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4034 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 8 bedroom holiday villa can comfortably accommodate a larger family or group of up to 16 people.
Home Features-
8 Bedrooms
6 Baths
Fully Equipped Kitchen with Granite Countertops and Stainless Steel Appliances
Wireless Internet
Patio with Outdoor Furniture and Spacious Deck
Private Screened-In Pool and Lanai
Spa-This is not a hot tub, this is only heated to the same temperature as the pool if pool heat is added
Game Room in Loft with 50" Flat Screen Cable TV, Pool Table and Foosball
Full Size Washer/Dryer
Dishwasher
Central Air
DVD Bluray Player in Great Room and Loft
Towels and Bed Linens
Telephone with FREE Local Calls
60" Flat Screen Cable T.V. in Great Room
50" Flat Screen Cable T.V. in Loft Game Room
43" Flat Screen Cable T.V.s in King Suites and Queen Room
32" Flat Screen Cable T.V. in Full Bunk and Twin Rooms
4034 Square Feet
Pool Direction Northwest
Bedroom Configuration
1-King (Downstairs, Master Suite 1 on Floor Plan)
1-King (Upstairs, Master Suite 2 on Floor Plan)
1-King (Upstairs, Master Suite 3 on Floor Plan)
1-King (Upstairs, Bedroom 5 on Floor Plan)
1-Queen (Downstairs, Bedroom 2 on Floor Plan)
1-Bunkbed (Upstairs, Bedroom 7 on Floor Plan)
2-Twins (Upstairs, Bedroom 6 on Floor Plan)
2-Twins (Upstairs, Bedroom 4 on Floor Plan)
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.
No Booking or Service Fees
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Nov 30 - Dec 18 2025 | $230 | $1,610 | $5,520 | 3 nights | |
Dec 19 2025 - Jan 03 2026 | $385 | $2,695 | $9,240 | 4 nights | |
Jan 04 - Feb 05 2026 | $230 | $1,610 | $5,520 | 3 nights | |
Feb 06 - Mar 05 2026 | $275 | $1,925 | $6,600 | 3 nights | |
Mar 06 - Mar 26 2026 | $350 | $2,450 | $8,400 | 4 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 4 night(s) minimum
Stays under 99 nights require a $325.00 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 December 02, 2025
Shonna R.Awsome family vacation home
The owner Jane was easy to work with. House was everything described. Totally furnished and great for the 7 kids we had with us ages 15,8,7,6,6,5 and 3. Pool was warm Beds were comfy, property manager was helpful and available for all questions. Definitely would stay again.
Stayed: December 2021 Submitted: December 09, 2021
Host response
"Thank you for the terrific review, Shonna. We are so pleased to know you enjoyed your stay and appreciate the feedback! We look forward to welcoming your family back soon!"
Sonya S.Family vacation
Its was everything and more the house was very nice I would recommend to anyone who is planning s family getaway.
Stayed: June 2021 Submitted: June 20, 2021
Host response
"Thank you so much for letting me know how your stay was, and for sharing with others. Nothing makes me happier than knowing my guests have a great time!"
Carmen Z.Spacious place
It was nice to have enough bedrooms for our crowd of 8 adults and 6 kids. So nice to have a swimming pool with hot tub in back. Laundry room and nice kitchen to cook at were helpful. We loved the West side pool, lazy river, and area very much. Close to walk to.
Stayed: December 2019 Submitted: January 04, 2020
Felicia K.Kellum
Nice home with great accommodations to enjoy a great family gathering of fun and excitement. Home big enough to accommodate family and friends and very children friendly- gate around pool, high chair and crib. Washer and dryer and no problem with check in and access to the resort was much appreciated-24/7 gym. Owners did not hassle you- it felt like home away from home. Family enjoyed the experience.
Stayed: September 2019 Submitted: October 03, 2019
Host response
"I am so glad you and your family enjoyed your stay!!! Thank you for your kind review. I hope to hear from you again."
Wendy A.Magical!!
The house was clean and spacious the owners were so easy to work with! We go to Disney often and this house was my favorite thus far!
Stayed: January 2019 Submitted: January 26, 2019
Host response
"I am so glad you enjoyed the home, Wendy! I would love to work with you again."
Patty R.wonderful property at champions gate
We had a wonderful stay at this property. The house is spacious and can can accommodate many guests. The pool and hot tub are great after a long day at the parks. The house was spotless upon arrival, had ample kitchenware if you want to cook and a huge washer and dryer. Great location close to the parks, restaurants, supermarkets and Walmart. My kids enjoyed the pool, bar and lazy river. We happened to be home one afternoon when the pool company came, really great guys-they gave my husband some pointers on our pool. Would definitely stay again.
Stayed: May 2018 Submitted: May 09, 2018
Host response
"Thank you so much for sharing your experience with us. I am so thrilled to hear that you all enjoyed the house. You have been a pleasure to work with and I really hope to hear from you again."
Member since 2017
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