort, convenience, and a little magic during their Orlando adventure.

Superhost
A modern kitchen area is visible, featuring a sleek countertop with place settings for four. Two pendant lights hang above the bar stools. In the background, a living area is seen, illuminated by natural light from glass doors leading to a balcony.
Apartment in Davenport
4.91 out of 5 average rating, 124 reviews

Cozy Modern 1 Bedroom Apartment

Warm welcome to our modern one bedroom apartment. We are happy to be your host for your stay. Located minutes away from attractions such as Walt Disney World and Universal Studios. During your stay you will find comfort with a brew of a delicious cup of coffee as the sun rises. Book your next stay with us. We would love to be your host!

Popular amenities for Windsor Hills apartment rentals

Quick stats about apartment rentals in Windsor Hills

  • Total holiday rentals

    Explore 10 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 160 verified reviews to help you choose

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Windsor Hills holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Windsor Hills rentals

  • 4.9 Average rating

    Windsor Hills stays are highly rated by guests—averaging 4.9 out of 5!