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Windsor Hills Orlando Resort

Windsor Hills Resort is a 24-hour secure gated resort community located less than 2 miles from Walt Disney World making it the closest resort community to the major theme parks.  Easy to get to and only 20′ minutes drive from Disney by car or bus, it provides the optimal base for a full-on day at the parks l while providing some well-earned rest in the comfort of a vacation rental you’ll love.

Alternatively, the resort acts as the ideal golf holiday location, located next door to the excellent Mystic Dunes Golf Club and within easy reach of a wide array of golf courses in the Kissimmee area (across all ability levels and budgets) so there are plenty of options and a week or two of full-on golf, playing a different course every day, is easily achieved with Windsor Hills Orlando as your base.

Joselly – Portfolio Manager

Casiola’s Windsor Hills Rentals

Amenities Designed to Inspire

Taking time to relax, unwind, and enjoy a Florida getaway to the fullest is something everyone deserves to embrace once in a while. At Casiola Orlando, we’re committed to helping all of the guests we partner with enjoy a customized and elevated adventure by booking them into luxurious rentals that meet their needs and exceed their expectations too. That’s exactly what visitors can expect to find who book a stay in a Windsor Hills Resort rental while they’re in the Orlando area. While the resort amenities here are a delight at every turn, rentals are also designed to inspire. Guests will find that the vast majority of our vacation rental options in Windsor Hills in Orlando feature inviting and spacious layouts that promote open living designs. This makes it easy for solo travelers, couples, and small and large groups of guests alike to move with ease between living, dining, entertainment, and sleeping spaces during their stay. In many rentals, guests will also enjoy seamless access to large windows and vaulted ceilings throughout. These features frame a great view, promote that Florida sunshine, and enhance the overall sense of living space available to guests as well.

A collection of tasteful and stylish furnishings is always waiting for guests who book our rentals at the Windsor Hills Resort in Orlando. These collections are often incorporated to capture the comforts of home and pair it up with those one-of-a-kind Florida-inspired color palettes, patterns and designs too. Collections can include everything from large flat-screen televisions and plush sofas to cozy loveseats, recliners, accent chairs, area rugs, wall art, innovative lighting, and beyond. No matter what the collection may entail, guests will find it’s an inviting task to settle into the style and luxury they’ve found.

While dining out across Orlando and Kissimmee is a treat for the tastebuds, booking a Windsor Hills Resort rental means guests can also choose to serve up a home-style meal when it’s preferred. Many rentals are designed to include full kitchens where serving up breakfast, lunch, or dinner is a breeze. These culinary spaces are comprehensive and provide an exciting place for traveling chefs to put their skills to the test. Many enjoy spacious counters, high-end appliances, and even custom cabinetry already filled with the cookware and essentials guests might need.

At Casiola Orlando, we know that every trip to Orlando deserves to be a one-of-a-kind experience for travelers. Our team is fully committed to making sure every guest we partner with savors a customized stay that fits their unique sense of travel style! While some guests head this way to settle into the comfort and luxury of their Windsor Hills Resort stay, others are looking to spend as much time as possible in the fresh air, savoring the view and the moment too. That’s where our property options are sure to thrill. Many of our Windsor Hills Resort rentals can be booked to include access to private decks and furnished patios where guests can make the most of outdoor fun without going anywhere at all! Whether it’s taking time to socialize with family and friends while surrounded by spectacular lush scenery, or simply relaxing at your own pace, we have the home-away-from-home options that are designed to inspire ready, and available to rent. While these outdoor spaces are great for a quiet moment, they work just as well for al fresco dining when nothing sounds better than pairing a home-style dish with sunshine, warm weather, and an inviting view too.

While time out exploring the greater Orlando area and even Windsor Hills Resort itself is always a fun addition to an itinerary for guests, at Casiola Orlando, we also know how important it is for our guests to be able to rest up in style for another day of fun and Florida adventure ahead. To that end, many of our Windsor Hills Resort rentals come designed with large bedrooms included. These restful spaces are ideal for guests who are looking to unwind in comfort and style. Many host large bedroom sets topped with plush mattresses, high-quality linens, and stylish comforters too. It’s common for master suites to enjoy en suite baths and large closets as an added convenience for guests.

Guests who are looking for added luxury and style to their experience in Orlando won’t have to search far to find it. Simply ask about our property selections in Windsor Hills Resort that come with custom-built bedrooms, extra-large patios, and even game rooms included when a little friendly competition would certainly go a long way towards the vacation fun. At Casiola Orlando, we’re happy to help handle requests of all types when it comes to creating an unforgettable adventure and stay for our guests. Our team is excited to take care of the details while visitors focus on the well-deserved fun ahead.

Looking to customize your downtime after dinner? Be sure to inquire about our Windsor Hills Resort rental with access to Wi-Fi and high-speed internet included!

Windsor Hills Resort Orlando

2600 N Old Lake Wilson Rd, Kissimmee, FL 34747, United States

+1(800) 464-4104

Windsor Hills Resort amenities

24-hour security
Community pool
Hot tub
Game room
Daily valet trash service
Soccer field
Basketball court
Sundry shop

Opening hours

Clubhouse: daily from 8 am to 10 pm

Pool: daily from 8 am to 10 pm

Water slide & kids area: 10 am to 8 pm (6pm from October to March)

  • Walt Disney World: 12 minutes (3.9 miles / 6.2 km)
  • Universal Studios: 28 minutes (16 miles / 25.7 km)
  • SeaWorld Orlando: 23 minutes (11 miles / 17.7 km)
  • Legoland  Florida Resort: 52 minutes (31.4 miles / 50.5 km)
  • Bush Gardens Tampa: 83 minutes (64.2 miles / 103.3 km)
  • Aquatica: 23 minutes (13 miles / 20.9 km)
  • Discovery Cove: 24 minutes (11.6 miles / 18.6 km)
  • Orlando Vineland Premium Outlets: 18 minutes (9 miles / 28.9 km)
  • The Mall at Millenia: (29 minutes: 18 miles / 28.9 km)
  • The Wheel at ICON Park™: (27 minutes: 14.7 miles / 23.6 km)
  • Gatorland: 28 minutes (15.1 miles / 24.3 km)
  • Fun Spot America: 17 minutes (5.7 miles / 9.1 km)
  • Old Town, Kissimmee: 16 minutes (5.4 miles / 8.6 km)
  • Orlando Starflyer: 27 minutes (14.2 miles / 22.8 km)
  • Orlando International Airport (MCO): 33 minutes (24.2 miles / 38.9 km) 
  • Downtown Orlando: 34 minutes (23.3 miles / 37.4 km)
  • Amway Center: 30 minutes (22.4 miles / 36 km)
  • Citrus Bowl: 32 minutes (21.8 miles / 35 km)
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Windsor Hills Resort in Kissimmee is one of the top vacation rental resorts in the area. With a huge 140.000-gallon swimming pool next to the clubhouse, a hot tub that easily fits 10 people, a fitness area, basketball, tennis, and a mini golf court, you have all the sports amenities you could wish for.  If you prefer a more relaxed time passing, go to the game room or watch a movie at the movie theatre!

Orlando vacationers put proximity to parks at the top of their list. At Casiola, our team of experts makes sure to highlight the convenience of your rental’s location, and all other target amenities/perks/attributes that have been proven to entice prospective guests’ interest, and lead them to book. We also price your rental at attractive prices that guests can’t refuse, and that will also provide you with maximized earnings on your investment.

Stuart – Vacation Rental Expert