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Superb luxury 3 bedroom homes with pools 8 minutes from Disney

Bedrooms 3
Space 1,500 sq ft
Property type house
Minimum Stay 0 - 7 nights


About the property

Villa with private swimming pool & games room located close to Walt Disney World

Just one of a number of our beautiful 3 and 4 bedroom homes. Located in the much sought after 'Windward Cay' development. Excellently maintained to a very high standard, with furnishings to compliment the spacious design. The very best of Florida living. Please see our other properties on Holiday- Property- links to the other advert are found towards the bottom of this advert. Many thanks.

We offer a number of privately owned well appointed homes at 'Windward Cay.' Only minutes away from Disney, Epcot, Universal Studios and all the major attractions. We also rent homes at many of the other popular locations in Kissimmee from 3 to 5 bedrooms. All are furnished to a very high standard. Cribs and high chairs are available if required (call for fees). Each villa has its own private swimming pool, with outdoor patio furniture and sun loungers, which is screened to deter insects, leaves etc but still allows a great Tan. A local management company is on hand and will be more than willing to help with any problems.

More Details

Property Manager
DJW Rental
Member since: 1996
Speaks: english
Response time:
Within 2 days
Response rate:
Calendar last updated:
April 7, 2018


Windward Cay House Accommodation and Amenities

Property Type:
  • house (detached)
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 1500 sq ft
House Rules:
  • Max. occupancy: 6
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Town
  • Family
  • Tourist Attractions
  • Air Conditioning
  • Alarm Clock
  • Broadband Access
  • Ceiling Fans
  • Garage
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Paper Towels
  • Parking
  • Parking Off Street
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Tumble Dryer
  • Washing Machine
  • 4 Ring Stove
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Freezer
  • Ice Maker
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Child's Highchair
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom -
    Bathroom -
  • 3 Bedrooms, Sleeps 6
  • Audio Tape Player
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Games for Kids
  • Radio
  • Satellite / Cable
  • Stereo
  • Television
  • VCR
  • Lawn / Garden
  • Outdoor Grill
  • Patio
  • 6 garden chairs
  • 2 beach chairs
  • Long-term Renters Welcome
  • suitable for elderly or infirm
Pool / Spa:
  • Heated Pool
  • Outdoor Pool
  • Private Pool
  • churches
  • duty free shops
  • library
  • museums
  • playground
  • pond
  • theme parks
  • water parks
  • zoo
Leisure Activities:
  • bird watching
  • horseback riding
  • outlet shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundromat
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • mountain biking
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • swimming
  • tennis
  • water skiing
  • wind-surfing
All of our homes are equipped with linen and bath towels, although we do advise guests to provide there own beach towels for use around the pool area. All of our homes in Kissimmee have free high speed internet access via an ethernet cable, these should be present in the homes, although we do advise guests to provide there own (in case they are missing). Pool heating is optional during the cooler seasons, please contact us for prices.


Excellent! 4.6/5 -
(7 traveler reviews)

57% Complete
42% Complete
0% Complete
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Superb luxury 3 bedroom homes with pools 8 minutes from Disney
average rating of 4.571429 based on 7 reviews

Windward Cay.. great location and quiet area.

  • 4 of 5

we were very impressed with the property on Windwood Drive. It is in an ideal location for Disney parks, restaurants, shopping and all other amenities. We would definitely book again with homeaway (DJ.W rentals) it was stress free..

  • Submitted: Apr 17, 2017
  • Stayed: March 2017
  • Source: HomeAway
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5 0

Wonderful Experience.

  • 5 of 5

My wife and I have spent the month of February at Windward Cay and can only describe the experience as "Wonderful." The entire experience was effortless on our part. The home is well stocked, clean, and very comfortable. The amenities make it seem just like home but without two things, snow and cold!!! We enjoyed every minute. The location is great, very convenient to all that Orlando has to offer, yet on a street that is very quiet. The pool and lanai offer great privacy and lots of sunshine. We would recommend this property for anyone seeking to escape the cold winters and enjoy the Florida experience.

  • Submitted: Feb 28, 2014
  • Stayed: February 2014
  • Source: VRBO, from HomeAway
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15 0

Review Chapell Court 2207, Winward Cay

  • 5 of 5

We just arrived back from a wonderfull stay at Chapell Court 2207, a.k.a. rental no. 323.

The villa is conveniently situated in a quiet area, very close to the Disney Parks, only 10 miles away. This was our first stay in a villa like this but we were pleasantly surprised. It's clean, spacious and has everything a family needs for a nice vacation. 3 Bedrooms, a large living room with open kitchen, a garage (which is in fact a playroom with pool table and darts) and a very nice covered pool outside.

The screens around the pool area make sure there are no insects bugging you there.

The place is 'well kept'; very tidy and definately not worn or torn. It really has all the facilities to guarantee a comfortable stay. Washing machine, tumble dryer, dishwasher, you name it. Even fast wireless internet.

Honestly : We left the property with some pain in our heart and hope to be back next year !

Pascal & Marjolein, with Tim (10) and Noa (3) from the Netherlands.

