Upstay Family Retreat w Pool Cinema Games Room
Private Swimming Pool & Hot Tub
In-Home Movie Theater
Modern Design
Kids Bedroom with Bunkbed Slide and Ball Pit
Presented by Upstay
The Windsor Island Resort
10 Bedroom, 20 Guest Capacity Mansion
Private Swimming Pool
Furnished Patio
Poolside Dining Area with BBQ Grill
In-Home Arcade Games Room
StarWars Themed Arcade Games Room
Upstairs Movie Theater
In-Home Movie Theater and Designated Workstation
Movie Theater Lounge
Smart TV with High Speed WiFi
Family Dining Area
Large Capacity Dining Table
Full Dining Set
Stainless Steel Appliances
Fully Equipped Kitchen
Ground level King suite
Modern bathroom with standing shower
Modern bathroom with large standing shower
Kids Room with Bunkbed Slide and Ball Pit
Cool Mood Lighting and Murals
Ensuite Bathroom is shared with the Harry Potter Room
Disney's Frozen Themed Room
Disney's Frozen Themed Room
Upstay Family Retreat w Pool Cinema Games Room | Photo 31
Disney's The Lion King Themed Room
Disney's The Lion King Themed Room
King Bedroom with Ensuite and Smart TV
Spa-like soaker tub and standing shower
Upstay Family Retreat w Pool Cinema Games Room | Photo 36
Upstay Family Retreat w Pool Cinema Games Room | Photo 37
Upstay Family Retreat w Pool Cinema Games Room | Photo 38
Upstay Family Retreat w Pool Cinema Games Room | Photo 39
Harry Potter Themed Room
Harry Potter Themed Room
Shower-in-Bathtub Design
Upstay Family Retreat w Pool Cinema Games Room | Photo 43
Upstay Family Retreat w Pool Cinema Games Room | Photo 44
Upstay Family Retreat w Pool Cinema Games Room | Photo 45
Upstay Family Retreat w Pool Cinema Games Room | Photo 46
Upstay Family Retreat w Pool Cinema Games Room | Photo 47
Upstay Family Retreat w Pool Cinema Games Room | Photo 48
Upstay Family Retreat w Pool Cinema Games Room | Photo 49
Upstay Family Retreat w Pool Cinema Games Room | Photo 50
Upstay Family Retreat w Pool Cinema Games Room | Photo 51
The Resort Waterslides
Resort Swimming Pool and Sun Loungers
Outdoor Astro Turf with Sun Loungers
Outdoor Astro Turf with Sun Loungers
Resort Swimming Pool
Jacuzzi Hot Tub at the Resort
Lazy River at the Resort
Waterslides at the Resort
The Resort Waterslides
Children's Splash Pad Playground at the Resort
The Resort Restaurant and Lawn Games Area
Mini Golf at the Resort
The Resort Clubhouse Lobby
Resort Gym
The Fitness Center at the Resort
The Arcade Games Room at the Resort Clubhouse
The Arcade Games Room at the Resort Clubhouse
The Arcade Games Room at the Resort Clubhouse
The Arcade Games Room at the Resort Clubhouse
The Arcade Games Room at the Resort Clubhouse
The Arcade Games Room at the Resort Clubhouse
The Arcade Games Room at the Resort Clubhouse
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House - Rating 5 (10)

Upstay Family Retreat w Pool Cinema Games Room

Bedroom 10 bedrooms
Bathroom 8 baths
Guests 20 guests
Pets Not Allowed Pets Not Allowed
  • Location: Orlando, Florida
  • Type: House
Location Location
Description Description
Perfect for families and large groups, this spacious 10-bedroom, 8-bathroom home is packed with immersive features—like themed kids’ rooms, a Star Wars game room, and a private movie theater. Located in the brand-new Windsor Cay community, guests enjoy full access to Windsor Cay Resort’s incredible Hawaiian-style water park and clubhouse amenities.

