Upstay Disney Family Adventure with Pool Hot Tub
Bright living area perfect for relaxing, family time, or cozy movie nights together
Dine in style at a table for 10 ready for meals and gatherings with family and friends
Kids can race into fun in a Toy Story-themed room with car-shaped beds and space to play
Second-floor living area with billiards and sofa for families, kids, and friends to relax and play
Presented by Upstay
Large pool with hot tub for family fun, swimming, and relaxing together
Relax by the pool while enjoying the view and spending time with family and friends
Relax by the pool while enjoying meals, entertainment, and quality time with family and friends
Spacious living area for relaxing, connecting, and making memories with family and friends
Dining area for families or groups to gather, enjoy meals, and share special moments
Kitchen with full setup and center island ideal for cooking, prepping, and sharing meals
Kitchen island with high chairs for casual meals, chatting, or extending dining and relaxing together
Open first-floor layout connecting living, dining, kitchen, and pool for seamless family fun
Hallway connecting to the second floor and main area, guiding guests through spacious, open living
Marvel-themed playroom featuring ping pong and air hockey for fun with family and friends
Full game room with TV, game chairs, and activities for fun with family and friends
Open living area with comfy seating, perfect for gathering, relaxing, and spending time together
Billiard table connected to round table and chairs for fun, meals, and socializing with guests
Round table for 6 with surrounding seating, perfect for meals, gatherings, and socializing together
Billiard table flowing into living area where family and friends can relax, play, and connect
King-size bedroom with cozy linens and space to relax, unwind, and enjoy comfort
Spacious king bedroom with 65-inch smart TV, perfect for relaxing, unwinding, and settling in
Bathroom with bathtub and walk-in shower, perfect for relaxing and refreshing after a long day
Well-lit bathroom with double sinks and mirror, ideal for getting ready with ease and comfort
Ocean-inspired bedroom with king bed, headboard, bedside lamps, and ceiling fan for cozy comfort
King bedroom with 65-inch smart TV and bathroom, perfect for relaxing, watching shows, and recharging
Well-lit bathroom with walk-in shower and amenities for a refreshing and comfortable stay
King bedroom with cozy lighting and headboard, perfect for relaxing, reading, or unwinding
King bedroom with 65-inch TV and sliding closet, perfect for relaxing, enjoying shows, and unwinding
Bathroom with walk-in shower, sink area, and essentials for refreshing and getting ready
King bedroom with headboard, ceiling fan, and bedside lamps, perfect for relaxing and unwinding
Tropical-themed king bedroom with 65-inch TV, perfect for relaxing, watching shows, and unwinding
Bathroom with walk-in shower and essentials, ready for a refreshing and convenient stay
Toy Story room with two single car-shaped beds where kids can play, imagine, and drift to sleep
Toy Story room with TV for shows and bathroom for quick, fun, and easy refresh
Bathroom with walk-in shower, perfect for easy, fun, and kid-friendly refresh
Harry Potter room with two single beds, where young wizards can play, imagine, and rest
Harry Potter room with magical candle-style lamps, perfect for young wizards to imagine and play
Harry Potter room with 55-inch TV and bathroom access, perfect for relaxing and enjoying shows
Jack and Jill bathroom with walk-in shower connecting to Moana room, share the fun and refresh
Moana room with a boat-shaped queen bed where kids can sail into adventure
Moana room with 55-inch TV, perfect for kids to watch shows and sail into adventure
Star Wars room with two single beds, surrounded by starships, where young Jedi can battle and play
Star Wars room where kids can imagine battling with fighter jets in an epic galactic adventure
Star Wars room with 55-inch TV, perfect for young Jedi to watch shows and plan galactic battles
Bathroom with walk-in shower, tub, and double sinks, perfect for fun and easy refresh
Step into a Frozen ice castle with double-deck beds, where kids can sleep, play, and imagine
Spacious Frozen room with character-framed walls and wardrobe, perfect for kids to imagine and play
Frozen room with 55-inch TV, where kids can watch shows and imagine adventures from their beds
Bedroom with two queen beds and headboards, perfect for relaxing, unwinding, and restful sleep
Bedroom with 55-inch TV and cozy corner chair, perfect for relaxing, watching shows, and unwinding
Bathroom with walk-in shower and essentials, perfect for a refreshing and convenient stay
Washer and dryer available for guest use, making your stay easy and convenient
Modern two-story home with garage and parking space for 2 cars
Enjoy Windsor Island Resort with a pool, lazy river, splash zone, and sports courts—perfect for family fun and unforgettable memories.
Enjoy Windsor Island Resort with a pool, lazy river, splash zone, and sports courts—perfect for family fun and unforgettable memories.
Enjoy Windsor Island Resort with a pool, lazy river, splash zone, and sports courts—perfect for family fun and unforgettable memories.
Enjoy Windsor Island Resort with a pool, lazy river, splash zone, and sports courts—perfect for family fun and unforgettable memories.
Enjoy Windsor Island Resort with a pool, lazy river, splash zone, and sports courts—perfect for family fun and unforgettable memories.
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House

