Windsor Hills Resort community is a distinct vacation rental home community.  Known for its incredibly close distance to Walt Disney World and family friendly resort-style amenities. With owners and staff devoted to providing a secure, comfortable, and pleasurable atmosphere for families visiting World-famous attractions in Central Florida. 

The 5-star resort-style community is only two miles from Walt Disney World, places to shop, World class restaurants, supermarkets, and everything in between.  Windsor Hills Resort provides guests with an abundance of fun amenities, including: a resort-style pool, clubhouse, and hot tub. A kids splash park and slide area are close by. With a welcome center & guest services featuring computers, printers, and fax machines. The community features many large grassy areas and a few recreation parks. It is one of the most well-kept and a premier destination for guests year after year.

By the clubhouse you have a movie theater, fitness center, marketplace and grill, game room, and ping-pong. There are sand volleyball and basketball courts, as well as kids’ playgrounds, tennis courts, community charcoal grills, and more. This perfect vacation rental destination in Central Florida has everything you need for an unforgettable holiday, or staycation. If you’re looking to stay at the World-famous Windsor Hills, continue reading for the most frequently asked questions. 

Each booking at Windsor Hills Resort, Orlando is permitted a maximum of 3 vehicles. This number includes visitor vehicles. Visitors and guests to the rental home will be required to provide a valid driver’s license if driving. Guests will be issued a temporary entry pass to show on their vehicle's windshield. The parking pass is valid till midnight on the arrival date. Parking is plentiful in Windsor Hills. The homes have 2 driveway spots available for parking. As well as close overflow parking available. There is also an oversized parking lot near the Clubhouse of Windsor Hills Resort, Florida.

Please note that street parking is not authorized within the Resort; parking is only permitted in designated places, and parked vehicles are not allowed to obstruct sidewalks. Windsor Hills Resort has active security vehicles on-site 24/7. All cars discovered to violate the Windsor Hills Resort rules and regulations will be towed. Owners will be fined by the Homeowners Association and that is billable back to guests.

Walt Disney World is merely a 2-mile drive away if you’re headed to Animal Kingdom. Guests are about 5 miles to Blizzard Beach and downtown Disney. Then you’re only about 5 to 7 miles from Disney’s Transportation and Ticket Center, Magic Kingdom, or Epcot. Windsor Hills sits as one of the closest vacation rental destinations off Disney property. You can’t beat the price, amenities, or location!

Windsor Hills is only a 16-mile drive from Windsor Hills Resort to Universal Studios, Island of Adventure, Volcano Bay. Legoland Florida is about 40 miles from Windsor Hills. Sea World and International Drive (where the Orlando eye Ferris wheel is) are only about an 11 to 15-mile drive from Windsor Hills. If you’re looking to get out and go to Busch Gardens in Tampa, Florida. You’re looking at around 64 miles, which is never far for a day trip! Depending on traffic and time of year travel time fluctuates.

Windsor Hills Resort is a gated community with security guards on duty 24 hours a day, seven days a week. They have a computerized system that tracks every visitor and vendor that comes and goes. Security cameras are placed in key places across the neighborhood. When you book your rental, you will receive all check-in instructions. As well as communication from your host on the security protocol and information they require. You must present a valid driver’s license if you are driving the vehicle and plan to drive in and out of the community.

Guards will deny access to anyone without a valid physical driver’s license, or ID. Valid photo ID required still even if you are arriving via a ride share like UBER, or LYFT. Registration of primary driver’s will be required prior to arrival. This will make sure guests have a smooth check-in process.

Windsor Hills Resort-style and Community amenities include the oversized clubhouse, resort swimming pool, kids splash park and slide area, welcome center & guest services, recreation park, movie theater, fitness center, Windsor marketplace & grill, game room, ping-pong, sand volleyball court, basketball courts, kids’ playground, tennis, community charcoal grill, and ATM. Guests can be entitled to use all these free of charge. Some may require a small cash deposit if they require equipment from the clubhouse.

Walt Disney World is merely a 2-mile drive away if you’re headed to Animal Kingdom. Guests are about 5 miles to Blizzard Beach and Disney Springs (formerly known as Downtown Disney). Then you’re only about 5 to 7 miles from Disney’s Transportation and Ticket Center, Magic Kingdom, or Epcot. Windsor Hills sits as one of the closest vacation rental destinations off Disney property.

Windsor Hills Resort pool hours are 8:00 AM to 10:00 PM daily (except on bad weather days). The water slide is open from 10:00 AM - 8:00 PM in summer and 10:00 AM - 6:00 PM in winter.

