Upstay Family Fun 5BR Retreat w Pool & Games Room provides amenities like a gym and a hot tub. Guests can connect to in-room WiFi.
Entire home
5 bedrooms5 bathrooms211 sq m
Popular amenities
Washer
Fireplace
Gym
Air conditioning
Hot Tub
Pool
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Upstay Family Fun 5BR Retreat w Pool & Games Room
Summary: Upstay presents this spacious 5BR retreat at Windsor Cay Resort, perfect for families and groups. Kids will love the Harry Potter and Toy Story themed bunk rooms, while everyone can enjoy the game room with PS5, air hockey, and arcade games. Relax by your private pool or explore resort-style amenities including a lazy river, waterslides, mini golf, and sports courts—everything you need for the ultimate Orlando getaway!
The Space: Magical Memories Start Here! This vibrant 5-bedroom, 4.5-bathroom getaway in Windsor Cay Resort is a dream come true for families and Disney fans alike. With themed kids’ rooms, a private pool, game room, and access to resort-style amenities, it’s the perfect launchpad for your next Orlando adventure.
From lazy days by the pool to movie nights and magical bunk beds, this home is packed with fun for all ages — and just minutes from the magic of Disney.
Soak Up the Sun & Splash into Fun: • Private outdoor swimming pool with spacious sundeck • Poolside loungers and shaded dining area • Indoor & outdoor dining tables for group meals • Complimentary access to resort waterpark, lazy river, & splash pad
Play All Day: • Game room with PS5, arcade games & air hockey • Toy Story–themed bunk room with slide • Harry Potter–themed bunk room for little wizards & witches • Smart TVs in every room for endless entertainment
Eat, Lounge & Connect: • Fully equipped chef’s kitchen with stainless steel appliances • Open-concept living room with large sectional & Smart TV • Indoor dining for 10, plus island seating for 4 • High-speed WiFi & central A/C throughout the home
Dream Big, Sleep Easy: • 5 spacious bedrooms / 4.5 bathrooms • Custom kids’ rooms with themed décor and bunk beds • Comfortable King and Queen bedrooms with modern furnishings • In-home washer & dryer for added convenience
Bedroom Breakdown:
First Floor: • Bedroom 1: King bed | Private ensuite bath • Bedroom 2: Queen bed | Shared half bath
Second Floor: • Bedroom 3: Toy Story-themed bunk room | 2 Twin bunks + slide • Bedroom 4: Harry Potter-themed bunk room | 2 Twin bunks • Bedroom 5: King bed | Shared hallway bath
Resort-Style Amenities Just Steps Away: As a guest of Windsor Cay, you’ll have full access to the resort’s world-class amenities: • Lagoon-style pool & lazy river • Waterslides & kids' splash playground • Outdoor hot tub & fire pit with Disney fireworks views • Mini golf, basketball, volleyball & sports courts • Game room, fitness center & oversized yard games • Poolside cabanas, hammocks & umbrella seating • Onsite café, ice cream shop, Blue Marlin Grille & Rumbrellas Pool Bar • Aloha Clubhouse with store & guest services
Perfectly Located: • 10–15 minutes to Disney World • 25 minutes to Universal Studios • 30 minutes to Orlando International Airport (MCO) • Nearby shopping, dining, and grocery options
Check-In, Parking & More: • Gated resort with 24/7 security • Free onsite parking (driveway and street) • Contactless check-in for your convenience
Why Stay With Us? This isn’t just a vacation home — it’s an experience designed for fun, comfort, and connection. Whether you're chasing thrills at the theme parks or relaxing poolside, this Windsor Cay retreat is your family’s perfect Orlando home base.
Book your stay now and get ready to create magical memories that last a lifetime!
Guest Access: - Full access to the entire home - Complimentary Windsor Cay Resort access (8:00 AM–8:00 PM) - Free Onsite Parking
The Neighborhood: Windsor Cay Resort is the newest vacation home community in the Orlando Disney area, just a short drive to all the major theme parks like Disney World and Universal Studios. Great news! The Reef Club at Windsor Cay Resort officially opens on July 2. All guests staying at Windsor Cay should now use the brand-new amenities at The Reef Club rather than Windsor Island Resort.
