The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
8 bedrooms6 bathroomsSleeps 21
Popular amenities
Private pool
Spa pool on site
Garage 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.)
40 min drive
Rooms & beds
8 bedrooms (sleeps 21)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 King Bed
Bedroom 4
1 Double Bed and 1 Single Bed
Bedroom 5
2 Queen Beds
Bedroom 6
1 Queen Bed
Bedroom 7
1 Double Bed and 1 Single Bed
Bedroom 8
1 Single Bunk Bed
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
Deck or patio
Kitchen
Garden
Dining area
About this property
Upstay Lake View Villa with Hot Tub, Pool & Resort
Summary:
Make magical memories near Walt Disney World at this spacious 8 bedroom retreat in Windsor at Westside Resort. Perfect for large families and groups, enjoy a private pool, spillover hot tub, themed bedrooms that sleep up to 21 guests, outdoor lounge spaces, a fully equipped kitchen, and convenient parking throughout your stay. Take advantage of resort amenities like hot tub, lazy river, kids splash, water slides, and sports courts to stay active. Book your Disney getaway today.
The Space:
Your Private Outdoor Escape
• Exclusive private pool and spillover hot tub
• Comfortable outdoor lounge seating and sofa for up to 6 guests
• Expansive patio space
• Pool safety fence for added peace of mind
• Ambient outdoor lighting
• Peaceful, quiet-street residential setting
Relax, Gather, and Feel at Home Indoors
• Spacious open-concept living area
• Cool and comfortable stay with Central air conditioning
• High-speed, reliable WiFi
• Open layout designed for seamless group socializing
• Cozy and comfortable seating arrangements
Share Meals, Stories, and Special Moments
• Dining table seats up to 10 guests
• Fully equipped culinary kitchen stocked with essentials
• Modern appliances and essential cooking tools provided
• Open layout that keeps cooking and dining connected
Rest Easy in Comfortable and Themed Bedrooms
• Bedroom 1: King bed with a 40 inch Smart TV and large private ensuite with separate bathtub
• Bedroom 2: King bed with mountain inspired décor, a 40 inch Smart TV and private ensuite
• Bedroom 3: King bed with city themed décor and a 40 inch Smart TV (shared ensuite with the Star Wars room)
• Bedroom 4: Full and twin bed in a Star Wars themed bedroom (shared ensuite with the city room)
• Bedroom 5: Two queen beds in a Batman themed bedroom with 32 inch Smart TV and private ensuite
• Bedroom 6: Queen bed with Mickey Mouse theme and 32 inch Smart TV
• Bedroom 7: Full and twin bed in a Harry Potter themed bedroom with a 32 inch Smart TV
• Bedroom 8: Princess themed bunk room (queen bed and twin bed)
Guest Access:
Easy entry and full access to resort style amenities
• Exclusive use of the entire property
• Garage parking and driveway parking fit 2 vehicles each, and available street parking
• Contactless self check in and check out
• Access to Windsor at Westside Resort amenities from 9am to 9pm daily: resort pool and hot tub, kids splash area and water slides, playground, fitness gym, volleyball court, tennis court, basketball court, spa and relaxation areas
• Secure gated resort community with easy guest access
The Neighborhood:
Driving is the most convenient way to explore the area, especially for visiting Disney parks, shopping outlets, and nearby attractions at your own pace. Your own vehicle or a rental car is highly recommended. If you prefer not to drive, taxis and private transfers can be arranged from the airport and major hubs. Rideshare services like Uber and Lyft are also widely available and commonly used for quick trips to theme parks and dining areas.
• Disney Springs ~10 miles
• Old Town Kissimmee ~11 miles
• Orlando Vineland Premium Outlets ~14 miles
• SeaWorld Orlando ~16 miles
• Universal Orlando Resort ~20 miles
• Orlando International Airport (MCO) ~28 miles
Getting Around:
Easy access to Orlando attractions with flexible transport options
Driving is the most convenient way to explore the area, especially for visiting Disney parks, shopping outlets, and nearby attractions at your own pace. Rideshare services like Uber and Lyft are also widely available and commonly used for quick trips to theme parks and dining areas. If you prefer not to drive, taxis and private transfers can be arranged from the airport and major hubs.
• Universal Orlando Resort ~20 miles
• SeaWorld Orlando ~16 miles
• Orlando Vineland Premium Outlets ~14 miles
• Old Town Kissimmee ~11 miles
• Disney Springs ~10 miles
• Orlando International Airport (MCO) ~28 miles
Best way to get around: A rental car is highly recommended for maximum flexibility, convenience, and easier access to all major attractions.
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!
• 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.
• 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.
4. Firearms and weapons are strictly prohibited on the property.
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.
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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 cha...
Important information
You need to know
Property # 5352748vb
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
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. Old Town and Disney Springs™ are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Animal Kingdom® Theme Park. Check out an event or a game at ESPN Wide World of Sports Complex, and consider making time for Disney's Hollywood Studios®, a top attraction not to be missed.
Walt Disney World® Resort - 11 min drive - 11.4 km
Disney's Animal Kingdom® Theme Park - 16 min drive - 14.4 km
Getting around
Kissimmee Station - 30 min drive
Kissimmee, FL (ISM-Kissimmee Gateway) - 45 min drive
Restaurants
Wawa - 5 min drive
McDonald's - 5 min drive
7-Eleven - 5 min walk
Twistee Treat Berry Town - 5 min drive
Dutch Bros Coffee - 5 min drive
Frequently asked questions
Does Upstay Lake View Villa with Hot Tub, Pool & Resort have a pool?
Yes, this property has an outdoor pool.
Is Upstay Lake View Villa with Hot Tub, Pool & Resort pet-friendly?
No, pets are not allowed at this property.
How much is parking at Upstay Lake View Villa with Hot Tub, Pool & Resort?
On-site parking is available at the property.
What time is check-in at Upstay Lake View Villa with Hot Tub, Pool & Resort?
Check-in begins at 4:00 PM.
What time is check-out at Upstay Lake View Villa with Hot Tub, Pool & Resort?
Checkout is at 10:00 AM.
Where is Upstay Lake View Villa with Hot Tub, Pool & Resort located?
Located in the heart of Kissimmee, this holiday home is within 3 miles (5 km) of Lake Davenport, Four Corners FC and Highland Reserve Golf Club. Northeast Regional Park is 2.8 mi (4.6 km) away.