Upstay Lake View Villa with Hot Tub, Pool & Resort — Kissimmee, FL — vacation rental

Upstay Lake View Villa with Hot Tub, Pool & Resort

Nightly
📍 Kissimmee, FL, US
GGuesty$392
Per night · ~ estimatesHow we estimate

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 with lake views, 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. Book your Disney getaway today.

About the Home

Your Private Outdoor Escape • Exclusive private pool with relaxing lake views 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)

Good to know

• 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! 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. Please let us know at least 24 hours in advance so we can have everything ready for you to enjoy the grill. • 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.

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

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

House Rules and Terms

1. Parties, events, and smoking/vaping are prohibited in or around our property. 2. Please check-out on time. 3. Outside of service animals, pets are not permitted at this property. 4. Firearms and weapons are strictly prohibited on the property.

What this place offers

Safety & cleaning 5Family, pets & fun 6Parking & access 4Views & setting 4Tech & work 3Pool & outdoors 10Kitchen & dining 14Comfort & essentials 19Rules & details 1
Carbon monoxide detector
Emergency exit
Enhanced cleaning practices
High touch surfaces disinfected
Smoke detector
Foosball table
Game room
Gym
Pool table
Suitable for children (2-12 years)
Suitable for infants (under 2 years)
Free parking on premises
Free parking on street
Garage
Private entrance
Downtown
Lake
Resort access
Town
Internet
TV
Wireless Internet
BBQ grill
Communal pool
Garden or backyard
Hot tub
Outdoor pool
Outdoor seating (furniture)
Patio or balcony
Private pool
Spa
Swimming pool
Blender
Coffee maker
Dining table
Dishes and silverware
Dishwasher
Freezer
Kettle
Kitchen
Microwave
Oven
Refrigerator
Stove
Toaster
Wine glasses
Air conditioning
Bathtub
Bed linens
Body soap
Ceiling fan
Clothing storage
Conditioner
Dryer
Essentials
Hair dryer
Hangers
Heating
Hot water
Iron
Mosquito net
Shampoo
Shower gel
Towels provided
Washer
Long term stays allowed

Booking and price

Book on
the host's own site (upstayreservation.guestybookings.com). CielStay links you there and charges no fee.
Nightly rate
Above the typical rate for the 735 homes we list in Kissimmee

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Explore around Kissimmee

Kissimmee & the Orlando Theme Park Area, Florida
Travel guide · Florida
Kissimmee & the Orlando Theme Park Area, Florida
Kissimmee and the surrounding Orlando area communities — Davenport, ChampionsGate, and south Orlando — form the heartland of American family vacation travel. Walt Disney World, Universal Orlando, and SeaWorld anchor a destination where multi-bedroom villas with private heated pools, themed bedrooms, and resort-community water parks have become the defining accommodation. Whether your group wants a six-bedroom villa with a game room five minutes from Disney, an eight-bedroom resort estate with twin theaters at ChampionsGate, or a condo near International Drive, this guide covers where to stay, what to expect from the resort communities, and how to plan a trip centered on the world's most famous concentration of theme parks.

Property sourced from Guesty • Listing stale? Update it!

$392/ night
GuestsUp to 21
Bedrooms8
Bathrooms6
Guests2
Pets · not listed as allowed0
📅 No current calendar from the host's site
GGuesty$392
Per night · ~ estimatesHow we estimate