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
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May 2026
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June 2026
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  1 2 3 4 5 $254 6
7 8 9 10 11 12 $316 13
$278 14 $278 15 $279 16 $240 17 18 19 20
$302 21 $288 22 $281 23 $285 24 $345 25 $438 26 $391 27
$283 28 $297 29 $303 30        
July 2026
Su Mo Tu We Th Fr Sa
      $358 1 $544 2 $603 3 4
5 6 7 $358 8 $426 9 10 11
12 13 14 15 16 $496 17 $480 18
19 20 21 22 23 $470 24 $469 25
$340 26 $272 27 $264 28 $313 29 $331 30 $383 31  
August 2026
Su Mo Tu We Th Fr Sa
            $387 1
$293 2 $240 3 $230 4 $239 5 $276 6 $311 7 $305 8
$250 9 $210 10 $200 11 $208 12 $229 13 14 15
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23 24 25 $150 26 $169 27 $250 28 $250 29
$159 30 $150 31          
September 2026
Su Mo Tu We Th Fr Sa
    $150 1 $150 2 $164 3 $251 4 5
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13 14 $150 15 $150 16 $150 17 $250 18 19
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October 2026
Su Mo Tu We Th Fr Sa
        1 2 $250 3
$160 4 $150 5 $179 6 $200 7 $199 8 $250 9 $250 10
$241 11 $226 12 $210 13 14 15 16 17
18 19 $152 20 $180 21 $185 22 $250 23 $250 24
$169 25 $150 26 $150 27 $150 28 $175 29 $250 30 $250 31
November 2026
Su Mo Tu We Th Fr Sa
$163 1 2 3 4 5 6 7
8 $190 9 $209 10 $206 11 $214 12 $277 13 $250 14
15 16 17 18 19 20 21
$365 22 $415 23 $422 24 $740 25 $743 26 $591 27 $509 28
$248 29 30          
December 2026
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6 $155 7 $155 8 $166 9 $198 10 $250 11 $251 12
$193 13 $189 14 $189 15 $220 16 $414 17 $752 18 $546 19
20 21 22 23 24 25 $841 26
$779 27 $779 28 $765 29 $756 30 $775 31    
January 2027
Su Mo Tu We Th Fr Sa
          $718 1 $656 2
$400 3 $350 4 $350 5 $350 6 $245 7 $268 8 $250 9
$204 10 $174 11 $174 12 $174 13 $174 14 $250 15 $268 16
$268 17 $174 18 $174 19 $174 20 $184 21 $250 22 $250 23
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February 2027
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 $199 8 $198 9 $215 10 $257 11 $402 12 $447 13
$442 14 $273 15 $245 16 $251 17 $278 18 $283 19 $250 20
$207 21 $213 22 $211 23 $217 24 $242 25 $250 26 $250 27
$199 28            
March 2027
Su Mo Tu We Th Fr Sa
  $179 1 $178 2 $182 3 $266 4 $282 5 $287 6
$280 7 $302 8 $293 9 $321 10 $314 11 $416 12 $420 13
$426 14 $427 15 $402 16 $419 17 $417 18 $437 19 $453 20
$440 21 $306 22 $291 23 $300 24 $427 25 $588 26 $588 27
$588 28 $422 29 $413 30 $460 31      
April 2027
Su Mo Tu We Th Fr Sa
        $540 1 $498 2 $498 3
$457 4 $297 5 $314 6 $379 7 $426 8 $515 9 $463 10
$458 11 $266 12 $273 13 $278 14 $280 15 $303 16 $497 17
$517 18 $532 19 $522 20 $530 21 $588 22 $588 23 $588 24
$588 25 $534 26 $535 27 $513 28 $508 29 $467 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
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