Apartment holiday rentals in Windsor Hills

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.

4.91 out of 5 average rating, 69 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

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.

4.94 out of 5 average rating, 126 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!!

5.0 out of 5 average rating, 12 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.

A welcoming living area features orange accent chairs and plush beige sofas arranged around a glass coffee table. Decorative mirrors adorn the walls, while vibrant floral arrangements add a touch of color. Natural light filters through the window, draped with patterned curtains.

4.87 out of 5 average rating, 409 reviews

Superb Townhouse Newly Renovated 1 mile to Disney

This 2-bedroom rental in Kissimmee is just 1 mile from Walt Disney and only 14 miles from Universal. This home has been completely renovated as of May 2017 with all brand new furniture and linens. This gated community is ideal for families and features plenty of updated, modern conveniences. Take advantage of the many on-site resort amenities including a swimming pool, hot tub, fitness center, tennis and basketball courts, and a fully-equipped game room with a pool table and air hockey.

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.

4.9 out of 5 average rating, 109 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

5.0 out of 5 average rating, 4 reviews

3BR First Floor | Free Water Park | 5 Min Disney

“Enjoy the perfect family getaway in this spacious 3-bedroom first-floor condo, just 5 minutes from Disney! Your stay includes FREE access to the resort’s amazing water park and pool, just steps from your apartment. Relax in a beautiful resort setting while staying close to Disney, shopping, restaurants and everything Orlando has to offer. Perfect for families looking for comfort, convenience and fun in one location.” Walmart, Starbucks, pharmacy justo 2 minutes driving

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, 106 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

Top Guest favourite

4.96 out of 5 average rating, 120 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 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.

4.56 out of 5 average rating, 27 reviews

Family Disney Condo｜Free Water Park｜Sleeps 7*

Your family's Disney getaway starts inside gated Windsor Hills Resort — just 2.5 miles (5 min) from Walt Disney World. This bright 3-bedroom, 2-bath condo sleeps 7 (king, queen + kids' themed bunk room). After a day at the parks, cool off at the resort water park with two big slides, splash in the zero-entry pool, catch a movie at the outdoor theater, or let the kids run the playground — every resort amenity included, no resort fee. Welcome!

Top Guest favourite

A dining table is set for six, adorned with teal plates and drinking glasses. The living area features a comfortable gray sofa and a TV mounted on the wall, with natural light filtering in from the balcony doors, which lead to a green outdoor seating area.

4.94 out of 5 average rating, 426 reviews

Great Full Apartment. Just 5' from Disney Orlando

Fantastic apartment in a nice and quiet place. Private gate area with security, locate in the best resort of Kissimmee: Legacy Dunes. Only 4 milles from Disney Parks. Full kitchen, laundry, central A/C, 2 bedroom, 2 bathrooms. Living room, dining room, balcony. Climatized pool, club house, fitness area, tennis court, childs área, free parking and wifi.