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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February 2025
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$186 2 $178 3 $172 4 $212 5 $212 6 $248 7 $251 8
$246 9 $216 10 $194 11 $212 12 $230 13 $363 14 $365 15
$323 16 $266 17 $268 18 $254 19 $262 20 $319 21 $284 22
$266 23 $241 24 $228 25 $244 26 $282 27 $356 28  
March 2025
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            $446 1
$402 2 $334 3 $336 4 $340 5 $411 6 $458 7 $474 8
$415 9 $442 10 $458 11 $458 12 $498 13 $502 14 $549 15
$420 16 $369 17 $372 18 $389 19 $434 20 $500 21 $525 22
$433 23 $435 24 $438 25 $478 26 $538 27 $537 28 $453 29
$366 30 $347 31          
April 2025
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    $370 1 $382 2 $445 3 $436 4 $372 5
$320 6 $305 7 $349 8 $408 9 $461 10 $535 11 $685 12
$676 13 $657 14 $568 15 $564 16 $582 17 $691 18 $672 19
$665 20 $374 21 $275 22 $301 23 $336 24 $391 25 $358 26
$283 27 $238 28 $256 29 $263 30      
May 2025
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        $299 1 $326 2 $308 3
$263 4 $274 5 $207 6 $215 7 $250 8 $267 9 $259 10
$230 11 $191 12 $251 13 $248 14 $246 15 $288 16 $286 17
$247 18 $204 19 $198 20 $210 21 $249 22 $411 23 $410 24
$409 25 $210 26 $205 27 $219 28 $273 29 $323 30 $317 31
June 2025
Su Mo Tu We Th Fr Sa
$305 1 $287 2 $295 3 $294 4 $305 5 $361 6 $341 7
$284 8 $244 9 $254 10 $276 11 $332 12 $425 13 $418 14
$324 15 $346 16 $283 17 $377 18 $394 19 $446 20 $434 21
$488 22 $410 23 $429 24 $404 25 $472 26 $512 27 $407 28
$317 29 $293 30          
July 2025
Su Mo Tu We Th Fr Sa
    $315 1 $397 2 $761 3 $708 4 $751 5
$403 6 $316 7 $325 8 $398 9 $496 10 $510 11 $443 12
$476 13 $482 14 $579 15 $554 16 $467 17 $631 18 $524 19
$355 20 $302 21 $286 22 $304 23 $420 24 $507 25 $475 26
$326 27 $280 28 $351 29 $304 30 $390 31    
August 2025
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          $428 1 $383 2
$278 3 $245 4 $245 5 $271 6 $328 7 $355 8 $320 9
$289 10 $272 11 $283 12 $269 13 $282 14 $283 15 $262 16
$221 17 $212 18 $214 19 $228 20 $240 21 $256 22 $249 23
$231 24 $203 25 $196 26 $238 27 $236 28 $315 29 $316 30
$317 31            
September 2025
Su Mo Tu We Th Fr Sa
  $148 1 $146 2 $149 3 $159 4 $240 5 $240 6
$171 7 $153 8 $149 9 $144 10 $154 11 $240 12 $240 13
$193 14 $180 15 $180 16 $194 17 $234 18 $240 19 $240 20
$218 21 $180 22 $182 23 $170 24 $171 25 $240 26 $240 27
$165 28 $155 29 $147 30        
October 2025
Su Mo Tu We Th Fr Sa
      $156 1 $177 2 $240 3 $240 4
$179 5 $166 6 $160 7 $174 8 $199 9 $240 10 $240 11
$239 12 $241 13 $241 14 $255 15 $240 16 $245 17 $240 18
$194 19 $170 20 $189 21 $204 22 $204 23 $240 24 $240 25
$178 26 $153 27 $151 28 $160 29 $188 30 $240 31  
November 2025
Su Mo Tu We Th Fr Sa
            $240 1
$189 2 $190 3 $159 4 $165 5 $186 6 $240 7 $240 8
$234 9 $293 10 $315 11 $357 12 $295 13 $303 14 $261 15
$242 16 $236 17 $250 18 $201 19 $396 20 $443 21 $392 22
$281 23 $279 24 $426 25 $723 26 $705 27 $711 28 $602 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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