Book Direct & Save - No Booking Fees
4369 sq. ft. For last minute rentals or longer extended rentals, please inquiry about our discounted rates.
This luxury vacation home is located in the Windsor at Westside upscale resort community - A perfect destination for DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends. It features 4369 sq. ft. living space and is luxuriously furnished with top line furniture, large screen LED TV in family room and LED TV in all bedrooms. Cable TV and high-speed Wi-Fi internet are all provided. This beautiful villa is close to the luxury clubhouse.
There are three master suites (two on the 1st floor and one on the 2nd floor). There are 4 king beds (1 on the first floor in 1 bedroom, 3 on the 2nd floor in 3 bedrooms). 2 queen bed (on 2nd floor in 2 bedrooms), 2 bunk beds with 2 fulls 2 twins (on the 1st floor in 1 bedroom), and 4 twins (on the 2nd floor in 3 bedrooms). Twin beds provide flexible combination for your need (two twin beds can be easily combined into a king size bed). Plus two folding beds. It sleeps 24 people in total! New wooden floor has been installed throughout the house.
The Kitchen has equipped with granite count tops and stainless-steel appliances. There is a 4 seating pull up bar in the kitchen beside the 10-seating dining table, 4 seating breakfast table, and 8 seating patio table.
A gas BBQ grill makes poolside living even easier. A ceiling fan circulates air, keeping the cool, and recessed lighting allows dining to go late into the night with
several lounge chairs surrounding the sparkling pool and SPA. The pool faces southeast, which ensures plenty of sun exposure in the morning and avoid hot sun in the afternoon with the full width lanai providing a shady retreat from the sun when required. A full width child safety fence is installed in front of the pool and the whole outside area is under an accessible full width pool screen enclosure. Washer/dryer, and dishwasher are available.
Also provided are strollers, highchairs & Pac ’n’ Play cribs for the very young ones. Air-conditioned game room has pool table and a full-size ping pong table for further enjoyment after full day theme park visit. A drink/wine cooler is available in the game room area for convenience of gamers and jet lag walkers.
The home is also equipped with unlimited high-speed Wi-Fi and unlimited long-distance calls with US and Canada. The super energy efficient design ensures your total comfort no matter how warm the Florida sunshine becomes.
You're close to all the attractions too. Disney is 15 mins away; shops are 5 minutes away. Universal is 30 minutes, Busch Gardens is 1 hour, Lego-Land is 45 minutes, Interstate 4 (55) is 5 minutes away.
This stunning vacation rental resort community features all the popular resort amenities of its sister communities - Windsor Hills Resort and Windsor Palms Resort, AND more! An extraordinary 10,000 sq.ft. clubhouse is the centerpiece and includes a huge resort-style pool complete with a water slide – perfect for families to enjoy for hours. When it’s time for a drink or a bite to eat, the tiki bar serves both your favorite libation along with a tempting menu for poolside dining. With all the latest in cardio and strength building equipment, the fitness center will keep you tone while on vacation. For some friendly competition, there are volleyball courts and a multi-purpose sports court. In addition, a sundry shop is located in the clubhouse along with a video arcade. Windsor at Westside is a gated community, with an attendant, to ensure the safety for all our visiting guests.
Windsor at Westside Resort is strategically located in the Kissimmee area, with easy access to the theme parks, dining and shopping. For those who love to visit Disney, the location is ideal as you gain easy access to all the Walt Disney World parks via Toll Road 429 and the Western Way Blvd.
Resort Amenities
Extraordinary 10000 sq.ft. clubhouse
Huge Resort-style pool
Lazy River
Water slide
Tiki Bar
Fitness Center
Volleyball courts
Multi-purpose sports courts (tennis, basketball)
Soccer field
Sundry shop
Video arcade
Gated community with attendant
Windsor at Westside Resort is strategically located in the Kissimmee area, with easy access to the theme parks, dining and shopping. For those who love to visit Disney, the location is ideal as you gain easy access to all the Walt Disney World parks via Toll Road 429 and the Western Way Blvd.
No Booking or Service Fees
Save up to 25% compared to other websites - no hidden costs.
Connect Directly with Hosts
Book with confidence and get the best rates.
Florida's #1 Vacation Rental Site
Trusted by millions - your go-to for the perfect Florida getaway.
| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
May 01 - May 31 2026 | $319 | $339 | $2,299 | 3 nights | |
Sep 08 - Nov 20 2026 | $319 | $339 | $2,299 | 3 nights | |
Nov 29 - Dec 18 2026 | $319 | $339 | $2,299 | 3 nights |
Fees:
Notes:
*** The rate is for one villa, please contact us for quotes for two or more villas ***
Rates for Holidays vary depending on demand.
Our calendar is not updated here, please contact us for availability and exact rate for your stay, special rate, and last minute discount.
* A 13% tourist tax is applied.
* $500 (for 1 villa, it will be higher for longer bookings ) security deposit is required at the time of booking.
* Optional pool/spa heat is $35/day (for 1 villa, discount rate is available for rental a week or longer).
* Pets fee and cleaning fee to be applied.
* Rates for Holidays vary depending on demand.
* All rate is subject to change without notice.
