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
October 2026
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 $120 26 $120 27 $120 28 $120 29 $250 30 $250 31
November 2026
Su Mo Tu We Th Fr Sa
$120 1 $120 2 $120 3 $120 4 $120 5 $225 6 $225 7
$124 8 $120 9 $120 10 $122 11 $132 12 $250 13 $250 14
$135 15 $135 16 $135 17 $135 18 $135 19 $263 20 $296 21
$224 22 $214 23 24 25 26 27 $521 28
$180 29 30          
December 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 $135 7 $135 8 $138 9 $164 10 $250 11 $250 12
$155 13 14 15 16 17 $303 18 $475 19
$751 20 $831 21 $845 22 23 24 25 26
27 28 29 $862 30 $863 31    
January 2027
Su Mo Tu We Th Fr Sa
          $644 1 $629 2
$295 3 $239 4 $197 5 $199 6 $165 7 $250 8 $250 9
$166 10 $150 11 12 13 14 $250 15 $250 16
$232 17 $154 18 $150 19 $150 20 $165 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 $194 8 $209 9 $207 10 $231 11 $315 12 $363 13
$351 14 $256 15 $229 16 $236 17 $265 18 $255 19 $250 20
$192 21 $200 22 $201 23 $206 24 $229 25 $250 26 $250 27
$216 28            
March 2027
Su Mo Tu We Th Fr Sa
  $216 1 $181 2 $233 3 $211 4 $290 5 $305 6
$319 7 $320 8 $312 9 $251 10 $335 11 $414 12 $411 13
$393 14 $388 15 $396 16 $410 17 $407 18 $441 19 $456 20
$449 21 $347 22 $296 23 $304 24 $445 25 $478 26 $520 27
$504 28 $487 29 $508 30 $500 31      
April 2027
Su Mo Tu We Th Fr Sa
        $507 1 $456 2 $420 3
$365 4 $317 5 $332 6 $395 7 $439 8 $422 9 $346 10
$278 11 $260 12 $267 13 $271 14 $296 15 $338 16 $475 17
$505 18 $534 19 $538 20 $550 21 $589 22 $613 23 $619 24
$605 25 $551 26 $549 27 $550 28 $557 29 $563 30  
May 2027
Su Mo Tu We Th Fr Sa
            $374 1
$279 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 $313 19 $320 20 $333 21 $261 22
$258 23 $255 24 $276 25 $276 26 $276 27 $383 28 $381 29
$366 30 $288 31          
June 2027
Su Mo Tu We Th Fr Sa
    $288 1 $288 2 $288 3 $292 4 $296 5
$307 6 $313 7 $321 8 $346 9 $284 10 $328 11 $329 12
$342 13 $360 14 $342 15 $361 16 $420 17 $444 18 $445 19
$457 20 $460 21 $460 22 $419 23 $413 24 $468 25 $442 26
$452 27 $451 28 $472 29 $480 30      
July 2027
Su Mo Tu We Th Fr Sa
        $493 1 $624 2 $619 3
$616 4 $480 5 $405 6 $451 7 $447 8 $530 9 $481 10
$460 11 $305 12 $304 13 $303 14 $418 15 $511 16 $483 17
$354 18 $297 19 $282 20 $298 21 $400 22 $482 23 $458 24
$346 25 $340 26 $272 27 $311 28 $364 29 $386 30 $390 31
August 2027
Su Mo Tu We Th Fr Sa
$315 1 $427 2 $285 3 $349 4 $349 5 $314 6 $309 7
$256 8 $224 9 $210 10 $215 11 $235 12 $262 13 $255 14
$220 15 $193 16 $170 17 $168 18 $197 19 $250 20 $250 21
$167 22 $163 23 $163 24 $163 25 $163 26 $250 27 $250 28
$189 29 $189 30 $189 31        
September 2027
Su Mo Tu We Th Fr Sa
      $215 1 $215 2 $265 3 $257 4
$243 5 $215 6 $215 7 $215 8 $215 9 $250 10 $250 11
$212 12 $212 13 $209 14 $209 15 $209 16 $250 17 $250 18
$208 19 $208 20 $204 21 $204 22 $204 23 $250 24 $250 25
$204 26 $176 27 $176 28 $176 29 $204 30    
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