House - Rating 5 (9)

Upstay 16 Guest Mansion w Pool Hot Tub Billiards


Bedroom 8 bedrooms
Bathroom 6 baths
Guests 16 guests
Pets Allowed Pets Allowed

  • Location: Orlando, Florida
  • Type: House

Location Location

Description Description
This pet-friendly, 16-guest capacity home is perfect for large families or big groups of friends! But, let me first tell you about the resort it's located in. Windsor by Westside is a secure, gated, family-friendly resort close to Disney and other Orlando attractions. The resort has an incredible clubhouse packed with amenities – think a romantic pier with lake views, a huge resort-style swimming pool, and concierge service. Your kids will go bonkers for the awesome water playground and splash zone. And for you? How about lounging on the sundeck with a drink in hand from the TuCasa Tiki bar. Or, maybe you'd rather float down the lazy river while soaking up the Florida sunshine. Looking for something more active? We've got your fitness covered too with a top-notch gym, plus beach volleyball and sports courts for some friendly competition. Our guests get access to the clubhouse and all of its amenities.

The house itself though, is so loaded with goodies that you may never want to leave! Starting with the garden-facing screened-in back patio - you'll love the added privacy of no rear facing neighbours. Imagine stretching out on a sun lounger by your own private swimming pool. The spill-over jacuzzi hot tub is perfect for those winter months, or in the evening any time of year. After a swim, why not indulge in a home-made BBQ meal cooked right off your patio grill? You can enjoy it poolside at the covered outdoor dining area.

Had enough sun? Well step inside to the garage-turned-games-room. That's right - we've converted the garage into a fun room filled with games like billiards and foosball. We've even added some puzzles and board games to play! Not to worry about the lack of a garage though - there's still plenty of free onsite parking on the driveway, and any overflow cars are welcome to park at the clubhouse.

Now, step inside the kitchen! The open concept design feels spacious and airy, while the large kitchen island provides extra room for prepping meals, additional dining space, serving food, or just resting your elbows! There's plenty of cupboard space for everyone's snacks and lots of countertop space for chopping, slicing and dicing!

The amenities continue on the second floor, where you and your crew can enjoy a movie night-in in the theater room, complete with a huge projector screen and cozy seating. All of the bedrooms are located upstairs as well, with the exception of one master suite, located on the ground floor. This bedroom has a King sized bed and features a sparkling ensuite bathroom.

So, what are you waiting for? Gather up your gang and prepare for the ultimate family getaway. The only thing missing is you! Come on over and let the good times roll at this jaw-dropping paradise. Trust us, this slice of vacation heaven is an opportunity you won't want to miss!

Home Features:
• 8 bedrooms (10 beds in total)
• 6 Bathrooms (including 4 en suite)
• Garage-turned-games-room (pool table, foosball table, and board games)
• In-home movie theatre with large projection screen
• Private pool with removable safety fence
• Spill-over jacuzzi hot tub
• Screened-in garden-facing furnished patio
• Sun loungers
• Outdoor dining area
• BBQ grill
• Fully equipped kitchen with high end appliances
• Large dining room with seating for up to 10
• Additional dining space at the kitchen island seating (for up to 4) and outdoor patio
• Smart TV's with complimentary cable
• High speed internet
• Central air conditioning
• In-home laundry machines
• Free onsite parking
• Complimentary resort access

Windsor at Westside Resort Features:
• 24hr gated entrance with security guard
• Clubhouse with licensed restaurant and lounge
• Lazy river for floating
• Resort-style heated pool with shallow-entry
• Children's splash zone with waterslide
• Outdoor jacuzzi hot tub
• Tiki bar
• State-of-the-art fitness center
• Children's playground
• Video arcade
• Market and Deli/Sundries Shop
• Tennis/Basketball court

*IMPORTANT NOTICE *

Please note that the ice maker is not available. We are sorry for the inconvenience this may cause. Do not hesitate to contact us if you have nay concerns.

• There is basic cookware available in the house.

Additional Services:
• Pool and hot tub heating is an additional service that is not included in your booking price. It's an additional fee of $35/day per service and $60/day for both, which we provide upon request. Please note that heating service is available with a minimum stay of 2 nights. Feel free to reach out for more details.

