House - Rating 5 (3)

Upstay 20 Guest Mansion THE BEST Resort


Bedroom 9 bedrooms
Bathroom 6 baths
Guests 20 guests
Pets Not Allowed Pets Not Allowed

  • Location: Orlando, Florida
  • Type: House
  • View: Downtown

Location Location

Description Description
Home Highlights:
- 9 bedrooms / 6 bathrooms
- Smart TVs
- High speed WiFi connection
- Private swimming pool and outdoor hot tub
- Large furnished sundeck
- In-home games room with billiards, air hockey and foosball
- Spacious group-friendly layout
- Fully equipped kitchen
- BBQ grill
- Large capacity indoor and outdoor dining areas
- In-home laundry machines
- Free onsite parking (for 4 vehicles)
- Resort access
- Proximity to Disney (only 8 miles)

Windsor at Westside Resort Features:
- 24hr gated entrance with security guard
- Clubhouse with restaurant, bar & lounge
- State-of-the-art fitness centre
- Lazy river and inflatable doughnuts for floating
- Shallow entry resort-style pool and outdoor hot tub
- Children’s water playground with waterslides
- Large sundeck with poolside loungers, cabanas and umbrella shading
- Poolside Tiki bar and ice cream shop
- Children’s centre with staff run activities
- Video arcade
- Sundries shop
- Sand volleyball court and tennis/basketball courts

This amazing 9 bedroom home comes with lovely pond-views, and has a fantastic back patio complete with a sparkling swimming pool and a jacuzzi hot tub. There are 6 bathrooms and the home is large enough to host up to 20 guests at a time.

The kitchen is fully equipped with all the tools you'll need to whip up a great meal, and a full dining set to enjoy it. Plus, you can add BBQ to the menu, thanks to your outdoor grill.

Each bedroom has its own smart TV for your entertainment, and the home is connected to high speed wifi. You'll find the primary King bedroom suite on the ground level of the home. It has a beautiful ensuite bathroom and spacious design. There is also a bunk-bed room on this floor, but all the other bedrooms are located upstairs on the 2nd level. You'll also find a loft lounge up here, that includes the popular games of billiards, and foosball.

All the comforts of home are included, such as central A/C, in-home laundry machines, and free onsite parking. Our guests also get access to the resort amenities at the clubhouse.

Windsor at Westside is a gated vacation rental community close to Disney featuring an extraordinary clubhouse, lake and pier, zero-entry resort-style pool complete with a waterslide, lazy river, and children’s water playground. The Tiki bar offers poolside food and drink service, while the TuCasa bar and fireplace lounge has indoor and outdoor dining. There is also a fitness centre, sand volleyball courts, multi purpose sports courts, a video arcade and sundries shop. The resort is perfectly located to give you easy access in to the back entrance of Disney World. Close to shops, supermarkets and restaurants it's a great location to explore all the Orlando theme park attractions.

