Condo vacation rentals in Windsor Hills

A spacious pool area is featured, surrounded by palm trees and lounge chairs. The expansive waterpark includes vibrant waterslides, providing a lively atmosphere. A relaxing hot tub is also visible nearby, complemented by a well-maintained landscaping that enhances the resort's inviting ambiance.

4.98 out of 5 average rating, 199 reviews

Poolside, 3Br Windsor Hills, Waterpark, By Disney

Your Windsor Hills Getaway starts here! This beautiful condo overlooks the resort pool, waterpark with waterslides, lake and just minutes from Disney World! New appliances and updated furnishings, this 3rd floor condo sleeps 8 with plenty of parking. The screened-in balcony can’t be beat, overlooking the pool and Lake! The clubhouse is steps away, with a store, food, drinks, game room arcade, movie theater and fitness center. No resort, parking, or hidden fees. Full access to all amenities!

4.94 out of 5 average rating, 104 reviews

Poolside 3 Bed Vacation Retreat in Windsor Hills

All the comforts of home will be with you in this modern poolside unit within this premium Windsor Hills Vacation Resort location. This spacious 3 bed/2bath ground floor condo overlooking the pool offers over 1440 sq. ft that features a full kitchen, in-suite laundry, dining area, as well as living area with cable, wifi, and Xbox. Located just 4 miles from Disney World and 25 miles from Orlando airport. Close to many amenities and shopping. This is the perfect spot for your next vacation.

4.85 out of 5 average rating, 209 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)

A modern kitchen is showcased with sleek cabinetry and stainless-steel appliances. A large island with seating for three is featured, complemented by pendant lighting. Countertops are clear, and utensils are neatly arranged. An archway leads to another area of the home, enhancing the open layout.

4.92 out of 5 average rating, 167 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).

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.

4.86 out of 5 average rating, 214 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.

A bright living area features a comfortable brown sofa and loveseat, accented with decorative pillows. A modern coffee table is centered on tiles that enhance the spaciousness. Natural light filters through large windows, while a flat-screen TV is mounted on the wall, framed by stylish light curtains.

4.85 out of 5 average rating, 162 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.

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.

4.91 out of 5 average rating, 233 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.

4.98 out of 5 average rating, 123 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.

4.88 out of 5 average rating, 103 reviews

Themed 3bd/2ba Condo_Water Park_ 2 miles to Disney

¡Welcome to Mickey’s Casa! Located just 2 miles away from Disney World, Windsor Hills is an upscale gated community resort offering: Resort with 24hr Security Giant Resort Pool + Sun Deck 2 Story Water Slide & Children Splash Area Gaming and Arcade Center Family Activities at Clubhouse Movie Theatre Professional Fitness Center Basketball, Tennis, Pickle Ball, and Sand Volleyball Putting Green Grills and picnic pavilion Multiple playgrounds Newly renovated Market Grill and Cafe

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.

4.91 out of 5 average rating, 177 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.

4.93 out of 5 average rating, 216 reviews

Magical Stay Near Disney & ESPN

🏰 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!

A spacious pool area is surrounded by palm trees and tropical landscaping. Sun loungers line the pool deck, and a water park with slides is visible nearby. The multi-level condo buildings create a vibrant backdrop, ensuring a family-friendly environment.

4.8 out of 5 average rating, 158 reviews

Lovely vacation condo close to Disney & Universal!

Family friendly 3 bedroom 2 bath condo on first level (handicap accessible) at Windsor Hills Resort. Gated access with private parking. Go straight to the condo with Lockbox access code. 7 minute drive to all Disney parks. As a guest you have access to the beautiful pool, hot tub, Water Park, gym, movie theater, Community Center at no extra cost. Everything is open and available.

Popular amenities for Windsor Hills condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.99 out of 5 average rating, 87 reviews

Renovated Luxury Condo in Windsor Hills Resort!

4.93 out of 5 average rating, 27 reviews

Lovely Place at Windsor Hills - Condo 2 bd / 2 bh

Superhost

4.67 out of 5 average rating, 55 reviews

Renovated 3BR | Superhost | close to Disney

The image captures a vibrant outdoor resort area featuring a lagoon-style pool and waterslides in shades of blue and green. Sun loungers are arranged around the pool, surrounded by palm trees and open green spaces. A two-story condo building stands in the background.

4.95 out of 5 average rating, 39 reviews

Sunny Condo Retreat~Clean, Cozy, & Convenient!

