Upstay Family Villa for 12 w Pool Games BBQ

Location

Description

Sunshine, space, and resort-style fun! Welcome to this beautiful 6-bedroom, 5-bathroom family villa at the highly sought-after Windsor at Westside Resort in Kissimmee. With over 3,100 sq. ft. of living space and room for up to 12 guests, this two-storey getaway is perfect for families, friends, or small group vacations just minutes from Disney.

From a private pool to a fully loaded garage game room and full access to world-class resort amenities, this home is made for memory-making.

Outdoor Living at Its Best:
• Private screened-in pool with safety fence
• Furnished patio with loungers & shaded seating
• BBQ grill for outdoor cooking
• Dining area for sunny meals or evening BBQs

It's Game Time, Anytime:
• Garage game room with pool table, foosball & darts
• Smart TVs throughout for movie nights or morning cartoons
• High-speed WiFi + Roku & cable for your streaming needs

Eat, Chill & Connect:
• Fully equipped kitchen with stainless steel appliances
• Spacious kitchen island & indoor dining for 8
• Open-concept living area with cozy seating & 64" Smart TV
• Upstairs loft with another 64" Smart TV – perfect for kids or extra hangout space

Sleep Soundly – 6 Bedrooms / 5 Bathrooms:
First Floor:
• Bedroom 1: King bed | Ensuite bathroom | 50" TV

Second Floor:
• Bedroom 2: King bed | Ensuite bathroom | 50" TV
• Bedroom 3: Queen bed | Shares bath w/ BR 4 | 43" TV
• Bedroom 4: Queen bed | Shares bath w/ BR 3 | 43" TV
• Bedroom 5: Queen bed | Shares bath w/ BR 6 | 43" TV
• Bedroom 6: Queen bed | Shares bath w/ BR 5 | 43" TV
(All bathrooms include fresh towels, hairdryers & shower amenities.)

Windsor at Westside Resort Amenities (included):
• Gated 24/7 security with access via Lima Gate
• Clubhouse with pool, lazy river, splash pad & waterslides
• Hot tub, fitness centre, spa & business center
• Tu Casa Bar & Lounge (open 11am–8pm)
• Volleyball, basketball & tennis courts
• Arcade room, playground, and movie theatre
(Clubhouse Hours: 9:00 AM – 8:00 PM)

Parking & Practical Info:
• Driveway parking for 2 vehicles
• Overflow parking available at clubhouse (limited)
• Washer & dryer available in-unit
• Trash pickup daily – place bins outside

Unbeatable Location:
• 10 minutes to Disney parks
• 25 minutes to Universal Studios & SeaWorld
• 5 minutes to shopping, groceries, and restaurants
• 35 minutes to Orlando International Airport (MCO)

Why Stay With Us?
As experienced & professional hosts, we pride ourselves on delivering top-notch guest experiences. Our home is professionally cleaned, well-stocked, and thoughtfully designed for comfort, fun, and togetherness.

Book now and make unforgettable Orlando memories with your crew!

Important 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!
• Please note that we do not provide washcloths. Please bring your own washcloths to make use of during your stay.

Add-On Services:
• Pool heating: $35/night

Convenience Rentals:
• 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!
• Pack 'N Play crib: $40
• Highchair: $40
(Please reach out after booking to arrange any add-ons or upgrades.)

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

Available

Unavailable

Check-In

Check-Out

March 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	26	27	28
29	30	31

April 2026

Su	Mo	Tu	We	Th	Fr	Sa
			1	2	$561 3	$565 4
$552 5	$510 6	$492 7	$514 8	$605 9	$560 10	$480 11
$209 12	$190 13	$186 14	$209 15	$246 16	$407 17	$406 18
$247 19	$243 20	$209 21	$233 22	$271 23	$452 24	$397 25
$251 26	$251 27	$184 28	$186 29	$215 30

May 2026

Su	Mo	Tu	We	Th	Fr	Sa
					$330 1	$315 2
$230 3	$195 4	$173 5	$177 6	7	8	9
10	$199 11	$197 12	$202 13	$233 14	$311 15	$332 16
$263 17	$222 18	$206 19	$274 20	$269 21	$452 22	$458 23
$451 24	$334 25	$323 26	$332 27	$324 28	$368 29	$394 30
$315 31

