A family-friendly stay in the heart of Kissimmee awaits you at this holiday home. You'll be 4 km (2.5 mi) from Lake Davenport and 4.7 km (2.9 mi) from Highland Reserve Golf Club. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features 6 bathrooms, a balcony and a TV. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A coffee/tea maker, a hairdryer and an iron/ironing board are also available. .Enjoy the indoor swimming pool, gym and Hot tub. Additionally, you'll find laundry facilities, a games room and barbecues. .Attractions within a 15-minute drive of this Kissimmee holiday home include Walt Disney World® Resort and Flamingo Crossings Town Center.
Reunion Resort Golf Course - 13 min drive - 10.4 km
Disney's Animal Kingdom® Theme Park - 15 min drive - 12.4 km
Getting around
Kissimmee Station - 31 min drive
Kissimmee, FL (ISM-Kissimmee Gateway) - 41 min drive
Restaurants
Dutch Bros Coffee - 6 min drive
McDonald's - 5 min drive
7-Eleven - 18 min walk
Twistee Treat Berry Town - 5 min drive
Giovanni's Pizzeria & Kichen - 5 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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 private movie theater and an upgraded games room, this home now 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. Book now!
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—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* • To help ensure a safe and trusted experience for all guests, ID verification may be required after booking. • 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: - Your BBQ comes with a complimentary full propane tank at check-in! Running low? Get a one-time refill for just $55 and keep the grill going! - 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.
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.
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
General
Property located in a resort
Unit size: 4,391 square feet
Policies
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Rules
1. Parties, events and smoking/vaping of any kind are prohibited in or around our property and risk a fine of $150 and/or your full deposit will be...
Pets
No pets allowed
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property accepts cash. On-site parties or group events are strictly prohibited. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher and a smoke detector in all accommodation.
Property is also known as
66b23d96f650240043cd268f
Frequently asked questions
Are there any beaches close to Upstay: Renovated 9BR Home w Theater & Games Room?
The closest beach to Upstay: Renovated 9BR Home w Theater & Games Room is Melt-Away Bay (8 km).
Does Upstay: Renovated 9BR Home w Theater & Games Room have a pool?
Take your pick from a pool, a communal pool and an indoor pool.
What makes Upstay: Renovated 9BR Home w Theater & Games Room a romantic place to stay?
1 hot tub, private pools, and private balconies all help set the scene for a sizzling getaway at Upstay: Renovated 9BR Home w Theater & Games Room.
Is Upstay: Renovated 9BR Home w Theater & Games Room family-friendly?
You bet! With amenities such as an arcade and laundry facilities, as well as highchairs and travel cots, it's no surprise that Upstay: Renovated 9BR Home w Theater & Games Room is a winner with our family travellers.
Is there a private hot tub at Upstay: Renovated 9BR Home w Theater & Games Room?
Yep, there is a hot tub.
Is there a free airport shuttle available at Upstay: Renovated 9BR Home w Theater & Games Room?
No, Upstay: Renovated 9BR Home w Theater & Games Room does not offer an airport shuttle service.
Are pets allowed at Upstay: Renovated 9BR Home w Theater & Games Room?
No, pets are not allowed.
Reviews
Upstay: Renovated 9BR Home w Theater & Games Room Reviews
9.6
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
10/10
Cleanliness
Rating 10 - Excellent. 5 out of 7 reviews
10 - Excellent
5
Rating 8 - Good. 2 out of 7 reviews
8 - Good
2
Rating 6 - Okay. 0 out of 7 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 7 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 7 reviews
2 - Terrible
0
Reviews
8/10 Good
Tracey O.
10 Oct 2025
Liked: Cleanliness
All great.
Tracey O.
Stayed 5 nights in Oct 2025
10/10 Excellent
Dre
30 Sept 2025
Liked: Cleanliness
Wonderful home, felt safe with family and had a lot of fun.
Dre
Stayed 2 nights in Sep 2025
10/10 Excellent
Lillian R.
29 Jul 2025
Liked: Cleanliness
Excellent vacation family home
" We had a wonderful stay at your vacation rental home! The spacious home provided plenty of room for a family of 20, and there was something for every age group to enjoy. The open kitchen was fantastic—it had enough space for everyone to eat together, making our family gatherings even more special. The whole family enjoyed the pool and the amenities at the clubhouse, which added to our fun! Highly recommend for a memorable and comfortable getaway!"
Lillian R.
Stayed 4 nights in Jul 2025
8/10 Good
Froilan S.
22 Jun 2025
Liked: Cleanliness
Great Vacation house
Overall, this was a great vacation home spacious and comfortable, with more than enough bedrooms and bathrooms for our group of 14. The kids especially loved the arcade room, swimming pool, and the home movie theater. A few things to note: the listing mentioned parking for four cars, but since the garage has been converted into an arcade, only two cars can actually fit in the driveway. We had three cars and were told that street parking isn’t allowed and could result in towing. Management recommended the “Parkopedia” app, but the nearest available parking was about two miles away, and we weren’t sure if overnight parking was allowed there. We ended up parking on the street and took our chances.We also had a bit of an issue at check-in. We were told we could check in at noon, but when we arrived, we were informed of a maintenance delay. The house wasn’t ready until around 2 PM, and we ended up waiting outside unnecessarily. Clearer communication would’ve been helpful so we can plan accordingly. We would have preferred an answer of no early check in, vice waiting there until we are allowed to go in. Lastly, basic supplies like toilet paper and trash bags were not stocked adequately. For 14 people staying 8 days, we had to go out and buy extras pretty quickly.Despite these issues, we still really enjoyed the house and the location, just 20–30 minutes from Disney. We would consider staying here again in the future with a few adjustments.
Froilan S.
Stayed 7 nights in Jun 2025
10/10 Excellent
Jacques J., Conyers, GA, USA
14 Jun 2025
Liked: Cleanliness
Amazing Accomodations!
Beautiful home. Close to the Clubhouse. Great communication with property manager. Amenities Galore! Highly Recommend!
Jacques J.
Stayed 5 nights in Jun 2025
10/10 Excellent
Albert N.
23 Apr 2025
Liked: Cleanliness
Orlando family trip
Great property. Very engaged host
Albert N.
Stayed 3 nights in Apr 2025
10/10 Excellent
Arthur V.
9 Mar 2025
Liked: Cleanliness
Spacious Vacation Home for large groups!
Did a family trip to Disney with a total of 18 kids/adults. Primarily used for the basics (sleep/shower/breakfast) so it was perfect for that as everyone had their own space. Property manager was on top of their game and very responsive. Thanks for a great trip!