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Upstay: Renovated 9BR Home w Theater & Games Room

Family-friendly holiday home with fitness centre and indoor pool

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Outdoor Private Swimming Pool with Sun Loungers
Bedroom 1 (King Bed, Ensuite): A serene master suite with a king-size bed, flat-screen TV, and private ensuite — designed for comfort and relaxation.
Disney Themed Large Family Movie Theater
Open-Concept Lounge: Relax in the stylish main lounge featuring plush sofas, a large smart TV, and a stunning feature wall with modern lighting — perfect for movie nights or family hangouts.
Billiards Table in Games Room

Reviews

9.6 out of 10
Exceptional
9 bedrooms6 bathroomsSleeps 204391 sq ft

Popular amenities

  • Parking available
  • Hot tub
  • Dryer
  • Washer
  • Outdoor space
  • Barbecue grill

Explore the area

View in a map
Kissimmee, FL
  • Place, ChampionsGate Golf Club
    ‪11 min drive‬
  • Place, Mystic Dunes Golf Club
    ‪12 min drive‬
  • Place, Disney's Animal Kingdom® Theme Park
    ‪16 min drive‬
  • Airport, Kissimmee, FL (ISM-Kissimmee Gateway)
    ‪33 min drive‬

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

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Bathroom 6

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Dining area

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 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.

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.
Our prices include all fees. No hidden fees.

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Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Air conditioning

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House Rules

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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
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...

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Kissimmee

Located in Kissimmee, this holiday home is in the city centre. Mystic Dunes Golf Club and Reunion Resort Golf Course 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™. Travelling with kids? Make time for Walt Disney World® Resort, or head to an event or a match at ESPN Wide World of Sports Complex.
Map
Kissimmee, FL

What's nearby

  • Highland Reserve Golf Club - 7 min drive - 4.0 km
  • ChampionsGate Golf Club - 11 min drive - 9.1 km
  • Mystic Dunes Golf Club - 12 min drive - 10.4 km
  • Reunion Resort Golf Course - 15 min drive - 12.1 km
  • Disney's Animal Kingdom® Theme Park - 16 min drive - 13.8 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
  • ‪Twistee Treat Berry Town - ‬5 min drive
  • ‪7-Eleven - ‬18 min walk
  • ‪Giovanni's Pizzeria & Kichen - ‬5 min drive

Frequently asked questions

Does Upstay: Renovated 9BR Home w Theater & Games Room have a pool?

Yes, this property has an indoor pool.

Is Upstay: Renovated 9BR Home w Theater & Games Room pet-friendly?

No, pets are not allowed at this property.

Where is Upstay: Renovated 9BR Home w Theater & Games Room located?

This family-friendly holiday home is located in the city centre, within 3 mi (5 km) of Lake Davenport, Four Corners FC and Highland Reserve Golf Club. Surfari Water Park and Mighty Jungle Golf are also within 6 miles (10 km).

About the host

Hosted by Upstay

Host profile image
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