House - Rating 5 (8)

Resort Home w Private Pool Hot Tub Games Movies


Bedroom 8 bedrooms
Bathroom 6 baths
Guests 16 guests
Pets Allowed Pets Allowed

  • Location: Kissimmee, Florida
  • Type: House

Location Location

Description Description
Looking for a fantastic Orlando vacation rental that will house the whole crew? Needing a place with loads of indoor and outdoor entertainment for all ages? Hoping to find somewhere that's close to Disney and other Orlando attractions? Well look no further!

With 8 bedrooms and room for 16 of your nearest and dearest, this house is meant to be shared with those who mean most and even can fit the friends of friends who you don’t actually know that well.

Let's kick things off with the amazing back deck. Picture this: a lake-facing private screened-in patio, featuring a sparkling swimming pool and spill-over jacuzzi hot tub. We've even got comfy lounge chairs and sun recliners for your total relaxation. There's an inflatable slide for the little ones, and removable safety fence when you're not able to keep an eye on them. Plus, there's a poolside dining space, and BBQ grill, perfect for a quick meal after a swim.

We've taken the garage, and turned it into your own personal arcade games room! Packed full of favourites like billiard and foosball, plus a big screen TV and comfy furniture. It's sure to be the fav hang out spot when you've had too much sun for the day.

Now, let's talk about the kitchen. It's an absolute masterpiece! You'll find top-of-the-line stainless steel appliances, granite countertops, and plenty of cupboard space for everyone's snacks. Whether you're a culinary genius or a fan of takeout, we've got you covered.

Need some space to chill? Our open-concept living area is designed with plenty of room to spread out and relax. The smart TV's come with complimentary cable, Netflix, and high speed internet.

And if that's not enough, just wait until you see the second floor. We've got a full-blown movie theater with plush modular seating, a massive projection screen, and cool mood lighting. Movie night, anyone?

The home is located at Windsor at Westside Resort, a community of luxury Orlando vacation rentals just 8 miles from Disney World with its own 10,000 sqft resort style clubhouse with lazy river, zero entry pool, fitness center, tiki bar and much more. Our guests get full access to the clubhouse and all of its amenities.

So what are you waiting for? Book your dream vacation today!

You'll love the indoor space:
• 8 bedrooms (11 beds in total)
• 6 Bathrooms including 4 ensuite
• Theater loft with plenty of seating and a 135" smart projector
• Private games room (pool table, foosball table, and arcade console)
• Fully equipped kitchen with high end appliances
• Large dining table (seating for up to 10) / Kitchen island (seating for up to 4)
• Smart TV's with complimentary Cable, Netflix, plus high speed internet
• Central air conditioning
• Laundry room in house
• Private pool and hot tub (removable safety fence included)
• Spacious patio with furniture/loungers
• Outdoor dining (plenty of seating)
• BBQ Grill
• Free onsite parking
• Complimentary resort access

Windsor at Westside Resort Features:
• 24hr gated entrance with security guard
• 10,000 square foot clubhouse with restaurant, bar & lounge
• State-of-the-art fitness center
• Lazy river for floating
• Zero entry resort-style pool
• Waterslide
• Outdoor jacuzzi hot tub
• Tiki bar
• Video arcade
• Sundries shop
• Volleyball court
• Multi-purpose sports courts