Upstay Disney Family Adventure with Pool Hot Tub

Bedroom 10 bedrooms
Bathroom 8 baths
Guests 20 guests
Pets Allowed Pets Allowed
  • Location: Orlando, Florida
  • Type: House
  • View: Downtown
Location Location
Description Description
Create Magical Memories
After a day at Disney, unwind in a space designed for fun and connection
• Private pool for adults to relax
• Hot tub for extra relaxation
• BBQ grill, sun loungers, and dining area for outdoor fun

Gather, Dine, and Connect
Enjoy shared meals and family time in a space designed for connection
• Fully equipped kitchen with center island for easy prep and serving
• Dining table comfortably seats 10, with essentials included
• Gather on comfortable seating for 8 and watch your favorite shows
• Stay connected with high-speed WiFi for work, play, and family fun
• Refreshment station with bar chiller, between dining area and patio

Play, Laugh, and Compete
Have fun with a variety of games at the property:
• Ping pong
• Pool table
• Air hockey

Rest, Dream, and Play
This home offers 10 bedrooms designed for comfort and fun:
• King Room with Bathtub – king bed, private ensuite bathroom with tub, perfect for relaxing and soaking after a day at Disney
• Toy Story Room – two single beds let kids play alongside Woody and Buzz, watch adventures, and enjoy their own private ensuite shower
• Frozen Room – twin bunk beds in an Arendelle-inspired space for movie nights with Anna and Elsa and a private ensuite shower
• Moana Room – tropical-inspired space with a queen bed and Jack and Jill bath shared with the Harry Potter room
• Harry Potter Room – young wizards can relax with two single beds and a Jack and Jill bath connecting to the Moana room
• Other King Bedrooms – king beds with private ensuite walk-in showers, bright, spacious, and ideal for unwinding
• Queen Bedroom – queen bed with private ensuite walk-in shower, comfortable and inviting for a restful stay
All bedrooms are equipped with Smart TVs for streaming your favorite shows

Windsor Island Resort Amenities (Included):
• Massive resort pool with lazy river & dual waterslides
• Kids' splash zone and playground
• Fitness center, sports courts, and arcade
• Clubhouse with restaurant & bar
• Daily entertainment & family activities (some may require a fee, including mini-golf)

• 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.

