House - Rating 5 (18)

Upstay Family Retreat w Pool 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
Bedroom 2: Two (2) Queen beds with ensuite

Second Floor:
Bedroom 3: King bed with ensuite
Bedroom 4: Bunk-bed (twin/full)
Bedroom 5: King bedroom suite
Bedroom 6: King bedroom suite
Bedroom 7: Bunk bed (twin/full)
Bedrooms 8&9: Two 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.

• 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 may park in the driveway while extra parking is available at the clubhouse. The garage is not available, and a maximum of 5 vehicles is allowed per residence.
• Please note that washcloths are not provided—kindly bring your own for your stay.

Additional Services:
• Pool and hot tub heating are available upon request and are not included in the booking price. The fee is $45/night per service or $79/night for both, with a 2-night minimum. At least 24 hours’ notice is required if you would like to add this service.
• 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!
• Rent a Pack 'n play for $39 (one-time fee)
• Rent a highchair for $29 (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.

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
November 2026
Su Mo Tu We Th Fr Sa
1 2 3 $140 4 $140 5 6 7
$154 8 $154 9 $154 10 11 12 13 14
$154 15 $154 16 $154 17 $154 18 $178 19 20 21
22 23 24 25 26 $497 27 28
29 30          
December 2026
Su Mo Tu We Th Fr Sa
    1 2 3 $240 4 5
6 7 8 $198 9 $198 10 11 12
13 $198 14 $198 15 $198 16 $198 17 $308 18 $394 19
$464 20 $520 21 $728 22 23 24 25 26
$896 27 $901 28 $906 29 $878 30 $879 31    
January 2027
Su Mo Tu We Th Fr Sa
          $694 1 $683 2
$220 3 $220 4 $220 5 $220 6 $220 7 $279 8 $323 9
$220 10 $220 11 $220 12 $220 13 $220 14 15 16
17 $220 18 $220 19 $220 20 21 22 23
$220 24 $220 25 26 27 28 29 30
31            
February 2027
Su Mo Tu We Th Fr Sa
  1 $220 2 $223 3 $260 4 $309 5 $322 6
$291 7 $286 8 $283 9 $288 10 $312 11 $538 12 $554 13
$538 14 $368 15 $311 16 $329 17 $347 18 $403 19 $382 20
$321 21 $343 22 $328 23 $349 24 $367 25 $384 26 $390 27
$295 28            
March 2027
Su Mo Tu We Th Fr Sa
  $257 1 $262 2 $278 3 $300 4 $379 5 6
7 8 9 10 11 12 $650 13
$609 14 $611 15 $599 16 $616 17 $627 18 $641 19 $672 20
$539 21 $528 22 $454 23 $462 24 $623 25 $808 26 $754 27
$785 28 $675 29 $664 30 $668 31      
April 2027
Su Mo Tu We Th Fr Sa
        $722 1 $689 2 $596 3
$517 4 $506 5 $525 6 $633 7 $703 8 $649 9 $535 10
$418 11 $408 12 $426 13 $433 14 $438 15 $472 16 $760 17
$809 18 $890 19 $939 20 $942 21 $978 22 $1013 23 $1010 24
$983 25 $847 26 $837 27 $856 28 $862 29 $855 30  
May 2027
Su Mo Tu We Th Fr Sa
            $558 1
$433 2 $383 3 $290 4 $286 5 $393 6 $405 7 $387 8
$328 9 $265 10 $258 11 $268 12 $317 13 $350 14 $366 15
$314 16 $290 17 $258 18 $508 19 $518 20 $538 21 $348 22
$308 23 $288 24 $270 25 $305 26 $364 27 $552 28 $541 29
$532 30 $365 31          
June 2027
Su Mo Tu We Th Fr Sa
    $398 1 $333 2 $413 3 $440 4 $465 5
$497 6 $509 7 $524 8 $558 9 $565 10 $574 11 $566 12
$568 13 $573 14 $574 15 $635 16 $707 17 $707 18 $707 19
$740 20 $750 21 $754 22 $757 23 $735 24 $773 25 $707 26
$779 27 $800 28 $804 29 $803 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 $684 5 $663 6 $686 7 $728 8 $792 9 $739 10
$808 11 $806 12 $803 13 $778 14 $781 15 $826 16 $769 17
$593 18 $485 19 $613 20 $579 21 $646 22 $774 23 $721 24
$539 25 $506 26 $506 27 $451 28 $549 29 $617 30 $602 31
August 2027
Su Mo Tu We Th Fr Sa
$487 1 $416 2 $470 3 $463 4 $456 5 $497 6 $472 7
$418 8 $362 9 $348 10 $354 11 $398 12 $437 13 $398 14
$364 15 $365 16 $291 17 $305 18 $335 19 $379 20 $360 21
$326 22 $274 23 $257 24 $268 25 $293 26 $352 27 $337 28
$299 29 $272 30 $257 31        
September 2027
Su Mo Tu We Th Fr Sa
      $266 1 $294 2 $441 3 $424 4
$410 5 $252 6 $233 7 $236 8 $266 9 $296 10 $288 11
$260 12 $240 13 $233 14 $317 15 $317 16 $294 17 $294 18
$261 19 $270 20 $264 21 $264 22 $278 23 $316 24 $298 25
$256 26 $262 27 $232 28 $244 29 $279 30    
October 2027
Su Mo Tu We Th Fr Sa
          $301 1 $313 2
$267 3 $249 4 $245 5 $258 6 $285 7 $360 8 $356 9
$359 10 $301 11 $265 12 $265 13 $298 14 $328 15 $349 16
$352 17 $301 18 $301 19 $238 20 $403 21 $381 22 $381 23
$403 24 $268 25 $221 26 $269 27 $403 28 $324 29 $346 30
$403 31            
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:
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