Upstay Family Fun 5BR Retreat w Pool Games Room
Enjoy a fast-paced game of air hockey, level up in the dedicated console area, or spectate from the high-chair bar and lounge zone
Sit back on the comfortable sofa, turn on your favorite show, and enjoy the warm glow of the electric fireplace
A sleek and inviting dining area for eight with a modern chandelier that sets the perfect mood
This themed Toy Story room features a playful bunk bed where waking up means sliding right into the day
Presented by Upstay
Relax by the water with fun pool floats, comfortable lounge chairs, and an outdoor dining setup perfect for sunny days
Enjoy family dinners at this spacious eight-seat dining area positioned directly alongside the pool for a relaxed, resort-style vibe
A spacious eight-seat dining area directly alongside the pool, offering the ultimate setup for open-air group dinners
Keep everyone entertained with air hockey, retro arcade games, a console setup, and a comfortable high-chair seating area to watch the fun
Bring back the nostalgia with a dedicated arcade machine loaded with multiplayer retro favorites
The ultimate entertainment zone complete with fast-paced air hockey, retro arcades, a console setup with an ergonomic gaming chair, and a stylish high-chair lounge area to kick back and socialize
A spacious living area featuring a large family couch and center table with a seamless view of the kitchen island and adjacent dining setup
Sit back and relax with your favorite shows on the smart TV, paired with the warm, comforting glow of the electric fireplace
A seamless open layout that beautifully blends the comfortable living area and spacious dining setup for effortless entertaining
Gather around this stylish six-person dining table, illuminated by a stunning designer chandelier that serves as the perfect centerpiece
Enjoy meals in this chic dining nook, where elegant wall frames and a hanging chandelier bring character and warmth to the space
The heart of the home, beautifully connecting the modern kitchen with the living area for a seamless, spacious feel
The ultimate breakfast bar and prep space, showcasing a large central island complete with four stylish high chairs
A beautifully designed kitchen layout highlighted by a large central island that offers both ample workspace and extra seating
A seamless transition from the central island breakfast bar right into the heart of the cozy living space
See how it all connects: the dining space, TV lounge, kitchen, and the staircase to the second floor
Unwind in a king bed with high-quality sheets and elegant bedside lighting on both sides
Catch your favorite shows from the comfort of your king bed, complete with a stylish wall mirror
The ultimate suite view: a king bed, built-in TV, stylish accent lounge couch, and a room-brightening mirror
A plush king bed featuring a classic statement headboard and warm, inviting bedside lamps
Enjoy movie nights from the king bed, complete with a flat-screen TV and a stylish low console underneath
A peaceful king bedroom setup framed by soft bedside lamps and elegant, floor-to-ceiling window curtains
Unwind in this stylish king room, complete with cozy side lamps, premium curtains, and ample cupboard storage
Enjoy late-night movies on the wall-mounted smart TV right from the comfort of your king bed
An immersive Toy Story kids' paradise, featuring a fun bunk bed and an exciting built-in slide
Fuel their imagination with sturdy, comfortable bunk beds framed by colorful Toy Story theme
The ultimate kids' hangout spot, blending whimsical Toy Story decor with a dedicated smart TV
A spellbinding kids' room featuring cozy bunk beds styled with magical Harry Potter details
Step into wizarding magic with custom bunk beds set in a fully immersive Harry Potter themed room
A welcoming room entrance featuring a large statement mirror that bridges the foyer directly to the main living area
The beautiful main exterior of the house, capturing its striking architectural design from the front yard
Get a birds-eye look at everything Windsor Cay Resort has to offer, from the massive clubhouse to the water park
A colorful and safe kiddie splash zone packed with water fountains and playful dumping buckets
Make a splash on the winding resort water slides, surrounded by a spacious, tropical pool deck
Windsor Cay Resort
Soak up the Florida sunshine from comfortable deck loungers surrounding the heated pool
Relax on the sun loungers overlooking the gorgeous main pool area at Windsor Cay
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House - Rating 5 (22)

Upstay Family Fun 5BR Retreat w Pool Games Room

Bedroom 5 bedrooms
Bathroom 4 baths
Guests 14 guests
Pets Not Allowed Pets Not Allowed
  • Location: Orlando, Florida
  • Type: House
  • View: Downtown
Location Location
Description Description
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!

