House - Rating 5 (7)

Windsor at Westside Resort Home w Pool Hot Tub


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

  • Location: Orlando, Florida
  • Type: House

Location Location

Description Description
Your dream group getaway starts here! This spacious 8-bedroom, 6-bathroom home sleeps up to 16 guests and delivers fun at every turn — with a private pool, bubbling hot tub, game room, and even a home theater. Located in the sought-after Windsor at Westside Resort, you’ll enjoy luxury living, resort perks, and a prime location just minutes from Disney and Orlando’s top attractions.

Poolside Paradise:
• Private screened-in patio with swimming pool & jacuzzi-style spa
• No rear-facing neighbors for added peace and privacy
• Sun loungers for soaking up the rays
• Covered outdoor dining area with BBQ grill — perfect for alfresco meals

Game On & Movie Nights:
• Garage-turned-games room with pool table, foosball & board games
• Private home theater with large projector screen & cozy seating
• High-speed WiFi + Smart TVs with cable for all your streaming needs

Cook, Dine & Chill:
• Fully equipped kitchen with high-end appliances & oversized island
• Indoor dining table for 10 + island seating & outdoor dining area
• Open-concept living space with plush seating and a large Smart TV
• In-home laundry machines and central A/C for ultimate convenience

8 Bedrooms / 6 Bathrooms:
With four ensuite bathrooms and thoughtful bedroom layouts, everyone in your group can enjoy comfort and privacy.

Bedroom Breakdown:

First Floor
• Bedroom 1: King bed | Private ensuite bath (ideal for guests avoiding stairs)

Second Floor
• Bedroom 2: King bed | Ensuite
• Bedroom 3: Queen bed | Shared bath
• Bedroom 4: 2 Full beds | Shared bath
• Bedroom 5: King bed | Ensuite
• Bedroom 6: 2 Twin beds | Shared bath
• Bedroom 7: Queen bed | Shared bath
• Bedroom 8: King bed | Ensuite

Windsor at Westside Resort Amenities:
• 24/7 gated entrance with security guard
• Massive resort-style heated pool with shallow-entry access
• Lazy river, kids’ splash zone & water slide
• Outdoor hot tub & sundeck with loungers
• Tiki bar (TuCasa) with cocktails and snacks
• Full-service clubhouse with restaurant & lounge
• Fitness center, tennis & basketball courts
• Playground, arcade & sundries shop

Whether you're floating in the lazy river, grabbing a cocktail poolside, or taking a break in the private theater, this home has something for everyone. Plus, you're just a short drive to Disney, Universal, shopping, dining, and more.

Extras & Essentials:
• Free driveway parking + additional guest parking at the clubhouse
• Pet-friendly — bring your furry companions along!
• Complimentary resort access for all registered guests

Why Stay With Us?
We make family vacations easy and unforgettable. From stylish interiors to resort-level entertainment, this home is designed for comfort, connection, and fun.

Book your Orlando adventure today!

• 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!
• Please note that washcloths are not provided—kindly bring your own for your stay.
• The fridge ice maker is currently unavailable, but a separate ice maker is available on the kitchen counter for your use.

Pet Friendly:
• Pets are welcome at our property. A maximum of two pets under 60 lbs. is permitted. A pet fee of $139 per pet applies and will be collected after booking.

