House - Rating 5 (18)

Upstay Renovated 9BR Home w Theater 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
This newly renovated 9-bedroom, 6-bathroom home at Windsor at Westside has been enhanced with a brand-new private movie theater and upgraded games room with a PlayStation—making it the ultimate group getaway. Enjoy a private pool, outdoor hot tub, and a large sundeck with serene pond views. The home sleeps up to 20 guests comfortably, with smart TVs in every bedroom and high-speed WiFi throughout.

Enjoy pond-facing views and no rear neighbors while you soak up the Florida sunshine from your private screened-in patio. Cool off in the sparkling swimming pool, unwind in the jacuzzi hot tub, or enjoy BBQ lunches around the outdoor dining area—there’s plenty of space for everyone.

Inside, the fully equipped kitchen features double fridge/freezer combo units, two large-capacity dishwashers, quartz countertops, stainless steel appliances, and a deep double sink. Dine together at the 10-person indoor dining table, with additional seating for 4 at the kitchen island and even more outdoors.

Every bedroom has a Smart TV, and high-speed internet keeps everyone connected.

Bedroom breakdown:
First Floor:
Bedroom 1: King bed with ensuite
Bedroom 2: Queen bed with ensuite
Bedroom 3: Queen bed with ensuite
Also on this floor: A popular bunk-bed room, great for kids!

Second Floor:
Bedroom 4: King bedroom suite
Bedroom 5: Queen bedroom suite
Bedroom 6: Bunk bed (twin/full)
Bedrooms 7–9: Three rooms, each with 2 twin beds
Bonus: Upstairs loft lounge now enhanced with air hockey, billiards, and foosball

Need to throw in a load of laundry? No problem—this home includes in-home washers and dryers, central A/C, and free parking for up to 4 vehicles on-site.

As part of your stay, you’ll also enjoy full access to the incredible Windsor at Westside Resort, complete with a lazy river, water slides, a Tiki bar, and so much more. Whether you're heading to Disney (just 8 miles away), relaxing poolside, or enjoying a movie night at home—this property offers a vacation experience unlike any other.

*IMPORTANT NOTE*
• For a smooth and secure check-in experience, all guests may be required to complete ID and Enso Boarding Pass verification before arrival. Check-in instructions will be shared once verification is completed. Thank you for helping us ensure a seamless stay!
• Up to 2 vehicles can park in the driveway. There is additional parking at the clubhouse if needed. Please note: the garage is not available, and the resort's policy limits a maximum of 5 vehicles per residence.
• Please note that we do not provide washcloths. Please bring your own washcloths to make use of during your stay.

