House - Rating 5 (22)

Family Friendly Villa w Pool Hot Tub Game Room


Bedroom 6 bedrooms
Bathroom 4 baths
Guests 12 guests
Pets Not Allowed Pets Not Allowed

  • Location: Orlando, Florida
  • Type: House

Location Location

Description Description
Family-Friendly 6BR Home w/ Pool, Hot Tub & Game Room

Spacious and stylish, this 6-bedroom, 4.5-bath retreat is perfect for group getaways! Enjoy two master suites (one on each floor), a private pool & hot tub, and a Mario-themed game room. Whip up meals in the fully equipped kitchen, relax across two living areas, and dine indoors or al fresco.

Home Highlights:
• 2 Ensuite King Bedrooms – Great for multi-gen stays
• Private Pool & Hot Tub (heating optional)
• Game Room with Foosball, Billiards & Mario Fun
• Smart TVs & blackout curtains in all bedrooms
• High-speed WiFi + central A/C
• Free on-site parking

Traveling with kids? We've got you covered with a high chair, Pack ‘n Play, stroller, baby dinnerware, toys & more—at no extra cost!

Access to Windsor at Westside Resort:
• Water park, lazy river, & waterslides
• Tiki bar, arcade, fitness center & more

Unbeatable Location:
• Just 15 mins to Disney, 25 to SeaWorld, 30 to Universal.

Book now for the ultimate Florida family getaway!

• 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!
• The resort's policy limits a maximum of 4 vehicles for this residence.
• The air hockey table is temporarily unavailable and will be fixed soon. Thank you for your understanding.
• Please note that washcloths are not provided—kindly bring your own for your stay.

Additional Services:
• 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!
• Pool and hot tub heating are available upon request and are not included in the booking price. The fee is $35/night per service or $59/night for both, with a 2-night minimum. At least 24 hours’ notice is required if you would like to add this service.
• 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
April 2026
Su Mo Tu We Th Fr Sa
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5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 $126 27 28 $142 29 $152 30    
May 2026
Su Mo Tu We Th Fr Sa
          $200 1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 $224 16
$188 17 18 19 20 21 $357 22 23
24 25 26 27 $169 28 $286 29 $292 30
$188 31            
June 2026
Su Mo Tu We Th Fr Sa
  $185 1 $189 2 $195 3 $202 4 $276 5 6
7 8 9 10 11 12 $310 13
$236 14 $225 15 $228 16 17 18 19 20
$363 21 $332 22 $334 23 $336 24 $361 25 $460 26 $429 27
$380 28 $378 29 $368 30        
July 2026
Su Mo Tu We Th Fr Sa
      $389 1 $671 2 $685 3 $679 4
$478 5 $433 6 $389 7 $418 8 $452 9 $556 10 $478 11
$378 12 $422 13 $395 14 $387 15 $381 16 $447 17 $446 18
$341 19 $316 20 $303 21 $383 22 $387 23 $488 24 $487 25
$364 26 $294 27 $288 28 $317 29 $372 30 $465 31  
August 2026
Su Mo Tu We Th Fr Sa
            $456 1
$334 2 $364 3 $331 4 $340 5 $349 6 $376 7 $365 8
$303 9 $315 10 $245 11 $271 12 $289 13 $308 14 $300 15
$239 16 $198 17 18 19 20 21 22
23 24 25 26 27 28 $202 29
$156 30 $150 31          
September 2026
Su Mo Tu We Th Fr Sa
    $145 1 $151 2 $177 3 $303 4 $312 5
$305 6 $174 7 $171 8 $175 9 $202 10 $223 11 12
13 14 15 16 17 18 $208 19
$151 20 21 22 23 $193 24 $208 25 $210 26
$205 27 $193 28 $183 29 $180 30      
October 2026
Su Mo Tu We Th Fr Sa
        $190 1 2 3
4 $176 5 $170 6 $173 7 $185 8 $257 9 10
11 12 $176 13 $172 14 15 16 17
18 19 20 21 $164 22 $233 23 24
25 26 27 28 29 30 $260 31
November 2026
Su Mo Tu We Th Fr Sa
$199 1 $202 2 $203 3 $200 4 $198 5 6 7
8 9 10 11 12 $267 13 $275 14
$224 15 $186 16 $188 17 $184 18 $225 19 $289 20 $377 21
$357 22 $393 23 $412 24 $591 25 $606 26 $488 27 $462 28
$223 29 $192 30          
December 2026
Su Mo Tu We Th Fr Sa
    $205 1 $213 2 3 4 5
6 $186 7 $187 8 $187 9 $224 10 $257 11 $260 12
$229 13 $234 14 $239 15 $238 16 $250 17 $374 18 $507 19
$663 20 $714 21 $715 22 $832 23 $854 24 $862 25 $884 26
$719 27 $719 28 $718 29 $850 30 $849 31    
January 2027
Su Mo Tu We Th Fr Sa
          $753 1 $720 2
$413 3 $366 4 $341 5 $341 6 $341 7 $269 8 $301 9
$263 10 $224 11 $200 12 $200 13 $227 14 $287 15 $315 16
$308 17 $222 18 $189 19 $192 20 $204 21 $226 22 $226 23
$208 24 $201 25 $186 26 $190 27 $199 28 $227 29 $220 30
31            
February 2027
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $332 6
$229 7 $236 8 $249 9 $249 10 $258 11 $348 12 $386 13
$385 14 $261 15 $251 16 $254 17 $277 18 $302 19 $272 20
$252 21 $248 22 $246 23 $259 24 $275 25 $278 26 $267 27
$216 28            
March 2027
Su Mo Tu We Th Fr Sa
  $211 1 $208 2 $217 3 $230 4 $304 5 $297 6
$287 7 $280 8 $300 9 $302 10 $330 11 $373 12 $387 13
$378 14 $304 15 $420 16 $421 17 $421 18 $415 19 $464 20
$519 21 $526 22 $518 23 $511 24 $512 25 $876 26 $859 27
$741 28 $501 29 $495 30 $502 31      
Swipe Swipe for Availability