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 $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.
• Rent a Pack 'n play for $39 (one-time fee)
• Rent a highchair for $29 (one-time fee)
• We offer 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
13 14 $150 15 $150 16 $150 17 $250 18 19
20 21 22 23 24 25 $250 26
$135 27 $135 28 $135 29 $135 30      
October 2026
Su Mo Tu We Th Fr Sa
        $135 1 2 3
4 5 $135 6 $137 7 $135 8 $250 9 $250 10
$156 11 $150 12 $150 13 $164 14 $172 15 $250 16 $250 17
$150 18 $150 19 $150 20 $150 21 $159 22 23 24
25 $150 26 $150 27 $150 28 $156 29 $250 30 $250 31
November 2026
Su Mo Tu We Th Fr Sa
$150 1 2 3 4 5 6 7
8 $150 9 $193 10 $195 11 $203 12 $250 13 $250 14
$208 15 $170 16 $179 17 $150 18 $182 19 $326 20 $359 21
$344 22 $372 23 $386 24 $672 25 $685 26 $666 27 $580 28
$226 29 30          
December 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 $150 7 $150 8 $162 9 $195 10 $250 11 $250 12
$183 13 $175 14 $152 15 $174 16 $212 17 $359 18 $538 19
$814 20 $857 21 $851 22 23 24 25 26
27 28 29 $747 30 $748 31    
January 2027
Su Mo Tu We Th Fr Sa
          $727 1 $691 2
$338 3 $233 4 $223 5 $217 6 $175 7 $253 8 $250 9
$169 10 $150 11 $150 12 $150 13 $158 14 $250 15 $261 16
$255 17 $157 18 $150 19 $150 20 $169 21 $250 22 $250 23
24 25 26 27 28 29 30
31            
February 2027
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 $192 8 $195 9 $205 10 $233 11 $349 12 $412 13
$408 14 $270 15 $234 16 $245 17 $287 18 $285 19 20
21 22 23 24 25 26 $250 27
$202 28            
March 2027
Su Mo Tu We Th Fr Sa
  $182 1 $181 2 $230 3 $211 4 $294 5 $297 6
$282 7 $299 8 $306 9 $252 10 $283 11 $407 12 $413 13
$403 14 $404 15 $396 16 $405 17 $413 18 $441 19 $460 20
$465 21 $354 22 $293 23 $306 24 $416 25 $588 26 $588 27
$588 28 $526 29 $560 30 $560 31      
April 2027
Su Mo Tu We Th Fr Sa
        $550 1 $506 2 $498 3
$457 4 $292 5 $320 6 $375 7 $424 8 $410 9 $331 10
$458 11 $265 12 $268 13 $273 14 $289 15 $365 16 $456 17
$478 18 $564 19 $558 20 $588 21 $588 22 $604 23 $620 24
$608 25 $558 26 $549 27 $562 28 $546 29 $535 30  
May 2027
Su Mo Tu We Th Fr Sa
            $287 1
$260 2 $242 3 $242 4 $221 5 $221 6 $250 7 $250 8
$221 9 $221 10 $238 11 $238 12 $238 13 $250 14 $250 15
$221 16 $221 17 $246 18 $323 19 $328 20 $332 21 $261 22
$258 23 $255 24 $276 25 $276 26 $276 27 $406 28 $403 29
$369 30 $288 31          
June 2027
Su Mo Tu We Th Fr Sa
    $288 1 $288 2 $288 3 $302 4 $296 5
$332 6 $332 7 $360 8 $396 9 $392 10 $410 11 $440 12
$400 13 $425 14 $397 15 $407 16 $429 17 $461 18 $445 19
$430 20 $412 21 $440 22 $413 23 $419 24 $475 25 $431 26
$447 27 $465 28 $478 29 $488 30      
July 2027
Su Mo Tu We Th Fr Sa
        $510 1 $637 2 $642 3
$639 4 $472 5 $463 6 $459 7 $441 8 $530 9 $469 10
$310 11 $308 12 $307 13 $301 14 $404 15 $504 16 $483 17
$377 18 $360 19 $281 20 $287 21 $386 22 $463 23 $427 24
$344 25 $340 26 $253 27 $293 28 $364 29 $373 30 $370 31
August 2027
Su Mo Tu We Th Fr Sa
$309 1 $427 2 $285 3 $349 4 $349 5 $317 6 $308 7
$252 8 $220 9 $209 10 $217 11 $244 12 $271 13 $255 14
$223 15 $195 16 $201 17 $198 18 $197 19 $250 20 $250 21
$180 22 $163 23 $163 24 $163 25 $166 26 $250 27 $250 28
$189 29 $189 30 $189 31        
Swipe Swipe for Availability


