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3281 sq. ft. Windsor at Westside - Kissimmee, Florida is an upscale gated community located just 10 minutes from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and has quickly become one of the most desired locations in the Orlando area. During your stay, you will enjoy this well-appointed home that has been designed and decorated to provide you and your family an abundance of luxury amenities and leaves you well equipped to vacation with all the usual items you would expect to find at home. Windsor at Westside is only a 30-minute drive from the Orlando International Airport and is situated central to all of Orlando’s famous attractions. This spacious 7 bedroom holiday villa can comfortably accommodate a larger family or group of up to 14 people.
Home Features -
7 Bedrooms
5.5 Baths
Fully Equipped Kitchen with Granite Countertops and Stainless Steel Appliances
Wireless Internet
Patio with Outdoor Furniture and Spacious Deck
Spa - This is not a hot tub, this is only heated to the same temperature as the pool if pool heat is added
Full-Size Washer/Dryer
Dishwasher
Central Air
DVD Player
Towels and Bed Linens
Telephone with FREE Local Calls
55" Flat Screen Cable TV in Living Room, 50" Flat Screen in Upstairs Loft
32" Flat Screen Cable TVs in All Bedrooms
3281 Square Feet
Pool Direction West
Bedroom Configuration:
1-King (Downstairs, Owner's Ensuite on Floor Plan)
1-King (Upstairs, Ensuite 2 on Floor Plan)
1-Queen (Upstairs, Ensuite 3 on Floor Plan)
1-Queen (Upstairs, Bedroom 5 on Floor Plan)
1-Queen (Upstairs, Bedroom 6 on Floor Plan)
2-Twins (Upstairs, Bedroom 4 on Floor Plan)
2-Twins (Upstairs, Bedroom 7 on Floor Plan)
Unique Benefits
Windsor at Westside - Kissimmee, Florida is an upscale gated community located just 10 minutes from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and has quickly become one of the most desired locations in the Orlando area. During your stay, you will enjoy this well-appointed home that has been designed and decorated to provide you and your family an abundance of luxury amenities and leaves you well equipped to vacation with all the usual items you would expect to find at home. Windsor at Westside is only a 30-minute drive from the Orlando International Airport and is situated central to all of Orlando’s famous attractions. This spacious 7 bedroom holiday villa can comfortably accommodate a larger family or group of up to 14 people.
Come stay in this wonderfully designed resort where you’ll enjoy luxury living at its finest. Whether you want to escape for peace and quiet, or would rather explore for a bit of adventure, Windsor at Westside can fulfill all of your desires. This resort community was developed with the discerning vacationer in mind offering privacy and peace, all just minutes away from Orlando’s famed attractions. Windsor at Westside was developed to ensure that it was close enough to access all that Orlando has to offer as well as to make certain there was plenty to do right within its gates. The neighborhood caters to groups, both family, and business oriented, and continues to be one of the best and most sought-after accommodations in the Orlando, Florida area.
Clubhouse Amenities
Resort Style Pool w/ Lazy River
Outdoor Spa
Children's Water Playground
Tiki Bar
Sand Volleyball
Fitness center
Game Room
Sundry shop
Beach Access
Central Florida's renowned coastal region is only a short drive from Windsor at Westside! Within an hour you can be sunbathing at the Sunshine States fabulous Atlantic Coast and within only 50 miles you can enjoy the amazing waters of the Gulf Coast.
Why rent with us?
Head for Orlando is led by a small hardworking team who focuses on customer service. Open daily from 8AM-10PM EST (including weekends and holidays), we strive to promptly help our guests.
When you inquire about a home, you will receive information about the homes along with payment information. We try to be as transparent as possible with the reservation process.
When you reserve, you will be emailed your confirmation and arrival instructions which have all the information you need for your stay.
Other benefits:
The photos you see in the ad are recent photos of the actual property you will rent.
Our homes are in safe communities.