4.96 out of 5 average rating, 25 reviews

A spacious bedroom is furnished with a large bed covered in a blue quilt, complemented by light-colored walls and natural light filtering through the window. A combined living area features a comfortable sofa and a television, while kids' water slides are visible in the outdoor pool area, surrounded by palm trees.

Condo in Four Corners

Windsor Hills Star Wars Retreat with Lake View

5 out of 5 average rating, 16 reviews

Family Friendly II

4.98 out of 5 average rating, 51 reviews

Windsor Hills, 3 Bedrooms, Disney, 24/7 Security

Superhost

Aerial view of a spacious heated pool surrounded by lounge chairs and palm trees. Adjacent to the pool, a vibrant water park features slides and play areas. Lush greenery and a tranquil lake create a serene backdrop.

4.74 out of 5 average rating, 86 reviews

INCREDIBLE CONDO ..NEWLY RENOVATED

Pet-friendly condo rentals

4.96 out of 5 average rating, 119 reviews

The living room features large sliding glass doors that open to the balcony, providing a view of the lake. A contemporary electric fireplace sits beneath a 65-inch smart TV. Comfortable seating includes a sofa, an armchair, and a coffee table, with warm curtains adding a touch of color.

Condo in Orlando

Penthouse Lakeview Minutes to Disney/ Universal

The living room features a spacious sectional sofa and a flat-screen TV mounted on a wooden console. Large glass doors provide a view of the patio and golf course, while natural light fills the room through the sheer curtains. A potted plant adds a touch of greenery.

4.95 out of 5 average rating, 148 reviews

3 Bedroom w/large patio on Resort Golf Course

4.79 out of 5 average rating, 264 reviews

A spacious bedroom features a plush, tufted headboard and a large window allowing natural light to fill the room. Two bedside lamps provide additional illumination, while modern furnishings add contemporary flair. A round mirror is mounted above the bed, reflecting the inviting ambiance.

Condo in Davenport

Brand New AwardWinning Renovated Condo Near Disney

4.97 out of 5 average rating, 172 reviews

Condo in Orlando

Magically Close to Disney- Serene LakeView Condo

4.9 out of 5 average rating, 136 reviews

A resort-style area is depicted, featuring a circular pool surrounded by lush palm trees and vibrant landscaping. The building is visible in the background, with a clear blue sky above. A purple text overlay states 'No Resort Fees' across the image.

Condo in Celebration

Pet Friendly in Orlando Area near Disney.

The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.

4.92 out of 5 average rating, 156 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

A modern living area is presented with a dining table and four chairs positioned beside a kitchenette. A green sofa adds a pop of color, while large windows provide ample natural light. The space opens to a bedroom area, creating an inviting atmosphere.

4.88 out of 5 average rating, 433 reviews

Family Apartment Near to Disney Orlando Universal

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.

4.93 out of 5 average rating, 163 reviews

Remodeled 2BR/2BA Near Disney, Pool +WiFi +Parking

Condo rentals with a pool

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

4.87 out of 5 average rating, 141 reviews

Stylish Condo 20 mins to Disney/King Bed

Superhost

The open-concept living area features a large sectional sofa with soft cushions and a glass coffee table. A flat-screen Smart TV is mounted on the wall, displaying a beach scene. Natural light fills the room through large windows with light curtains.

4.57 out of 5 average rating, 54 reviews

Resort Oasis! 3BR w Pool Access near Disney World

A cozy dormitory space features two bunk beds draped with red fabric. A wooden door leads to the room, where a starry ceiling complements golden light fixtures. A Victorian-style chair and a small trunk add charm, while natural light filters through a window with red curtains.

4.94 out of 5 average rating, 62 reviews

Fully Themed Harry Potter Magical Experience!

An aerial view of a large lagoon-style pool area surrounded by lush greenery. Water slides and water park features are visible alongside a spacious deck with lounge chairs. The clubhouse is tucked behind the pool, offering additional resort amenities.

4.74 out of 5 average rating, 58 reviews

2 MI TO DISNEY WITH POOL, WATER PARK & WATER SLIDE

4.95 out of 5 average rating, 132 reviews

Condo in Orlando

Modern Lake view Condo 1 mile from Disney

5 out of 5 average rating, 26 reviews

*Pixie Dust Penthouse* Totally Remodeled, Luxury

4.98 out of 5 average rating, 51 reviews

Harry Potter - Windsor Hills! Near Disney + Pool

A spacious living room is highlighted by a large television mounted on the wall, displaying a serene tropical scene. Comfortable seating arrangements include dark leather sofas and a coffee table, with natural light filtering through the large windows adorned with blinds.