House in Osceola County, FL
20 guests · 9 bedrooms · 6 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
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About this house rental
Summary:
Upstay presents this newly renovated 9-bedroom home at the sought-after Windsor at Westside Resort—just 8 miles from Disney! Recently updated to include a brand-new movie theater and an upgraded games room with a PlayStation, this home offers even more space for fun and relaxation. Enjoy your own private swimming pool, jacuzzi hot tub, and a spacious, fully furnished sundeck. Inside, you’ll find modern, airy rooms and entertainment for all ages, including air hockey, billiards, and foosball.
The Space:
This newly renovated 9-bedroom, 6-bathroom home at Windsor at Westside has been enhanced with a brand-new private movie theater and upgraded games room with a PlayStation—making it the ultimate group getaway. Enjoy a private pool, outdoor hot tub, and a large sundeck with serene pond views. The home sleeps up to 20 guests comfortably, with smart TVs in every bedroom and high-speed WiFi throughout.
Enjoy pond-facing views and no rear neighbors while you soak up the Florida sunshine from your private screened-in patio. Cool off in the sparkling swimming pool, unwind in the jacuzzi hot tub, or enjoy BBQ lunches around the outdoor dining area—there’s plenty of space for everyone.
Inside, the fully equipped kitchen features double fridge/freezer combo units, two large-capacity dishwashers, quartz countertops, stainless steel appliances, and a deep double sink. Dine together at the 10-person indoor dining table, with additional seating for 4 at the kitchen island and even more outdoors.
Every bedroom has a Smart TV, and high-speed internet keeps everyone connected.
Bedroom breakdown:
First Floor:
First Floor:
Bedroom 1: King bed
Bedroom 2: Two (2) Queen beds with ensuite
Second Floor:
Bedroom 3: King bed with ensuite
Bedroom 4: Bunk-bed (twin/full)
Bedroom 5: King bedroom suite
Bedroom 6: King bedroom suite
Bedroom 7: Bunk bed (twin/full)
Bedrooms 8&9: Two rooms, each with 2 twin beds
Bonus: Upstairs loft lounge now enhanced with air hockey, billiards, and foosball
Need to throw in a load of laundry? No problem—this home includes in-home washers and dryers, central A/C, and free parking for up to 4 vehicles on-site.
As part of your stay, you’ll also enjoy full access to the incredible Windsor at Westside Resort, complete with a lazy river, water slides, a Tiki bar, and so much more. Whether you're heading to Disney (just 8 miles away), relaxing poolside, or enjoying a movie night at home—this property offers a vacation experience unlike any other.
Guest Access:
You'll have private access to the property, so please make yourself at home. You can park 2 cars in the driveway. Our guests also get access to the resort clubhouse and its amenities, they are open from 9am to 9pm daily.
The Neighborhood:
Windsor at Westside is a brand new Mediterranean-themed community of luxury Orlando vacation rentals just 8 miles from Disney World. Guests get full access to the clubhouse and all of its amenities.
Getting Around:
Windsor at Westside is perfectly located to give you easy access in to the back entrance of Disney World via Black Lake Road followed by Sherbeth Road, so you will experience very minimal traffic. Close to shops, supermarkets (publix) and restaurants it's a great location to explore all the Orlando theme park attractions.
Windsor at Westside is just 30 miles from Orlando International Airport via the 417 toll road which normally takes about 35 minutes and only costs a few Dollars for the convenience.
Other Things to Note:
• 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!
• Up to 2 vehicles may park in the driveway while extra parking is available at the clubhouse. The garage is not available, and a maximum of 5 vehicles is allowed per residence.
• Please note that washcloths are not provided—kindly bring your own for your stay.
Additional Services:
• 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.
• 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!
• Rent a Pack 'n play for $39 (one-time fee)
• Rent a highchair for $29 (one-time fee)
• 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.
House Rules:
1. Parties, events, and smoking/vaping are prohibited in or around our property.
2. Please check-out on time. Late departures will result in a charge for each additional hour the property cannot be accessed for turnover.
3. Outside of service animals, pets are not permitted at this property. Any evidence of pets will result in a fine and/or forfeiture of your full deposit.