June 2026

Su	Mo	Tu	We	Th	Fr	Sa
	$307 1	$269 2	$272 3	$318 4	$385 5	$368 6
$307 7	$288 8	$379 9	$297 10	$350 11	$397 12	$414 13
$389 14	$374 15	$376 16	$396 17	$502 18	$499 19	$510 20
$525 21	$551 22	$608 23	$583 24	$623 25	$635 26	$593 27
$518 28	$429 29	$426 30

July 2026

Su	Mo	Tu	We	Th	Fr	Sa
			$453 1	$940 2	$986 3	$982 4
$725 5	$664 6	$614 7	$638 8	$762 9	$736 10	$729 11
$448 12	$391 13	$391 14	$620 15	$622 16	$624 17	$621 18
$429 19	$361 20	$361 21	$435 22	$499 23	$588 24	$585 25
$420 26	$414 27	$434 28	$371 29	$444 30	$495 31

August 2026

Su	Mo	Tu	We	Th	Fr	Sa
						$480 1
$349 2	$314 3	$326 4	$332 5	$368 6	$407 7	$400 8
$321 9	$283 10	$281 11	$286 12	$310 13	$341 14	$332 15
$327 16	$294 17	$286 18	$263 19	$254 20	$311 21	$304 22
$260 23	$209 24	$198 25	$200 26	$225 27	$283 28	$285 29
$243 30	$193 31

September 2026

Su	Mo	Tu	We	Th	Fr	Sa
		$184 1	$191 2	$227 3	$374 4	$381 5
$379 6	$195 7	$180 8	$191 9	$231 10	$275 11	$275 12
$227 13	$227 14	$193 15	$240 16	$230 17	$275 18	$275 19
$232 20	$243 21	$233 22	$239 23	$233 24	$275 25	$275 26
$241 27	$218 28	$259 29	$229 30

October 2026

Su	Mo	Tu	We	Th	Fr	Sa
				$258 1	$278 2	$275 3
$228 4	$210 5	$206 6	$223 7	$259 8	$327 9	$328 10
$330 11	$278 12	$278 13	$278 14	$285 15	$333 16	$313 17
$246 18	$221 19	$209 20	$225 21	$268 22	23	24
25	26	27	28	29	30	$285 31

November 2026

Su	Mo	Tu	We	Th	Fr	Sa
$231 1	$200 2	$261 3	$194 4	$248 5	$292 6	$290 7
$262 8	$271 9	$312 10	$314 11	$321 12	$330 13	$329 14
$289 15	$235 16	$245 17	$206 18	$381 19	$415 20	$466 21
$507 22	23	24	25	26	27	28
$291 29	$245 30

December 2026

Su	Mo	Tu	We	Th	Fr	Sa
		$259 1	$365 2	$388 3	$403 4	$335 5
$244 6	$231 7	$236 8	$246 9	$272 10	$312 11	$332 12
$322 13	$317 14	$358 15	$400 16	$281 17	$537 18	$751 19
$999 20	$1040 21	$1052 22	$1147 23	$1149 24	$1146 25	$1159 26
$1098 27	$1091 28	$1092 29	$1132 30	$1130 31

January 2027

Su	Mo	Tu	We	Th	Fr	Sa
					$993 1	$953 2
$589 3	$442 4	$249 5	$278 6	$376 7	$334 8	$319 9
$265 10	$235 11	$218 12	$223 13	$235 14	$306 15	$340 16
$346 17	$303 18	$271 19	$272 20	$269 21	$278 22	$284 23
$253 24	$269 25	$269 26	$269 27	$268 28	$275 29	$275 30
$248 31

February 2027

Su	Mo	Tu	We	Th	Fr	Sa
	$225 1	$221 2	$236 3	$278 4	$320 5	$367 6
$340 7	$283 8	$279 9	$298 10	$316 11	$524 12	$580 13
$582 14	$360 15	$328 16	$325 17	$341 18	$393 19	$413 20
$365 21	$316 22	$301 23	$312 24	$335 25	$366 26	$340 27
$329 28