Availability Calendar Availability Calendar
Available
Unavailable
Check-In
Check-Out
February 2024
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 23 24
25 26 $165 27 $169 28 29    
March 2024
Su Mo Tu We Th Fr Sa
          1 2
$232 3 $245 4 $249 5 $254 6 $259 7 8 9
$280 10 $285 11 $343 12 $361 13 $380 14 $441 15 $405 16
$285 17 $273 18 $278 19 $301 20 $379 21 $541 22 $590 23
$584 24 25 26 27 28 $778 29 $795 30
$761 31            
April 2024
Su Mo Tu We Th Fr Sa
  $684 1 $603 2 $597 3 $626 4 $672 5 $524 6
$513 7 $570 8 $570 9 $570 10 $542 11 $542 12 $542 13
$343 14 $329 15 $351 16 $468 17 $468 18 $606 19 $606 20
$570 21 $597 22 $625 23 $625 24 $625 25 $654 26 $688 27
$557 28 $557 29 $557 30        
May 2024
Su Mo Tu We Th Fr Sa
      1 2 3 4
5 6 7 $258 8 $278 9 $371 10 $364 11
$306 12 $253 13 $239 14 $228 15 $258 16 $368 17 $416 18
$346 19 $273 20 $221 21 $218 22 $256 23 $542 24 25
26 27 28 29 30 31  
June 2024
Su Mo Tu We Th Fr Sa
            $410 1
$408 2 $403 3 $399 4 $414 5 $424 6 $407 7 $366 8
9 10 11 12 13 $481 14 $616 15
$640 16 $517 17 $550 18 $544 19 $558 20 $749 21 $560 22
$588 23 $464 24 $528 25 $466 26 $538 27 $556 28 $603 29
$465 30            
July 2024
Su Mo Tu We Th Fr Sa
  $503 1 $472 2 $700 3 $791 4 $807 5 $753 6
$569 7 $547 8 $511 9 $517 10 $557 11 $570 12 $567 13
$446 14 15 16 17 18 19 $521 20
$553 21 $556 22 $531 23 $662 24 $483 25 $517 26 $490 27
$383 28 $375 29 $354 30 $347 31      
August 2024
Su Mo Tu We Th Fr Sa
        $381 1 $411 2 $396 3
$372 4 $388 5 $367 6 $372 7 $336 8 $365 9 $365 10
$348 11 $370 12 $333 13 $403 14 $427 15 $387 16 $473 17
$461 18 $405 19 $423 20 $401 21 $396 22 $420 23 $413 24
$336 25 $283 26 $263 27 $251 28 $283 29 $404 30 $404 31
September 2024
Su Mo Tu We Th Fr Sa
$400 1 $419 2 $192 3 $188 4 $242 5 $326 6 $314 7
$255 8 $199 9 $186 10 $191 11 $246 12 $294 13 14
15 16 17 18 19 20 $302 21
$237 22 23 24 25 26 27 28
29 30          
October 2024
Su Mo Tu We Th Fr Sa
    1 2 3 $278 4 $261 5
$229 6 $251 7 $267 8 $326 9 $350 10 $338 11 12
13 14 15 16 17 18 $314 19
$333 20 $242 21 $235 22 $235 23 $309 24 $321 25 $345 26
$275 27 $237 28 $246 29 $320 30 $320 31    
November 2024
Su Mo Tu We Th Fr Sa
          $333 1 $330 2
$272 3 $272 4 $211 5 6 7 8 9
$397 10 $397 11 $294 12 $295 13 $316 14 $353 15 $338 16
$325 17 $431 18 $288 19 $388 20 $462 21 $536 22 $556 23
$401 24 $494 25 $513 26 $920 27 $912 28 $911 29 $750 30
December 2024
Su Mo Tu We Th Fr Sa
$297 1 $228 2 $229 3 $232 4 $387 5 $376 6 $326 7
$262 8 $236 9 $271 10 $299 11 $299 12 $354 13 $415 14
$633 15 $635 16 $605 17 $591 18 $644 19 $1094 20 $1141 21
$1194 22 $1372 23 $1393 24 $1419 25 $1305 26 $1205 27 $1222 28
$1176 29 $1237 30 $1152 31        
January 2025
Su Mo Tu We Th Fr Sa
      $957 1 $859 2 $661 3 $506 4
$414 5 $346 6 $315 7 $297 8 $281 9 $323 10 $302 11
$258 12 $219 13 $215 14 $226 15 $244 16 $288 17 $302 18
$293 19 $256 20 $306 21 $276 22 $274 23 $307 24 $309 25
$269 26 $255 27 $251 28 $264 29 $279 30 $316 31  
Swipe Swipe for Availability


Amenities 68 Amenities
  • Air conditioning
  • Bathtub
  • BBQ grill
  • Bed linens
  • Cable TV
  • Carbon monoxide detector
  • Cleaning Disinfection
  • Coffee maker
  • Cookware
  • Dishes and silverware
  • Dishwasher
  • Downtown
  • Dryer
  • Enhanced cleaning practices
  • Essentials
  • Extra pillows and blankets
  • Family/kid friendly
  • Fire extinguisher
  • Flat smooth pathway to front door
  • Free parking on premises
  • Garden or backyard
  • Grab-rails for shower and toilet
  • Gym
  • Hair dryer
  • Hangers
  • Heating
  • High touch surfaces disinfected
  • Hot tub
  • Hot water
  • Internet
  • Iron
  • Kettle
  • Kitchen
  • Lake
  • Lake access
  • Lake Front
  • Laptop friendly workspace
  • Microwave
  • Oven
  • Path to entrance lit at night
  • Patio or balcony
  • Pets allowed
  • Private entrance
  • Refrigerator
  • Resort
  • Room-darkening shades
  • Shampoo
  • Smoke detector
  • Step-free access
  • Stove
  • Suitable for children (2-12 years)
  • Suitable for infants (under 2 years)
  • Toaster
  • Towels provided
  • Town
  • TV
  • Washer
  • Water View
  • Waterfront
  • Wide clearance to bed
  • Wide clearance to shower and toilet
  • Wide doorway
  • Wide hallway clearance
  • Wireless Internet
  • Communal pool
  • Outdoor pool
  • Private pool
  • Swimming pool

