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
September 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
$125 13 $125 14 $125 15 $125 16 $125 17 18 19
20 $132 21 $132 22 23 24 25 26
$154 27 $154 28 $154 29 $154 30      
October 2026
Su Mo Tu We Th Fr Sa
        $162 1 $223 2 3
4 $176 5 $176 6 $176 7 $176 8 $287 9 10
11 12 13 $198 14 $198 15 $259 16 $250 17
$194 18 $192 19 $194 20 $176 21 22 23 24
25 $198 26 $198 27 $198 28 $221 29 $271 30 $277 31
November 2026
Su Mo Tu We Th Fr Sa
$220 1 $220 2 $220 3 $220 4 5 6 7
$220 8 $220 9 $220 10 11 12 13 14
$294 15 $238 16 $256 17 $220 18 $278 19 $481 20 $572 21
$590 22 $489 23 $534 24 $828 25 $839 26 $798 27 $643 28
$334 29 $235 30          
December 2026
Su Mo Tu We Th Fr Sa
    $263 1 $229 2 $250 3 $344 4 5
6 7 8 $243 9 $292 10 $374 11 $374 12
$221 13 $220 14 $220 15 $220 16 $303 17 $496 18 $701 19
$798 20 $863 21 $866 22 23 24 25 26
$1037 27 $1033 28 $1007 29 $930 30 $1007 31    
January 2027
Su Mo Tu We Th Fr Sa
          $1052 1 $946 2
$416 3 $318 4 $305 5 $220 6 $245 7 $311 8 $367 9
$280 10 $227 11 $226 12 $266 13 $266 14 $362 15 $403 16
$392 17 $267 18 $235 19 $240 20 $271 21 $299 22 $300 23
$277 24 $279 25 26 27 28 29 30
31            
February 2027
Su Mo Tu We Th Fr Sa
  1 $243 2 $271 3 $298 4 $323 5 $329 6
$287 7 $320 8 $304 9 $340 10 $381 11 $569 12 $665 13
$658 14 $449 15 $398 16 $394 17 $434 18 $446 19 $418 20
$344 21 $363 22 $344 23 $369 24 $390 25 $407 26 $407 27
$338 28            
March 2027
Su Mo Tu We Th Fr Sa
  $288 1 $290 2 $306 3 $329 4 $462 5 $527 6
$453 7 $407 8 $522 9 $557 10 $577 11 $684 12 $690 13
$652 14 $658 15 $642 16 $651 17 $655 18 $745 19 $726 20
$732 21 $658 22 $516 23 $516 24 $662 25 $841 26 $893 27
$887 28 $886 29 $888 30 $887 31      
April 2027
Su Mo Tu We Th Fr Sa
        $885 1 $812 2 $685 3
$724 4 $724 5 $724 6 $641 7 $720 8 $681 9 $583 10
$523 11 $523 12 $523 13 $523 14 $523 15 $523 16 $753 17
$811 18 $952 19 $964 20 $974 21 $1019 22 $1098 23 $1124 24
$1100 25 $946 26 $921 27 $933 28 $927 29 $915 30  
May 2027
Su Mo Tu We Th Fr Sa
            $386 1
$358 2 $290 3 $290 4 $273 5 $299 6 $387 7 $387 8
$320 9 $258 10 $258 11 $258 12 $298 13 $339 14 $363 15
$297 16 $259 17 $258 18 $506 19 $508 20 $517 21 $344 22
$307 23 $338 24 $344 25 $355 26 $362 27 $531 28 $530 29
$493 30 $304 31          
June 2027
Su Mo Tu We Th Fr Sa
    $297 1 $333 2 $397 3 $439 4 $463 5
$572 6 $574 7 $591 8 $607 9 $623 10 $693 11 $746 12
$656 13 $661 14 $657 15 $657 16 $707 17 $716 18 $707 19
$724 20 $707 21 $718 22 $665 23 $702 24 $745 25 $664 26
$748 27 $737 28 $736 29 $752 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 $729 5 $745 6 $746 7 $695 8 $801 9 $728 10
$563 11 $703 12 $489 13 $497 14 $693 15 $812 16 $776 17
$579 18 $462 19 $454 20 $484 21 $633 22 $736 23 $679 24
$509 25 $506 26 $506 27 $437 28 $542 29 $604 30 $578 31
August 2027
Su Mo Tu We Th Fr Sa
$497 1 $454 2 $463 3 $451 4 $468 5 $524 6 $491 7
$414 8 $356 9 $341 10 $345 11 $399 12 $442 13 $403 14
$365 15 $354 16 $313 17 $311 18 $310 19 $335 20 $327 21
$298 22 $259 23 $239 24 $243 25 $272 26 $317 27 $301 28
$282 29 $243 30 $280 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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