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
Check-Out
September 2026
Su Mo Tu We Th Fr Sa
    1 $162 2 $162 3 4 5
6 $162 7 $162 8 $162 9 $162 10 $300 11 $300 12
$162 13 $162 14 $162 15 $162 16 $185 17 $277 18 19
20 21 $180 22 $180 23 $180 24 25 26
27 28 29 30      
October 2026
Su Mo Tu We Th Fr Sa
        1 $300 2 3
4 5 6 7 8 9 $300 10
$208 11 12 13 14 15 16 17
18 19 20 21 22 $320 23 $318 24
$244 25 $245 26 $245 27 $206 28 $247 29 $305 30 $309 31
November 2026
Su Mo Tu We Th Fr Sa
$251 1 $203 2 $189 3 $213 4 $273 5 $300 6 $303 7
$250 8 $244 9 $258 10 $258 11 $264 12 $318 13 $337 14
$263 15 $208 16 $218 17 $186 18 $243 19 $453 20 $488 21
$475 22 $496 23 $604 24 25 26 27 28
$344 29 $231 30          
December 2026
Su Mo Tu We Th Fr Sa
    $253 1 $208 2 $261 3 $334 4 $322 5
$276 6 $225 7 $219 8 $229 9 $276 10 $352 11 $372 12
$263 13 $237 14 $219 15 $227 16 $324 17 $458 18 $579 19
$882 20 $960 21 $987 22 $1044 23 $1047 24 $1049 25 26
27 28 29 30 31    
January 2027
Su Mo Tu We Th Fr Sa
          1 $767 2
$242 3 $198 4 5 6 7 8 9
$272 10 $221 11 $210 12 $219 13 $289 14 $340 15 $378 16
$371 17 $289 18 $207 19 20 21 22 23
24 25 26 $224 27 $256 28 $300 29 $300 30
$255 31            
February 2027
Su Mo Tu We Th Fr Sa
  $272 1 $227 2 $279 3 $283 4 $309 5 $313 6
$293 7 $287 8 $266 9 $284 10 $333 11 $421 12 $485 13
$477 14 $364 15 $329 16 $335 17 $350 18 $390 19 $360 20
$311 21 $290 22 $284 23 $312 24 25 26 27
28            
March 2027
Su Mo Tu We Th Fr Sa
  1 $251 2 $267 3 $307 4 $419 5 $433 6
$448 7 $448 8 $437 9 $437 10 $452 11 $558 12 $571 13
$548 14 $557 15 $547 16 $552 17 $563 18 $550 19 $545 20
$481 21 $478 22 $597 23 $597 24 $597 25 $681 26 $717 27
$717 28 $717 29 $645 30 $645 31      
April 2027
Su Mo Tu We Th Fr Sa
        $697 1 $627 2 $614 3
$717 4 $717 5 $669 6 $515 7 $616 8 $557 9 $520 10
$717 11 $717 12 $717 13 $717 14 $717 15 $619 16 $651 17
$747 18 $904 19 $891 20 $892 21 $894 22 $899 23 $903 24
$881 25 $816 26 $808 27 $804 28 $801 29 $760 30  
May 2027
Su Mo Tu We Th Fr Sa
            $361 1
$284 2 $249 3 $236 4 $250 5 $285 6 $326 7 $329 8
$274 9 $241 10 $241 11 $241 12 $287 13 $344 14 $336 15
$321 16 $241 17 $241 18 $475 19 $493 20 $500 21 $354 22
$372 23 $257 24 $241 25 $289 26 $355 27 $455 28 $448 29
$424 30 $371 31          
June 2027
Su Mo Tu We Th Fr Sa
    $378 1 $398 2 $360 3 $411 4 $440 5
$467 6 $482 7 $479 8 $545 9 $589 10 $514 11 $478 12
$519 13 $591 14 $571 15 $550 16 $585 17 $555 18 $596 19
$573 20 $571 21 $584 22 $533 23 $615 24 $667 25 $645 26
$673 27 $677 28 $673 29 $680 30      
July 2027
Su Mo Tu We Th Fr Sa
        $701 1 $878 2 $857 3
$854 4 $641 5 $640 6 $641 7 $635 8 $704 9 $640 10
$473 11 $422 12 $415 13 $438 14 $595 15 $655 16 $618 17
$555 18 $546 19 $493 20 $486 21 $540 22 $625 23 $583 24
$475 25 $416 26 $416 27 $416 28 $460 29 $558 30 $514 31
August 2027
Su Mo Tu We Th Fr Sa
$439 1 $362 2 $339 3 $384 4 $406 5 $463 6 $421 7
$348 8 $305 9 $293 10 $308 11 $363 12 $393 13 $358 14
$317 15 $282 16 $278 17 $273 18 $291 19 $315 20 $312 21
$312 22 $215 23 $199 24 $312 25 $312 26 $328 27 $328 28
$328 29 $260 30 $180 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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