4. Firearms and weapons are strictly prohibited on the property.
5. We do not assume liability for any injuries sustained by using the pool. Please follow all safety precautions and use at your own discretion.
If any of these house rules are broken, you and your group may be subject to additional charges or be requested to vacate the property immediately without refund.
Interaction with Guests:
We work with a team of dedicated hospitality professionals who will assist us in providing you with 5-star quality service. Your recommendations and questions are important to us and we're here 24/7 to assist you. Please don't hesitate to reach out to us at any time.
Upstay presents this newly renovated 9-bedroom home at the sought-after Windsor at Westside Resort—just 8 miles from Disney! Recently updated to include a brand-new movie theater and an upgraded games room with a PlayStation, this home offers even more space for fun and relaxation. Enjoy your own private swimming pool, jacuzzi hot tub, and a spacious, fully furnished sundeck. Inside, you’ll find modern, airy rooms and entertainment for all ages, including air hockey, billiards, and foosball.
The Space:
This newly renovated 9-bedroom, 6-bathroom home at Windsor at Westside has been enhanced with a brand-new private movie theater and upgraded games room with a PlayStation—making it the ultimate group getaway. Enjoy a private pool, outdoor hot tub, and a large sundeck with serene pond views. The home sleeps up to 20 guests comfortably, with smart TVs in every bedroom and high-speed WiFi throughout.
Enjoy pond-facing views and no rear neighbors while you soak up the Florida sunshine from your private screened-in patio. Cool off in the sparkling swimming pool, unwind in the jacuzzi hot tub, or enjoy BBQ lunches around the outdoor dining area—there’s plenty of space for everyone.
Inside, the fully equipped kitchen features double fridge/freezer combo units, two large-capacity dishwashers, quartz countertops, stainless steel appliances, and a deep double sink. Dine together at the 10-person indoor dining table, with additional seating for 4 at the kitchen island and even more outdoors.
Every bedroom has a Smart TV, and high-speed internet keeps everyone connected.
Bedroom breakdown:
First Floor:
First Floor:
Bedroom 1: King bed
Bedroom 2: Two (2) Queen beds with ensuite
Second Floor:
Bedroom 3: King bed with ensuite
Bedroom 4: Bunk-bed (twin/full)
Bedroom 5: King bedroom suite
Bedroom 6: King bedroom suite
Bedroom 7: Bunk bed (twin/full)
Bedrooms 8&9: Two rooms, each with 2 twin beds
Bonus: Upstairs loft lounge now enhanced with air hockey, billiards, and foosball
Need to throw in a load of laundry? No problem—this home includes in-home washers and dryers, central A/C, and free parking for up to 4 vehicles on-site.
As part of your stay, you’ll also enjoy full access to the incredible Windsor at Westside Resort, complete with a lazy river, water slides, a Tiki bar, and so much more. Whether you're heading to Disney (just 8 miles away), relaxing poolside, or enjoying a movie night at home—this property offers a vacation experience unlike any other.
Guest Access:
You'll have private access to the property, so please make yourself at home. You can park 2 cars in the driveway. Our guests also get access to the resort clubhouse and its amenities, they are open from 9am to 9pm daily.
The Neighborhood:
Windsor at Westside is a brand new Mediterranean-themed community of luxury Orlando vacation rentals just 8 miles from Disney World. Guests get full access to the clubhouse and all of its amenities.
Getting Around:
Windsor at Westside is perfectly located to give you easy access in to the back entrance of Disney World via Black Lake Road followed by Sherbeth Road, so you will experience very minimal traffic. Close to shops, supermarkets (publix) and restaurants it's a great location to explore all the Orlando theme park attractions.
Windsor at Westside is just 30 miles from Orlando International Airport via the 417 toll road which normally takes about 35 minutes and only costs a few Dollars for the convenience.
Other Things to Note:
• 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!
• Up to 2 vehicles may park in the driveway while extra parking is available at the clubhouse. The garage is not available, and a maximum of 5 vehicles is allowed per residence.
• Please note that washcloths are not provided—kindly bring your own for your stay.
Additional Services:
• 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.
• 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!