  • Submitted: Feb 8, 2013
  • Stayed: January 2013
  • Source: HomeAway
Owner's Response: We are so pleased to hear that you enjoyed the home located on Windward Cay, please let us know if we can be of assistance in the future.
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17 0

Great Kissammee Villa stay

  • 5 of 5

We spent a delightful week in a lovely 3 bedroom bungalow with a pool and spa.

4 adults and 2 children enjoyed our stay just a short drive to all DisneyWorld sites and nearby Outlet shops as well as a 45 min drive to Kennedy Space Centre . Great value !!

  • Submitted: Oct 7, 2012
  • Stayed: September 2012
  • Source: HomeAway
Owner's Response: Thank you for your kind comments, we are pleased to hear you enjoyed the home. Please let me know if we can of assistance in the future.
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7 0


  • 4 of 5

Very comfortable villa, and very well placed for access to Kissimmee entertainment/dining facilities. Only a short drive to all the Orlando theme parks. The tall pine trees at the back provide welcome relief from the direct afternoon sun.

  • Submitted: Oct 18, 2011
  • Stayed: October 2011
  • Source: HomeAway
Owner's Response: Thank you for your kind comments if we can be of assisitance in the future please let us know.
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4 0
Brighton, Mi

Nice Place

  • 4 of 5

The property was top notch, with fantastic amenities. My only complaint was that they needed to do a better job on the "pre-arrival" check list to esnure that all was in order. The water heater was off-line (I fixed it), cable was out (which took out the wireless). The cable/wireless was a big problem for me because I needed to execute some business while away from home, which I had to manage through alternate means. This is very correctable and I will certainly be back again to rent this property!

  • Submitted: Jul 27, 2009
  • Stayed: June 2009
  • Source: HomeAway
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11 1


Wings on the Run
Fast Food Restaurant
Medieval Times Dinner & Tournament
Dinner Theater
M&M's Cafe
Dominican Restaurant
Poblanos Mexican Restaurant
Mexican Restaurant
China Bell Asian Restaurant
Asian Restaurant
Taqueria Casas
Mexican Restaurant
192 Flea Market
Jonae's Island Twist
Caribbean Restaurant
Congo River Golf
Osceola County Welcome Center and History Museum
Kosher Eatery
Kosher Restaurant
Rosies Smokin Hot BBQ
Barbecue Restaurant
Taste of Punjab
Indian Restaurant
Pizzeria Italia
Pizza Restaurant
Smokey Bones Bar & Fire Grill
Jerusalem Middle Eastern Restaurant
Middle Eastern Restaurant
China Restaurant
Chinese Restaurant
Booka Bar & Food
Bar & Grill
The British Chippy
Fish & Chips Restaurant
Café Colombia Company
Colombian Restaurant
Schiano Pizza
Pizza Restaurant
Tasty Lemon - Acai Bowl & Juice Bar
Health Food Restaurant
Slice of Italian Heaven
Pizza Delivery
Tabbouleh Halal Restaurant
Mediterranean Restaurant
Fish Taco
Seafood Restaurant
Eastern Pearl Restaurant
Chinese Restaurant
El Arepazoo
Venezuelan Restaurant
King O Falafel
Mediterranean Restaurant
Pollo Tropical
Chicken Restaurant
El Cilantrillo Restaurant
Latin American Restaurant
Mexican Restaurant
My Friend's Pizza Restaurant
Pizza Restaurant
Coach's Corner
Ichiban Buffet
Buffet Restaurant
Romano's Macaroni Grill
Italian Restaurant
The WingHouse of Kissimmee
Bar & Grill
La Alegria
Dominican Restaurant
Boston Market
American Restaurant
Uno Pizzeria & Grill
Delicias Cafe
Colombian Restaurant
Fast Food Restaurant
Osaka Japanese Steak House
Japanese Restaurant
Happy Garden
Chinese Restaurant
Fast Food Restaurant
Tropico Mofongo
Latin American Restaurant
Sharky's Sports Bar
Sports Bar
Rio Mexican Grille
Mexican Restaurant
Al dente Italian & Mediterranean halal cuisine
Halal Restaurant
Caribbean Jerk & Grille. Food Court- Bld D
Jamaican Restaurant
Punjab Kitchen
Indian Restaurant
Nearest Airport
25 Miles
Orlando International Airport
Nearest Ferry
55 Miles
Port Canaveral
Nearest Train
4 Miles
Nearest Motorway
3 Miles
Nearest Beach
50 Miles
Cocoa Beach
Car: necessary

Winward Cay is conveniently located within 2 minutes from Highway 192 containing hundreds of restaurants, shops, bars and activities. Disney and Universal Studios are situated nearby allowing you to return to your home should you require a rest before returning for the evening events

Other Activities: Walt Disney World, Universal Studios, Florida Mall, Crazy Golf, Go Carting, Waterparks, Themed Dinner shows and many other great attractions


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Fees No additional mandatory fees

Pool heating is optional please call our office for rates and further information.

We require a 30% deposit at time of confirmation, unless travel is within 10 weeks when we shall require full payment along with the refundable security deposit. Please contact our office for a copy of our booking form/rental agreement.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.

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