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:
- Planning a BBQ? A propane tank is available for a one-time $69 charge. Let us know in advance, and we’ll make sure you’re all set to grill and enjoy!
- 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
Check-Out
March 2026
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 $263 23 $263 24 $273 25 $291 26 27 28
$382 29 $372 30 31        
April 2026
Su Mo Tu We Th Fr Sa
      1 2 3 4
5 6 7 8 9 10 11
$271 12 $220 13 $220 14 $247 15 $322 16 $447 17 18
19 20 21 22 23 24 25
26 27 28 $306 29 $295 30    
May 2026
Su Mo Tu We Th Fr Sa
          $325 1 $305 2
$273 3 $227 4 $223 5 $290 6 $292 7 $305 8 $300 9
$266 10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 $223 27 $264 28 $389 29 $398 30
31            
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $420 6
$404 7 $330 8 $415 9 $341 10 $426 11 $497 12 $479 13
$475 14 $459 15 $459 16 $480 17 $653 18 $647 19 $646 20
$685 21 $713 22 $718 23 $721 24 $749 25 26 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 $970 3 $963 4
$714 5 $669 6 $679 7 $739 8 $789 9 $828 10 11
12 13 14 15 16 17 $915 18
$654 19 $457 20 $440 21 $487 22 $615 23 $755 24 $674 25
$530 26 $500 27 $500 28 $450 29 $529 30 $609 31  
August 2026
Su Mo Tu We Th Fr Sa
            $565 1
$475 2 $405 3 $382 4 $377 5 $423 6 $459 7 $444 8
$410 9 $379 10 $413 11 $418 12 $425 13 $418 14 $408 15
$377 16 $287 17 $272 18 $283 19 $314 20 $338 21 $334 22
$291 23 $238 24 $220 25 $222 26 $267 27 $309 28 $316 29
$274 30 $220 31          
September 2026
Su Mo Tu We Th Fr Sa
    $220 1 $220 2 $242 3 $394 4 $415 5
$389 6 $220 7 $220 8 9 10 11 12
$292 13 $292 14 $292 15 $292 16 $283 17 $309 18 $311 19
$262 20 $230 21 $224 22 $262 23 $262 24 $309 25 $305 26
$262 27 $226 28 $222 29 $220 30      
October 2026
Su Mo Tu We Th Fr Sa
        $250 1 $294 2 $319 3
$283 4 $246 5 $279 6 $299 7 $330 8 $377 9 $376 10
$381 11 $345 12 $326 13 $333 14 $317 15 $336 16 $339 17
$296 18 $309 19 $289 20 $285 21 $270 22 $297 23 $287 24
$246 25 $220 26 $220 27 $222 28 $268 29 $317 30 $324 31
November 2026
Su Mo Tu We Th Fr Sa
$277 1 $276 2 $277 3 $282 4 $305 5 $309 6 $309 7
$253 8 $222 9 $323 10 $320 11 $326 12 $342 13 $348 14
$298 15 $236 16 $275 17 $223 18 $274 19 $471 20 $537 21
$542 22 $593 23 $611 24 $1246 25 $1244 26 $1035 27 $865 28
$305 29 $253 30          
December 2026
Su Mo Tu We Th Fr Sa
    $274 1 $249 2 $250 3 $441 4 $352 5
$260 6 $255 7 $255 8 $262 9 $290 10 $372 11 $362 12
$348 13 $355 14 $394 15 $281 16 $394 17 $614 18 $953 19
$1250 20 $1311 21 $1293 22 $1612 23 $1649 24 $1645 25 $1648 26
$1515 27 $1321 28 $1319 29 $1205 30 $1200 31    
January 2027
Su Mo Tu We Th Fr Sa
          $1155 1 $1025 2
$892 3 $578 4 $462 5 $450 6 $444 7 $374 8 $328 9
$335 10 $241 11 $233 12 $220 13 $248 14 $328 15 $364 16
$361 17 $304 18 $271 19 $271 20 $270 21 $281 22 $279 23
$262 24 $228 25 $223 26 $232 27 $253 28 $282 29 $280 30
$263 31            
February 2027
Su Mo Tu We Th Fr Sa
  $240 1 $229 2 $248 3 $280 4 $379 5 $389 6
$367 7 $334 8 $307 9 $348 10 $387 11 $575 12 $626 13
$576 14 $401 15 $328 16 $360 17 $380 18 $414 19 $421 20
$442 21 $422 22 $422 23 $423 24 $420 25 $447 26 $436 27
$331 28            
Swipe Swipe for Availability


Amenities 56 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 fireplace
  • 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
  • Suitable for children (2-12 years)
  • Suitable for infants (under 2 years)
  • Toaster
  • Towels provided
  • Town
  • TV
  • Washer
  • Wireless Internet
Resorts
  • WindsorWestside
  • Communal pool
  • Game room
  • Outdoor pool
  • Private pool
  • Swimming pool