Amenities 53 Amenities
  • Air conditioning
  • Baking sheet
  • Bathtub
  • BBQ grill
  • Bed linens
  • Carbon monoxide detector
  • Cleaning Disinfection
  • Coffee maker
  • Dishes and silverware
  • Dishwasher
  • 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
  • Kitchen
  • Long term stays allowed
  • Microwave
  • Oven
  • Patio or balcony
  • Private entrance
  • Refrigerator
  • Resort
  • Shampoo
  • Shower gel
  • Smoke detector
  • Stove
  • Suitable for children (2-12 years)
  • Suitable for infants (under 2 years)
  • Toaster
  • Towels provided
  • TV
  • Washer
  • Wireless Internet
Resorts
  • WindsorWestside
  • Communal pool
  • Game room
  • In-Home Games Room
  • Nintendo Theme Room
  • Outdoor pool
  • Private pool
  • Swimming pool

Reviews Rating 5 (22) Reviews
Rating 5
Enjoyed our time. Great communication. Thank you.
Anonymous - Posted: 3/4/2026
We're so glad to hear that you enjoyed your time with us! It was a pleasure to communicate with you and ensure your stay was as comfortable as possible. Thank you for choosing Upstay, and we hope to welcome you back in the future!
Upstay staff
Posted: 3/6/2026
Rating 5
Perfect host even with them needing to change my rental at the last minute due to an issue at my other rental
Anonymous - Posted: 3/3/2026
Thank you for your understanding and flexibility during the last-minute change. We always strive to provide our guests with the best experience possible, and we're glad we could accommodate you. It means a lot to us that you appreciated our efforts. We hope you enjoyed your stay in Kissimmee and would love to welcome you back in the future!
Upstay staff
Posted: 3/6/2026
Rating 5
Great stay and plenty of room.
Anonymous - Posted: 2/28/2026
We're so glad to hear that you enjoyed your stay and found the space to be ample for your needs. It’s always our goal to provide a comfortable and spacious environment for our guests. Thank you for choosing Upstay, and we hope to welcome you back for another great experience in Kissimmee!
Upstay staff
Posted: 3/3/2026
Rating 5
Host is very responsive and friendly . Any wrongs were quickly corrected . Would stay with them again . House was nicely laid out with alot of space .
Anonymous - Posted: 2/20/2026
Thank you, Stephanie, for your kind words! We're glad to hear that you found our communication helpful and that we could address any issues promptly. It’s great to know you enjoyed the spacious layout of the house. We would love to welcome you back anytime for another stay!
Upstay staff
Posted: 2/22/2026
Rating 5
Very satisfied with our stay. Would recommend and will look to book if we are back in the area
Anonymous - Posted: 2/14/2026
Thank you for your kind words, Matthew! It’s wonderful to hear that you were satisfied with your stay at Upstay. We always strive to create a welcoming environment for our guests, and knowing that you would recommend us means a lot to us. We’d love to host you again if you find yourselves back in Kissimmee! Safe travels!
Upstay staff
Posted: 2/22/2026
Rating 5
Very responsive and clear instructions throughout booking and stay. Lovely outside area with pool and hot tub and everything needed for a long holiday. Thank you!
Anonymous - Posted: 2/1/2026
Thank you for your kind words, Nichola! We're delighted to hear that you found our communication helpful and that you enjoyed the outdoor space, including the pool and hot tub. It’s great to know that our place met your needs for a long holiday. We hope to welcome you back for another relaxing stay in the future!
Upstay staff
Posted: 2/3/2026
Rating 5
Great host! Attentive and responsive. Location was ideal. House itself was clean and had everything listed in description. Would definitely stay here again.
Anonymous - Posted: 1/29/2026
Thank you, Rebecca! It’s wonderful to hear that you enjoyed your stay with us. We take pride in providing a clean and well-equipped space, and we’re glad it met your expectations. Knowing that our location worked well for you makes us happy, too. We would love to welcome you back anytime!
Upstay staff
Posted: 1/30/2026
Rating 5
Great place to stay in a private neighborhood! Close enough to Disney parks as well. Highly recommend using the pool heater during the winter months. It worked great for us!
Anonymous - Posted: 1/11/2026
Rating 5
This Host was great!!! We made a same day reservation because another Airbnb was terrible. He let us check in early to help us get started on our vacation. There were a few issues and he got them corrected immediately. He was a fast responding proactive host. Absolutely loved his home and the experience. 5stars across the board💫💫💫💫💫
