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Upstay: Renovated 9BR Home w Theater & Games RoomHouse in Kissimmee, Florida

Managed by Upstay

Overview

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.

20 guests · 9 bedrooms · 6 baths · 4391 sqft

Good for: large groups · families with children · entertainment seekers

Pricing

From $220/night + tax · $369 cleaning fee · 1-night minimum · View rate calendar

Amenities

Foosball table · Game room · Pool table

Location

4 mins to Windsor at Westside Resort · 22 mins to Disney World · 13 mins to Publix Supermarket · 39 mins to Orlando International Airport

Reviews

4.6/5 from 27 reviews · Read all reviews

Popular with: Family: 4.9/5 (10 reviews) · Large_group: 4.9/5 (7 reviews)

Guests mention: Amazing_host · Spacious · Close_to_town · Accurate_listing · Spotless_clean

Policies

No pets · Check-in 16:00 · Check-out 10:00

FAQ

Is this property pet-friendly? No, pets are not allowed.

How far is this from local attractions? 4 mins to Windsor at Westside Resort, 22 mins to Disney World, 13 mins to Publix Supermarket, 39 mins to Orlando International Airport.

What are check-in and check-out times? Check-in: 16:00, Check-out: 10:00

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Upstay: Renovated 9BR Home w Theater & Games Room

Kissimmee, Florida
9 bedrooms · 14 beds · 6 bathrooms · Sleeps 20

Where you’ll sleep

2x Bunk (Twin/Twin)
Bedroom
King
Bedroom
2x Twin
Bedroom
King
Bedroom
Queen
Bedroom
Queen
Bedroom
King
Bedroom
King
Bedroom
2x Twin
Bedroom

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.

About this property

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
Bedroom 2: Two (2) Queen beds with ensuite

Second Floor:
Bedroom 3: King bed with ensuite
Bedroom 4: Bunk-bed (twin/full)
Bedroom 5: King bedroom suite
Bedroom 6: King bedroom suite
Bedroom 7: Bunk bed (twin/full)
Bedrooms 8&9: Two 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.

The area

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.

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.

Notes from your host

• 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 may park in the driveway while extra parking is available at the clubhouse. The garage is not available, and a maximum of 5 vehicles is allowed per residence.
• Please note that washcloths are not provided—kindly bring your own for your stay.

Additional Services:
• Pool and hot tub heating are available upon request and are not included in the booking price. The fee is $45/night per service or $79/night for both, with a 2-night minimum. At least 24 hours’ notice is required if you would like to add this service.
• 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!
• Rent a Pack 'n play for $39 (one-time fee)
• Rent a highchair for $29 (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.

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.

full description, the area, host notes




Managed by Upstay

Upstay
4.5

18,070 reviews

Upstay is a vacation rental management company offering hand-picked, uniquely designed properties across multiple destinations including Orlando, Austin, Costa Rica, Canada, and Colorado. They provide curated accommodations ranging from family retreats to luxury villas, emphasizing comfort, style, and personalized travel experiences.



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