• 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)
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
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July 2026
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$209 27 $196 28 $186 29 $195 30      
October 2026
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November 2026
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$220 15 $202 16 $211 17 $199 18 $222 19 $273 20 $377 21
$363 22 $363 23 $363 24 $546 25 $556 26 $539 27 $514 28
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December 2026
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$226 6 $209 7 $211 8 $210 9 $255 10 $291 11 $294 12
$244 13 $233 14 $238 15 $218 16 $266 17 $398 18 $501 19
$591 20 $666 21 $667 22 $793 23 $809 24 $787 25 26
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January 2027
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$316 17 $269 18 $234 19 $241 20 $249 21 $275 22 $285 23
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$254 31            
February 2027
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$275 7 $296 8 $307 9 $316 10 $341 11 $450 12 $498 13
$522 14 $363 15 $329 16 $319 17 $351 18 $407 19 $411 20
$329 21 $329 22 $325 23 $326 24 $376 25 $403 26 $395 27
$344 28            
March 2027
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$426 7 $469 8 $480 9 $389 10 $420 11 $556 12 $557 13
$543 14 $560 15 $558 16 $580 17 $602 18 $650 19 $625 20
$613 21 $478 22 $499 23 $544 24 $567 25 $635 26 $606 27
$597 28 $608 29 $560 30 $526 31      
April 2027
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$431 4 $385 5 $404 6 $413 7 $504 8 $525 9 $450 10
$345 11 $319 12 $326 13 $418 14 $418 15 $430 16 $412 17
$340 18 $571 19 $576 20 $575 21 $576 22 $541 23 $539 24
$536 25 $540 26 $542 27 $552 28 $571 29 $577 30  
May 2027
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$360 2 $360 3 $352 4 $343 5 $344 6 $355 7 $345 8
$302 9 $323 10 $320 11 $267 12 $301 13 $339 14 $323 15
$293 16 $259 17 $255 18 $466 19 $468 20 $473 21 $317 22
$303 23 $281 24 $267 25 $279 26 $310 27 $396 28 $395 29
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June 2027
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$367 6 $373 7 $402 8 $415 9 $417 10 $435 11 $416 12
$416 13 $438 14 $442 15 $453 16 $458 17 $510 18 $500 19
$477 20 $477 21 $482 22 $456 23 $488 24 $527 25 $530 26
$584 27 $553 28 $553 29 $553 30      
Swipe Swipe for Availability
Amenities 51 Amenities
  • Air conditioning
  • Baking sheet
  • Bathtub
  • Bed linens
  • Carbon monoxide detector
  • Cleaning Disinfection
  • Coffee maker
  • Cookware
  • Dishwasher
  • Downtown
  • Enhanced cleaning practices
  • Essentials
  • Free parking on premises
  • Free parking on street
  • Gym
  • Hair dryer
  • Hangers
  • Heating
  • High touch surfaces disinfected
  • Hot tub
  • Hot water
  • Indoor fireplace
  • Internet
  • Iron
  • Kettle
  • Kitchen
  • Laptop friendly workspace
  • 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
  • Town
  • TV
  • Washer
  • Wireless Internet
  • Communal pool
  • Game console
  • Outdoor pool
  • Private pool
  • Swimming pool
Reviews Rating 5 (22) Reviews
Rating 5
Nuestra experiencia fue muy buena. La casa es hermosa, amplia y muy cómoda, ideal para familias y grupos grandes. Está bien equipada y tiene todo lo necesario para una estadía agradable después de días intensos en los parques. Disfrutamos mucho los espacios comunes y la tranquilidad del lugar. La comunicación fue clara y el proceso fue sencillo. Sin duda es un alojamiento que recomendamos y al que volveríamos felices en un próximo viaje.
Anonymous - Posted: 2/28/2026
We are so happy to hear that your experience with us was so positive. It's great that they found the house beautiful, and a comfortable place to enjoy with the family. We strive to provide a welcoming environment, so it's gratifying to know that we meet your expectations. We look forward to the opportunity to welcome you back on your next trip. Thank you for recommending us!
Upstay staff
Posted: 3/5/2026
Rating 5
Location was gorgeous! Also the host was very nice, even when we left one of our bags she met with us to give them back.
Anonymous - Posted: 2/26/2026
Thank you for your kind words, Henry! We're so glad to hear that you enjoyed your stay. We’re always here to help our guests have a great experience. We hope to welcome you back soon!
Upstay staff
Posted: 3/5/2026
Rating 5
We really enjoyed our stay! The kids loved the game room and themed bedrooms. The location was perfect for our trip to the theme parks and any communication was answered quickly. We would definitely stay again!
Anonymous - Posted: 1/29/2026
It’s wonderful to hear that you and your family had such a great time during your stay! We’re glad the kids enjoyed the game room and themed bedrooms—those are always a hit with families. We appreciate your kind words about our communication and would love to welcome you back for another visit!
Upstay staff
Posted: 2/5/2026
Rating 5
The house was an amazing felt like I was right at home, I will definitely recommend and book again !!!
Anonymous - Posted: 1/26/2026
It’s wonderful to hear that you felt right at home during your stay! Thank you for your kind words and for recommending us. We would love to host you again in the future!