Outdoor Living at Its Best
• Private screened-in pool and hot tub
• Furnished sundeck with loungers and covered seating
• Outdoor dining area and BBQ grill for poolside meals
• Fully fenced-in for privacy and peace of mind

Entertainment for Everyone
• Star Wars–themed game room with billiards and air hockey
• Private in-home movie theater with projection screen and theater seating
• Smart TV in the living room + high-speed WiFi
• Multiple laptop-friendly workstations throughout the home

Cook, Dine & Gather
• Fully equipped kitchen with stainless steel appliances
• Large kitchen island with bar seating
• Indoor dining table + outdoor patio dining area
• Stocked with cookware, dishware, and utensils

Dream Big, Sleep Easy – 10 Bedrooms | Sleeps up to 22
First Floor
• Bedroom 1: King bed
• Bedroom 2: King bed | Private ensuite

Second Floor
• Bedroom 3: Queen bed | Ensuite
• Bedroom 4: 2 Twin beds | Ensuite – Harry Potter Room
• Bedroom 5: Queen bed | Ensuite
• Bedroom 6: 2 Twin beds – The Lion King Room
• Bedroom 7: 2 Twin beds – Frozen Room
• Bedroom 8: King bed | Ensuite
• Bedroom 9: Bunk bed + ball pit – Pixar Room
• Bedroom 10: 2 Twin beds

8 full bathrooms total – with fresh towels, hairdryers & toiletries provided

Resort-Style Amenities – Windsor Cay Access Included!
Guests enjoy full access to the brand-new Reef Club at Windsor Cay Resort, featuring modern amenities perfect for family fun and relaxation.

Resort Features:
• Brand-new Reef Club clubhouse & convenience store
• Zero-entry resort pool & relaxing lazy river
• Waterslides & kids’ splash zone
• 9-hole mini golf course, game room & outdoor hot tub
• Poolside cabanas, umbrellas & fire pits
• Blue Lagoon Tavern & Grille, poolside bar, café & ice cream shop
• Sand volleyball, cornhole, sports & basketball courts
• Fitness center & arcade room

Location Highlights
• Just 8 miles from Walt Disney World
• Close to Universal Orlando, SeaWorld & major attractions
• A short drive to Lake Louisa State Park for hiking, kayaking & nature escapes

Please Note:
Our home is located in a newly developed community. While the property is fully ready for your stay, you may notice some ongoing landscaping work in nearby areas as the neighborhood completes final development stages.

Why Stay With Us?
We’re dedicated to creating amazing stays for families and large groups—offering high-quality design, curated amenities, and responsive local support. Whether you're here for theme parks or poolside downtime, you’ll find everything you need to make unforgettable memories.

Book your group getaway today!

• To ensure a smooth and secure check-in, guests may be required to complete ID and Enso Boarding Pass verification before arrival. Check-in details will be shared once completed.

• To access Windsor Cay Resort, all guests must be registered in advance. The HOA office operates 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+ ahead of time so we can complete this for you.

• Pool service is scheduled weekly and may occur during your stay. This is a brief visit, and technicians will only access the pool area.

Pet Friendly:
• Up to 2 pets allowed (under 60 lbs each)
• Pet fee: $139 per pet, per stay (collected after booking)

Additional Services:
• Pool and hot tub heating (optional): $45/night per service or $79/night for both
(2-night minimum, 24-hour notice required)
• BBQ propane tank: one-time $69 charge (please request in advance)
• Pack ’n play rental: $39 (one-time fee)
• Highchair rental: $29 (one-time fee)
• Mid-stay cleaning (for stays over 3 nights): available for an additional fee (advance booking required)
Cancellation Policy 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.


