House - Rating 5 (5)

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:
- Your BBQ comes with a complimentary full propane tank at check-in! Running low? Get a one-time refill for just $55 and keep the grill going!
- 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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April 2025
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May 2025
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June 2025
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$271 8 $255 9 $256 10 $257 11 $312 12 $367 13 14
15 16 17 18 19 20 $440 21
$393 22 $386 23 $364 24 $417 25 $414 26 27 28
29 $303 30          
July 2025
Su Mo Tu We Th Fr Sa
    $309 1 $350 2 $646 3 $614 4 $621 5
$327 6 $323 7 $334 8 $368 9 $423 10 $468 11 $440 12
$373 13 14 15 16 17 18 $461 19
$363 20 $319 21 $303 22 $326 23 $418 24 $505 25 $468 26
$380 27 $303 28 $299 29 $312 30 $390 31    
August 2025
Su Mo Tu We Th Fr Sa
          $438 1 $418 2
$326 3 $336 4 $405 5 $329 6 $349 7 $376 8 $361 9
$285 10 $260 11 $268 12 $276 13 $294 14 $309 15 $298 16
$216 17 $209 18 $216 19 $223 20 $237 21 $318 22 $295 23
$253 24 $213 25 $201 26 $193 27 $209 28 $282 29 $279 30
$279 31            
September 2025
Su Mo Tu We Th Fr Sa
  $153 1 $144 2 $148 3 $163 4 $240 5 $240 6
$178 7 $153 8 $146 9 $146 10 $170 11 $240 12 $240 13
$190 14 $149 15 $149 16 $151 17 $199 18 $240 19 $240 20
$167 21 $156 22 $152 23 $157 24 $175 25 $240 26 $240 27
$167 28 $158 29 $148 30        
October 2025
Su Mo Tu We Th Fr Sa
      $152 1 $178 2 $240 3 $240 4
$177 5 $189 6 $190 7 $208 8 $254 9 $240 10 $240 11
$230 12 $193 13 $194 14 $181 15 $201 16 $240 17 $240 18
$187 19 $165 20 $165 21 $167 22 $180 23 $240 24 $240 25
$179 26 $165 27 $163 28 $175 29 $212 30 $240 31  
November 2025
Su Mo Tu We Th Fr Sa
            $241 1
$193 2 $218 3 $226 4 $224 5 $226 6 $265 7 $262 8
$257 9 $279 10 $192 11 $250 12 $243 13 $299 14 $298 15
$252 16 $241 17 $202 18 $172 19 $307 20 $424 21 $389 22
$403 23 $410 24 $419 25 $699 26 $674 27 $667 28 $637 29
30            
December 2025
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $240 6
$193 7 $174 8 $187 9 $196 10 $237 11 $290 12 $293 13
$222 14 $246 15 $199 16 $258 17 $371 18 $559 19 $644 20
$760 21 $813 22 $870 23 $825 24 $774 25 $842 26 $865 27
$854 28 $862 29 $873 30 $757 31      
January 2026
Su Mo Tu We Th Fr Sa
        $728 1 $677 2 $677 3
$368 4 $300 5 $318 6 $290 7 $290 8 $281 9 $293 10
$195 11 $259 12 $182 13 $238 14 $212 15 $253 16 $283 17
$282 18 $174 19 $153 20 $189 21 $183 22 $240 23 $240 24
$190 25 $192 26 $190 27 $174 28 $193 29 $240 30 $240 31
February 2026
Su Mo Tu We Th Fr Sa
$196 1 $178 2 $179 3 $189 4 $211 5 $244 6 $257 7
$229 8 $204 9 $194 10 $208 11 $238 12 $370 13 $413 14
$413 15 $271 16 $243 17 $239 18 $248 19 $285 20 $298 21
$257 22 $221 23 $217 24 $228 25 $253 26 $266 27 $351 28
March 2026
Su Mo Tu We Th Fr Sa
$312 1 $312 2 $316 3 $320 4 $347 5 $361 6 $358 7
$319 8 $293 9 $293 10 $301 11 $346 12 $373 13 $409 14
$365 15 $334 16 $332 17 $338 18 $380 19 $430 20 $412 21
$412 22 $340 23 $344 24 $344 25 $359 26 $395 27 $380 28
$314 29 $346 30 $371 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 (5) Reviews
Rating 5
We had a great stay!
Anonymous - Posted: 1/28/2025
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
Thank you for your kind words, David! We’re thrilled to hear that you found the home spacious and clean, and that the resort amenities were easily accessible. We're glad it worked well for your large family group and that the kids had a great time. We’re also happy to know that you found us polite and responsive. We always strive to provide excellent service, and we truly appreciate you taking the time to share your positive experience. We look forward to hosting you again in the future!
Upstay staff
Posted: 2/6/2025
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
Thank you so much for your heartfelt review, Valerie! We’re so glad to hear that you had a wonderful Thanksgiving weekend and that the home provided more than enough space for your family. We’re also thrilled that we were able to assist you quickly and make your stay even more enjoyable. It would be our pleasure to host you again in the future, and we really appreciate your recommendation. Thank you for choosing us for your memorable weekend!
Upstay staff
Posted: 2/6/2025
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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