• Rent a Pack 'n play for $39 (one-time fee)
• Rent a highchair for $29 (one-time fee)
• 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.
House Rules:
1. Parties, events, and smoking/vaping are prohibited in or around our property.
2. Please check-out on time. Late departures will result in a charge for each additional hour the property cannot be accessed for turnover.
3. Outside of service animals, pets are not permitted at this property. Any evidence of pets will result in a fine and/or forfeiture of your full deposit.
4. Firearms and weapons are strictly prohibited on the property.
5. We do not assume liability for any injuries sustained by using the pool. Please follow all safety precautions and use at your own discretion.
If any of these house rules are broken, you and your group may be subject to additional charges or be requested to vacate the property immediately without refund.
Interaction with Guests:
We work with a team of dedicated hospitality professionals who will assist us in providing you with 5-star quality service. Your recommendations and questions are important to us and we're here 24/7 to assist you. Please don't hesitate to reach out to us at any time.
Amenities at Upstay Family Retreat w Pool, Theater & Games Room
Non-smoking
No pets allowed
Family friendly
Map of Osceola County, FL
Ratings and reviews
8 / 10Excellent·Apr 2026
I’ll start by saying the house was very clean and that is probably my number 1 priority when staying anywhere besides home. Check in was not at the exact location I was given and also didn’t even take a gate code I was given. You’d think they’d know thThe house is huge There was ample room to move around with 18 of us. That being said, there were a few things that need to be addr:The listing is inaccurate. In one section abut there being a room with two sets of bunk beds. We got there and the beds were separated, taking up an entire room where there was supposed to be a queen bed. It wouldn’t have been a big deal that they were separated if one of them had a queen bed like states. This caused an adult to have to sleep in a twin bed which I was unhappy with because I had told her she’d have a queen. First world problems, yes, but I ended up giving her money back because I felt bad she had to sleep in a twin bed along with another adult. The ice machine stopped working one night and we were sent a technician to repair it. It seemed to work for another day and then stopped working again. We didn’t bother getting it fixed again we just went out and bought our own ice. I don’t know what it is about housing in Florida but the lowest temperature setting is 68. We are from Maine and so on the hotter days it felt warm inside. I was told to shut my door to keep it cooler inside but that made my room even hotter. I was uncomfortable but the fans kept me OK for my stay.
10 / 10Outstanding·Jan 2026
I wish I could give more stars to be honest! The pictures on this listing do not give this house justice! The house is breathtaking! So much space! My family and I stayed for my PhD graduation at Disney and we had so much fun! The host is wonderful and super responsive. If you are on the fence with booking this listing, let this review help you make the decision to book! I would definitely stay here again.
10 / 10Outstanding·Oct 2025
Everything Was On Point except tha AC Was not working up stairs
6 / 10Average·Mar 2026
The first issue is that the address is wrong and it took me 45 minutes of driving around, trying to contact host, speaking to security and going to clubhouse for them to tell me it was 8828 and not 8228 like it’s written on this website. The lack of communication with parking was a big deal. They told me to park in clubhouse and security said that was not an option. Everyone parks in the side of the street and I was told not to. Obviously we had more than two cars. The house was nice and comfortable but needs to be updated with basic stuff that makes it look very bad. I cannot fathom how a bathroom has a shower curtain lining with major mold and a hole when that’s only 2.00 for a loner and can be quickly fixed. It’s disgusting to take a shower and see mold on it. That’s in the connecting M&M room bathroom. Dining room chairs were falling apart. The ocean bedroom on first floor had a broken bed. I had to contact host. We had to put stuff under to hold bed. We pad 7 to heat pool and it was only hot at certain times. There is no light for the pool area only a small light where the table is. So the pool was totally dark at night. No broom anywhere around so if you want to pick up something you can’t. There’s little foxes that would make noise and stay more pleasant. Theatre was great so was the play room. There’s plenty of places for people to hang out.
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Top rated by guests
8.6Excellent
(19 Ratings)
"I wish I could give more stars to be honest! The pictures on this listing do not give this house justice! The house is breathtaking! So much space! My family and I stayed for my PhD graduation at Disn..."
Aaliyah M.Don't miss out! Price and availability may change
