House - Rating 5 (18)

Upstay Family Villa for 12 w Pool Games BBQ


Bedroom 6 bedrooms
Bathroom 4 baths
Guests 12 guests
Pets Not Allowed Pets Not Allowed

  • Location: Orlando, Florida
  • Type: House

Location Location

Description Description
Sunshine, space, and resort-style fun! Welcome to this beautiful 6-bedroom, 5-bathroom family villa at the highly sought-after Windsor at Westside Resort in Kissimmee. With over 3,100 sq. ft. of living space and room for up to 12 guests, this two-storey getaway is perfect for families, friends, or small group vacations just minutes from Disney.

From a private pool to a fully loaded garage game room and full access to world-class resort amenities, this home is made for memory-making.

Outdoor Living at Its Best:
• Private screened-in pool with safety fence
• Furnished patio with loungers & shaded seating
• BBQ grill for outdoor cooking
• Dining area for sunny meals or evening BBQs

It's Game Time, Anytime:
• Garage game room with pool table, foosball & darts
• Smart TVs throughout for movie nights or morning cartoons
• High-speed WiFi + Roku & cable for your streaming needs

Eat, Chill & Connect:
• Fully equipped kitchen with stainless steel appliances
• Spacious kitchen island & indoor dining for 8
• Open-concept living area with cozy seating & 64" Smart TV
• Upstairs loft with another 64" Smart TV – perfect for kids or extra hangout space

Sleep Soundly – 6 Bedrooms / 5 Bathrooms:
First Floor:
• Bedroom 1: King bed | Ensuite bathroom | 50" TV

Second Floor:
• Bedroom 2: King bed | Ensuite bathroom | 50" TV
• Bedroom 3: Queen bed | Shares bath w/ BR 4 | 43" TV
• Bedroom 4: Queen bed | Shares bath w/ BR 3 | 43" TV
• Bedroom 5: Queen bed | Shares bath w/ BR 6 | 43" TV
• Bedroom 6: Queen bed | Shares bath w/ BR 5 | 43" TV
(All bathrooms include fresh towels, hairdryers & shower amenities.)

Windsor at Westside Resort Amenities (included):
• Gated 24/7 security with access via Lima Gate
• Clubhouse with pool, lazy river, splash pad & waterslides
• Hot tub, fitness centre, spa & business center
• Tu Casa Bar & Lounge (open 11am–8pm)
• Volleyball, basketball & tennis courts
• Arcade room, playground, and movie theatre
(Clubhouse Hours: 9:00 AM – 8:00 PM)

Parking & Practical Info:
• Driveway parking for 2 vehicles
• Overflow parking available at clubhouse (limited)
• Washer & dryer available in-unit
• Trash pickup daily – place bins outside

Unbeatable Location:
• 10 minutes to Disney parks
• 25 minutes to Universal Studios & SeaWorld
• 5 minutes to shopping, groceries, and restaurants
• 35 minutes to Orlando International Airport (MCO)

Why Stay With Us?
As experienced & professional hosts, we pride ourselves on delivering top-notch guest experiences. Our home is professionally cleaned, well-stocked, and thoughtfully designed for comfort, fun, and togetherness.

Book now and make unforgettable Orlando memories with your crew!

• For a smooth and secure check-in experience, all guests may be required to complete ID and Enso Boarding Pass verification before arrival. Check-in instructions will be shared once verification is completed. Thank you for helping us ensure a seamless stay!
• Please note that washcloths are not provided—kindly bring your own for your stay.

Additional Services:
• Planning a BBQ? A propane tank is available for a one-time $69 charge. Let us know in advance, and we’ll make sure you’re all set to grill and enjoy!
• Pool heating is available upon request and is not included in the booking price. The fee is $35/night with a 2-night minimum. At least 24 hours’ notice is required if you would like to add this service.
• Rent a Pack 'n play for $39 (one-time fee)
• Rent a highchair for $29 (one-time fee)

Cancellation Policy Cancellation Policy
We offer flexible cancellations for all reservations made on upstay.com

  • 0-4 bedroom properties - Free cancellation until 5 days prior to arrival (4pm eastern time)
  • 5-8 bedroom properties - Free cancellation until 7 days prior to arrival (4pm eastern time)
  • 9+ bedroom properties - Free cancellation until 14 days prior to arrival (4pm eastern time)

For longer stays (up to 30 days) or monthly leases, we require at least 30 days notice to cancel or modify without fees.

Booking On Other Sites

Booking directly with us offers more flexible cancellation policies compared to other sites. Always double-check the cancellation policy before booking elsewhere, and consider booking with us directly for the best price on your rental.


