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Upstay: Renovated 9BR Home w Theater & Games Room
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Reviews
8.8 out of 10
Excellent
9 bedrooms6 bathroomsSleeps 204391 sq ft
Popular amenities
Rooms & beds
9 bedrooms (sleeps 20)
Bedroom 1
2 Single Bunk Beds
Bedroom 2
1 King Bed
Bedroom 3
2 Single Beds
Bedroom 4
1 King Bed
Bedroom 5
1 Queen Bed
Bedroom 6
1 Queen Bed
Bedroom 7
1 King Bed
Bedroom 8
1 King Bed
Bedroom 9
2 Single Beds
6 bathrooms
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Bathroom 3
Bathtub · Toilet · Shower only
Bathroom 4
Bathtub · Toilet · Shower only
Bathroom 5
Bathtub · Toilet · Shower only
Bathroom 6
Bathtub · Toilet · Shower only
Spaces
Kitchen
Balcony
About this property
Upstay: Renovated 9BR Home w Theater & Games Room
Summary:
Upstay presents this newly renovated 9-bedroom home at the sought-after Windsor at Westside Resort—just 8 miles from Disney! Recently updated to include a brand-new movie theater and an upgraded games room with a PlayStation, this home offers even more space for fun and relaxation. Enjoy your own private swimming pool, jacuzzi hot tub, and a spacious, fully furnished sundeck. Inside, you’ll find modern, airy rooms and entertainment for all ages, including air hockey, billiards, and foosball.
The Space:
This newly renovated 9-bedroom, 6-bathroom home at Windsor at Westside has been enhanced with a brand-new private movie theater and upgraded games room with a PlayStation—making it the ultimate group getaway. Enjoy a private pool, outdoor hot tub, and a large sundeck with serene pond views. The home sleeps up to 20 guests comfortably, with smart TVs in every bedroom and high-speed WiFi throughout.
Enjoy pond-facing views and no rear neighbors while you soak up the Florida sunshine from your private screened-in patio. Cool off in the sparkling swimming pool, unwind in the jacuzzi hot tub, or enjoy BBQ lunches around the outdoor dining area—there’s plenty of space for everyone.
Inside, the fully equipped kitchen features double fridge/freezer combo units, two large-capacity dishwashers, quartz countertops, stainless steel appliances, and a deep double sink. Dine together at the 10-person indoor dining table, with additional seating for 4 at the kitchen island and even more outdoors.
Every bedroom has a Smart TV, and high-speed internet keeps everyone connected.
Bedroom breakdown:
First Floor:
Bedroom 1: King bed with ensuite
Bedroom 2: Queen bed with ensuite
Bedroom 3: Queen bed with ensuite
Also on this floor: A popular bunk-bed room, great for kids!
Second Floor:
Bedroom 4: King bedroom suite
Bedroom 5: Queen bedroom suite
Bedroom 6: Bunk bed (twin/full)
Bedrooms 7–9: Three rooms, each with 2 twin beds
Bonus: Upstairs loft lounge now enhanced with air hockey, billiards, and foosball
Need to throw in a load of laundry? No problem—this home includes in-home washers and dryers, central A/C, and free parking for up to 4 vehicles on-site.
As part of your stay, you’ll also enjoy full access to the incredible Windsor at Westside Resort, complete with a lazy river, water slides, a Tiki bar, and so much more. Whether you're heading to Disney (just 8 miles away), relaxing poolside, or enjoying a movie night at home—this property offers a vacation experience unlike any other.
Guest Access:
You'll have private access to the property, so please make yourself at home. You can park 2 cars in the driveway. Our guests also get access to the resort clubhouse and its amenities, they are open from 9am to 9pm daily.
The Neighborhood:
Windsor at Westside is a brand new Mediterranean-themed community of luxury Orlando vacation rentals just 8 miles from Disney World. Guests get full access to the clubhouse and all of its amenities.
Getting Around:
Windsor at Westside is perfectly located to give you easy access in to the back entrance of Disney World via Black Lake Road followed by Sherbeth Road, so you will experience very minimal traffic. Close to shops, supermarkets (publix) and restaurants it's a great location to explore all the Orlando theme park attractions.
Windsor at Westside is just 30 miles from Orlando International Airport via the 417 toll road which normally takes about 35 minutes and only costs a few Dollars for the convenience.
Other Things to Note:
*IMPORTANT NOTE*
• 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!
• Up to 2 vehicles can park in the driveway. There is additional parking at the clubhouse if needed. Please note: the garage is not available, and the resort's policy limits a maximum of 5 vehicles per residence.
• Please note that we do not provide washcloths. Please bring your own washcloths to make use of during your stay.
Additional Services:
• Pool and hot tub heating is an additional service that is not included in your booking price. It's an additional fee of $35/night per service and $60/night for both, which we provide upon request. Please note that heating service is available with a minimum stay of 2 nights. Feel free to reach out for more details.
