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Apartment holiday rentals in Windsor Hills

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Top-rated apartment rentals in Windsor Hills

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Top guest favourite
The living area features a modern sectional sofa adorned with decorative pillows. A sleek coffee table is positioned on a patterned rug, while large sliding doors lead to a balcony, enhancing natural light. An adjacent dining area with stylish chairs is visible in the background.
Flat in Kissimmee
4.97 out of 5 average rating, 170 reviews

3121-402 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Guest favourite
Flat in Citrus Ridge
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 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.
Flat in Citrus Ridge
4.95 out of 5 average rating, 110 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
Flat in Citrus Ridge
4.96 out of 5 average rating, 99 reviews

Disney Family Vacation Special! 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 resort fees - Family & kid-friendly rooms with Disney themes - Fully equipped kitchen Superhost (nearly 100 reviews!) , Guest Favorite, Excellent customer service!

Guest favourite
A modern living area is showcased with a sectional sofa, lounge chairs, and a coffee table. Open shelving displays decorative items. The kitchen area is visible in the background, featuring pendant lighting and sleek appliances. Natural light enhances the neutral tones of the space.
Flat in Citrus Ridge
4.93 out of 5 average rating, 157 reviews

Luxury condo near Walt Disney Parks - Kissimmee FL

Entire family will enjoy this luxury condominium located in Kissimmee Florida. Minutes away from all Walt Disney parks, quick drive to Disney Springs and close to major highways. Many attractions within walking distance such as water parks, Studio Grille movie theater, grocery stores, pharmacies, gift shops and plenty restaurants. The condominium includes two primary bedroom suites with en-suite fully remodeled bathrooms. Entire condo is beautifully remodeled to make you feel at home.

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.
Flat in Kissimmee
4.99 out of 5 average rating, 144 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.
Flat in Orlando
4.97 out of 5 average rating, 101 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
A living room is presented with green accent walls and hardwood flooring. A comfortable sofa with orange throw pillows faces two small coffee tables. Wall decorations include woven art pieces. A ceiling fan hangs above, and a door leads to a balcony, allowing natural light into the space.
Flat in Kissimmee
4.95 out of 5 average rating, 151 reviews

Cozy 2Bed Boho Hideaway 10 Min to Parks Allows Pet

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 8 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Guest favourite
Flat in Kissimmee
4.89 out of 5 average rating, 106 reviews

Cozy Apartment Close to Disney

Welcome to our charming apartment in the heart of Kissimmee! Perfectly situated near Disney & Animal Kingdom, Shopping, Dining and Entertainment are at your fingertips. This delightful accommodation is an ideal choice for couples, solo adventurers, extended stay, and business travelers. Whether you're in town for a magical vacation, a business trip, or a romantic getaway, our apartment provides the perfect home base for your adventures.

Top guest favourite
A bright and inviting living and dining area features a large table set for dinner, surrounded by colorful decorations. A blue mural and modern light fixtures enhance the atmosphere. Nearby, playful artifacts and themed elements add charm, contributing to a family-friendly environment.
Flat in Citrus Ridge
4.92 out of 5 average rating, 60 reviews

Walt’s Vision – Disney-Inspired 3BR Condo

Top 10% of homes on Airbnb ⭐️ Highly rated for reviews, reliability & guest satisfaction. Walt’s Vision is a ground-floor 3BR condo in Windsor Hills Resort, just 2 miles from Walt Disney World. Skip stairs and long walks—this walk-out unit is steps from the pool, clubhouse & water park. Perfect for families, grandparents & multi-gen Disney trips who want comfort, location, and zero hassle. Homes this close book fast—don’t miss it.

Guest favourite
Flat in Citrus Ridge
5 out of 5 average rating, 5 reviews

°o° Modern 3B/2B Condo in Windsor Hills by Disney

Welcome to your perfect vacation getaway! This beautifully updated 3-bedroom, 2-bathroom condo is located in the highly sought-after Windsor Hills Resort, just minutes from the entrance to Walt Disney World. With new upgrades, spacious bedrooms, and unbeatable resort amenities, this home offers comfort, convenience, and fun for the whole family.

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.
Flat in Davenport
4.93 out of 5 average rating, 121 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 flat rentals in Windsor Hills

  • Total holiday rentals

    Explore 10 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at £38 per night before taxes and fees

  • Verified guest reviews

    Over 150 verified reviews to help you choose

  • Holiday rentals with a pool

    10 properties feature pools

  • Wifi availability

    10 of Windsor Hills holiday rentals include wifi 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!

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Four Corners
  6. Windsor Hills
  7. Flat rentals