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:
- 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
Available
Unavailable
Check-In
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March 2025
Su Mo Tu We Th Fr Sa
            1
2 3 4 5 6 7 8
9 10 11 $147 12 $147 13 $252 14 15
16 17 18 19 20 $318 21 $343 22
$280 23 24 25 26 27 28 29
30 31          
April 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 $262 9 $357 10 $372 11 $461 12
$492 13 $508 14 $484 15 $431 16 $435 17 $540 18 $537 19
$516 20 $401 21 $260 22 $290 23 $321 24 $355 25 $332 26
$225 27 28 29 30      
May 2025
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 $185 13 $192 14 $211 15 $255 16 $265 17
$238 18 $198 19 $193 20 $201 21 $235 22 $359 23 $366 24
$368 25 $246 26 $237 27 $241 28 $256 29 $307 30 $308 31
June 2025
Su Mo Tu We Th Fr Sa
$256 1 $215 2 $213 3 $264 4 $269 5 $312 6 $298 7
$256 8 $227 9 $237 10 $236 11 $292 12 $361 13 14
15 16 17 18 19 20 $392 21
$462 22 $376 23 $314 24 $489 25 $440 26 $467 27 $388 28
$333 29 $347 30          
July 2025
Su Mo Tu We Th Fr Sa
    $348 1 $357 2 $794 3 $729 4 $778 5
$318 6 $304 7 $323 8 $379 9 $477 10 $517 11 $438 12
$419 13 $461 14 $427 15 $452 16 $445 17 $647 18 $469 19
$339 20 $289 21 $281 22 $299 23 $410 24 $482 25 $454 26
$367 27 $338 28 $398 29 $332 30 $371 31    
August 2025
Su Mo Tu We Th Fr Sa
          $414 1 $397 2
$292 3 $264 4 $269 5 $286 6 $319 7 $330 8 $313 9
$254 10 $240 11 $248 12 $266 13 $283 14 $291 15 $264 16
$202 17 $196 18 $200 19 $213 20 $228 21 $296 22 $275 23
$244 24 $206 25 $200 26 $236 27 $235 28 $278 29 $272 30
$272 31            
September 2025
Su Mo Tu We Th Fr Sa
  $153 1 $146 2 $150 3 $162 4 $240 5 $240 6
$187 7 $188 8 $155 9 $181 10 $164 11 $240 12 $240 13
$170 14 $160 15 $155 16 $151 17 $160 18 $240 19 $240 20
$188 21 $187 22 $186 23 $159 24 $181 25 $240 26 $240 27
$170 28 $161 29 $153 30        
October 2025
Su Mo Tu We Th Fr Sa
      $157 1 $176 2 $240 3 $240 4
$183 5 $170 6 $168 7 $226 8 $235 9 $240 10 $263 11
$231 12 $241 13 $247 14 $225 15 $204 16 $240 17 $240 18
$195 19 $167 20 $162 21 $165 22 $185 23 $240 24 $240 25
$181 26 $157 27 $151 28 $161 29 $196 30 $240 31  
November 2025
Su Mo Tu We Th Fr Sa
            $240 1
$197 2 $209 3 $220 4 $227 5 $200 6 $241 7 $244 8
$238 9 $263 10 $180 11 $274 12 $381 13 $381 14 $381 15
$381 16 $381 17 $198 18 $173 19 $332 20 $435 21 $397 22
$451 23 $422 24 $444 25 $753 26 $719 27 $718 28 $643 29
30            
December 2025
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $240 6
$195 7 $172 8 $187 9 $199 10 $241 11 $299 12 $281 13
$247 14 $279 15 $212 16 $222 17 $406 18 $558 19 $636 20
$753 21 $842 22 $936 23 $970 24 $929 25 $965 26 $786 27
$763 28 $843 29 $815 30 $726 31      
January 2026
Su Mo Tu We Th Fr Sa
        $705 1 $662 2 $666 3
$322 4 $191 5 $191 6 $178 7 $231 8 $240 9 $240 10
$177 11 $147 12 $148 13 $156 14 $173 15 $282 16 $314 17
$313 18 $209 19 $188 20 $188 21 $189 22 $240 23 $240 24
$182 25 $160 26 $153 27 $158 28 $174 29 $240 30 $240 31
February 2026
Su Mo Tu We Th Fr Sa
$192 1 $176 2 $172 3 $183 4 $208 5 $256 6 $270 7
$237 8 $204 9 $199 10 $211 11 $246 12 $368 13 $410 14
$414 15 $312 16 $280 17 $263 18 $279 19 $296 20 $328 21
$287 22 $278 23 $278 24 $257 25 $286 26 $294 27 $344 28
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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