Reviews Rating 5 (8) Reviews
Rating 5
This was probably my top two places to stay! So clean and had everything you could ever imagine to have a fun and relaxing stay. The beds were amazing, the kitchen was fully loaded, it was so clean, safe and peaceful area, I want to stay here again! It’s not often that the home is actually as beautiful as they say it is. I’m so grateful ??
Anonymous - Posted: 2/9/2024
Thank you for your wonderful review, Dana! I'm glad you enjoyed your stay and found the place clean, well-equipped, and peaceful. You're always welcome back, and I look forward to hosting you again!
Upstay staff
Posted: 2/11/2024
Rating 5
Hosts were very responsive reaching out to us prior to our trip, once we checked in, any questions we had, and preparation for departure. Very friendly and professional. The house was larger than we expected. Plenty of room for a large family. You can park up to 6 vehicles, 3 in the drive way in front of the house, and 3 along the curb as long as the vehicle is not on the grass. So, the house and parking accomomdated our 3 vehicles. We used the heated hot tub and it was well worth the extra cost. We cooked meals in the kitchen, DoorDashed a couple, and hit several restaurants in the local area. The location is great, close enough to everything Orlando. Highly recommend and we would stay here again with our large group.
Anonymous - Posted: 1/19/2024
Thank you for the great feedback! We're thrilled that the house, parking, and amenities met your expectations. Your recommendation means a lot, and we'd love to host your group again. If you have any questions or need assistance in the future, feel free to reach out. Looking forward to welcoming you back! ?
Upstay staff
Posted: 1/19/2024
Rating 5
Amazing stay! Thanks for having this beautiful property available
Anonymous - Posted: 12/18/2023
Thank you for your awesome feedback, Robert! It was a pleasure hosting your stay. We hope to host you again in the future. Safe travels, and thank you for choosing our place!
Upstay staff
Posted: 12/19/2023
Rating 5
Es un muy buen sitio para pasar unos dias , reunidos con la Familia ! , nos gusto mucho la zona de billar y el cine!Seguro que volveremos!
Anonymous - Posted: 11/30/2023
Glad to know that you and your family had a great time, Edwin! Happy to have the chance to host your stay. Wishing you all the best on all of your travels!
Upstay staff
Posted: 12/3/2023
Rating 5
We had an awesome time, the home was cozy and very welcoming. I wish the price included the heating of the pool and the hot tub so we could enjoy more. Overall, we had a great time. Mark and Lyndsey were great host. Their home was absolutely beautiful. We cant wait to book with them again in the future.
Anonymous - Posted: 11/25/2023
Thank you for your review! I want to assure you that we have addressed the concerns you raised. Hosting your stay was a pleasure, and I'm grateful for the care you took with my property.
Upstay staff
Posted: 12/10/2023
Rating 5
This is the best place I have ever stayed in. It is huge and for the price it was well worth it. Plenty of rooms and beds. The movie area was amazing as well as the pool, and game room. Perfect place for a large number of guests or just a few!
Anonymous - Posted: 11/17/2023
Thank you for your review! We are happy to hear you have enjoyed your stay. We appreciate you taking the time to rate your experience!
Upstay staff
Posted: 12/5/2023
Rating 5
MY FAMILY AND I HAD A VACATION. THE HOUSE WAS BEAUTIFUL. IT WAS VERY CLEAN. BEDROOMS WERE COMFORTABLE. MY GRANDCHILDREN WERE DISAPPOINTED THAT TV IN THE THEATER ROOM DID NOT WORK. THE OVERALL APPEARANCE WAS EXCELLENT.
Anonymous - Posted: 11/14/2023
Thank you for choosing our property for your family vacation, Jacqueline. We're thrilled to hear that you found the house beautiful and very clean. We apologize for any disappointment regarding the TV in the theater room and appreciate your understanding. Please know that it is now in working order as per my team. Your feedback is invaluable, and we're pleased to know that the overall appearance of the house met your expectations. We hope to have the opportunity to welcome you and your family again, ensuring a seamless and enjoyable stay.
Upstay staff
Posted: 12/4/2023
Rating 5
Definitely recommended
Anonymous - Posted: 1/31/2022
Hello Marcones, Thank you for your review! We are happy to hear you have enjoyed your stay. As hosts, we appreciate you taking the time in rating your experience. We look forward to hosting you again in the future!
Upstay staff
Posted: 2/13/2022
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