The clubhouse pool and hot tub are heated all year for guests to enjoy. Normally the clubhouse pool heats between 82-85 degrees. Hot tub will heat to normal spa temperatures. The splash pad at Windsor Hills is not heated.

Windsor Hills Resort does not allow pets inside the condominiums at all. However, there are weight restrictions for the houses and townhouses.  We do not allow pets regardless of weight limits.

We offer a complimentary starter pack with EVERY booking! We provide starter pack of laundry pods, dishwasher pods, bars of soap, conditioning shampoos, as well as a roll of toilet paper per bathroom, and a starter trash bag in each can. We also provide cleaning items such as a broom, dustpan, and vacuum.

Please understand that our vacation rentals are "self-catering" accommodations. We leave consumable items and groceries up to the guests. We provide a basic starter pack of soaps and detergents to get you started as mentioned above. We recommend purchasing what you need at the local grocery stores or ordering online. Self-catering accommodations are the best way to get the biggest discount on your stay.

Enjoy a round of golf at one of Orlando's top tier championship courses, including the Mystic Dunes Golf Club located right next door! Golfers can also enjoy the magnificent Disney courses such as Lake Buena Vista, The Palm, Magnolia, and Oak Trail Golf Courses. All some of the most sought after and most played courses around the area.

Championship level courses are close by at Reunion and Champions Gate, which are both less than 20 minutes away. Golf Courses near Windsor Hills in Kissimmee have superb deals. Don’t feel like going out on a course? Windsor Hills proximity is near Top Golf on I-Drive only 15 miles away! No matter what your play style is. There will be a course nearby for you and your family.

Yes, guests can order food and groceries to Windsor Hills if the delivery driver has a valid driving license and the correct address of the rental location. Windsor Hills Resort and Community has a list of preferred vendors for food, grocery, and shuttle services.  The community also has a convenience store where you can grab something quick. Restaurants near Windsor Hills are also available for guests to enjoy countless eating options.  You’ll never run out of options!

Yes, Windsor Hills Resort has preset quiet hours from 11:00 PM until 7:00 AM, and all guests must adhere to this.

Yes, Windsor Hills has a sundry shop located inside the Clubhouse. During the summertime Windsor Hills grocery store is open from 8:00 AM to 9:00 PM. During wintertime, hours of operations are 8:00 AM to 9:00 PM. Guests can find Walmart, Target, and Publix within a few minutes of driving range from Windsor Hills Resort Private Rentals. Including many more great places to sit down and eat with the Family!

Windsor Hills is a gated community and the safety of the guests is taken very seriously.  

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For your first check-in you must keep to the left gate at the guard house.  Be prepared to wait at peak times. You only need to go through this process one time. 

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-All drivers must have a valid driver's license or a military ID (with proof of insurance).

-Uber/Taxi drivers must have a valid Windsor Hills address and a driver's license.  Pin dots are not acceptable addresses. 

-All vehicles must have valid license plates & tags.

-The first time a vehicle enters the resort, it must be driven by a driver registered on the security system by the owners. After the first time the guards will issue a paper parking pass, then any licensed driver can come in and out using that vehicle.

-Paper parking passes may not be shared between vehicles (the guards will revoke the pass).

-Guests must have their reservation paperwork with the property address ready for review.  This can be on a smartphone but not in text message format.

-You will be given a parking pass which must not be shared. 

One week before your trip you'll receive a message with your door code.  If you you haven't heard from us please make sure to check your spam folder!

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You can always send a quick email with any questions: alwaysbebookedrentals@gmail.com.

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If you're at the resort and need any help please call the Property Management team: PROPERTY CHEKKER (201-724-1018).

CHECK IN

Welcome to your vacation home!! Check in is from 4pm onwards on the day of your arrival.  Please remember that you will need to register at the guard house upon first arrival (don't forget your booking confirmation document).  Your door code will be provided to you by email but in case of any miscommunication, please contact the Management Company at (201-724-1018).

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CHECK OUT

Check out time is 10 am on the day of departure.

Please make sure you do vacate the home promptly. The management company will charge a $50 re-scheduling fee should the cleaner arrive and the home not be vacated. Late check outs must have prior consent from the owner before the day of departure. There may be a small charge for this. Please leave all trash in bags in the trash bins provided. Please do not leave trash bags on the floor outside as you may not be leaving on a day when there is a trash pick-up and any left at the curbside will be shredded by wildlife or attacked by ants. Please keep any opened food items in the fridge and do not fill garbage bags full of raw food for the above reasons.

