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.

*IMPORTANT NOTE*
• To help ensure a safe and trusted experience for all guests, ID verification may be required after booking.

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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July 2025
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August 2025
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September 2025
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$160 28 $151 29 $144 30        
October 2025
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$228 12 $198 13 $197 14 $184 15 $201 16 $240 17 18
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$181 26 $164 27 $160 28 $172 29 $206 30 $240 31  
November 2025
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$202 2 $219 3 $222 4 $217 5 $228 6 $275 7 $267 8
$263 9 $288 10 $191 11 $243 12 $242 13 $295 14 $283 15
$237 16 $237 17 $186 18 $167 19 $283 20 $403 21 $410 22
$418 23 $418 24 $427 25 $660 26 $642 27 $640 28 $616 29
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December 2025
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  1 2 3 4 5 $240 6
$198 7 $182 8 $189 9 $203 10 $234 11 $274 12 $292 13
$223 14 $250 15 $265 16 $258 17 $357 18 $552 19 $640 20
$751 21 $803 22 $848 23 $761 24 $736 25 $804 26 $810 27
$841 28 $840 29 $825 30 $764 31      
January 2026
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$195 11 $172 12 $170 13 $160 14 $163 15 $240 16 $266 17
$273 18 $219 19 $152 20 $190 21 $189 22 $240 23 $240 24
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February 2026
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$196 1 $179 2 $181 3 $196 4 $218 5 $244 6 $276 7
$251 8 $222 9 $212 10 $234 11 $257 12 $366 13 $418 14
$417 15 $304 16 $260 17 $254 18 $254 19 $289 20 $294 21
$260 22 $228 23 $222 24 $234 25 $246 26 $268 27 $351 28
March 2026
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$304 1 $272 2 $272 3 $278 4 $334 5 $351 6 $354 7
$304 8 $286 9 $280 10 $286 11 $328 12 $366 13 $402 14
$373 15 $332 16 $326 17 $331 18 $359 19 $412 20 $393 21
$387 22 $367 23 $366 24 $367 25 $405 26 $404 27 $429 28
$370 29 $386 30 $406 31        
April 2026
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      $471 1 $513 2 $739 3 $671 4
$685 5 $354 6 $380 7 $420 8 $475 9 $515 10 $489 11
$331 12 $298 13 $287 14 $321 15 $367 16 $396 17 $393 18
$342 19 $297 20 $291 21 $311 22 $345 23 $381 24 $338 25
$287 26 $235 27 $294 28 $319 29 $238 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 (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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