Upstay Family Fun 5BR Retreat w Pool & Games Room — Clermont, FL — vacation rental

Upstay Family Fun 5BR Retreat w Pool & Games Room

Nightly
📍 Clermont, FL, US
GGuesty$305
Per night · ~ estimatesHow we estimate

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(OOO), 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!

About the Home

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 is currently unavailable • 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: • Bedroom 1: King bed | Private ensuite bath • Bedroom 2: Queen bed | Shared half bath • 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 Windsor Cay Resort — Operating Hours Update • Opening hours remain unchanged • The Pool Deck and Restaurant will now close at 6:00 p.m. • Mini Golf and Volleyball will also close at 6:00 p.m. • The Clubhouse will remain open until 7:30 p.m.

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! • 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. • Not pet friendly; violations may result in fees or loss of deposit Additional Services (Available Upon Request) • Pool heating: USD 35/night (2-night minimum, 24-hour notice required)

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 Windsor Cay Resort — Operating Hours Update Starting September 12: • Opening hours remain unchanged • Pool deck & restaurant close at 7:00 PM • Clubhouse closes at 7:30 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)

Guest Access

- Full access to the entire home - Complimentary Windsor Cay Resort access (8:00 AM–8:00 PM) - Free Onsite Parking

House Rules and Terms

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 forfeited. 2. Please check-out on time. Late departures will result in a fine of $150 for each additional hour the property cannot be accessed for turnover. 3. Large messes will result in an additional cleaning fee. Please clean up after yourselves and any pets. 4. We do not assume liability for any injuries sustained by using the pool. Please follow all safety precautions and use at your own discretion. 5. 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.

What this place offers

Safety & cleaning 6Family, pets & fun 4Parking & access 4Views & setting 4Tech & work 4Pool & outdoors 6Kitchen & dining 15Comfort & essentials 19Rules & details 1
Carbon monoxide detector
Cleaning Disinfection
Cleaning before checkout
Enhanced cleaning practices
High touch surfaces disinfected
Smoke detector
Game console
Gym
Suitable for children (2-12 years)
Suitable for infants (under 2 years)
EV charger
Free parking on premises
Free parking on street
Private entrance
Downtown
Resort
Resort access
Town
Internet
Laptop friendly workspace
TV
Wireless Internet
Communal pool
Hot tub
Outdoor pool
Outdoor seating (furniture)
Private pool
Swimming pool
Baking sheet
Blender
Coffee maker
Cookware
Dining table
Dishwasher
Freezer
Kettle
Kitchen
Microwave
Oven
Refrigerator
Stove
Toaster
Wine glasses
Air conditioning
Bathtub
Bed linens
Body soap
Ceiling fan
Clothing storage
Conditioner
Essentials
Hair dryer
Hangers
Heating
Hot water
Indoor fireplace
Iron
Room-darkening shades
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
Close to the typical rate for the 105 homes we list in Clermont

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Property sourced from Guesty • Listing stale? Update it!

$305/ night
GuestsUp to 14
Bedrooms5
Bathrooms4.5
Guests2
Pets · not listed as allowed0
📅 No current calendar from the host's site
GGuesty$305
Per night · ~ estimatesHow we estimate