If there are any dirty dishes please put them in the dish washer and start the cycle. We will gladly put them away.

Our cleaners would greatly appreciate it if you could start the laundry of towels.

Please turn off all lights and ceiling fans and please ensure that all windows and patio doors are secured. Please lock the door behind you and make sure you lock the door.

Thank you. Your co-operation is greatly appreciated.

ALL GOOD THINGS COME TO AN END.HAVE A SAFE JOURNEY AND WE LOOK FORWARD TO SEEING YOU AGAIN!!

Windsor Hills is under 2 miles to Disney and less than a mile to many shopping and dining options.  Car hire/rental is the best option to navigate the area but Uber and Lyft are readily accessible options in the area and are very reasonably priced for those who choose not to drive.

Most guests now prefer the convenience of Uber or Lyft.  An Uber to Epcot for 4 people is usually around 12$ plus tip.  In advance of an Uber or Lyft vehicle arriving at the gate you should notify security in advance and ensure the driver has your details including address you are staying at in the resort.

When ordering an Uber/Lyft to pick you up at WH:

1. Put the address of your villa, townhome or condo into Uber/Lyft as the pick up.  We'd recommend you build in an extra 15 minutes for pick-up because of the check-in process at the guardhouse and chance of long lines.

2. Then message the driver with the resort address (2600 N Old Lake Wilson Road, Kissimmee, 34747) so that they will arrive at the guard house (not the back entrance - it is not accessible to guests).

3. Call the guard house on 407-397-1464 and advise that you have ordered an Uber/Lyft (leave a message if no one answers)

4. Do not use the Pick Me Up Here option (it relies on GPS - the guards require a physical address)

5. Advise Uber/Lyft that the driver’s license will be checked at the guard house. Cars/drivers without a valid driver’s license will not be allowed into the community.

Windsor Hills enjoys an optimum location at the heart of Kissimmee. Within close proximity are all the major theme parks and both Orlando international airports. Kissimmee sits to the south west of the greater Orlando conurbation. Windsor Hills is the nearest vacation rental resort community to the main WDW entrance gates (around 2 miles and 10 minutes by car). Other major theme park attractions are equally accessible: Universal Orlando, also known as Universal Studios, (15 miles and 18 minutes by car on the main I4 interstate) and Sea World (12 miles and 20 minutes by car again north east along the I4).

You'll hear the term 'rope drop' when holidaymakers talk about the Disney theme parks. At 9am each morning the rope is dropped and entry to car parking associated with the various parks becomes accessible. Ensuring you are at Disney in advance of this happening is important if you want to make the most of your day at Disney. Getting from Windsor Hills to the parks is a relatively simple affair; 8 minute drive to Animal Kingdom, 10 minutes to Epcot, 15minutes to Magic Kingdom. Consult the latest opening times before planning your journey times. Leaving on average around 45 minutes before opening is best advised. While driving to the parks takes little time getting parked and through the various security checks takes time and ideally you want to do all of this before 9am.

The wider Orlando area accommodates over 50 million visitors each year, with the majority attracted to the world's most famous theme parks. Golf is another huge draw and for many it's simply the year round sunny climate that brings them each year to central Florida. Two major airports serve the greater Orlando area. Orlando International (MCO) is located to the north east of the Orlando conurbation and, in relation to Windsor Hills, is best accessed along the I4 (around 23 miles and 30 minutes by car). Further to the north of MCO is Orlando Sanford International (SFB) easily reached along the 417 or I4 (around 50 miles and 55 minutes by car).

Florida's stunning gulf coast beaches are easily accessible to the west along the I4 to Clearwater and St Petersburg (around 1hr 30mins and 85 miles by car). To the east you'll find the beautiful beaches of the Atlantic coast. On the west coast Kennedy Space Centre can be reached in around 1hr 10mins 64 miles by car along the 528. Windsor Hills is located south of Orlando so access to both coasts does not require you to traverse the Orlando city area.

Windsor Hills is located at the heart of Florida golf country. The closest course, the excellent Mystic Dunes, is a mere 1.8miles and 6 mins drive by car. The resort is encircled by top class golf courses and if you are planning a trip to central Florida for a week or two of golf you have a huge selection of golf courses to choose from around Orlando.

Welcome to Windsor Hills’ Spectacular NEW water park where you’ll find gallons of fun!  You’ll love our new water park equipped with 2 large dueling slides and 2 smaller slides for the little ones.  Opened to the world in late 2018, you'll find it adjacent to the existing community pool and clubhouse area.  The facility is free to all guests in the resort unlike many other resort water parks in the Orlando area.  The multi-million dollar development is a fantastic addition to what is already the most popular short term rental resort in the area.