• We're happy to deliver:
- 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!
- a "Pack 'N Play Crib" for $40 (one-time fee).
- a Highchair for $40 (one-time fee).
- Mid-stay cleaning for reservations over 3 days in duration. This service is available for an extra fee and will need to be booked in advance.
Quality Assurance:
• Your wellbeing is our top priority. We have built upon our foundation of pre-existing high cleaning standards with additional COVID-19 specific recommendations from the WHO, CDC and Canadian Public Health Agency guidelines.
House Rules:
1. Parties, events, and smoking/vaping are prohibited in or around our property.
2. Please check-out on time. Late departures will result in a charge for each additional hour the property cannot be accessed for turnover.
3. Outside of service animals, pets are not permitted at this property. Any evidence of pets will result in a fine and/or forfeiture of your full deposit.
4. Firearms and weapons are strictly prohibited on the property.
5. We do not assume liability for any injuries sustained by using the pool. Please follow all safety precautions and use at your own discretion.
If any of these house rules are broken, you and your group may be subject to additional charges or be requested to vacate the property immediately without refund.
Interaction with Guests:
We work with a team of dedicated hospitality professionals who will assist us in providing you with 5-star quality service. Your recommendations and questions are important to us and we're here 24/7 to assist you. Please don't hesitate to reach out to us at any time.
Upstay presents this newly renovated 9-bedroom home at the sought-after Windsor at Westside Resort—just 8 miles from Disney! Recently updated to include a brand-new movie theater and an upgraded games room with a PlayStation, this home offers even more space for fun and relaxation. Enjoy your own private swimming pool, jacuzzi hot tub, and a spacious, fully furnished sundeck. Inside, you’ll find modern, airy rooms and entertainment for all ages, including air hockey, billiards, and foosball.
The Space:
This newly renovated 9-bedroom, 6-bathroom home at Windsor at Westside has been enhanced with a brand-new private movie theater and upgraded games room with a PlayStation—making it the ultimate group getaway. Enjoy a private pool, outdoor hot tub, and a large sundeck with serene pond views. The home sleeps up to 20 guests comfortably, with smart TVs in every bedroom and high-speed WiFi throughout.
Enjoy pond-facing views and no rear neighbors while you soak up the Florida sunshine from your private screened-in patio. Cool off in the sparkling swimming pool, unwind in the jacuzzi hot tub, or enjoy BBQ lunches around the outdoor dining area—there’s plenty of space for everyone.
Inside, the fully equipped kitchen features double fridge/freezer combo units, two large-capacity dishwashers, quartz countertops, stainless steel appliances, and a deep double sink. Dine together at the 10-person indoor dining table, with additional seating for 4 at the kitchen island and even more outdoors.
Every bedroom has a Smart TV, and high-speed internet keeps everyone connected.
Bedroom breakdown:
First Floor:
Bedroom 1: King bed with ensuite
Bedroom 2: Queen bed with ensuite
Bedroom 3: Queen bed with ensuite
Also on this floor: A popular bunk-bed room, great for kids!
Second Floor:
Bedroom 4: King bedroom suite
Bedroom 5: Queen bedroom suite
Bedroom 6: Bunk bed (twin/full)
Bedrooms 7–9: Three rooms, each with 2 twin beds
Bonus: Upstairs loft lounge now enhanced with air hockey, billiards, and foosball
Need to throw in a load of laundry? No problem—this home includes in-home washers and dryers, central A/C, and free parking for up to 4 vehicles on-site.
As part of your stay, you’ll also enjoy full access to the incredible Windsor at Westside Resort, complete with a lazy river, water slides, a Tiki bar, and so much more. Whether you're heading to Disney (just 8 miles away), relaxing poolside, or enjoying a movie night at home—this property offers a vacation experience unlike any other.
Guest Access:
You'll have private access to the property, so please make yourself at home. You can park 2 cars in the driveway. Our guests also get access to the resort clubhouse and its amenities, they are open from 9am to 9pm daily.
The Neighborhood:
Windsor at Westside is a brand new Mediterranean-themed community of luxury Orlando vacation rentals just 8 miles from Disney World. Guests get full access to the clubhouse and all of its amenities.
Getting Around:
Windsor at Westside is perfectly located to give you easy access in to the back entrance of Disney World via Black Lake Road followed by Sherbeth Road, so you will experience very minimal traffic. Close to shops, supermarkets (publix) and restaurants it's a great location to explore all the Orlando theme park attractions.
Windsor at Westside is just 30 miles from Orlando International Airport via the 417 toll road which normally takes about 35 minutes and only costs a few Dollars for the convenience.
Other Things to Note:
*IMPORTANT NOTE*
• 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!
