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Upstay Family Fun 5BR Retreat w Pool & Games Room

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Pool - Upstay Family Fun 5BR Retreat w Pool & Games Room (Clermont)
Interior - Upstay Family Fun 5BR Retreat w Pool & Games Room (Clermont)
A modern kitchen with dark cabinetry, stainless steel appliances, a granite countertop island, and pendant lighting. - Upstay Family Fun 5BR Retreat w Pool & Games Room (Clermont)
Exterior - Upstay Family Fun 5BR Retreat w Pool & Games Room (Clermont)
Fridge, microwave, oven, stovetop - Upstay Family Fun 5BR Retreat w Pool & Games Room (Clermont)
Upstay Family Fun 5BR Retreat w Pool & Games Room provides amenities, such as a gym and a hot tub. Guests can connect to in-room WiFi.

Reviews

8.0 out of 10
Very good

Entire home

5 bedrooms5 bathrooms211 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Gym

Add dates for prices

About this property

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.



    Resort Access:

    Guests enjoy complimentary access to the Windsor Cay Resort clubhouse and amenities:

    • The Reef Club (Clubhouse): Mon–Wed: 8:00 AM – 5:00 PM ; Thu–Sun: 8:00 AM – 8:00 PM

    • Resort Pool & Waterpark: Mon–Wed: 12:00 PM – 5:00 PM ; Thu–Sun: 10:00 AM – 6:00 PM

    • Blue Lagoon Bar & Grille (Dining at the Clubhouse):

    • Mon–Wed: 12:00 PM – 5:00 PM

    • Thu–Sun: 11:00 AM – 6:00 PM

    • Ordering: Scan the QR code to place your order

    • Pickup: Collect your meal at the clubhouse

    •Mini Golf Course: Daily: 10:00 AM – 4:30 PM

    •HOA Office: Mon–Fri: 8:30 AM – 5:00 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:

    • 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!



    • To ensure smooth access to Windsor Island, guests must 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+ in a timely manner so we can assist with registration. Thank you!



    • Pool maintenance is scheduled weekly and may occur during your stay. Technicians will briefly access the pool area only. Thank you for your understanding.



    Additional Services (Available Upon Request)

    • Pool heating: USD 35/night (2-night minimum, 24-hour notice required)



    House Rules



    No parties, events, or smoking/vaping. Violations may result in a USD 150 fine and/or forfeiture of deposit.

    Check-out is on time. Late departures will be charged USD 150 per additional hour.

    Excessive mess will result in additional cleaning fees. Please leave the home tidy.

    No liability is assumed for injuries related to pool use. Please use at your own risk and follow safety guidelines.

    Firearms and weapons are strictly prohibited on the property.



    • Violation of house rules may result in additional charges or immediate removal 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.

Property amenities

Pool/Spa

  • Communal pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: WiFi

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • TV
  • Video games

Laundry

  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

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)

General

  • Property located in a resort
  • Unit size: 2,276 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 18

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

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
On-site parties or group events are strictly prohibited
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 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

About the area

Located in Four Corners, this holiday home is in the city centre. Mystic Dunes Golf Club and ChampionsGate Golf Club 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™. Check out an event or a game at ESPN Wide World of Sports Complex, and consider making time for Walt Disney World® Resort, a top attraction not to be missed. Visit our Clermont travel guide
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Map
Clermont, FL

What's nearby

  • Lake Louisa State Park
    Lake Louisa State Park
    7 min drive - 9.2 km
  • Lake Davenport
    5 min drive - 5.7 km
  • Northeast Regional Park
    5 min drive - 6.5 km
  • beach near The Oaks at Southlake Commons
    5 min drive - 5.7 km
  • Four Corners FC
    6 min drive - 6.8 km

Getting around

  • Kissimmee Station
    31 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    43 min drive

Restaurants

  • Checkers
    4 min drive
  • Wawa
    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?

Checkout 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 holiday home is within 6 miles (10 km) of Northeast Regional Park, Four Corners FC and Lake Davenport. Surfari Water Park and Highland Reserve Golf Club are also within 6 miles (10 km).

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Upstay Family Fun 5BR Retreat w Pool & Games Room Reviews

Reviews

Very good

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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Rating 10 - Excellent. 0 out of 1 reviews
Rating 8 - Good. 1 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

10

Cleanliness

Reviews

Verified

8/10 Good

Dan D.

Liked: Cleanliness, check-in, communication, listing accuracy
The home was beautiful and the location was great. It not as practical as it could be. Basics like salt and pepper a would be helpful
Stayed 11 nights in Jan 2026