Upstay staff
Posted: 1/28/2026
Rating 5
Loved the home and how spacious it was! Thank you for making us feel so at home!
Anonymous - Posted: 1/21/2026
It’s wonderful to hear that you loved the spaciousness of our home! We always strive to create a welcoming atmosphere, and we’re delighted that you felt at home during your stay. Thank you for choosing us, and we hope to host you again in the future!
Upstay staff
Posted: 1/28/2026
Rating 5
This place is very nice, the only thing is that when we got the house the cleaner was placing towels and we had to wait for them to finish. We ask for one more hour the day of the check out and they did not accept our request and I think it was not fair. Otherwise, I will give them 5 starts. We had a good time there.
Anonymous - Posted: 1/18/2026
Thank you for your feedback, Eiden. We're glad to hear that you enjoyed your time at our place and found it nice. We apologize for the inconvenience you experienced with the cleaning schedule upon your arrival. We strive to ensure that our guests have a seamless check-in experience, and we appreciate your understanding. Regarding your checkout request, we do have specific policies in place to ensure that we can prepare the home for the next guests on time. We appreciate your input and will action on this as we continue to improve our services. We hope to welcome you back soon!
Upstay staff
Posted: 1/22/2026
Rating 5
The house is as listed. We were a big group…3 families and felt very comfortable not crowded at all. It was great for adults and children. Game room and themed rooms were a big hit.
Anonymous - Posted: 1/6/2026
Rating 5
We had a great family stay! The home was very spacious, extremely clean, and perfect for traveling with kids. There was plenty of room for everyone to relax comfortably, and everything was well maintained. It felt safe, welcoming, and truly like a home away from home. We would absolutely stay here again and highly recommend it to other families.
Anonymous - Posted: 1/3/2026
Rating 5
A fun place for a large family like ours. Fun things to do for all ages, both within the home as well as at the community amenities.
Anonymous - Posted: 12/28/2025
It’s wonderful to hear that your family had a great time! We designed the space with families in mind, so it’s fantastic to know that everyone found something enjoyable to do. We hope to welcome you all back for another fun-filled stay in the future!
Upstay staff
Posted: 12/30/2025
Rating 5
Everything was as advertised! Clean home and superior furnishings/kitchen equipment. Host was very attentive.
Anonymous - Posted: 12/21/2025
Thank you, Kierra, for your wonderful feedback! We always strive to provide a comfortable and enjoyable experience for our guests, and your kind words about our attentiveness mean a lot to us. We hope to welcome you back in the future!
Upstay staff
Posted: 12/23/2025
Rating 5
loved it!
Anonymous - Posted: 12/14/2025
It’s wonderful to hear that you loved your stay with us! We hope to welcome you back soon!
Upstay staff
Posted: 12/18/2025
Rating 5
Luciana was very communicative throughout our stay, will definitely stay again.
Anonymous - Posted: 12/8/2025
Thank you, Aimee! We're so glad to hear that you found our communication helpful during your stay. It’s always our goal to ensure our guests feel supported and informed. We can’t wait to welcome you back for another visit!
Upstay staff
Posted: 12/10/2025
Rating 5
The host was super responsive. Kudos! Clear instructions and super clean home. Everything was just perfect!
Anonymous - Posted: 11/30/2025
Thank you for your wonderful feedback! We always strive to provide a seamless experience for our guests, and your kind words about our responsiveness mean a lot to us. We hope to welcome you back in the future!
Upstay staff
Posted: 12/5/2025
Rating 5
We had a great stay! The place was exactly as described—clean, comfortable, and well-kept. The host was extremely responsive and made everything easy from check-in to check-out. The location was convenient and the home had everything we needed for a smooth and enjoyable visit. Highly recommend and would happily stay again!
Anonymous - Posted: 11/24/2025
Thank you, Seif, for your wonderful review! It’s fantastic to hear that you found our place clean, comfortable, and well-kept. We always strive to provide a seamless experience for our guests, so knowing that our responsiveness made your stay easier is incredibly rewarding. We're glad you enjoyed the convenient location and that the home had everything you needed. Your recommendation means a lot to us, and we would love to welcome you back anytime!
Upstay staff
Posted: 11/25/2025
Rating 5
Beautiful home! The pictures do not do this place justice. Looks even better in person! The host was friendly and easy to reach. Overall great experience.
Anonymous - Posted: 11/9/2025
Thank you, Darlene! We’re so glad to hear that you found our home even more beautiful in person. It’s always our goal to provide a welcoming and comfortable experience for our guests, and we appreciate your kind words about our communication. We hope to welcome you back for another great stay in the future!
