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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July 2026
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August 2026
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$157 30 $150 31          
September 2026
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October 2026
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        1 2 $250 3
$158 4 $151 5 $168 6 $181 7 $190 8 $250 9 $250 10
$231 11 $183 12 $178 13 14 15 16 17
18 19 $187 20 $185 21 $185 22 $250 23 $250 24
$165 25 $150 26 $150 27 $150 28 $176 29 $250 30 $250 31
November 2026
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8 $150 9 $208 10 $206 11 $208 12 $250 13 $250 14
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$368 22 $391 23 $415 24 $683 25 $680 26 $663 27 $598 28
$239 29 30          
December 2026
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6 $150 7 $150 8 $162 9 $194 10 $250 11 $250 12
$188 13 $150 14 $157 15 $215 16 $201 17 $363 18 $643 19
$754 20 $807 21 $818 22 23 24 25 26
27 28 29 $700 30 $700 31    
January 2027
Su Mo Tu We Th Fr Sa
          $667 1 $637 2
$352 3 $287 4 $236 5 $239 6 $193 7 $259 8 $250 9
$192 10 $159 11 $152 12 $157 13 $179 14 $250 15 $263 16
$258 17 $174 18 $174 19 $174 20 $184 21 $250 22 $250 23
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February 2027
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7 $200 8 $201 9 $215 10 $249 11 $370 12 $426 13
$419 14 $254 15 $227 16 $243 17 $267 18 $268 19 20
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$207 28            
March 2027
Su Mo Tu We Th Fr Sa
  $189 1 $185 2 $192 3 $266 4 $305 5 $302 6
$299 7 $309 8 $312 9 $312 10 $317 11 $414 12 $422 13
$420 14 $420 15 $412 16 $424 17 $418 18 $439 19 $458 20
$450 21 $342 22 $292 23 $297 24 $424 25 $588 26 $588 27
$588 28 $462 29 $460 30 $462 31      
April 2027
Su Mo Tu We Th Fr Sa
        $540 1 $498 2 $498 3
$457 4 $316 5 $338 6 $397 7 $448 8 $515 9 $463 10
$458 11 $266 12 $274 13 $278 14 $279 15 $316 16 $472 17
$498 18 $580 19 $583 20 $606 21 $642 22 $672 23 $686 24
$667 25 $584 26 $584 27 $590 28 $583 29 $580 30  
May 2027
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            $304 1
$280 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 $328 19 $338 20 $334 21 $261 22
$258 23 $255 24 $276 25 $276 26 $276 27 $403 28 $402 29
$371 30 $288 31          
June 2027
Su Mo Tu We Th Fr Sa
    $288 1 $288 2 $293 3 $307 4 $296 5
$320 6 $347 7 $376 8 $400 9 $403 10 $415 11 $409 12
$380 13 $391 14 $378 15 $377 16 $416 17 $438 18 $435 19
$413 20 $403 21 $409 22 $389 23 $424 24 $472 25 $443 26
$464 27 $463 28 $462 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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