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'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).
- 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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December 2024
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January 2025
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$140 5 $140 6 $140 7 $140 8 $140 9 $240 10 $240 11
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26 27 $140 28 $140 29 $142 30 $240 31  
February 2025
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$183 2 $177 3 $170 4 $212 5 $210 6 $249 7 $253 8
$245 9 $213 10 $193 11 $210 12 $227 13 $360 14 $363 15
$321 16 $267 17 $269 18 $256 19 $261 20 $318 21 $287 22
$266 23 $239 24 $229 25 $244 26 $285 27 $353 28  
March 2025
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            $455 1
$401 2 $338 3 $344 4 $346 5 $430 6 $454 7 $483 8
$434 9 $461 10 $477 11 $483 12 $519 13 $496 14 $548 15
$425 16 $370 17 $375 18 $391 19 $435 20 $497 21 $519 22
$437 23 $440 24 $437 25 $480 26 $533 27 $537 28 $454 29
$367 30 $347 31          
April 2025
Su Mo Tu We Th Fr Sa
    $370 1 $386 2 $442 3 $439 4 $370 5
$314 6 $305 7 $348 8 $391 9 $458 10 $533 11 $677 12
$683 13 $655 14 $556 15 $553 16 $568 17 $681 18 $667 19
$663 20 $381 21 $274 22 $298 23 $334 24 $393 25 $357 26
$279 27 $238 28 $256 29 $260 30      
May 2025
Su Mo Tu We Th Fr Sa
        $297 1 $328 2 $305 3
$258 4 $267 5 $205 6 $217 7 $251 8 $271 9 $265 10
$234 11 $195 12 $258 13 $258 14 $250 15 $293 16 $285 17
$245 18 $206 19 $197 20 $208 21 $246 22 $407 23 $407 24
$406 25 $206 26 $200 27 $213 28 $263 29 $313 30 $307 31
June 2025
Su Mo Tu We Th Fr Sa
$291 1 $281 2 $290 3 $294 4 $306 5 $360 6 $341 7
$285 8 $244 9 $254 10 $276 11 $332 12 $424 13 $412 14
$323 15 $354 16 $282 17 $373 18 $394 19 $444 20 $429 21
$445 22 $395 23 $400 24 $401 25 $475 26 $504 27 $403 28
$319 29 $294 30          
July 2025
Su Mo Tu We Th Fr Sa
    $321 1 $407 2 $755 3 $711 4 $753 5
$489 6 $447 7 $432 8 $448 9 $506 10 $518 11 $455 12
$514 13 $538 14 $603 15 $590 16 $468 17 $598 18 $535 19
$364 20 $303 21 $285 22 $306 23 $417 24 $509 25 $468 26
$325 27 $274 28 $328 29 $296 30 $385 31    
August 2025
Su Mo Tu We Th Fr Sa
          $426 1 $381 2
$276 3 $246 4 $248 5 $272 6 $327 7 $346 8 $317 9
$276 10 $235 11 $236 12 $253 13 $272 14 $274 15 $258 16
$211 17 $204 18 $202 19 $222 20 $235 21 $254 22 $247 23
$253 24 $251 25 $249 26 $257 27 $255 28 $316 29 $316 30
$318 31            
September 2025
Su Mo Tu We Th Fr Sa
  $148 1 $147 2 $151 3 $160 4 $240 5 $240 6
$173 7 $154 8 $151 9 $148 10 $156 11 $240 12 $240 13
$194 14 $180 15 $180 16 $208 17 $222 18 $240 19 $240 20
$205 21 $163 22 $155 23 $149 24 $167 25 $240 26 $240 27
$166 28 $156 29 $147 30        
October 2025
Su Mo Tu We Th Fr Sa
      $155 1 $176 2 $240 3 $240 4
$178 5 $167 6 $161 7 $172 8 $198 9 $240 10 $240 11
$239 12 $241 13 $241 14 $256 15 $242 16 $247 17 $240 18
$192 19 $171 20 $188 21 $204 22 $204 23 $240 24 $240 25
$176 26 $153 27 $150 28 $159 29 $187 30 $240 31  
November 2025
Su Mo Tu We Th Fr Sa
            $240 1
$186 2 $189 3 $158 4 $164 5 $184 6 $240 7 $240 8
$233 9 $292 10 $316 11 $360 12 $297 13 $304 14 $259 15
$241 16 $236 17 $248 18 $200 19 $393 20 $441 21 $391 22
$279 23 $279 24 $425 25 $720 26 $702 27 $707 28 $599 29
$254 30            
Swipe Swipe for Availability


Amenities 54 Amenities
  • Air conditioning
  • Baking sheet
  • Bathtub
  • BBQ grill
  • Bed linens
  • Carbon monoxide detector
  • Cleaning Disinfection
  • Coffee maker
  • Cookware
  • Dishes and silverware
  • Dishwasher
  • Downtown
  • Dryer
  • Enhanced cleaning practices
  • Essentials
  • Family/kid friendly
  • Fire extinguisher
  • Free parking on premises
  • 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
  • Refrigerator
  • Resort
  • Room-darkening shades
  • Shampoo
  • Shower gel
  • Smoke detector
  • Stove
  • Toaster
  • Towels provided
  • Town
  • TV
  • Washer
  • Wireless Internet
Resorts
  • WindsorWestside
  • Communal pool
  • Game room
  • Outdoor pool
  • Private pool
  • Swimming pool

Reviews Rating 5 (3) Reviews
Rating 5
Words cannot express the Thanksgiving weekend we had in this great home. We had more than enough room for everyone and the response from Upstay was amazing. They answered any questions we had and so quickly. My family and I will definitely be back and would recommend this home to anyone looking for a home away from home. Thank you Upstay for a weekend we won't forget.
Anonymous - Posted: 12/5/2024
Rating 5
The best house in Davenport ! Amazing ?
Anonymous - Posted: 11/28/2024
Thank you for your glowing review! We're thrilled you had an amazing experience and consider it the best house in Davenport. We'd be delighted to host you again in the future! ?
Upstay staff
Posted: 12/13/2024
Rating 5
The Place was very nice, and Spacious. The Pictures Matched the house, and the house is was not far from the Entry Gate. Great Location, The Host were very quick to respond and assist. Me and family would definitely stay here again :)
Anonymous - Posted: 11/25/2024
Thank you for your kind words! We're thrilled to hear you found the place spacious and true to the photos. It's great that the location and quick responses from our team added to your positive experience. We would love to host you and your family again in the future!
Upstay staff
Posted: 12/13/2024
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