Swipe for Availability

Amenities 51

Air conditioning
Baking sheet
BBQ grill
Bed linens
Carbon monoxide detector
Cleaning Disinfection
Coffee maker
Cookware
Desk
Dishes and silverware
Dishwasher
Dryer
Enhanced cleaning practices
Essentials
Family/kid friendly
Fire extinguisher
Free parking on premises
Garden or backyard
Gym
Hair dryer
Hangers
Heating
High touch surfaces disinfected
Hot tub
Hot water
Internet
Iron
Kettle
Kitchen
Long term stays allowed
Microwave
Oven
Patio or balcony
Private entrance
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
TV
Washer
Wireless Internet

Resorts

WindsorWestside

Game room
Private pool

Reviews 5 (18)

Casa hermosa. Muy bien equipada.
Anonymous - Posted: 2/27/2026

We are very happy to hear that you enjoyed your stay in our house. We strive to provide a comfortable and well-equipped space for our guests, and it is rewarding to know that we meet your expectations. We look forward to the opportunity to host you again in the future. Thank you for your review!
Upstay staff

Posted: 3/3/2026

The house was very clean and spacious. We paid for the pool heat since we stayed in February and it was worth it, the pool was a very comfortable temperature. Upstay was very responsive and helpful whenever we reached out. We enjoyed our stay and can’t wait to visit FL again.
Anonymous - Posted: 2/19/2026

Thank you for sharing your experience with us! We're delighted to hear that you found the house clean and spacious, and that the pool heat made your February stay enjoyable. It’s great to know that our team was able to assist you promptly. We appreciate your kind words and look forward to welcoming you back to Florida for another memorable visit!
Upstay staff

Posted: 2/22/2026

10/10 stay! The host was very helpful and their response time was great. Would definitely recommend!
Anonymous - Posted: 2/6/2026

Thank you for your wonderful feedback! It’s fantastic to hear that you had a 10/10 experience with us. We always strive to be responsive and helpful, and we’re glad that it made a positive impact on your stay. Your recommendation means a lot to us, and we hope to welcome you back to Upstay in Kissimmee soon!
Upstay staff

Posted: 2/10/2026

The home was beautiful and accommodated my group of 6 greatly! It is truly a beautiful home, and I would definitely book again. The check in process was very smooth, the house was easy to find, it is in a lovely neighborhood, and the host were very responsive! Thank you for having us
Anonymous - Posted: 1/29/2026

Thank you for your wonderful feedback, Jasmine! We're delighted to hear that our home was a great fit for your group of six and that you enjoyed the beautiful surroundings. It’s fantastic to know that the check-in process was smooth and that you found the house easily. We take pride in being responsive to our guests, and we appreciate your kind words. We would love to welcome you back anytime!
Upstay staff

Posted: 1/30/2026

Big house, plenty of spaces and rooms, super clean, communication was great. Would recommend to everyone!
Anonymous - Posted: 1/29/2026

Thank you, Chaoyi, for your wonderful review! We're delighted to hear that you enjoyed the spaciousness and cleanliness of our home. It’s always our goal to provide a comfortable and welcoming environment for our guests. We appreciate your kind words about our communication and your recommendation means a lot to us. We hope to welcome you back for another stay in the future!
Upstay staff

Posted: 1/30/2026

Great host and home for a family vacation. Very responsive. Will definitely book again
Anonymous - Posted: 1/10/2026

Very nice home, well communicated, and very close to everything
Anonymous - Posted: 1/7/2026

Highly recommended, this place was exactly what I was looking for in my family loved it as well Alfredo is a great host, very attentive, overall great experience!
Anonymous - Posted: 12/31/2025

Thank you for your wonderful review, Victor! It brings us so much joy to hear that you and your family had a great experience at Upstay. We strive to create a welcoming environment, and it’s fantastic to know that our efforts made a positive impact on your stay. Your recommendation means a lot to us, and we hope to welcome you back for another memorable visit in the future!
Upstay staff

Posted: 1/2/2026

My family and I loved staying here. It had plenty of room and it was a fun place to stay. It was in a gated community, the security guard got us an access card to the gate with a minute or two of the first time we pulled up to the gate. Entry in and out of the community was flawless during our stay. We accessed the home via pass code so it was all painless checking in. The home has a kitchen that is well equipped and it was very fun to have a private pool. We paid the extra $35 a day to heat the pool, it took about 20-30 hours to really warm up but it got nice and warm and my kids loved it. We spent one of the days of our stay just hanging out at the house. It was fun to have the pool table and the foosball table. I was pleased with our experience here.
Anonymous - Posted: 12/26/2025