Upstay staff
Posted: 11/10/2025
Rating 5
Amazing house! The ambiance was wonderful, clean & pristine, fun themed rooms, gaming area, and refreshing pool. The resort amenities were also fun, and gated community felt very safe. Our host made us feel like family, responded immediately, and I'd book again just for their service! We visited Disney & Universal, with a car it took 30-40min drive depending on the theme park. This house has everything you would need, they planned ahead for sure! Be sure to use the QR-code (photo) at the gates, typing the code did not always work, but the QR did (bottom of dial-pad). You'll have to drive 10min for good restaurants, but it's worth it! We spent 2 days relaxing at the house, and you'll make memories here, just the same as the theme parks! 6 STARS is my rating, they went above & beyond, we would gladly book again :)
Anonymous - Posted: 11/6/2025
Thank you for your wonderful review! It brings us so much joy to hear that you enjoyed the ambiance and amenities of our home. We take great pride in creating a clean and welcoming environment, and it’s fantastic to know that you appreciated the themed rooms and gaming area. We're glad you felt safe in our gated community and that our service made you feel like family. Your tips about the QR code are super helpful, and we appreciate you sharing that with future guests. It sounds like you had a great time exploring the nearby theme parks and relaxing by the pool. We would love to host you again in the future and help create more memorable moments! Thank you for the 6-star rating!
Upstay staff
Posted: 11/6/2025
Rating 5
Above and beyond!!! The home was beautiful, clean and exactly as pictured. Luciana went above and beyond to make my daughter’s birthday weekend special. Amenities of the resort were great, pool Area was amazing and a hit with the kids and adults. Definitely will be booking again.
Anonymous - Posted: 10/27/2025
Thank you for your wonderful review, Kristin! It brings us so much joy to hear that you and your family had a fantastic time celebrating your daughter's birthday with us. We take great pride in maintaining our home and ensuring it meets our guests' expectations, so it's rewarding to know that you found it beautiful and clean. We're also glad you enjoyed the resort amenities and the pool area—it's always a favorite for both kids and adults alike! We can't wait to welcome you back for another memorable stay.
Upstay staff
Posted: 10/27/2025
Rating 5
We loved this property! The kids loved the Toy Story room and the slide, it was perfect for a long weekend getaway!
Anonymous - Posted: 10/20/2025
It’s wonderful to hear that you and your family enjoyed your stay with us! The Toy Story room and slide are definitely favorites for kids, and we’re glad they added to your long weekend getaway. We hope to welcome you back for another fun-filled visit soon!
Upstay staff
Posted: 10/23/2025
Rating 5
Our host was amazing, the place was beautiful and we had a great time! We will definitely stay again!
Anonymous - Posted: 10/15/2025
Thank you so much for your kind words, Kelly! It brings us immense joy to hear that you enjoyed your stay at Upstay. We take great pride in providing a beautiful space for our guests, and knowing that you had a great time truly makes our efforts worthwhile. We can’t wait to welcome you back for another memorable experience!
Upstay staff
Posted: 10/15/2025
Rating 5
Excellent home to spend time, and create beautiful memories with family and friends, Luciana is a great host… she was always attentive to everything
Anonymous - Posted: 10/12/2025
We’re thrilled to hear that you had an excellent time at our home and that it served as a backdrop for creating beautiful memories with your family and friends. It means a lot to us that you found our attentiveness helpful during your stay. We strive to make every guest's experience special, and your kind words motivate us to keep doing our best. We hope to welcome you back soon for more memorable moments!
Upstay staff
Posted: 10/13/2025
Rating 5
Great place and responsive hosts!
Anonymous - Posted: 10/6/2025
Thank you so much for your kind words! We're thrilled to hear that you enjoyed your stay and that you found us responsive. It was a pleasure hosting you, and we hope to welcome you back again soon!
Upstay staff
Posted: 10/6/2025
Rating 5
Absolutely best AirBnB we've ever stayed in !! from start to finish, the host was accommodating and the house was perfection. For a group of 14, it was perfectly spaced out, great locating ( easy to get to everywhere) and the house amenities were exactly what we needed. Host went above and beyond and the checkin process was seamless and easy ( never had to wait at the gate). House was spotless and we felt right at home. we highly recommend and will be booking again soon!
Anonymous - Posted: 9/22/2025
Thank you so much for your wonderful review! We’re thrilled to hear that you and your group had such a fantastic experience at Upstay. It’s great to know that the space worked perfectly for your needs and that you found the location convenient. We always strive to make the check-in process as smooth as possible, so we’re glad that you appreciated it. Your kind words about the cleanliness and our efforts to accommodate you mean a lot to us. We can’t wait to welcome you back for another stay soon!
Upstay staff
Posted: 9/25/2025
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