• Up to 2 vehicles can park in the driveway. There is additional parking at the clubhouse if needed. Please note: the garage is not available, and the resort's policy limits a maximum of 5 vehicles per residence.
• Please note that we do not provide washcloths. Please bring your own washcloths to make use of during your stay.
Additional Services:
• Pool and hot tub heating is an additional service that is not included in your booking price. It's an additional fee of $35/night per service and $60/night for both, which we provide upon request. Please note that heating service is available with a minimum stay of 2 nights. Feel free to reach out for more details.
• We're happy to deliver:
- 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!
- a "Pack 'N Play Crib" for $40 (one-time fee).
- a Highchair for $40 (one-time fee).
- Mid-stay cleaning for reservations over 3 days in duration. This service is available for an extra fee and will need to be booked in advance.
Quality Assurance:
• Your wellbeing is our top priority. We have built upon our foundation of pre-existing high cleaning standards with additional COVID-19 specific recommendations from the WHO, CDC and Canadian Public Health Agency guidelines.
House Rules:
1. Parties, events, and smoking/vaping are prohibited in or around our property.
2. Please check-out on time. Late departures will result in a charge for each additional hour the property cannot be accessed for turnover.
3. Outside of service animals, pets are not permitted at this property. Any evidence of pets will result in a fine and/or forfeiture of your full deposit.
4. Firearms and weapons are strictly prohibited on the property.
5. We do not assume liability for any injuries sustained by using the pool. Please follow all safety precautions and use at your own discretion.
If any of these house rules are broken, you and your group may be subject to additional charges or be requested to vacate the property immediately without refund.
Interaction with Guests:
We work with a team of dedicated hospitality professionals who will assist us in providing you with 5-star quality service. Your recommendations and questions are important to us and we're here 24/7 to assist you. Please don't hesitate to reach out to us at any time.
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Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
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About the area
Kissimmee
Located in Kissimmee, this holiday home is in the city centre and near theme parks. ChampionsGate Golf Club and Mystic Dunes Golf Club are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Old Town and Disney Springs™. Check out an event or a game at ESPN Wide World of Sports Complex, and consider making time for Walt Disney World® Resort, a top attraction not to be missed.

Kissimmee, FL
What's nearby
- Northeast Regional Park - 3 min drive - 2.7 km
- Lake Davenport - 3 min drive - 2.7 km
- Four Corners FC - 5 min drive - 5.0 km
- Highland Reserve Golf Club - 6 min drive - 4.0 km
- Orange Lake Golf - 7 min drive - 8.5 km
Getting around
Restaurants
- McDonald's - 5 min drive
- 7-Eleven - 18 min walk
- Dutch Bros Coffee - 6 min drive
- Circle K - 7 min drive
- Twistee Treat Berry Town - 5 min drive
Frequently asked questions
Reviews
8.8
Excellent
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
8.4/10
Check-in
9.2/10
Communication
10/10
Location
8.0/10
Listing accuracy
Reviews
30 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Sep 2025
8/10 Good
Tracey O.
10 Oct, 2025
Liked: Cleanliness, check-in, communication, location
Tracey O.
Stayed 5 nights in Oct 2025
6/10 Okay
Stephanie G.
14 Jan, 2026
Liked: Cleanliness, location
Disliked: Check-in, listing accuracy
Stephanie G.
Stayed 3 nights in Dec 2025
10/10 Excellent
Lillian R.
29 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent vacation family home
Lillian R.
Stayed 4 nights in Jul 2025
10/10 Excellent
Albert N.
23 Apr, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Orlando family trip
Albert N.
Stayed 3 nights in Apr 2025
10/10 Excellent
Jacques J.
14 Jun, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Accomodations!
Jacques J.
Stayed 5 nights in Jun 2025
10/10 Excellent
Sandra S.
26 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Sandra S.
Stayed 2 nights in Oct 2025
6/10 Okay
Cynthia G.
1 Dec, 2025
Liked: Location
Disliked: Check-in, listing accuracy
Cynthia G.
Stayed 4 nights in Nov 2025
10/10 Excellent
Arthur V.
9 Mar, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Spacious Vacation Home for large groups!
Arthur V.
Stayed 6 nights in Feb 2025
8/10 Good
Froilan S.
22 Jun, 2025
Liked: Cleanliness, communication, location
Great Vacation house
Froilan S.
Stayed 7 nights in Jun 2025
6/10 Okay
Charity J.
8 Feb, 2026
Charity J.
Stayed 7 nights in Jan 2026
10/10 Excellent
Aaliyah M.
31 Jan, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Aaliyah M.
Stayed 3 nights in Jan 2026
About the host
Hosted by Upstay
Upstay provides modern vacation homes and urban retreats with 5-star hospitality. Our promise is to provide exceptional experiences by offering anticipatory hospitality services and innovative spaces that inspire and delight our guests.
Languages:
English, Spanish, Portuguese
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