Joanne G.Great place for large family
We were pleased with the size and location of the house. It was walking distance to the community amenities including the water park. The park is very well kept. We had heated pool heat and BBQ included and I highly recommend it. We got to cook outside while the kids played in the heated pool. We were a group of 19 and were able to co-habit easily in this house thanks to the design of it. Strongly recommend. The house is not new but also not very old. The beds were very comfortable. Quick note it was recommended that we purchase water and not drink from the tap. Did not question it just bought big water bottles.
Stayed: January 2024 Submitted: January 28, 2024
Host response
"Thanks Joanne and welcome back!"
Debbie Ann P.Awesome Thanksgiving 2022
My family and I had an awesome Thanksgiving this year. It was one of the best I like to say thank you to our host Mr. Larry and his team for making our state one of the best ones they made sure that our pool was hot that our snacks were there in the home and that we had everything that we need it even and if we have to call them late at night, they have phone numbers available for everything I like to say thank you to Larry and his team for helping our Thanksgiving being one of the best that we will remember we had an awesome time, we also like to say thank you due to we were kind of late preparing and planning but the team step right into our last minute and they helped us find a beautiful home and a nice neighborhood that we enjoy. We felt safe in the home it was clean and everything was right there. Awesome team awesome job. Thank you so much. We didn’t know that the traveling was going to be extremely long due to so many travelers out but because of what we were expecting, we travel in peace Joy we made it there safely and back home and Larry made sure that he called us every step of the way to greet us at the home was a awesome experience. Thank you we love you guys and will be seeing you again in 2023. May God bless you and continue to keep you with lift up your business and growth opportunity there in Orlando keep them safe. Oh God in Jesus name amen. Dr. Debbie Pinckney
Stayed: November 2022 Submitted: December 02, 2022
Gerald M.The most trusted, genuine, secure, comfortable and excellent rentals in Florida!
Jane has the best rentals and excellent customer care! She was very concerned and organized. She provided all the helpful information before the trip, ensured security, resourceful tips and information with guided instructions. This was very helpful to us that we never struggled with anything. The house was super excellent with ample facilities and rooms as indicated in the pictures! Being in a gated community, one has nothing to worry about security! I can certainly prove that Florida Rentals has the best houses with wonderful and awesome Owners compared to others. Choose this house with confidence, it will be a great relief to your endless vacation rentals search! The Owner is Great and dedicated to ensure a wonderful experience for your vacation!
Stayed: July 2022 Submitted: July 20, 2022
Sandy S.Plenty of room
My family (18 of us) stayed in this large home. At one point I was watching everyone in the kitchen area packing lunches, washing dishes, putting dishes away and realized it was just like the movie Home Alone with everyone running this way and that! There is plenty of room for everyone. There were some minor issues upon arrival. I called and advised the property manager and things were taken care of within a couple of days. The pool was awesome at the house. There were too many people at the resort pool for us to enjoy but we never really missed it. Went to Disney and was within 15-20 min. Discovery Cove, sea world was 20-25 min away. Great location. Only thing I would suggest is more silverware, glassware, dishcloths. Overall a great and convenient place to stay.
Stayed: July 2022 Submitted: July 05, 2022
Host response
"Glad to know you had a wonderful time and thanks for your feedback!"
Jeffrey M.Terrible
In our opinion, this rental was terrible, was dirty and in disrepair - faucets falling off the hinges, carpet stained throughout, dirt all over banisters, etc. Pool and spa were cold, even after paying an additional $ to have it heated for the week. On the second day, after returning from the day out, it appeared someone entered the house, left a door open, and took some food. The front window latch was broken and did not lock, so it could be opened easily from the outside. We called the Sheriff and they took an incident report. At that point we had enough and left the property after 2 days into our week long stay as we did not feel safe with our young children in this property. Management and owner had no sympathy and refused to refund any part of our payment. Worst rental experience we have ever had.
Stayed: April 2022 Submitted: June 02, 2022
Doreen F.Terrible Experience, Home Does Not Match Pictures
2183 Tripoli Court, Kissimmee,FL missed the mark completely! The home was not clean (carpets, walls, baseboards, lanai, and pool) were caked up with dirt / grime and grease. There was a dead RAT in the pool - Health Alert! When I reached out to the owner Ann and Gary they refused to respond. I asked for a refund - no response. Carpets are so dirty we had to wear socks the whole time. DO NOT STAY HERE!
Stayed: December 2021 Submitted: December 13, 2021
Tasha H.Excellent Stay
Very comfortable home , very spacious this is my 2nd stay at this Vacation Rental Home ,I will always recommend my family and friends ! Thanks for making our stay welcoming
Stayed: July 2020 Submitted: July 22, 2020
Host response
"Thanks Tasha! Welcome back any time ! :)"
Mike and B.Family Vacation
We had 19 family members for this reunion. The size of the house was perfect. The kids enjoyed the pool very much.Having four master suites was perfect.The upstairs loft area was a great hangout area for the older kids.The clubhouse with the pool, lazy river and children’s area is amazing. We wish that we would have spent more time enjoying this.The sand volleyball was a hit also.We would definitely recommend for a family vacation!
Stayed: July 2019 Submitted: July 21, 2019
Host response
"Thanks Bev!"
Larry H.
Facebook
Twitter
Email