Booking Deposit

50% of the total cost of the reservation is due at the time of booking, the other 50% must be paid once the cancellation policy kicks in.



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Swipe Swipe for Availability


Amenities 51 Amenities
  • Air conditioning
  • Baking sheet
  • BBQ grill
  • Bed linens
  • Carbon monoxide detector
  • Cleaning Disinfection
  • Coffee maker
  • Cookware
  • Desk
  • Dishes and silverware
  • Dishwasher
  • Dryer
  • Enhanced cleaning practices
  • Essentials
  • Family/kid friendly
  • Fire extinguisher
  • Free parking on premises
  • Garden or backyard
  • Gym
  • Hair dryer
  • Hangers
  • Heating
  • High touch surfaces disinfected
  • Hot tub
  • Hot water
  • Internet
  • Iron
  • Kettle
  • Kitchen
  • Long term stays allowed
  • Microwave
  • Oven
  • Patio or balcony
  • Private entrance
  • Refrigerator
  • Resort
  • Room-darkening shades
  • Shampoo
  • Shower gel
  • Smoke detector
  • Stove
  • Suitable for children (2-12 years)
  • Suitable for infants (under 2 years)
  • Toaster
  • Towels provided
  • TV
  • Washer
  • Wireless Internet
Resorts
  • WindsorWestside
  • Game room
  • Private pool