Keep cool and refreshed as you slide, splash, twirl and squirt your way around our super fun water park.

There’s so much to see and do:

Explore the pink and green waterbug!

Beware the rooster tails and ground geysers located throughout. You never know when they’ll spray.

Aim our 360 degree tube to blast your friends

Spin the Ombrello Twirls to create your own spiral water effect.

Stand under the Wavy Palm and enjoy the view.

Keen for a super soak?  Stand under our giant water wheel and try to guess when it will land a massive wave of water on you. 

Feeling really brave? Try out our dueling flume slides for a wild and wet ride.  One is faster and steeper than the other. Can you guess which one? Each provides an unique ride experience.

All riders must be 42” tall to ride the blue and green slides.

April 1 thru September 30 10am until 8pm

October 1 thru March 31 10am until 6pm

(excluding any unforeseen closures due to maintenance or bad weather).

Our condos are one of the reasons behind Windsor Hills success.  Our condos area adjacent to the first class resort pool and clubhouse, Windsor Hills offers a range of styles that cover every party size and budget.

The Condo comes with 2 bedrooms. The master bedroom comes with an en-suite bathroom while there is an additional main bathroom. You'll also find a balcony off the living/dining area.

Our townhome at Windsor Hills are 3 bed / 3 bath with floor space varying slightly based on whether the townhome is sandwiched between two other townhomes (interior) or on the end of a block (exterior).

3 BED TOWNHOME

Our townhome is a two story property coming with 3 bedrooms and 3 bathrooms with 1 bedroom and 1 bathroom located on the ground floor. Upon entering the home the bedroom/bathroom are first on the left. You then pass through the kitchen into the main living/dining area and out onto the patio with private plunge pool. Unlike most townhomes in Orlando those at Windsor Hills benefit from a private plunge pool. The remaining 2 bedrooms and bathrooms are located on the second floor.

We have basic grocery items to ensure a comfortable stay with us at Windsor Hills! Grab a bite at our Grill! Enjoy fresh sandwiches & assorted beverages!

• SANDWICHES & LITE BITES
  *Substitute Chips for French Fries for only $1.75.
  
  • HOTDOG W/ CHIPS  $4.25
  • GRILLED CHEESE SANDWICH W/CHIPS  $4.25
  • CHEESEBURGER W/ CHIPS $7.50 Quarter pound burger, cheese, lettuce, tomatoes, onions, pickles
  • WINDSOR HILLS DELUXE  $12.95 Double quarter pounder, double cheese, double bacon, lettuce, tomato, onion, pickles served w/Chips
  • VEGETARIAN BLACK BEAN CHIPOTLE BURGER $7.50 Lettuce, tomatoes, onions, pickles served w/Chips
  • CHICKEN SANDWICH W/ CHIPS $7.50 Breaded Chicken, lettuce, tomato, mayo
  • CLUB SANDWICH W/CHIPS  $7.85 Turkey, bacon, lettuce, tomato, may, cheese
  • CAESAR SALAD  $7.50 Romaine lettuce, croutons, parmesan, ceasar dressing. Add Chicken $2
  • BLT SANDWICH W/ CHIPS $6.95 Bacon, lettuce, tomato, mayo
  • CHICKEN TENDERS & FRENCH FRIES  $8.95

• STONEBAKED ITALIAN PIZZAS
  
  • CHEESE PIZZA
    • 12"  $10.99
  • PEPPERONI PIZZA
    • 12"  $11.99
• KID'S CORNER
  All meals served with juice drink, yoghurt, fruit snack, & tattoo.
  
  • GRILLED CHEESE WITH FRIES  $5.99
  • HOT DOG W/ FRIES  $5.99
  • CHICKEN NUGGETS (4) W/ FRIES  $5.99
  • CHICKEN NUGGETS (6) W/ FRIES  $6.99

NOW SERVING DELICIOUS ICE CREAM

AVAILABLE IN CUPS OR CONE

Mint Choc Chip, Vanilla, Strawberry, Rocky Road, Cookies n Cream, Chocolate, Butter Pecan, & Cookie Dough

DRINKS MENU AT THE MARKET

Stella Artios, Bud, Bud Light, Bud Light Lime, Cider, Longboard, Michelob Ultra, Spiked Seltzer, Cocktails, Wine by the glass.  Frozen Pina Colada & Strawberry Daiquiri,Sodas, Icee, Milkshakes, Latte, Cappuccino, Hot Chocolate