Amenities 63 Amenities
  • 24-hour check-in
  • Air conditioning
  • Baking sheet
  • Barbecue utensils
  • Bathtub
  • BBQ grill
  • Bed linens
  • Cable TV
  • Carbon monoxide detector
  • Cleaning Disinfection
  • Coffee maker
  • Cookware
  • Dishes and silverware
  • Downtown
  • Dryer
  • Dvd player
  • Enhanced cleaning practices
  • Essentials
  • Family/kid friendly
  • Fire extinguisher
  • Flat smooth pathway to front door
  • Free parking on premises
  • Garden or backyard
  • Gym
  • Hair dryer
  • Hangers
  • Heating
  • High touch surfaces disinfected
  • Hot tub
  • Hot water
  • Indoor pool
  • Internet
  • Kettle
  • Kitchen
  • Long term stays allowed
  • Microwave
  • Oven
  • Patio or balcony
  • Pets allowed
  • Private entrance
  • Private living room
  • 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
  • Trash can
  • TV
  • Washer
  • Wireless Internet
Resorts
  • WindsorWestside
  • Communal pool
  • Game room
  • Outdoor pool
  • Private pool
  • Swimming pool

Reviews Rating 5 (7) Reviews
Rating 5
Our stay was wonderful! The space was clean, well-maintained, and exactly as described. The host went above and beyond to accommodate us and ensure we had everything we needed. We would happily stay here again!
Anonymous - Posted: 12/6/2025
Thank you for your kind words, Tram! It brings us so much joy to hear that you had a wonderful stay. We take great pride in maintaining a clean and welcoming space, and it’s fantastic to know that our efforts made a difference for you. Your satisfaction is our top priority, and we’re always here to ensure our guests have everything they need for a comfortable experience. We would love to host you again in the future!
Upstay staff
Posted: 12/8/2025
Rating 5
Great place to stay for a week while on a golf trip. Would stay here again!
Anonymous - Posted: 10/27/2025
We're so glad to hear that you enjoyed your stay with us during your golf trip! It’s wonderful to know that our place met your needs and provided a comfortable base for your adventures. We would love to welcome you back anytime for another round of golf or just to relax. Safe travels until we see you again!
Upstay staff
Posted: 10/28/2025
Rating 5
This was an amazing home, pictures do not do it justice! The host was very communicative and helpful. We really enjoyed our stay thank you for having us!
Anonymous - Posted: 6/13/2025
Thank you so much for the kind words! We’re thrilled to hear the home exceeded your expectations and that you had such a great experience. It was a pleasure hosting you, and we’d love to welcome you back anytime!
Upstay staff
Posted: 8/6/2025
Rating 5
Place was Perfect, beautiful home and great for big family vacations, definitely will recommend this place to family and friends.
Anonymous - Posted: 6/1/2025
Thank you for the wonderful feedback! We're so happy to hear the home was perfect for your family vacation. It means a lot that you'd recommend us to others—we truly appreciate it and would love to host you again in the future!
Upstay staff
Posted: 8/6/2025
Rating 5
Very nice
Anonymous - Posted: 5/25/2025
Thank you for your feedback! We’re glad you enjoyed your stay and would love to host you again anytime.
Upstay staff
Posted: 9/25/2025
Rating 5
Una maravillosa estancia la pasamos excelente
Anonymous - Posted: 5/15/2025
Muchas gracias por tus palabras. Nos alegra muchísimo que hayan tenido una estancia maravillosa y lo hayan pasado excelente. ¡Será un placer recibirlos nuevamente en el futuro!
Upstay staff
Posted: 9/25/2025
Rating 5
Planned a last minute 14th birthday weekend for my daughter and it turned out to be everything imagined . Thank you so much to our host Ryan and Carissa for an amazing stay . The home was absolutely beautiful and clean , the communication was on point , Ryan even accommodated my late check out request which I’m greatful. I will definitely be booking this home again in the near future!
Anonymous - Posted: 4/28/2025
Thank you so much for your wonderful review! We’re thrilled that your daughter’s birthday weekend turned out exactly as imagined and that the home, cleanliness, and communication all met your expectations. It was our pleasure to accommodate your late check-out request, and we’d be delighted to host you again anytime.
Upstay staff
Posted: 9/25/2025
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