Anonymous - Posted: 12/27/2025
Thank you, Marcus, for your wonderful review! We're so glad we could accommodate your last-minute reservation and help kick off your vacation on the right foot. It’s great to hear that you enjoyed your stay and appreciated our quick responses to any issues. We strive to create a welcoming environment, and knowing you loved our home means a lot to us. Your kind words and five-star rating truly motivate us to keep providing the best experience possible. We hope to welcome you back for another fantastic stay in the future!
Upstay staff
Posted: 12/30/2025
Rating 5
My family had an amazing time during our stay. The home is just as described and location was perfect. The home is walking distance to the water park entrance. The staff at the facility was so kind and friendly. The views are beautiful and we had a ball in the game room and pool. The location is also close to many attractions 10/10
Anonymous - Posted: 12/19/2025
Thank you, Donetta, for your wonderful review! It brings us so much joy to hear that your family had an amazing time at our home. We take pride in providing an accurate description and ensuring our guests have everything they need for a memorable stay. The proximity to the water park and other attractions is definitely a highlight, and we're glad you enjoyed the beautiful views and had fun in the game room and pool. Our team works hard to create a welcoming atmosphere, and your kind words about our staff mean a lot to us. We hope to welcome you back for another fantastic getaway in the future!
Upstay staff
Posted: 12/22/2025
Rating 5
Our host was absolutely amazing. Our flight got in early and they allowed us to check in early and our flight was delayed and they let us stay late! I would defiantly recommend this host to to other guest. We also enjoyed the pool and the water park
Anonymous - Posted: 12/8/2025
Thank you for your wonderful review! It was our pleasure to accommodate your early check-in and late check-out. We always strive to make our guests' experiences as smooth and enjoyable as possible. We're glad to hear you loved the pool and the water park—those are definitely highlights of staying with us. Your recommendation means a lot to us, and we hope to welcome you back for another fantastic stay in the future!
Upstay staff
Posted: 12/10/2025
Rating 5
Clean and simple exactly what my family needed for a short stay!
Anonymous - Posted: 10/7/2025
We’re so glad to hear that our place was a perfect fit for your family’s short stay! It’s always our goal to provide a clean and simple space where guests can feel at home. Thank you for choosing Upstay, and we hope to welcome you back in the future!
Upstay staff
Posted: 10/7/2025
Rating 5
The stay was nice, there was so much to do!
Anonymous - Posted: 7/31/2025
Thank you for your review Keyana! I'm so glad you had a nice stay and enjoyed all the activities in the area. We hope to welcome you back soon!
Upstay staff
Posted: 8/5/2025
Rating 5
We fell in love with this place. This home was nothing short of amazing! Very spacious and comfortable. We plan on coming back and renting this AIRBNB again. Also, the host was very responsive.
Anonymous - Posted: 7/23/2025
Thank you for the amazing feedback! We’re so glad you fell in love with the home and found it spacious and comfortable. It’s wonderful to hear you plan on returning—we’d be absolutely delighted to host you again. See you next time!
Upstay staff
Posted: 8/6/2025
Rating 5
We enjoyed staying at the house with the family.
Anonymous - Posted: 7/12/2025
Thank you so much for your review Samir! We're happy to hear you and your family enjoyed your stay with us. It was a pleasure hosting you, and we'd love to welcome you back anytime!
Upstay staff
Posted: 7/22/2025
Rating 5
We really enjoyed our stay with Upstay! Our kids loved the pool and game room. The community pool was relaxing and we all loved the lazy river. They were very responsive with any questions I had. We would stay with them again.
Anonymous - Posted: 6/27/2025
Thank you for your lovely review! We're so happy to hear your family had a great time, especially enjoying the pool, game room, and the lazy river. It’s great to know our team was helpful and responsive throughout your stay. We’d be delighted to host you again in the future!
Upstay staff
Posted: 8/6/2025
Rating 5
