House - Rating 5 (4)

Upstay 20Guest Mansion w Pool Hot tub Games Room


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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January 2025
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February 2025
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March 2025
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$277 9 $331 10 $327 11 $342 12 $344 13 $381 14 $411 15
$319 16 $289 17 $295 18 $302 19 $331 20 $416 21 $464 22
$360 23 $368 24 $366 25 $387 26 $420 27 $416 28 $378 29
$312 30 $287 31          
April 2025
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    $326 1 $324 2 $368 3 $365 4 $327 5
$274 6 $264 7 $326 8 $351 9 $488 10 $485 11 $583 12
$627 13 $637 14 $549 15 $509 16 $489 17 $641 18 $624 19
$628 20 $454 21 $290 22 $321 23 $358 24 $414 25 $380 26
$249 27 $220 28 $226 29 $232 30      
May 2025
Su Mo Tu We Th Fr Sa
        $275 1 $304 2 $287 3
$231 4 $204 5 $183 6 $184 7 $209 8 $240 9 $240 10
$202 11 $169 12 $178 13 $221 14 $214 15 $259 16 $260 17
$223 18 $182 19 $178 20 $191 21 $231 22 $387 23 $388 24
$385 25 $188 26 $185 27 $187 28 $239 29 $297 30 $299 31
June 2025
Su Mo Tu We Th Fr Sa
$262 1 $256 2 $251 3 $251 4 $265 5 $327 6 $302 7
$251 8 $215 9 $223 10 $231 11 $314 12 $378 13 $372 14
$290 15 $245 16 $245 17 $312 18 $328 19 $376 20 $356 21
$340 22 $355 23 $286 24 $351 25 $413 26 $447 27 $365 28
$301 29 $277 30          
July 2025
Su Mo Tu We Th Fr Sa
    $365 1 $379 2 $760 3 $696 4 $750 5
$373 6 $428 7 $451 8 $440 9 $502 10 $525 11 $437 12
$404 13 $375 14 $292 15 $320 16 $432 17 $507 18 $465 19
$333 20 $276 21 $262 22 $277 23 $375 24 $446 25 $423 26
$303 27 $314 28 $352 29 $318 30 $362 31    
August 2025
Su Mo Tu We Th Fr Sa
          $390 1 $353 2
$253 3 $233 4 $230 5 $255 6 $299 7 $316 8 $294 9
$281 10 $263 11 $289 12 $275 13 $274 14 $291 15 $264 16
$222 17 $190 18 $223 19 $206 20 $220 21 $262 22 $249 23
$226 24 $194 25 $190 26 $182 27 $196 28 $273 29 $270 30
$271 31            
September 2025
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  $152 1 $147 2 $149 3 $159 4 $240 5 $240 6
$170 7 $152 8 $148 9 $145 10 $152 11 $240 12 $240 13
$165 14 $166 15 $174 16 $198 17 $215 18 $240 19 $240 20
$182 21 $173 22 $156 23 $151 24 $166 25 $240 26 $240 27
$169 28 $157 29 $147 30        
October 2025
Su Mo Tu We Th Fr Sa
      $152 1 $180 2 $240 3 $240 4
$182 5 $164 6 $155 7 $209 8 $236 9 $240 10 $240 11
$257 12 $240 13 $238 14 $208 15 $198 16 $240 17 $240 18
$185 19 $161 20 $156 21 $164 22 $181 23 $240 24 $240 25
$170 26 $147 27 $145 28 $160 29 $191 30 $240 31  
November 2025
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            $240 1
$190 2 $191 3 $185 4 $160 5 $184 6 $240 7 $240 8
$224 9 $249 10 $238 11 $251 12 $368 13 $368 14 $368 15
$368 16 $368 17 $181 18 $170 19 $314 20 $422 21 $384 22
$348 23 $376 24 $398 25 $635 26 $634 27 $635 28 $617 29
$196 30            
December 2025
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  $163 1 $199 2 $165 3 $306 4 $289 5 $240 6
$165 7 $166 8 $176 9 $180 10 $190 11 $244 12 $254 13
$226 14 $255 15 $285 16 $319 17 $384 18 $518 19 $599 20
$710 21 $764 22 $780 23 $845 24 $847 25 $669 26 $667 27
$718 28 $780 29 $752 30 $668 31      
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 (4) Reviews
Rating 5
The host is polite and very responsive. The home is spacious and clean. The resort amenities are close and easily accessible. Great place for a large family group. Great for kids
Anonymous - Posted: 1/4/2025
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
Swipe Swipe for More Reviews

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