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!

• Please note that the fridge's ice maker is currently unavailable. However, for your convenience, a separate ice maker is provided on the kitchen counter.
• 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 we do not provide washcloths. Please bring your own washcloths to make use of during your stay.

Additional Services:
• Pool and hot tub heating is an additional service that is not included in your booking price. It's an additional fee of $35/night per service and $60/night for both, which we provide upon request. Please note that heating service is available with a minimum stay of 2 nights. Feel free to reach out for more details.
• 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.

Pet Friendly:
• Pets less than 60lbs. are very welcome at our home (maximum of 2 pets )
• A pet fee of $129/pet per stay will be added at the time of booking if the pet is added to the reservation. If no pet is declared during booking, we will collect the fee separately.

We're happy to deliver:
- 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!
- a "Pack 'N Play Crib" for $40 (one-time fee).
- a Highchair for $40 (one-time fee).

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
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March 2026
Su Mo Tu We Th Fr Sa
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29 $354 30 $364 31        
April 2026
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      $365 1 2 3 4
5 $405 6 $406 7 $416 8 9 10 11
$208 12 13 14 15 16 $376 17 18
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26 27 28 $190 29 $217 30    
May 2026
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June 2026
Su Mo Tu We Th Fr Sa
  $222 1 $232 2 $239 3 $254 4 $279 5 $269 6
7 8 9 10 11 12 $323 13
$318 14 $288 15 $294 16 $343 17 18 19 20
$443 21 $517 22 $544 23 $479 24 $445 25 $481 26 $436 27
$430 28 $445 29 $404 30        
July 2026
Su Mo Tu We Th Fr Sa
      $398 1 $618 2 $627 3 4
5 6 7 $450 8 $490 9 $525 10 $490 11
$318 12 13 14 15 16 $642 17 $509 18
$409 19 $278 20 $274 21 $300 22 $384 23 $472 24 $469 25
$335 26 $272 27 $262 28 $270 29 $334 30 $391 31  
August 2026
Su Mo Tu We Th Fr Sa
            $389 1
$282 2 $236 3 $227 4 $235 5 $276 6 $311 7 $298 8
$247 9 $240 10 $238 11 $237 12 $239 13 14 15
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23 24 25 $150 26 $169 27 $250 28 $250 29
$179 30 $150 31          
September 2026
Su Mo Tu We Th Fr Sa
    $150 1 $150 2 $167 3 $251 4 5
6 7 8 9 10 11 12
13 14 $150 15 $150 16 $150 17 $250 18 19
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27 28 29 30      
October 2026
Su Mo Tu We Th Fr Sa
        1 2 $250 3
$178 4 $150 5 $177 6 $189 7 $193 8 $250 9 $250 10
$241 11 $216 12 $202 13 $205 14 $215 15 $250 16 $250 17
$182 18 $154 19 $150 20 $154 21 $183 22 $250 23 $250 24
$167 25 $150 26 $150 27 $150 28 $169 29 $250 30 $250 31
November 2026
Su Mo Tu We Th Fr Sa
$171 1 2 3 4 5 6 7
8 $188 9 $204 10 $204 11 $206 12 $250 13 $250 14
15 16 17 18 19 20 21
$364 22 $400 23 $401 24 $735 25 $736 26 $602 27 $506 28
$202 29 30          
December 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 $160 7 $165 8 $168 9 $194 10 $250 11 $250 12
$232 13 $195 14 $221 15 $265 16 $205 17 $403 18 $649 19
20 21 22 23 24 25 $870 26
$823 27 $818 28 $818 29 $769 30 $770 31    
January 2027
Su Mo Tu We Th Fr Sa
          $750 1 $651 2
$445 3 $342 4 $273 5 $285 6 $270 7 $250 8 $250 9
$216 10 $154 11 $153 12 $150 13 $153 14 $250 15 $250 16
$239 17 $203 18 $176 19 $174 20 $175 21 $250 22 $250 23
$167 24 $170 25 $170 26 $170 27 $179 28 $250 29 $250 30
$165 31            
February 2027
Su Mo Tu We Th Fr Sa
  $150 1 $150 2 $153 3 $181 4 $250 5 $250 6
$231 7 $191 8 $193 9 $211 10 $233 11 $332 12 $370 13
$369 14 $262 15 $236 16 $231 17 $242 18 $262 19 $267 20
$253 21 $241 22 $242 23 $240 24 $261 25 $262 26 $260 27
$204 28            
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
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