Pet Friendly:
• Pets up to 70lbs. are very welcome at our home. The pet fee is $129/animal (one-time fee).

Additional Services:
• We're happy to deliver:
- a full BBQ propane tank upon request for $70/per tank.
- a "Pack 'N Play Crib" for $40 (one-time fee).
- a Highchair for $40 (one-time fee).
- We offer mid-stay cleaning for reservations over 3 days in duration. This service is available for an extra fee and will need to be booked in advance.

Quality Assurance:
• Your wellbeing is our top priority. We have built upon our foundation of pre-existing high cleaning standards with additional COVID-19 specific recommendations from the WHO, CDC and Canadian Public Health Agency guidelines.

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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November 2024
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December 2024
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22 $924 23 $934 24 $945 25 $839 26 $884 27 $963 28
$985 29 $1020 30 $975 31        
January 2025
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$225 26 $221 27 $225 28 $206 29 $227 30 $267 31  
February 2025
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            $264 1
$225 2 $198 3 $199 4 $212 5 $242 6 $297 7 $349 8
$304 9 $254 10 $258 11 $252 12 $296 13 $455 14 $456 15
$420 16 $334 17 $338 18 $336 19 20 21 22
23 24 25 26 $361 27 $441 28  
March 2025
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$338 2 $330 3 $313 4 $340 5 $383 6 $396 7 $366 8
9 10 11 $391 12 $392 13 $404 14 $412 15
$374 16 $360 17 $353 18 $370 19 $452 20 $490 21 $488 22
$403 23 $399 24 $391 25 26 27 28 29
$394 30 $359 31          
April 2025
Su Mo Tu We Th Fr Sa
    $354 1 $371 2 $441 3 $444 4 $402 5
$336 6 7 8 9 10 11 12
13 14 15 16 17 $773 18 $732 19
$798 20 $377 21 $303 22 $329 23 $340 24 $438 25 $427 26
$321 27 $286 28 $269 29 $280 30      
May 2025
Su Mo Tu We Th Fr Sa
        $269 1 $339 2 $324 3
$347 4 $226 5 $201 6 $258 7 $217 8 $298 9 $296 10
$213 11 $181 12 $172 13 $181 14 $223 15 $280 16 $300 17
$227 18 $177 19 $170 20 $179 21 $222 22 $431 23 $431 24
$432 25 $237 26 $266 27 $296 28 $366 29 $388 30 $350 31
June 2025
Su Mo Tu We Th Fr Sa
$361 1 $335 2 $281 3 $238 4 $346 5 $348 6 $321 7
$273 8 $229 9 $235 10 $288 11 $312 12 $380 13 $370 14
$315 15 $252 16 $258 17 $351 18 $377 19 $427 20 $418 21
$450 22 $376 23 $288 24 $363 25 $473 26 $488 27 $433 28
$317 29 $275 30          
July 2025
Su Mo Tu We Th Fr Sa
    $277 1 $355 2 $641 3 $616 4 $622 5
$323 6 $260 7 $278 8 $366 9 $503 10 $493 11 $414 12
$307 13 $439 14 $393 15 $394 16 $432 17 $458 18 $419 19
$332 20 $273 21 $352 22 $312 23 $405 24 $436 25 $412 26
$319 27 $326 28 $250 29 $273 30 $336 31    
August 2025
Su Mo Tu We Th Fr Sa
          $362 1 $343 2
$263 3 $237 4 $224 5 $231 6 $269 7 $301 8 $279 9
$215 10 $193 11 12 13 14 15 16
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24 25 $150 26 $155 27 $174 28 $272 29 $276 30
$275 31            
September 2025
Su Mo Tu We Th Fr Sa
  $142 1 $142 2 $142 3 $145 4 $263 5 $263 6
$163 7 $142 8 $142 9 $142 10 $142 11 $263 12 $263 13
$142 14 $155 15 $155 16 $142 17 $220 18 $263 19 $263 20
$187 21 $142 22 $171 23 $142 24 $143 25 $263 26 $263 27
$142 28 $142 29 $142 30        
October 2025
Su Mo Tu We Th Fr Sa
      $143 1 $150 2 $263 3 $263 4
$143 5 $154 6 $142 7 $155 8 $171 9 $263 10 $263 11
$255 12 $275 13 $275 14 $217 15 $238 16 $263 17 $263 18
$151 19 $142 20 $142 21 $142 22 $156 23 $263 24 $263 25
$155 26 $142 27 $142 28 $153 29 $163 30 $263 31  
Swipe Swipe for Availability