• Access to Windsor Island requires advance guest registration. 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+ in advance 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
(minimum 2-night stay required)
• BBQ propane tank: one-time $69 charge (please request at least 24 hours 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
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June 2026
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July 2026
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      $240 1 2 3 4
$245 5 $219 6 7 8 9 10 11
$338 12 $313 13 $323 14 $308 15 $342 16 17 18
19 20 21 22 $408 23 24 25
26 $281 27 $246 28 $261 29 $308 30 31  
August 2026
Su Mo Tu We Th Fr Sa
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2 $257 3 $243 4 $252 5 $298 6 $394 7 $361 8
$241 9 $214 10 $204 11 $223 12 $249 13 $331 14 $304 15
$241 16 $197 17 $189 18 $208 19 $234 20 $300 21 $300 22
$219 23 $190 24 $180 25 $181 26 $209 27 $300 28 $300 29
$235 30 $182 31          
September 2026
Su Mo Tu We Th Fr Sa
    $180 1 $185 2 $238 3 $352 4 $394 5
$369 6 $243 7 $180 8 $180 9 $223 10 $300 11 $300 12
$225 13 $185 14 $252 15 $232 16 $264 17 $300 18 $300 19
$234 20 $243 21 $253 22 $194 23 $241 24 $300 25 $300 26
$241 27 $192 28 $187 29 $202 30      
October 2026
Su Mo Tu We Th Fr Sa
        $257 1 $300 2 3
4 5 6 7 8 9 $364 10
$350 11 $277 12 $277 13 $277 14 $293 15 $301 16 $300 17
$259 18 $266 19 $272 20 $271 21 $268 22 $302 23 $300 24
$256 25 $211 26 $196 27 $211 28 $260 29 $300 30 $300 31
November 2026
Su Mo Tu We Th Fr Sa
$262 1 $262 2 $203 3 $270 4 $265 5 $307 6 $309 7
$273 8 $226 9 $317 10 $317 11 $325 12 $336 13 $352 14
$307 15 $252 16 $262 17 $221 18 $274 19 $368 20 $493 21
$533 22 $587 23 $643 24 $967 25 $967 26 $955 27 $839 28
$373 29 $296 30          
December 2026
Su Mo Tu We Th Fr Sa
    $267 1 $230 2 $272 3 $347 4 $317 5
$271 6 $224 7 $221 8 $239 9 $282 10 $353 11 $374 12
$295 13 $264 14 $235 15 $253 16 $309 17 $471 18 $674 19
$926 20 $995 21 $1000 22 $1024 23 $1028 24 $1033 25 26
27 28 29 30 31    
January 2027
Su Mo Tu We Th Fr Sa
          1 $788 2
$526 3 $447 4 $399 5 $301 6 $316 7 $378 8 $340 9
$297 10 $243 11 $229 12 $239 13 $272 14 $335 15 $378 16
$368 17 $258 18 $222 19 $236 20 $270 21 $300 22 $300 23
$260 24 $243 25 $273 26 $277 27 $280 28 $300 29 $300 30
$267 31            
February 2027
Su Mo Tu We Th Fr Sa
  $290 1 $290 2 $291 3 $287 4 $310 5 $323 6
$304 7 $287 8 $273 9 $304 10 $351 11 $450 12 $534 13
$517 14 $365 15 $324 16 $337 17 $365 18 $406 19 $361 20
$306 21 $292 22 $286 23 $304 24 $337 25 $358 26 $344 27
$289 28            
March 2027
Su Mo Tu We Th Fr Sa
  $260 1 $251 2 $256 3 $300 4 $424 5 $435 6
$459 7 $438 8 $440 9 $454 10 $470 11 $568 12 $587 13
$568 14 $575 15 $576 16 $580 17 $588 18 $600 19 $576 20
$580 21 $511 22 $597 23 $597 24 $616 25 $723 26 $717 27
$717 28 $717 29 $645 30 $669 31      
April 2027
Su Mo Tu We Th Fr Sa
        $734 1 $675 2 $633 3
$717 4 $717 5 $669 6 $669 7 $669 8 $616 9 $526 10
$717 11 $717 12 $717 13 $601 14 $579 15 $610 16 $576 17
$686 18 $853 19 $805 20 $806 21 $840 22 $880 23 $902 24
$800 25 $757 26 $757 27 $757 28 $759 29 $760 30  
May 2027
Su Mo Tu We Th Fr Sa
            $366 1
$279 2 $236 3 $234 4 $250 5 $288 6 $308 7 $329 8
$270 9 $313 10 $241 11 $241 12 $270 13 $327 14 $330 15
$321 16 $241 17 $241 18 $483 19 $508 20 $519 21 $367 22
$372 23 $257 24 $240 25 $289 26 $314 27 $431 28 $432 29
$418 30 $370 31          
Swipe Swipe for Availability
Amenities 60 Amenities
  • Air conditioning
  • Baking sheet
  • Bathtub
  • BBQ grill
  • Bed linens
  • Carbon monoxide detector
  • Cleaning Disinfection
  • Coffee maker
  • Cookware
  • Dishes and silverware
  • Dishwasher
  • Downtown
  • Dryer
  • Dryer in common space
  • Emergency exit
  • Enhanced cleaning practices
  • Essentials
  • Family/kid friendly
  • Fire extinguisher
  • Free parking on premises
  • Hair dryer
  • Hangers
  • Heating
  • High touch surfaces disinfected
  • Hot tub
  • Hot water
  • Internet
  • Kitchen
  • Long term stays allowed
  • Microwave
  • Oven
  • Pack ’n Play/travel crib
  • Patio or balcony
  • Pets allowed
  • 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
  • Washer in common space
  • Wireless Internet
Resorts
  • WindsorIslandResort
  • Communal pool
  • Game room
  • HarryPotter Theme Room
  • Outdoor pool
  • Princess Theme Room
  • Private pool
  • Swimming pool
  • Tropical Theme Room
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