Thank you, Richard, for sharing your experience with us! It’s wonderful to hear that you and your family enjoyed your stay and found the space to be both fun and accommodating. We’re glad the gated community provided you with a seamless entry and that the check-in process was easy. \n\nHaving a well-equipped kitchen and a private pool can really enhance a vacation, and we’re thrilled that your kids had a great time swimming after the pool was heated. It sounds like you made the most of your time with the pool table and foosball table, too! We appreciate your feedback and hope to welcome you back for another memorable stay in the future.
Upstay staff

Posted: 12/30/2025

Excellent Stay
Anonymous - Posted: 12/15/2025

Thank you, Tierra, for your wonderful review! We're so glad to hear that you had an excellent stay with us in Kissimmee. It brings us joy to know that our space met your expectations and contributed to a memorable experience. We hope to welcome you back soon for another fantastic getaway!
Upstay staff

Posted: 12/16/2025

Great stay! The place was clean, comfortable, and just like the pictures. Host was very responsive. Would stay again!
Anonymous - Posted: 12/9/2025

Thank you, Sheba! It’s wonderful to hear that you enjoyed your stay with us. We take pride in maintaining a clean and comfortable space, and we’re glad it met your expectations. Your kind words about our responsiveness mean a lot to us. We would love to welcome you back anytime!
Upstay staff

Posted: 12/10/2025

Alfredo is a great host! I highly recommend this home , very clean, spacious. I would definitely book again.
Anonymous - Posted: 11/20/2025

Thank you, Chanel, for your wonderful review! It brings us so much joy to hear that you found our home clean and spacious. We strive to create a welcoming environment for all our guests, and your recommendation means the world to us. We would love to host you again on your next visit to Kissimmee!
Upstay staff

Posted: 11/22/2025

Everything about this place was good stayed here with a total of 8 adults and we were comfortable and at home at all times. Perfect place to stay.
Anonymous - Posted: 10/30/2025

It’s wonderful to hear that you and your group of eight felt comfortable and at home during your stay! We strive to create a welcoming environment for all our guests, and it’s great to know that we succeeded in making your experience enjoyable. Thank you for choosing Upstay for your time in Kissimmee, and we hope to welcome you back in the future!
Upstay staff

Posted: 10/31/2025

THE STAY HERE WAS GREAT! MY FAMILY ENJOYED AND EVERYTHING AS DESCRIBED. THE HOME WAS BEAUTIFUL!
Anonymous - Posted: 10/14/2025

We’re thrilled to hear that you and your family had a great stay! It’s wonderful to know that you found everything as described and enjoyed the beauty of our home. We strive to create a welcoming environment for our guests, and your feedback truly means a lot to us. We hope to welcome you back for another memorable visit!
Upstay staff

Posted: 10/14/2025

We enjoyed our stay the pics liked exactly like the property. They allowed us to check in at 2pm which was a plus for those of us flying in.
Anonymous - Posted: 10/5/2025

We’re thrilled to hear that you enjoyed your stay and that the property met your expectations! It’s great to know that the early check-in made your arrival smoother, especially after a flight. We hope to welcome you back for another visit soon!
Upstay staff

Posted: 10/6/2025

Great stay, thank you for the express check-in and clear instructions!
Anonymous - Posted: 9/22/2025

We’re thrilled to hear that you had a great stay! It’s our pleasure to provide express check-in and clear instructions to make your experience as smooth as possible. Thank you for choosing Upstay, and we hope to welcome you back in the future!
Upstay staff

Posted: 9/22/2025

My family and I enjoyed our stay.
Anonymous - Posted: 9/3/2025

We’re thrilled to hear that you and your family enjoyed your stay with us! It was a pleasure hosting you, and we hope to welcome you back for another memorable visit in the future. Thank you for choosing Upstay!
Upstay staff

Posted: 9/4/2025

The house is very clean and beautifully decorated.
Letitia P. - Posted:

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