Amenities 65 Amenities
  • 24-hour check-in
  • Air conditioning
  • Baking sheet
  • Barbecue utensils
  • Bathtub
  • BBQ grill
  • Bed linens
  • Cable TV
  • Carbon monoxide detector
  • Children’s books and toys
  • Cleaning Disinfection
  • Coffee maker
  • Cookware
  • Dishes and silverware
  • Dishwasher
  • Downtown
  • Dryer
  • Dvd player
  • Enhanced cleaning practices
  • Essentials
  • Family/kid friendly
  • Fire extinguisher
  • Flat smooth pathway to front door
  • Free parking on premises
  • Garden or backyard
  • Gym
  • Hair dryer
  • Hangers
  • Heating
  • High touch surfaces disinfected
  • Hot tub
  • Hot water
  • Indoor pool
  • Internet
  • Iron
  • Kettle
  • Kitchen
  • Long term stays allowed
  • Microwave
  • Oven
  • Patio or balcony
  • Pets allowed
  • Private entrance
  • Private living room
  • 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
  • Trash can
  • TV
  • Washer
  • Wireless Internet
  • Communal pool
  • Game room
  • Outdoor pool
  • Private pool
  • Swimming pool

Reviews Rating 5 (9) Reviews
Rating 5
Perfect for our size of group.
Anonymous - Posted: 3/19/2024
Thank you for your kind review, Stacey! We're thrilled to hear that our property was a perfect fit for your group. We hope to have the opportunity to host you again in the future. Safe travels!
Upstay staff
Posted: 3/20/2024
Rating 5
Amazing spacious house for a big family. We had a great time. We felt just like home.
Anonymous - Posted: 2/28/2024
Rating 5
The house met all of our family's needs, eleven of us. However, the projector did not work and the ice maker did not work. This definitely did not deter our enjoying the house and all the amenities. The house was beautiful and location was perfect for our Disney adventures. I would most certainly stay again and encourage others with larger families to do the same. Pricing was so much better than Disney properties. The money we saved went to enjoying Disney more and that's what our family went for anyway. Thank you UpStay for being a great Host.
Anonymous - Posted: 2/8/2024
Thank you for choosing to stay with us, Nancy! We're glad to hear that our house met all of your family's needs and that you enjoyed the amenities and location. We apologize for the inconvenience with the projector and ice maker, and we appreciate your understanding. Rest assured that my team already checked and fixed them. We would be delighted to host you and your family again in the future. Thank you for your kind words and for being a great guest!
Upstay staff
Posted: 3/4/2024
Rating 5
Muy satisfecho
Anonymous - Posted: 9/30/2023
Rating 5
The place was huge and comfortable. Would stay again. Thanks for being a great host.
Anonymous - Posted: 9/27/2023
Rating 5
The house was better than expected and had more than we needed it was also super comfortable and clean would highly recommend highly recommended and would definitely book again. 10/10
Anonymous - Posted: 9/25/2023
Rating 5
Beautiful spacious home, great for big family gatherings. Pool was nice and clean. The projector tv screen was phenomenal with surround sound.
Anonymous - Posted: 9/12/2023
Thank you for your feedback, Gregory! We're delighted to hear that you found the home beautiful and spacious, making it perfect for big family gatherings. It's great that the pool was clean and enjoyable. We're especially pleased that you loved the projector TV screen with surround sound. If you ever decide to stay with us again, we'll be here to provide another phenomenal experience for you and your family.
Upstay staff
Posted: 9/15/2023
Rating 5
Valerie and Kyle were excellent hosts.
Anonymous - Posted: 7/30/2023
Rating 5
I absolutely enjoyed my stay at this house. It was so gorgeous.
Anonymous - Posted: 7/26/2023
Thank you, Trinity!
Upstay staff
Posted: 8/10/2023
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