Condo vacation rentals in Windsor Hills

Find and book unique condos on Airbnb

Quick stats about condo rentals in Windsor Hills

  • Total vacation rentals

    Explore 30 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at $167 CAD per night before taxes and fees

  • Verified guest reviews

    Over 50 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Vacation rentals with a pool

    30 properties feature pools

  • Wifi availability

    30 of Windsor Hills vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor Hills rentals

  • 4.7 Average rating

    Windsor Hills stays receive an average rating of 4.7 out of 5 from guests

Top-rated condo rentals in Windsor Hills

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

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Top guest favourite
Condo in Kissimmee
4.98 out of 5 average rating, 211 reviews

Poolside, Windsor Hills 3Br, Waterpark, By Disney

Welcome to beautiful Pool and Lake views at the heart of Windsor Hills Resort, just 2 miles to Disney! Our updated 3-bedroom, 2 bathroom condo for up to 8 guests is steps from the extensive amenities, including a clubhouse with a lagoon pool, waterpark with waterslides, arcade, fitness center, movie theater, and sports courts. As owner-hosts, we take pride in caring for our condo and providing warm, responsive service. Your stay includes full access to everything with no resort or hidden fees.

Guest favourite
A cheerful family bedroom is decorated in a Mickey Mouse theme, featuring two full-size beds with vibrant blue and patterned bedding. Wall art displays colorful Mickey images, complemented by a nightstand with a lamp. A plush Mickey toy rests on one bed, adding a playful touch.
Condo in Kissimmee
4.85 out of 5 average rating, 210 reviews

Luxurious Mickey's Dream Home!

Wonderful Mickey-themed 2 bed 2 bath condo in the Windsor Hills Resort located 2 miles from Disney World Entrance! Our Condo is a modern, clean & upgraded condo, that offers the comforts & convenience of home. Features: Granite counter-topped well-stocked kitchen, comfortable beds with clean linens, Smart TVs in all rooms, cable TV, free WiFi. Washer & dryer in unit, Valet trash pickup, with 2 elevators in the building. Free Parking, Free access to resort pool, waterpark & lots more (see below)

Guest favourite
Condo in Kissimmee
4.93 out of 5 average rating, 175 reviews

New Luxury Condo near Disney

A passos da piscina e parque aquático. Covid-19 safe. Wi-fi de 500 megabytes! O apartamento possui localização privilegiada: está no condomínio fechado Windsor Hills, o mais próximo dos parques. A 10 minutos do Animal Kingdom, Epcot, Hollywood Studios e Magic Kingdom e a 25 minutos dos parques da Universal. Além disso, possui fácil acesso ao aeroporto (US 192, FL 417 e I-4), Downtown Orlando, Miami e a todos os atrativos da região da Central Flórida (Daytona Beach, Clearwater, St. Petersburg).

Guest favourite
The aerial view showcases a spacious pool area surrounded by lush palm trees and lounge chairs. A bright water slide is visible in the background, leading to the pool. A serene lake serves as a picturesque backdrop, enhancing the resort's atmosphere.
Condo in Kissimmee
4.86 out of 5 average rating, 217 reviews

One in a Minion condo your kids will love +450Mbps

Enjoy of sophisticated and modern accommodations on your next visit to Orlando. This One in a Minion themed two bedroom condo boasts 1082 SQ FT of living space and it's fully equipped for 6 guests. Conveniently located on the ground floor and a short stroll to the clubhouse, pool and dueling water slides. It features a smart lock, High-speed WIFI Internet +450Mbps, cable TV, telephone line, linens & towels and washer/dryer. Slide and Water Park will not reopen until Wednesday, February 18th.

Guest favourite
Condo in Kissimmee
4.85 out of 5 average rating, 164 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

Welcome to our Star Wars themed rental in Kissimmee, FL, just 3 miles from Disney World! Experience the ultimate vacation in a galaxy far, far away. Located in Windsor Hills Resort with a heated community pool and two water slides. The kids bedroom has Star Wars decor, twin bunk beds, and an electronic pinball machine. The condo is decorated with Star Wars artwork and a half-sized Darth Vader figure. The kitchen is fully equipped. Don't miss this chance to live out your Star Wars fantasies.