Operating Hours: • The Reef Club: 8:00 AM – 8:00 PM • Blue Lagoon Tavern & Grille: 11:00 AM – 7:00 PM (Food service begins July 2) • Pool Deck & Water Amenities: 10:00 AM – 7:00 PM • Mini Golf, Cornhole & Volleyball: 10:00 AM – 7:00 PM
Please bring your own towels for the pool and water areas. A limited supply is available for purchase at the amenity center.
Available Amenities: • Brand-new clubhouse – The Reef Club • Lazy river & kids splash zone • Zero-entry resort pool + hot tub • Poolside cabanas (family & adult-only options) • Fitness center & game room • Mini golf (9 holes), cornhole, and sand volleyball • The Blue Lagoon Tavern & Grille (liquor license pending)
Other Things to Note: Important Note: • To help ensure a safe and trusted experience for all guests, ID verification may be required after booking. • To ensure smooth access to Windsor Island, guests need to be registered in advance. The HOA office is open Monday–Friday, 8:30 AM–5:00 PM, and last-minute registrations may not be processed. Please provide the names of all guests aged 18 and up in a timely manner so we can handle the registration for you. Thank you!
Add-On Services: • Pool heating is an additional service that is not included in your booking price. It's an additional fee of $35/night, which we provide upon request. • Please note that heating service is available with a minimum stay of 2 nights. Feel free to reach out for more details.
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
Pool/Spa
Communal pool
Hot tub
Private pool
Internet
Available in the house: WiFi
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Microwave
Oven
Refrigerator
Stovetop
Toaster
Bedrooms
5 bedrooms
Bedsheets provided
Bathroom
4.5 bathrooms
Hair dryer
Shower
Towels provided
Living spaces
Fireplace
Entertainment
TV
Video games
Laundry
Washing machine
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
Smoking not allowed
Services and conveniences
Iron/ironing board
Location highlights
In the city center
Things to do
Gym
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)
You will receive an email from the host with check-in and check-out instructions
Rules
1. Parties, events and smoking/vaping of any kind are prohibited in or around our property and risk a fine of $150 and/or your full deposit will be...
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
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
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
Property is also known as
6844a39ff58ce00013c5aaf7
About the neighborhood
FL, Clermont
What's nearby
Northeast Regional Park - 6 min drive - 6.1 km
Walt Disney World® Resort - 12 min drive - 11.9 km
Flamingo Crossings Town Center - 13 min drive - 14.5 km
Disney's Animal Kingdom® Theme Park - 16 min drive - 15.0 km
Magic Kingdom® Park - 23 min drive - 24.4 km
Getting around
Kissimmee Station - 31 min drive
Kissimmee, FL (ISM-Kissimmee Gateway) - 43 min drive
Restaurants
Wawa - 4 min drive
Checkers - 4 min drive
McDonald's - 3 min drive
Mcdonald's - 4 min drive
Chick-fil-A - 4 min drive
Frequently asked questions
Does Upstay Family Fun 5BR Retreat w Pool & Games Room have a pool?
Yes, this property has a pool.
Is Upstay Family Fun 5BR Retreat w Pool & Games Room pet-friendly?
No, pets are not allowed at this property.
What time is check-in at Upstay Family Fun 5BR Retreat w Pool & Games Room?
Check-in begins at 4:00 PM.
What time is check-out at Upstay Family Fun 5BR Retreat w Pool & Games Room?
Check-out is at 10:00 AM.
Where is Upstay Family Fun 5BR Retreat w Pool & Games Room located?
Located in the heart of Four Corners, this vacation home is within 6 mi (10 km) of Northeast Regional Park, Four Corners FC, and Lake Davenport. Surfari Water Park and Highland Reserve Golf Club are also within 6 mi (10 km).
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