A rare find — beach equipment ready to go for your days by the sea.
9 bedrooms6 bathroomsSleeps 20
Popular amenities
Private pool
Hot tub on site
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Explore the area
Kissimmee, FL
Northeast Regional Park
Place, Northeast Regional Park
3 min drive
Lake Davenport
Place, Lake Davenport
4 min drive
beach near Bahama Bay
Place, beach near Bahama Bay
4 min drive
Orlando, FL (MCO-Orlando Intl.)
Airport, Orlando, FL (MCO-Orlando Intl.)
41 min drive
Rooms & beds
9 bedrooms (sleeps 20)
Bedroom 1
1 King Bed
Bedroom 2
2 Queen Beds
Bedroom 3
1 King Bed
Bedroom 4
1 Single Bunk Bed
Bedroom 5
1 King Bed
Bedroom 6
1 King Bed
Bedroom 7
1 Single Bunk Bed
Bedroom 8
2 Single Beds
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
Garden
Dining area
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.
Our prices include all fees. No hidden fees.
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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.
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
About the area
Kissimmee
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.
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.
How much does it cost to stay at Upstay Family Retreat w Pool, Theater & Games Room?
As of 24 Aug 2026, prices found for a 1-night stay for 2 adults at Upstay Family Retreat w Pool, Theater & Games Room on 25 Aug 2026 start from £578, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
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).
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.