Location
Description
Sun-Drenched Poolside Sanctuary
• Private swimming pool + relaxing hot tub
• Fully enclosed private screened-in pool lanai
• Premium poolside loungers for soaking up the sun
• Shaded outdoor couch seating area
• Outdoor dining table for 10 for open-air meals
Unwind & Connect Headquarters
• The Living Room: Open-concept space built for gathering the whole group, featuring plush seating, an oversized 65" Smart TV, and ultra-fast high-speed Wi-Fi throughout the home
• The Culinary Social Hub: Fully equipped kitchen with modern stainless steel appliances, main dining table with seating for 10, plus additional kitchen island breakfast bar seating
The Ultimate Arcade & Wizarding Theater
• Harry Potter Theater Room: Upstairs loft with Hogwarts decor, mood lighting, life-sized props, PS5 console gaming station, and 65" Smart TV for movie marathons
• Downstairs Games Room: Full-sized billiard pool table, foosball table, retro arcade machines, and multiplayer gaming console setup
• Star Wars Gaming Nook: Additional arcade and gaming setup designed for young Padawans
Dream in Style – Immersive Themed Bedrooms
First Floor:
• Bedroom 1: King bed | Ensuite bath
• Bedroom 2: Bunk room with 6 Twins | Star Wars arcade theme
Second Floor:
• Bedroom 3: King bed | Ensuite bath
• Bedroom 4: Queen bed | Shared bath with Bedroom 5
• Bedroom 5: Queen bed | Shared bath with Bedroom 4
• Bedroom 6: King bed | Ensuite bath
• Bedroom 7: 2 Twin beds | Superhero theme
• Bedroom 8: 2 Twin beds | Frozen theme
• Bedroom 9: Queen bed | Ensuite bath
• Bedroom 10: Bunk room with 4 Twins | Lilo & Stitch theme
Complimentary Windsor Island Resort Access
• Resort Swimming Complex: Heated zero-entry lagoon pool, lazy river, dual water slides, children’s splash pad, and community spa
• Sports & Outdoor Recreation: Basketball court, sand volleyball court, 9-hole mini-golf, pickleball courts, and playground
• Aloha Clubhouse Access: Fitness center, video arcade room, outdoor hammock garden, and fire pit
• On-Site Dining & Amenities (Pay-as-you-go): Blue Marlin Grille restaurant, poolside bar, quick-service snack shop, and marketplace
• 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!
• We offer mid-stay cleaning for bookings over 3 days. This service is available for an additional fee and must be booked in advance.
• No pets, smoking, or parties are allowed on the property.
• Please note that pool service is scheduled weekly and may occur during your stay. It’s a brief visit to keep the pool clean, and technicians will only access the pool area. Thank you for your understanding.
• Heating service is currently unavailable.
• One of the arcades is currently unavailable to use. We sincerely apologize for the inconvenience and appreciate your patience while we get it fixed.
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. Please request at least 24 hours in advance.
• Rent a Pack ’n Play for $39 (one-time fee)
• Rent a highchair for $29 (one-time fee)
• Private swimming pool + relaxing hot tub
• Fully enclosed private screened-in pool lanai
• Premium poolside loungers for soaking up the sun
• Shaded outdoor couch seating area
• Outdoor dining table for 10 for open-air meals
Unwind & Connect Headquarters
• The Living Room: Open-concept space built for gathering the whole group, featuring plush seating, an oversized 65" Smart TV, and ultra-fast high-speed Wi-Fi throughout the home
• The Culinary Social Hub: Fully equipped kitchen with modern stainless steel appliances, main dining table with seating for 10, plus additional kitchen island breakfast bar seating
The Ultimate Arcade & Wizarding Theater
• Harry Potter Theater Room: Upstairs loft with Hogwarts decor, mood lighting, life-sized props, PS5 console gaming station, and 65" Smart TV for movie marathons
• Downstairs Games Room: Full-sized billiard pool table, foosball table, retro arcade machines, and multiplayer gaming console setup
• Star Wars Gaming Nook: Additional arcade and gaming setup designed for young Padawans
Dream in Style – Immersive Themed Bedrooms
First Floor:
• Bedroom 1: King bed | Ensuite bath
• Bedroom 2: Bunk room with 6 Twins | Star Wars arcade theme
Second Floor:
• Bedroom 3: King bed | Ensuite bath
• Bedroom 4: Queen bed | Shared bath with Bedroom 5
• Bedroom 5: Queen bed | Shared bath with Bedroom 4
• Bedroom 6: King bed | Ensuite bath
• Bedroom 7: 2 Twin beds | Superhero theme
• Bedroom 8: 2 Twin beds | Frozen theme
• Bedroom 9: Queen bed | Ensuite bath
• Bedroom 10: Bunk room with 4 Twins | Lilo & Stitch theme
Complimentary Windsor Island Resort Access
• Resort Swimming Complex: Heated zero-entry lagoon pool, lazy river, dual water slides, children’s splash pad, and community spa
• Sports & Outdoor Recreation: Basketball court, sand volleyball court, 9-hole mini-golf, pickleball courts, and playground
• Aloha Clubhouse Access: Fitness center, video arcade room, outdoor hammock garden, and fire pit
• On-Site Dining & Amenities (Pay-as-you-go): Blue Marlin Grille restaurant, poolside bar, quick-service snack shop, and marketplace
• 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!
• We offer mid-stay cleaning for bookings over 3 days. This service is available for an additional fee and must be booked in advance.
• No pets, smoking, or parties are allowed on the property.
• Please note that pool service is scheduled weekly and may occur during your stay. It’s a brief visit to keep the pool clean, and technicians will only access the pool area. Thank you for your understanding.
• Heating service is currently unavailable.
• One of the arcades is currently unavailable to use. We sincerely apologize for the inconvenience and appreciate your patience while we get it fixed.
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. Please request at least 24 hours in advance.
• Rent a Pack ’n Play for $39 (one-time fee)
• Rent a highchair for $29 (one-time fee)
Cancellation Policy
We offer flexible cancellations for all reservations made on upstay.com
- 0-4 bedroom properties - Free cancellation until 5 days prior to arrival (4pm eastern time)
- 5-8 bedroom properties - Free cancellation until 7 days prior to arrival (4pm eastern time)
- 9+ bedroom properties - Free cancellation until 14 days prior to arrival (4pm eastern time)
For longer stays (up to 30 days) or monthly leases, we require at least 30 days notice to cancel or modify without fees.
Booking On Other Sites
Booking directly with us offers more flexible cancellation policies compared to other sites. Always double-check the cancellation policy before booking elsewhere, and consider booking with us directly for the best price on your rental.
Booking Deposit
50% of the total cost of the reservation is due at the time of booking, the other 50% must be paid once the cancellation policy kicks in.
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Amenities 46
- Air conditioning
- Baking sheet
- Bathtub
- Bed linens
- Cable TV
- Dishes and silverware
- Dishwasher
- Downtown
- Dryer
- Essentials
- Fire extinguisher
- Free parking on premises
- Gym
- Hair dryer
- Hangers
- Heating
- Hot tub
- Hot water
- Indoor fireplace
- Internet
- Iron
- Kettle
- Kitchen
- Microwave
- Oven
- Private entrance
- Refrigerator
- Resort
- Room-darkening shades
- Shampoo
- Shower gel
- Smoke detector
- Stove
- Suitable for children (2-12 years)
- Suitable for infants (under 2 years)
- Toaster
- Towels provided
- TV
- Washer
- Wireless Internet
Resorts
- WindsorIslandResort
- Communal pool
- Game room
- Outdoor pool
- Private pool
- Swimming pool
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