Availability Calendar Availability Calendar
Available
Unavailable
Check-In
Check-Out
June 2026
Su Mo Tu We Th Fr Sa
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$395 21 $424 22 $387 23 $386 24 $433 25 $554 26 $526 27
$382 28 $386 29 $378 30        
July 2026
Su Mo Tu We Th Fr Sa
      $402 1 $707 2 3 4
5 $392 6 $367 7 $366 8 $400 9 10 11
12 $364 13 $544 14 $416 15 $586 16 $760 17 $745 18
$469 19 $519 20 $522 21 $530 22 $599 23 $697 24 $690 25
$427 26 $445 27 $426 28 $413 29 $490 30 $607 31  
August 2026
Su Mo Tu We Th Fr Sa
            $640 1
$426 2 $416 3 $333 4 $381 5 $394 6 7 8
9 $258 10 $261 11 12 13 14 15
16 17 $302 18 $316 19 $385 20 $416 21 $421 22
$343 23 $294 24 $272 25 $284 26 27 28 29
30 $253 31          
September 2026
Su Mo Tu We Th Fr Sa
    $225 1 $237 2 $325 3 $497 4 $496 5
$492 6 7 8 9 10 11 12
$290 13 $241 14 $226 15 $242 16 $309 17 $364 18 $378 19
$313 20 $308 21 $313 22 $313 23 $321 24 $379 25 $388 26
$299 27 $244 28 $245 29 $272 30      
October 2026
Su Mo Tu We Th Fr Sa
        $335 1 $385 2 $390 3
$311 4 $310 5 $319 6 7 8 9 10
$449 11 $351 12 $359 13 $352 14 $379 15 $459 16 17
18 19 20 21 22 23 24
$313 25 $250 26 $230 27 $247 28 $342 29 $397 30 $393 31
November 2026
Su Mo Tu We Th Fr Sa
$351 1 $340 2 $339 3 $340 4 $356 5 $397 6 $430 7
$355 8 $359 9 $450 10 $451 11 $460 12 $432 13 $455 14
$348 15 $272 16 $287 17 $278 18 $353 19 $471 20 $601 21
$646 22 $775 23 $841 24 $1223 25 $1224 26 $1218 27 $1186 28
$419 29 $360 30          
December 2026
Su Mo Tu We Th Fr Sa
    $379 1 $369 2 $375 3 $431 4 $457 5
$347 6 $329 7 $329 8 $345 9 $367 10 $431 11 $462 12
$401 13 $351 14 $351 15 $322 16 $431 17 $659 18 $1047 19
$1204 20 $1252 21 $1253 22 23 24 25 26
$1312 27 $1311 28 $1311 29 $1493 30 $1494 31    
January 2027
Su Mo Tu We Th Fr Sa
          $1428 1 $1295 2
$737 3 $664 4 $540 5 $458 6 $459 7 $544 8 $475 9
$406 10 $327 11 $309 12 $323 13 $368 14 $458 15 $503 16
$500 17 $347 18 $297 19 $311 20 $364 21 $408 22 $409 23
$361 24 $324 25 $305 26 $313 27 $372 28 $421 29 $415 30
$368 31            
February 2027
Su Mo Tu We Th Fr Sa
  $334 1 $307 2 $333 3 $397 4 $432 5 $438 6
$408 7 $413 8 $422 9 $426 10 $490 11 $632 12 $723 13
$720 14 $554 15 $472 16 $472 17 $489 18 $547 19 $501 20
$448 21 $422 22 $399 23 $415 24 $463 25 $538 26 $501 27
$442 28            
March 2027
Su Mo Tu We Th Fr Sa
  $433 1 $450 2 $433 3 $472 4 $596 5 $607 6
$537 7 $490 8 $509 9 $616 10 $561 11 $899 12 $907 13
$902 14 $909 15 $909 16 $884 17 $874 18 $912 19 $843 20
$753 21 $630 22 $592 23 $960 24 $985 25 $1041 26 $991 27
$1005 28 $973 29 $1009 30 $1037 31      
April 2027
Su Mo Tu We Th Fr Sa
        $1133 1 $1168 2 $916 3
$773 4 $746 5 $648 6 $778 7 $905 8 $914 9 $894 10
$636 11 $636 12 $520 13 $770 14 $558 15 $645 16 $967 17
$998 18 $1107 19 $1136 20 $1137 21 $1125 22 $1208 23 $1198 24
$1187 25 $1095 26 $1090 27 $1091 28 $1097 29 $1090 30  
May 2027
Su Mo Tu We Th Fr Sa
            $536 1
$439 2 $363 3 $348 4 $351 5 $418 6 $499 7 $477 8
$409 9 $345 10 $326 11 $418 12 $431 13 $499 14 $477 15
$389 16 $521 17 $541 18 $664 19 $665 20 $692 21 $533 22
$402 23 $393 24 $367 25 $562 26 $547 27 $732 28 $732 29
$745 30 $548 31          
Swipe Swipe for Availability
Amenities 58 Amenities
  • Air conditioning
  • Baking sheet
  • Bathtub
  • BBQ grill
  • Bed linens
  • Cable TV
  • Carbon monoxide detector
  • Cleaning Disinfection
  • Coffee maker
  • Cookware
  • Desk
  • Dishes and silverware
  • Dishwasher
  • Dryer
  • Enhanced cleaning practices
  • Essentials
  • Family/kid friendly
  • Fire extinguisher
  • Free parking on premises
  • Hair dryer
  • Hangers
  • Heating
  • High touch surfaces disinfected
  • Hot water
  • Indoor pool
  • Internet
  • Iron
  • Kettle
  • Kitchen
  • Long term stays allowed
  • 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
  • Disney Theme Room
  • Game room
  • HarryPotter Theme Room
  • In-Home Games Room
  • Pixar Theme Room
  • Princess Theme Room
  • Private Cinema - BEST
  • Private pool
  • StarWars Theme Room
  • Swimming pool
  • Tropical Theme Room
Reviews Rating 5 (10) Reviews
Rating 5
My family and I loved our stay at Upstay,! The cohost Luciana was very helpful during our stay, she helped me with anything I needed. The kids loved the game room and home theater. When we come back to Orlando Upstay is where we want to stay!
Anonymous - Posted: 12/26/2025