Reviews Rating 5 (18) Reviews
Rating 5
Casa hermosa. Muy bien equipada.
Anonymous - Posted: 2/27/2026
We are very happy to hear that you enjoyed your stay in our house. We strive to provide a comfortable and well-equipped space for our guests, and it is rewarding to know that we meet your expectations. We look forward to the opportunity to host you again in the future. Thank you for your review!
Upstay staff
Posted: 3/3/2026
Rating 5
The house was very clean and spacious. We paid for the pool heat since we stayed in February and it was worth it, the pool was a very comfortable temperature. Upstay was very responsive and helpful whenever we reached out. We enjoyed our stay and can’t wait to visit FL again.
Anonymous - Posted: 2/19/2026
Thank you for sharing your experience with us! We're delighted to hear that you found the house clean and spacious, and that the pool heat made your February stay enjoyable. It’s great to know that our team was able to assist you promptly. We appreciate your kind words and look forward to welcoming you back to Florida for another memorable visit!
Upstay staff
Posted: 2/22/2026
Rating 5
10/10 stay! The host was very helpful and their response time was great. Would definitely recommend!
Anonymous - Posted: 2/6/2026
Thank you for your wonderful feedback! It’s fantastic to hear that you had a 10/10 experience with us. We always strive to be responsive and helpful, and we’re glad that it made a positive impact on your stay. Your recommendation means a lot to us, and we hope to welcome you back to Upstay in Kissimmee soon!
Upstay staff
Posted: 2/10/2026
Rating 5
The home was beautiful and accommodated my group of 6 greatly! It is truly a beautiful home, and I would definitely book again. The check in process was very smooth, the house was easy to find, it is in a lovely neighborhood, and the host were very responsive! Thank you for having us
Anonymous - Posted: 1/29/2026
Thank you for your wonderful feedback, Jasmine! We're delighted to hear that our home was a great fit for your group of six and that you enjoyed the beautiful surroundings. It’s fantastic to know that the check-in process was smooth and that you found the house easily. We take pride in being responsive to our guests, and we appreciate your kind words. We would love to welcome you back anytime!
Upstay staff
Posted: 1/30/2026
Rating 5
Big house, plenty of spaces and rooms, super clean, communication was great. Would recommend to everyone!
Anonymous - Posted: 1/29/2026
Thank you, Chaoyi, for your wonderful review! We're delighted to hear that you enjoyed the spaciousness and cleanliness of our home. It’s always our goal to provide a comfortable and welcoming environment for our guests. We appreciate your kind words about our communication and your recommendation means a lot to us. We hope to welcome you back for another stay in the future!
Upstay staff
Posted: 1/30/2026
Rating 5
Great host and home for a family vacation. Very responsive. Will definitely book again
Anonymous - Posted: 1/10/2026
Rating 5
Very nice home, well communicated, and very close to everything
Anonymous - Posted: 1/7/2026
Rating 5
Highly recommended, this place was exactly what I was looking for in my family loved it as well Alfredo is a great host, very attentive, overall great experience!
Anonymous - Posted: 12/31/2025
Thank you for your wonderful review, Victor! It brings us so much joy to hear that you and your family had a great experience at Upstay. We strive to create a welcoming environment, and it’s fantastic to know that our efforts made a positive impact on your stay. Your recommendation means a lot to us, and we hope to welcome you back for another memorable visit in the future!
Upstay staff
Posted: 1/2/2026
Rating 5
My family and I loved staying here. It had plenty of room and it was a fun place to stay. It was in a gated community, the security guard got us an access card to the gate with a minute or two of the first time we pulled up to the gate. Entry in and out of the community was flawless during our stay. We accessed the home via pass code so it was all painless checking in. The home has a kitchen that is well equipped and it was very fun to have a private pool. We paid the extra $35 a day to heat the pool, it took about 20-30 hours to really warm up but it got nice and warm and my kids loved it. We spent one of the days of our stay just hanging out at the house. It was fun to have the pool table and the foosball table. I was pleased with our experience here.
Anonymous - Posted: 12/26/2025
Thank you, Richard, for sharing your experience with us! It’s wonderful to hear that you and your family enjoyed your stay and found the space to be both fun and accommodating. We’re glad the gated community provided you with a seamless entry and that the check-in process was easy. \n\nHaving a well-equipped kitchen and a private pool can really enhance a vacation, and we’re thrilled that your kids had a great time swimming after the pool was heated. It sounds like you made the most of your time with the pool table and foosball table, too! We appreciate your feedback and hope to welcome you back for another memorable stay in the future.
Upstay staff
Posted: 12/30/2025
Rating 5
Excellent Stay
Anonymous - Posted: 12/15/2025
Thank you, Tierra, for your wonderful review! We're so glad to hear that you had an excellent stay with us in Kissimmee. It brings us joy to know that our space met your expectations and contributed to a memorable experience. We hope to welcome you back soon for another fantastic getaway!
Upstay staff
Posted: 12/16/2025
Rating 5
Great stay! The place was clean, comfortable, and just like the pictures. Host was very responsive. Would stay again!
Anonymous - Posted: 12/9/2025
Thank you, Sheba! It’s wonderful to hear that you enjoyed your stay with us. We take pride in maintaining a clean and comfortable space, and we’re glad it met your expectations. Your kind words about our responsiveness mean a lot to us. We would love to welcome you back anytime!
Upstay staff
Posted: 12/10/2025
Rating 5
Alfredo is a great host! I highly recommend this home , very clean, spacious. I would definitely book again.
Anonymous - Posted: 11/20/2025
Thank you, Chanel, for your wonderful review! It brings us so much joy to hear that you found our home clean and spacious. We strive to create a welcoming environment for all our guests, and your recommendation means the world to us. We would love to host you again on your next visit to Kissimmee!
Upstay staff
Posted: 11/22/2025
Rating 5
Everything about this place was good stayed here with a total of 8 adults and we were comfortable and at home at all times. Perfect place to stay.
Anonymous - Posted: 10/30/2025
It’s wonderful to hear that you and your group of eight felt comfortable and at home during your stay! We strive to create a welcoming environment for all our guests, and it’s great to know that we succeeded in making your experience enjoyable. Thank you for choosing Upstay for your time in Kissimmee, and we hope to welcome you back in the future!
Upstay staff
Posted: 10/31/2025
Rating 5
THE STAY HERE WAS GREAT! MY FAMILY ENJOYED AND EVERYTHING AS DESCRIBED. THE HOME WAS BEAUTIFUL!
Anonymous - Posted: 10/14/2025
We’re thrilled to hear that you and your family had a great stay! It’s wonderful to know that you found everything as described and enjoyed the beauty of our home. We strive to create a welcoming environment for our guests, and your feedback truly means a lot to us. We hope to welcome you back for another memorable visit!
Upstay staff
Posted: 10/14/2025
Rating 5
We enjoyed our stay the pics liked exactly like the property. They allowed us to check in at 2pm which was a plus for those of us flying in.
Anonymous - Posted: 10/5/2025
We’re thrilled to hear that you enjoyed your stay and that the property met your expectations! It’s great to know that the early check-in made your arrival smoother, especially after a flight. We hope to welcome you back for another visit soon!
Upstay staff
Posted: 10/6/2025
Rating 5
Great stay, thank you for the express check-in and clear instructions!
Anonymous - Posted: 9/22/2025
We’re thrilled to hear that you had a great stay! It’s our pleasure to provide express check-in and clear instructions to make your experience as smooth as possible. Thank you for choosing Upstay, and we hope to welcome you back in the future!
Upstay staff
Posted: 9/22/2025
Rating 5
My family and I enjoyed our stay.
Anonymous - Posted: 9/3/2025
We’re thrilled to hear that you and your family enjoyed your stay with us! It was a pleasure hosting you, and we hope to welcome you back for another memorable visit in the future. Thank you for choosing Upstay!
Upstay staff
Posted: 9/4/2025
Rating 5
The house is very clean and beautifully decorated.
Letitia P. - Posted:
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