Top guest favourite
A vibrant outdoor water park is depicted, featuring two large water slides and a colorful kids' splash area. Surrounding palm trees provide shade, and a spacious pool area is visible in the background, inviting relaxation and fun.
Condo in Kissimmee
4.91 out of 5 average rating, 238 reviews

Disney's Doorstep, 3 Bed 2 Bath, Waterslides!

Welcome to your dream vacation! This 3 bedroom, 2 bath, is right on Disney's doorstep, this amazing vacation rental has all the amenities you'd put on your dream list. Two water slides, a kids splash park, walk in pool, movie theater with wheelchair access, game room, fitness center, putting green, playground, shop for snacks, and more! This condo also comes fully furnished with a washer/dryer, WiFi, elevator for wheelchair access, and more. This is sure to be your relaxation destination.

Top guest favourite
Condo in Kissimmee
4.98 out of 5 average rating, 125 reviews

11 am checkout, Windsor Hills, Family, Disney.

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.

Top guest favourite
An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.
Condo in Kissimmee
4.94 out of 5 average rating, 210 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

Guest favourite
An aerial view showcases a resort-style pool surrounded by lounge chairs. A colorful water park with slides is located nearby, complemented by lush greenery and palm trees. Multiple buildings are visible in the background, offering a welcoming atmosphere for families.
Condo in Kissimmee
4.85 out of 5 average rating, 189 reviews

WH Condo. Pool/Waterpark and close to Disney!

Take an elevator to unit 302 and witness beautifully decorated Disney themed rooms. Directly outside is a lovely pool and kid-friendly waterpark. All amenities included in cost: game room, theater, exercise room, tennis courts, play grounds, sand volleyball, putting green, basketball court and a marketplace and grill. Located 15 minutes to all 4 Disney parks and Sea World! Looking for more space? Check out our townhome also located in Windsor Hills at 7668 Fitzclarence

Guest favourite
A vibrant water park is illustrated in the background, featuring colorful slides and pools surrounded by lounge areas. In the foreground, a cozy sleeping area showcases a blue accent wall decorated with playful Disney characters. A billiards table is visible, inviting recreational activities.
Condo in Kissimmee
4.86 out of 5 average rating, 246 reviews

Superhero Retreat Near Disney Parks

Experience the magic of Disney and create memories for a lifetime at your very own “Superhero Retreat “. - 3 bedrooms and 2 bathrooms designed with Disney themes - Family-friendly atmosphere with kid amenities provided - Access to Windsor Hills Clubhouse with pools, water park, and gym - Free parking and no extra fees - Fully equipped kitchen with stainless steel appliances - Free WiFi with 400 Mbps speed - Located less than 2 miles from Walt Disney Resort

Guest favourite
An aerial view captures the resort's inviting pool area, featuring a large, curvilinear swimming pool surrounded by lounge chairs. Adjacent, a water park offers colorful slides and play structures. The three-story condo is visible in the background, highlighted by lush landscaping.
Condo in Kissimmee
4.91 out of 5 average rating, 180 reviews

Windsor Hills Resort - Disney Pool View Condo

Location, location, location! Windsor Hills pool view condo and only 2 miles to Disney World! This 3 bedroom pool view condo is in the beautiful Windsor Hills Resort gated community. The single level condo is located in the closest building to the pool, water park, clubhouse, hot tub, movie theater, and arcade. The condo has one of the best balcony views in the entire resort. Located on the third floor, the balcony looks directly over the resort pool and lake.

Top guest favourite
The living area features a comfortable sofa facing a large smart TV mounted on the wall. Natural light enters through windows, enhancing the space. A round coffee table sits in the center, surrounded by potted plants, with a dining area and a modern kitchen visible in the background.
Condo in Kissimmee
4.93 out of 5 average rating, 217 reviews

Magical Disney Retreat | Near ESPN | Pool | 3BR

🏰 Make magical memories just minutes from Disney & ESPN! Bright 3BR, 2BA condo for up to 6 guests in a safe, gated community—perfect for families or friends! Why you’ll love it: Family-friendly & ideal for kids 🏡 Relax in comfort after a fun day at the parks 🍳 Fully equipped kitchen for easy meals 🛍️ Close to restaurants, shopping & entertainment 🎢 Only 1.5 miles from Disney World & ESPN Stress-free, unforgettable family vacation awaits!

Popular amenities for Windsor Hills condo rentals