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Upstay Epic Windsor Home w Pool, Cinema & GamesHouse in Kissimmee, Florida

Managed by Upstay

Overview

Get ready for the ultimate Orlando getaway! This beautifully designed 10-bedroom themed villa is designed for big groups who love big fun.

28 guests · 10 bedrooms · 6 baths · 4391 sqft

Good for: families with young kids · large groups

Pricing

From $200/night + tax · $429 cleaning fee · 1-night minimum · View rate calendar

Amenities

Foosball table · Game room · Ping pong table · Pool table

Location

25 mins to Walt Disney World Resort · 38 mins to Universal Studios · 28 mins to Magic Kingdom Park · 26 mins to EPCOT

Reviews

4.9/5 from 7 reviews — "The house is absolutely beautiful" · Read all reviews

Popular with: Family: 5.0/5 (5 reviews)

Guests mention: Amazing_host · Spotless_clean

Policies

No pets · Check-in 16:00 · Check-out 10:00

FAQ

Is this property pet-friendly? No, pets are not allowed.

How far is this from local attractions? 25 mins to Walt Disney World Resort, 38 mins to Universal Studios, 28 mins to Magic Kingdom Park, 26 mins to EPCOT.

What are check-in and check-out times? Check-in: 16:00, Check-out: 10:00

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Upstay Epic Windsor Home w Pool, Cinema & Games

Kissimmee, Florida
10 bedrooms · 20 beds · 6 bathrooms · Sleeps 28

Where you’ll sleep

King
Bedroom
King
Bedroom 2
King
Bedroom 3
Queen
Bedroom 4
Queen
Bedroom 5
Queen · 2x Twin
Bedroom 6
2x Bunk (Twin/Twin)
Bedroom 7
Bunk (Twin/Twin)
Bedroom 8
Bunk (Twin/Twin)
Bedroom 9
2x Twin
Bedroom 10
2x Twin
Bedroom 10

Get ready for the ultimate Orlando getaway! This beautifully designed 10-bedroom themed villa is designed for big groups who love big fun.

About this property

Step into your own private slice of resort-style paradise. This spacious villa blends luxury, comfort, and non-stop entertainment — approximately 15 miles from Universal Studios — giving your group the perfect home base for an unforgettable Orlando stay. Whether you’re relaxing by the pool and hot tub, exploring the themed bedrooms, or enjoying the game-packed indoor spaces, this home is built for connection, comfort, and pure holiday happiness.

Soak up the sunshine on your private outdoor retreat:
• Private screened-in swimming pool and hot tub
• Comfortable loungers for tanning & relaxing
• Outdoor seating area perfect for morning coffee or evening downtime

Fun, Games & Movie Time:
• Vibrant in-home cinema lounge with a massive screen
• Games room with ping pong, foosball, air hockey & arcade games
• High-speed Wi-Fi + Smart TVs throughout the home

Eat, Lounge & Gather:
• Open-concept living room with large Smart TV & cozy seating
• Fully equipped kitchen with modern appliances
• Elegant dining table for group meals + bar seating at the island
• Bright, airy main space perfect for reconnecting after theme-park adventures

Dream Big, Sleep Easy:
Everyone gets their perfect place to recharge — including magical themed rooms the kids will love:

First Floor
• Bedroom 1: Queen bed + 2 Twins (Cars-themed)
• Bedroom 2: King bed | Ensuite

Second Floor
• Bedroom 3: Bunk room – 2 Twins + 2 Fulls (Barbie theme)
• Bedroom 4: Bunk room – 2 Fulls (Pirates of the Caribbean theme)
• Bedroom 5: Bunk room – 2 Fulls (Avatar theme)
• Bedroom 6: Queen bed
• Bedroom 7: Queen bed
• Bedroom 8: King bed | Ensuite
• Bedroom 9: King bed
• Bedroom 10: Bunk room – 2 Twins (Winnie the Pooh theme)
Every room is cozy, comfortable, and designed for rest — with playful touches that make bedtime its own adventure.

Unbeatable location—You’re perfectly placed to enjoy the best of Orlando:
• Minutes to restaurants, groceries & convenience stores
• ≈ 10 mi to Walt Disney World Resort
• ≈ 15 mi Universal Studios
• ≈ 9 mi to Universal Studios Florida
• ≈ 20 mi to Orlando International Airport (MCO

Check-In, Parking & Resort Access
• Gated community with 24/7 security
• Driveway parking + garage parking available
• No street parking permitted in the neighbourhood

As a guest, you’ll enjoy full access to Windsor at Westside Resort, including:
• Massive resort pool & lazy river
• Kids’ splash zone & waterslides
• Tiki bar, cabanas & sun deck
• Volleyball & basketball courts
• Arcade room, activity center & clubhouse lounge
• Fitness center, business center & more
(Please Note: Some amenities or rentals may require an additional fee.)

Why Stay With Us?
We’re experts at delivering unforgettable group getaways. Our homes are clean, spacious, and full of personality — from custom designs to immersive entertainment spaces. We handle the details, so you can focus on fun.

This villa is the perfect blend of comfort, style, and entertainment — designed to bring people together and ensure every day feels special. Book your stay today!

The area

Windsor is a friendly, residential neighborhood known for its tree-lined streets and relaxed atmosphere. It’s the kind of place where you’ll see people out for walks, kids playing at nearby parks, and neighbors saying hello as they pass by.

Guests enjoy Windsor because it’s quiet and comfortable while still offering easy access to cafés, casual restaurants, grocery stores, and everyday essentials. The area feels safe and welcoming, making it great for both short visits and longer stays. With convenient public transit and major roads close by, getting around the city is quick and simple.

Nearby Family Attractions:
• Walt Disney World ~ 10 miles.
• Universal Studios ~ 15 miles.
• Magic Kingdom Park ~ 15 miles.
• EPCOT ~ 15 miles.
• Hollywood Studios ~ 10 miles.
• SeaWorld ~ 16 miles.

Nearby Other Attractions:
• Highlands Reserve Golf Club ~ 3 miles.
• Lake Louisa State Park ~ 13 miles.
• Camping World Stadium ~ 32 miles.
• Orlando Science Center ~ 34 miles.
• Mennello Museum of American Art ~ 36 miles.

Notes from your host

• 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.
• 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)

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.

full description, the area, host notes




Managed by Upstay

Upstay
4.5

18,070 reviews

Upstay is a vacation rental management company offering hand-picked, uniquely designed properties across multiple destinations including Orlando, Austin, Costa Rica, Canada, and Colorado. They provide curated accommodations ranging from family retreats to luxury villas, emphasizing comfort, style, and personalized travel experiences.



Rules & Policies


Spaces


Location

Approximate location · exact address shared after booking

Nearby · 10

  • Walt Disney World Resort

    25 mins drive
  • Universal Studios

    38 mins drive
  • Magic Kingdom Park

    28 mins drive
  • EPCOT

    26 mins drive
  • Hollywood Studios

    20 mins drive
  • SeaWorld

    30 mins drive
  • Highlands Reserve Golf Club

    7 mins drive
  • Lake Louisa State Park

    31 mins drive
  • Camping World Stadium

    38 mins drive
  • Orlando Science Center