Reviews Rating 5 (18) Reviews
Rating 5
Alfredo was an amazing host very responsive. The house was absolutely beautiful every aspect of the home was beautiful we all enjoyed ourselves and will definitely return.
Anonymous - Posted: 12/16/2025
Thank you so much for your kind words, Tiffany! It brings us immense joy to hear that you and your group enjoyed your stay at Upstay. We take great pride in maintaining the beauty of our home, and it’s wonderful to know that it met your expectations. We’re looking forward to welcoming you back for another memorable visit!
Upstay staff
Posted: 12/17/2025
Rating 5
The pictures does not do justice. I rent homes at least twice a year, and this home is one of the top 5. The movie room was REMARKABLE!!!! I even played the games in the game room and I have NEVER played any games in any of the homes. This home was spacious for 12 adult women. My only complaint is the dining table needs replaced, as the chairs came apart, and you can tell they have been glued before, but we made the best of it…… I WOULD RENT AGAIN
Anonymous - Posted: 12/10/2025
Thank you for sharing your experience with us! It’s wonderful to hear that you and your group enjoyed the spaciousness of our home and had a great time in the movie and game rooms. We strive to create a memorable stay for our guests, and it’s rewarding to know we succeeded with you. We appreciate your feedback regarding the dining table and chairs. We’re always looking for ways to improve, and we’ll definitely take your comments into consideration as we make updates. We’d love to welcome you back for another stay in the future!
Upstay staff
Posted: 12/11/2025
Rating 5
This home was beautiful and was the perfect amount of space for my extended family. The kids enjoyed the game room, movie theater, and the pool/spa. To be honest, so did the adults! I was able to prepare meals just like I was at home. We brought most of our food, but the local grocery store (Publix) was only 5 minutes away. The kitchen was equipped with every kitchen gadget you could imagine. I eat a mostly Keto diet, and I enjoy easily prepared meals. The provided air fryer was a plus, thank you! Each room and bathroom were both neat and clean; there were also bath linens and extra towels for the pool. The host was responsive and also checked on us during our stay. This was our first getaway as an extended family, and we truly enjoyed ourselves. Thank you for making it a memorable one.
Anonymous - Posted: 9/13/2025
We’re thrilled to hear that you and your extended family had such a wonderful stay at Upstay! It’s great to know that everyone, from the kids to the adults, enjoyed the game room, movie theater, and pool/spa. We strive to create a home-like atmosphere, so we’re glad you found the kitchen well-equipped for your meal preparations, especially with your Keto diet in mind. It’s fantastic that the air fryer was a hit! We take pride in maintaining a clean and comfortable space, and we’re happy to hear that you appreciated the extra towels and linens. Thank you for recognizing our efforts to be responsive and check in during your stay. We’re honored to have been a part of your first getaway as an extended family and are delighted that it was a memorable experience for you all. We hope to welcome you back for more family adventures in the future!
Upstay staff
Posted: 9/16/2025
Rating 5
Host was very responsive and accommodating. Proactively communicated with me and prepared us for the stay. Will definitely book again.
Anonymous - Posted: 8/11/2025
Thank you for your kind words! We’re so glad our communication and preparation helped make your stay smooth and enjoyable. We’d be delighted to host you again anytime!
Upstay staff
Posted: 8/12/2025
Rating 5
Todo muy bien 👍
Anonymous - Posted: 7/24/2025
Thank you for your review Pedro! We are glad to hear everything went well. We hope to host you again soon.
Upstay staff
Posted: 8/11/2025
Rating 5
We had an amazing stay! From the moment we walked in, we were blown away by how spacious, fun, and beautifully designed everything was. The home has enough sleep space! Super comfortable beds more than perfect for our big group of 12. The kitchen is well-equipped and roomy, with plenty of seating to enjoy family meals. The game room is a definite highlight so fun and well set up! It kept us entertained, and there's even space to add more games if they ever want to expand. The TV setup in the game room is awesome, bring the game console! The movie room was cozy with super comfy chairs for everyone to relax and enjoy without feeling left out. The private pool is a good size which is important for large groups. The resort area is nice, though the Lazy River and slides felt a bit smaller than advertised. Still very fun, and adults can fit on the slide. Host communication was top tier they were very accommodating at all times. I’d definitely stay again. Everyone enjoyed the stay so much.
Anonymous - Posted: 7/22/2025
Thank you so much for your amazing and thoughtful review! We’re thrilled to hear the home exceeded your expectations and was such a great fit for your group. It’s wonderful to know you enjoyed everything from the spacious layout and comfortable beds to the game room, movie room, and private pool. Your feedback about the resort amenities and suggestions for future additions are greatly appreciated—we're always looking to improve! We’re especially glad our team could support your stay with great communication. It means a lot that you’d stay with us again, and we’d absolutely love to host you and your group anytime in the future!
Upstay staff
Posted: 8/6/2025
Rating 5
it was great....everything ready for a great vacations....
Anonymous - Posted: 6/26/2025
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: 2/7/2025
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: 2/7/2025
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: 12/14/2024
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: 12/14/2024
Rating 5
" We had a wonderful stay at your vacation rental home! The spacious home provided plenty of room for a family of 20, and there was something for every age group to enjoy. The open kitchen was fantastic—it had enough space for everyone to eat together, making our family gatherings even more special. The whole family enjoyed the pool and the amenities at the clubhouse, which added to our fun! Highly recommend for a memorable and comfortable getaway!"
Lillian R. - Posted:
Rating 5
Beautiful home. Close to the Clubhouse. Great communication with property manager. Amenities Galore! Highly Recommend!
Jacques J. - Posted:
Rating 5
Great property. Very engaged host
Albert N. - Posted:
Rating 5
Did a family trip to Disney with a total of 18 kids/adults. Primarily used for the basics (sleep/shower/breakfast) so it was perfect for that as everyone had their own space. Property manager was on top of their game and very responsive. Thanks for a great trip!
Arthur V. - Posted:
Rating 5
Wonderful home, felt safe with family and had a lot of fun.
Dre W. - Posted:
Rating 5
Everything Was On Point except tha AC Was not working up stairs
Sandra S. - Posted:
Swipe Swipe for More Reviews

Request More Info Request More Info

Want to know specifics? Ask anything in reference to vacationing at this property that you would like to know...

Example: "Are fresh linens provided?"

I agree