Loved this place! Very nice and cozy! Host was very responsive and met all of our concerns in a timely manner! Would highly recommend!
Anonymous - Posted: 6/22/2025
Thank you so much for the kind words! We're thrilled to hear you loved the place and felt comfortable and well taken care of. Your recommendation means a lot to us, and we’d be happy to host you again anytime!
Upstay staff
Posted: 8/6/2025
Rating 5
This place was so beautiful and me and my family had a ball. We enjoyed having free usage of the community pool and lazy river and our very own private pool. I would recommend replacing better cooking equipment and a bigger coffee machine because most of the pans were worn out. Also the iron should be replaced right along with having wash clothes. Other than that I have no complaints. My host was friendly and he responded in a timely manner. I will be booking again next year 🥰
Anonymous - Posted: 6/19/2025
Thank you for your kind feedback—we’re so glad to hear you and your family had such a wonderful time enjoying both the private pool and the community amenities! We appreciate your suggestions and wanted to share that we’ve already replaced the pans in the kitchen for future guests. The iron is kept inside the closet for easy access, and we’ll be sure to make that clearer going forward. We’re thrilled that you enjoyed your stay overall and that our timely communication made a difference. We’d be delighted to host you and your family again next year! 🥰
Upstay staff
Posted: 9/5/2025
Rating 5
Great place absolutely love it will recommend and hopefully can stay again
Anonymous - Posted: 4/27/2025
Thank you so much for your kind words, Jentry! We’re thrilled you loved the place and truly appreciate your recommendation. We’d be delighted to host you again whenever you’re back in the area.
Upstay staff
Posted: 9/25/2025
Rating 5
This is a 5 star place! Our stay at this Orlando home was perfect for our multi-family trip, including grandparents! The two master suites—one on each level—gave everyone their own space, and the other 2 king-sized bedrooms were roomy enough for our toddler to snuggle with us. Super clean! The kids adored the Disney-themed bedroom and the Mario game room with air hockey, skee ball, foosball, and 2 gaming consoles. The private pool was already warm, so no heating was needed, and the hot tub heating was free—a rare and much-appreciated perk! pool noodles, Blackout curtains, night lights, step stools, a stroller made things super convenient, especially for little ones. While we took the kids to Disney, the grandparents enjoyed the lazy river, the cocktail tiki bar and fitness center. I wanted toddler friendly dinner ware and the host delivered it! We didn’t use the BBQ, but it was nice to have the option. Thoughtful touches made this a true 5-star experience. We’ll definitely be back!
Anonymous - Posted: 3/3/2025
Thank you for sharing you experience, Peter! That sounds like an incredible stay! We’re so happy to hear that the home was a perfect fit for your multi-family trip and that everyone—from the little ones to the grandparents—had a fantastic time. It’s wonderful that the thoughtful touches, fun amenities, and warm pool made your experience even more special. We’d love to welcome you back for another amazing stay!
Upstay staff
Posted: 3/21/2025
Rating 5
We all very much enjoyed our stay ! The ONLY downfall was the jacuzzi not working the first two days but after being in contact about it our host was able to fix and accommodate me which made it better! Also, the grill is also available for a $70 fee which is not listed I was under the impression it was for use like the pool.. I would also buy trash bags as there were only 2 for our week stay of 7 people .. the house is absolutely beautiful! Spacious kitchen and rooms. Super comfy beds ! And such a cool game room !! We would deff recommend staying here and would love to return !
Anonymous - Posted: 12/15/2024
Hi Chelsea, we're so glad you enjoyed your stay and that the home met your expectations! We appreciate your patience with the jacuzzi and your feedback on the grill fee and trash bags. The grill fee is clearly stated in our listing description, along with other extra amenities we offer. Additional trash bags are available upon request, and we wish you had let us know so we could have sent someone to deliver them. We’d love to host you again and hope to see you back soon!
Upstay staff
Posted: 2/21/2025
Rating 5
It was perfect
Demarcus D. - Posted:
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