Entire home

Upstay Family Retreat w Pool, Theater & Games Room

Photo gallery for Upstay Family Retreat w Pool, Theater & Games Room

A large pool with clear blue water, surrounded by lounge chairs and umbrellas, and a building with a sign that reads "The Cove". - Upstay Family Retreat w Pool, Theater & Games Room (Kissimmee)
A spacious lobby with a reception desk, seating area, and a Game Room. - Upstay Family Retreat w Pool, Theater & Games Room (Kissimmee)
A modern kitchen with dark cabinets, a central island, and a built-in oven. - Upstay Family Retreat w Pool, Theater & Games Room (Kissimmee)
A bedroom with a large bed, a chandelier, a castle-themed wall mural, and a window with curtains. - Upstay Family Retreat w Pool, Theater & Games Room (Kissimmee)
A modern living room with a sofa, coffee table, and dining area. There is a staircase leading to an upper level. - Upstay Family Retreat w Pool, Theater & Games Room (Kissimmee)
A garden, an arcade/games room and laundry facilities are just a few of the amenities provided at Upstay Family Retreat w Pool, Theater & Games Room. For some rest and relaxation, visit the hot tub. Free in-room WiFi and a gym are available to all guests.

Reviews

8.6 out of 10
Excellent

Entire home

9 bedrooms6 bathrooms408 sq m

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Add dates for prices

About this property

Upstay Family Retreat w Pool, 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:

    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.



    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:

    • 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.



    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.

Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Communal pool
  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Electric car charging station on site
  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 9 bedrooms
  • Bedsheets provided

Bathroom

  • 6 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Hardwood flooring in public areas
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • Near a health/beauty spa

Things to do

  • Arcade/game room
  • Billiards/pool table
  • Foosball table
  • Gym
  • Table tennis
  • Theme park nearby

Safety features

  • 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

  • Electric car charging station
  • Garden
  • Property located in a resort
  • Unit size: 4,391 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 18

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

About the area

Located in Kissimmee, this holiday home is in the city centre and near theme parks. 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. Visit our Kissimmee travel guide
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Map
Kissimmee, FL

What's nearby

  • Northeast Regional Park
    3 min drive - 3.4 km
  • Lake Davenport
    4 min drive - 3.7 km
  • beach near Bahama Bay
    4 min drive - 3.7 km
  • Four Corners FC
    6 min drive - 5.7 km
  • Highland Reserve Golf Club
    7 min drive - 7.1 km

Getting around

  • Kissimmee Station
    30 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    47 min drive

Restaurants

  • Wawa
    9 min drive
  • Raising Cane's Chicken Fingers
    9 min drive
  • 7-Eleven
    16 min walk
  • Chick-fil-A
    10 min drive
  • Chick-Fil-A
    9 min drive

Frequently asked questions

Does Upstay Family Retreat w Pool, Theater & Games Room have a pool?

Yes, this property has an outdoor pool.

Is Upstay Family Retreat w Pool, Theater & Games Room pet-friendly?

No, pets are not allowed at this property.

How much is parking at Upstay Family Retreat w Pool, Theater & Games Room?

On-site parking is available at the property.

What time is check-in at Upstay Family Retreat w Pool, Theater & Games Room?

Check-in begins at 4:00 PM.

What time is check-out at Upstay Family Retreat w Pool, Theater & Games Room?

Checkout is at 10:00 AM.

Where is Upstay Family Retreat w Pool, Theater & Games Room located?

This family-friendly holiday home is located in the city centre, within 3 mi (5 km) of Highland Reserve Golf Club, Lake Davenport and Four Corners FC. Surfari Water Park and Island H2O Live! are also within 6 miles (10 km).

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Upstay Family Retreat w Pool, Theater & Games Room Reviews