House - Rating 5 (9)

Upstay 16 Guest Mansion w Pool Hot Tub Billiards


Bedroom 8 bedrooms
Bathroom 6 baths
Guests 16 guests
Pets Not Allowed Pets Not Allowed

  • Location: Orlando, Florida
  • Type: House

Location Location

Description Description
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

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!

*IMPORTANT NOTICE *
Please note that the fridge's ice maker is currently unavailable. However, we have provided a separate ice maker on the kitchen counter for your convenience.

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/night per service and $60/night 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.
• 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.

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

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).

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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February 2025
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March 2025
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April 2025
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$270 6 7 8 9 10 11 12
13 14 15 16 17 $743 18 $711 19
$701 20 $443 21 $355 22 $388 23 $411 24 $525 25 $531 26
$336 27 $297 28 $282 29 $287 30      
May 2025
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$279 4 $230 5 $195 6 $192 7 $209 8 $278 9 $281 10
$219 11 $186 12 $170 13 $174 14 $213 15 $268 16 $276 17
$228 18 $181 19 $173 20 $187 21 $234 22 $392 23 $406 24
$408 25 $252 26 $270 27 $259 28 $292 29 $374 30 $372 31
June 2025
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$314 1 $268 2 $220 3 $240 4 $293 5 $362 6 $328 7
$267 8 $225 9 $231 10 $257 11 12 13 14
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$361 22 $368 23 $284 24 $359 25 $456 26 $464 27 $408 28
$326 29 $273 30          
July 2025
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    $370 1 $385 2 $824 3 $797 4 $783 5
$322 6 $307 7 $321 8 $418 9 $573 10 $543 11 $481 12
$393 13 $425 14 $408 15 $369 16 $497 17 $515 18 $475 19
$372 20 $313 21 $315 22 $350 23 $460 24 25 26
27 28 29 $297 30 $361 31    
August 2025
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$310 3 $334 4 $319 5 6 7 8 9
$257 10 $236 11 12 13 14 15 16
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24 25 $158 26 $164 27 $191 28 $266 29 $268 30
$266 31            
September 2025
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  $143 1 $143 2 $142 3 $162 4 $263 5 $263 6
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$189 14 $186 15 $184 16 $192 17 $184 18 $263 19 20
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October 2025
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$166 5 $145 6 $150 7 $184 8 $192 9 $315 10 $315 11
$207 12 13 14 15 16 17 18
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26 $165 27 $162 28 $172 29 $193 30 $263 31  
November 2025
Su Mo Tu We Th Fr Sa
            $263 1
$201 2 $221 3 $208 4 $212 5 $205 6 $267 7 $263 8
$248 9 $273 10 $157 11 $173 12 $370 13 $370 14 $370 15
$370 16 $370 17 $192 18 $149 19 $280 20 $381 21 $306 22
$392 23 $390 24 $399 25 $580 26 $574 27 $566 28 $559 29
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December 2025
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  $152 1 $178 2 $242 3 $261 4 $269 5 $263 6
$224 7 $243 8 $255 9 $249 10 $252 11 $263 12 $263 13
$236 14 $170 15 $173 16 $181 17 $276 18 $512 19 $674 20
$832 21 $919 22 $890 23 $790 24 $697 25 $718 26 $759 27
$856 28 $910 29 $866 30 $738 31      
January 2026
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        $649 1 $706 2 $711 3
$315 4 $173 5 $171 6 $242 7 $242 8 $263 9 $263 10
$175 11 $146 12 $142 13 $182 14 $175 15 $263 16 $263 17
$252 18 $215 19 $193 20 $181 21 $183 22 $263 23 $263 24
$184 25 $154 26 $151 27 $156 28 $178 29 $263 30 $263 31
Swipe Swipe for Availability


Amenities 63 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
  • Private entrance
  • Private living room
  • Refrigerator
  • Resort
  • Room-darkening shades
  • Shampoo
  • Shower gel
  • Smoke detector
  • Stove
  • Toaster
  • Towels provided
  • Town
  • Trash can
  • TV
  • Washer
  • Wireless Internet
Resorts
  • WindsorWestside
  • 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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