It’s wonderful to hear that you and your family had such a great time! The game room and home theater are definitely favorites among our guests, and it’s fantastic that the kids had a blast there. We can’t wait to welcome you back on your next trip!
Upstay staff
Posted: 12/30/2025
Rating 5
Todo estuvo bien muchas gracias
Anonymous - Posted: 12/26/2025
We are happy to hear that everything was fine during your stay. We look forward to welcoming you again in the future!
Upstay staff
Posted: 12/30/2025
Rating 5
Great for family gatherings. We were a party of 20 and had plenty of space. Loved the pool!
Anonymous - Posted: 11/27/2025
It’s wonderful to hear that you and your family enjoyed your stay with us! Hosting a gathering of 20 can be a challenge, but we’re glad our space was able to accommodate everyone comfortably. The pool is definitely a highlight, and we’re thrilled that you loved it. We hope to welcome you back for another memorable family gathering in the future!
Upstay staff
Posted: 11/29/2025
Rating 5
I loved my stay at this beautiful home
Anonymous - Posted: 11/19/2025
It’s wonderful to hear that you loved your stay at our home! We take great pride in creating a beautiful and welcoming space for our guests. Your satisfaction means a lot to us, and we hope to have the pleasure of hosting you again in the future. Thank you for choosing to stay with us!
Upstay staff
Posted: 11/19/2025
Rating 5
Great place with great amenities, looks like the pictures. Host was very friendly and responsive. Definitely will book there again.
Anonymous - Posted: 10/23/2025
Thank you for your wonderful feedback! It’s fantastic to hear that you enjoyed the amenities and found everything to be just as depicted in the photos. We always strive to provide a welcoming experience, and we’re glad our responsiveness made a positive impact on your stay. We look forward to hosting you again in the future!
Upstay staff
Posted: 10/24/2025
Rating 5
Great house to celebrate our son’s 10th birthday! Beautiful house
Anonymous - Posted: 10/15/2025
Thank you, Antonio, for choosing our home to celebrate such a special occasion! We're delighted to hear that you found the house beautiful and that it was the perfect backdrop for your son's 10th birthday. It means a lot to us that our space could contribute to your family's memories. We hope to welcome you back for more celebrations in the future!
Upstay staff
Posted: 10/17/2025
Rating 5
Absolutely loved our stay here! The host was amazing—so sweet and welcoming. The house itself was beautiful, spacious, and everything worked perfectly. The water park was open, easy to find, and not crowded at all, which made it even more fun. Parking was plentiful, and the whole experience was just perfect. I’ll definitely be saving this house as a favorite for a future stay! If you’re considering booking this place, don’t hesitate—you won’t be disappointed!
Anonymous - Posted: 9/22/2025
We’re thrilled to hear that you absolutely loved your stay with us! It warms our hearts to know that you found our home beautiful and spacious, and that everything met your expectations. We’re glad you enjoyed the water park and appreciated the easy access and ample parking. Your kind words about our hospitality mean so much to us. Thank you for considering us for your future stays—we can’t wait to welcome you back!
Upstay staff
Posted: 9/23/2025
Rating 5
We had an amazing stay! The house is just as pictured. It was great having access to the resort amenities as well. My family and I really enjoyed them. Luciana and the team were great hosts. They were very responsive and attentive. The pool in the backyard is a great addition! I would recommend adding heat, as the water can get pretty cold at night. This is a place I would highly recommend and definitely book again!
Anonymous - Posted: 9/17/2025
Hi Brianna, Thank you so much for your wonderful feedback! We’re so happy to know you and your family had an amazing stay and enjoyed the house and resort amenities. 💛 We’d love to welcome you back anytime, it will be a pleasure to host you again!
Upstay staff
Posted: 9/17/2025
Rating 5
Everything was great, will definitely be back
MOISES A. - Posted:
Rating 5
Great property! Well maintained and great management team! Strongly recommend.
David P. - Posted:
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