Keyless entry allows you to check in directly to your home, without stopping at an office.
Smoke free and pet free properties.
Our homes have assigned, dedicated onsite property managers to assist you if any issues arise.
Home Features-
7 Bedrooms
5.5 Baths
Fully Equipped Kitchen with Granite Countertops and Stainless-Steel Appliances
Wireless Internet
Patio with Outdoor Furniture and Spacious Deck
Spa-This is not a hot tub, this is only heated to the same temperature as the pool if pool heat is added.
Full-Size Washer/Dryer
Dishwasher
Central Air
DVD Player
Towels and Bed Linens
Telephone with FREE Local Calls
55" Flat Screen Cable TV in Living Room, 50" Flat Screen in Upstairs Loft
32" Flat Screen Cable TVs in All Bedrooms
3281 Square Feet
Pool Direction West
Bedroom Configuration
1-King (Downstairs, Owner's Ensuite on Floor Plan)
1-King (Upstairs, Ensuite 2 on Floor Plan)
1-Queen (Upstairs, Ensuite 3 on Floor Plan)
1-Queen (Upstairs, Bedroom 5 on Floor Plan)
1-Queen (Upstairs, Bedroom 6 on Floor Plan)
2-Twins (Upstairs, Bedroom 4 on Floor Plan)
2-Twins (Upstairs, Bedroom 7 on Floor Plan)
Clubhouse Amenities
Resort Style Pool w/ Lazy River
Outdoor Spa
Children's Water Playground
Tiki Bar
Sand Volleyball
Fitness center
Game Room
Sundry shop
No Booking or Service Fees
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Apr 12 - Jun 04 2026 | $200 | 3 nights | |||
Jun 05 - Jun 30 2026 | $250 | 3 nights | |||
Jul 01 - Jul 05 2026 | $345 | 6 nights | |||
Jul 06 - Aug 14 2026 | $300 | 4 nights | |||
Aug 15 - Sep 30 2026 | $200 | 3 nights |
Fees:
Notes:
Please note: Low Season has a 3 night(s) minimum
Mid Season has a 3 night(s) minimum
High Season has a 4 night(s) minimum
Holiday Season has a 6 night(s) minimum
Stays under 99 nights require a $310.00 Cleaning fee.
If stay is 99 nights or longer, the cleaning fee is waived.
Pool heat is an extra $40.00 per day.
Tax/Service fee is 13.50%
Last updated on April 20, 2026
Michelle C.Great House for my family
Husband and I rented this home for us and our family (total of 13 people). The home was very close to Disney and worked great for us. We had plenty of room and it was very clean.The only issue we had was with the heating of the pool. It did not start getting warm till 8pm and would cut off around 8am. I think they AM / PM is off.
Stayed: December 2019 Submitted: January 01, 2020
In your confirmation email, you will receive a 4 digit random code. You will use this code to enter the property. There is not a need to visit our onsite location. This is great for late night arrivals!
All our homes are EXECUTIVE homes. The EXECUTIVE homes have all the extra amenities include at no additional charge . All linens, towels and washcloths are provided. Fully equipped kitchens with all the modern conveniences (microwave, dishwasher, disposal, refrigerator with icemaker, etc.), dishes, cookware, cutlery, coffee maker, blender, toaster.
The initial setup includes – toilet tissue in each bathroom, paper towels, a trash can liner, and small bars of soap for the baths. After you arrive, you will need to shop for the above supplies to last for your entire stay. You will also need to bring beach towels for the pool area.
After you complete the reservation form, You will receive a confirmation by email. All payment amounts and information will be in that email. The initial $200 toward payment of the rental is due within two weeks, with the balance due 35 days in advance. You can pay by check, money order or credit card. If you make a reservation inside 35 days, then the full payment will be due immediately. If you cancel outside of 35 days before arrival then there is a $200 administration fee. If you cancel within 35 days before arrival then your stay is non-refundable.
Member since 2017
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