Upstay Family Home w Cinema Pool BBQ Clermont

Location

Description

Treat your family or group to the ultimate Orlando escape! This 5-bedroom, 4-bathroom vacation home is packed with entertainment, comfort, and style—from a private pool and BBQ-ready patio to a full game room and an in-home movie theater. Nestled inside the gated Windsor Cay Resort, you’ll enjoy full access to brand-new resort amenities, including a lazy river, mini golf, splash zone, and more!

Relax, Unwind & Play:
• Private outdoor pool with lounge seating
• Shaded patio + BBQ grill for al fresco meals
• Indoor & outdoor dining areas – perfect for group meals
• Game room with shuffleboard, pool table & arcade games
• In-home movie theater for private screenings
• High-speed WiFi & Smart TVs
• Central air conditioning & heating
• In-home laundry & driveway parking for 2 vehicles

Cook, Dine & Gather:
• Fully equipped kitchen with full-sized appliances
• Coffee maker, cookware, utensils & more
• Indoor dining table + patio dining space for outdoor meals
• Open-concept layout for easy gathering & lounging

Dream Big, Sleep Easy – 5 Bedrooms | Sleeps up to 12
First Floor
• Bedroom 1: Queen bed | Shared ensuite (toilet/shower)

Second Floor
• Bedroom 2: Queen bed | Shared bath nearby
• Bedroom 3: 2 Twin beds
• Bedroom 4: King bed | Private ensuite (toilet/shower)
• Bedroom 5: Bunk bed (2 Full beds) | Ensuite (toilet/shower)
(4 full bathrooms total, stocked with towels, hairdryers & toiletries)

Resort Access – Windsor Cay Resort Perks
All guests enjoy complimentary access to Windsor Cay’s brand-new world-class amenities:
• Zero-entry resort-style pool + lazy river
• Kids splash zone & water playground
• Waterslides & relaxing hot tub
• Private poolside cabanas & fire pits
• Mini golf, arcade & game room
• Full-service fitness center
• Basketball, volleyball & cornhole courts

Location Perks:
• Just 8 miles from Walt Disney World
• Quick drive to Universal, SeaWorld, shopping & dining
• Easy access to Orlando’s top attractions

Why Stay With Us?
We specialize in creating memorable stays for families and groups, with thoughtfully designed homes, responsive communication, and spotless spaces. Whether you’re here for theme parks, relaxation, or reconnecting with loved ones—this home is ready to make your vacation unforgettable.

• 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!

• To access the resort, all adult guests (18+) must be registered in advance. The HOA office is open Monday–Friday, 8:30 AM–5:00 PM, so please provide names as soon as possible to ensure a smooth check-in process.

• Pool maintenance is scheduled weekly and may occur during your stay. Technicians will briefly access the pool area only. Thank you for your understanding.

Community & Resort Information – Windsor Cay

• Windsor Cay is a newly developed community and is now fully open, including all resort amenities.

• The home is fully prepared and stocked for your stay, while minor finishing touches may still be ongoing in the surrounding community.

• Guests have full access to the brand-new Windsor Cay Resort amenities during their stay.

• The community and resort facilities are open and welcoming guests for a complete vacation experience.

Additional Services (Available Upon Request)
• BBQ propane tank: USD 69 one-time charge (please request in advance)
• Pool heating: USD 35/night (2-night minimum, 24-hour notice required)
• Pack ’n play: USD 39 one-time fee
• Highchair: USD 29 one-time fee
• Mid-stay cleaning (for stays over 3 nights): available for an additional fee, must be booked in advance

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

September 2026

Su	Mo	Tu	We	Th	Fr	Sa
		1	2	3	4	5
6	7	8	$130 9	10	11	12
13	14	15	16	17	$186 18	19
20	$130 21	$130 22	$130 23	24	25	26
$161 27	28	29	30

October 2026

Su	Mo	Tu	We	Th	Fr	Sa
				1	2	3
4	5	6	7	8	9	10
$295 11	12	13	14	15	16	17
$144 18	$144 19	20	21	22	$234 23	$224 24
$142 25	$148 26	$130 27	$133 28	$153 29	$244 30	$246 31

November 2026

Su	Mo	Tu	We	Th	Fr	Sa
$160 1	$143 2	$146 3	$148 4	$174 5	$215 6	$246 7
$230 8	$178 9	$225 10	$225 11	$236 12	$246 13	$263 14
$210 15	$193 16	$207 17	$192 18	$232 19	$321 20	$367 21
$365 22	$365 23	$357 24	$434 25	$438 26	$431 27	$404 28
$239 29	$184 30

December 2026

Su	Mo	Tu	We	Th	Fr	Sa
		$201 1	$186 2	$193 3	$246 4	$242 5
$217 6	$202 7	$197 8	$198 9	$233 10	$262 11	$272 12
$229 13	$221 14	$220 15	$227 16	$243 17	$379 18	$504 19
$605 20	$663 21	$664 22	$700 23	$702 24	$703 25	$703 26
$768 27	$757 28	$751 29	$696 30	$697 31

January 2027

Su	Mo	Tu	We	Th	Fr	Sa
					$683 1	$649 2
$305 3	$241 4	$229 5	$203 6	$206 7	$262 8	$278 9
$219 10	$195 11	$189 12	$193 13	$203 14	$268 15	$286 16
$280 17	$238 18	$209 19	$236 20	$222 21	$244 22	$251 23
$238 24	$239 25	$243 26	$241 27	$241 28	$256 29	$254 30
$231 31

February 2027

Su	Mo	Tu	We	Th	Fr	Sa
	$223 1	$220 2	$231 3	$249 4	$261 5	$271 6
$242 7	$253 8	$252 9	$266 10	$288 11	$401 12	$458 13
$455 14	$318 15	$297 16	$294 17	$307 18	$352 19	$320 20
$282 21	$283 22	$280 23	$282 24	$300 25	$342 26	$341 27
$303 28

March 2027

Su	Mo	Tu	We	Th	Fr	Sa
	$291 1	$283 2	$275 3	$299 4	$412 5	$436 6
$435 7	$443 8	$442 9	$431 10	$460 11	$598 12	$624 13
$639 14	$661 15	$660 16	$644 17	$667 18	$698 19	$578 20
$532 21	$431 22	$455 23	$507 24	$590 25	$581 26	$583 27
$562 28	$511 29	$472 30	$455 31

April 2027

Su	Mo	Tu	We	Th	Fr	Sa
				$520 1	$553 2	$472 3
$413 4	$376 5	$376 6	$366 7	$423 8	$453 9	$392 10
$328 11	$284 12	$294 13	$296 14	$431 15	$432 16	$357 17
$302 18	$503 19	$512 20	$513 21	$516 22	$499 23	$506 24
$490 25	$493 26	$492 27	$486 28	$508 29	$508 30

May 2027

Su	Mo	Tu	We	Th	Fr	Sa
						$334 1
$321 2	$326 3	$310 4	$317 5	$313 6	$319 7	$310 8
$279 9	$255 10	$292 11	$291 12	$289 13	$323 14	$308 15
$280 16	$254 17	$249 18	$404 19	$407 20	$411 21	$321 22
$281 23	$303 24	$261 25	$268 26	$295 27	$392 28	$397 29
$397 30	$277 31

June 2027

Su	Mo	Tu	We	Th	Fr	Sa
		$321 1	$334 2	$326 3	$339 4	$340 5
$333 6	$285 7	$275 8	$293 9	$317 10	$384 11	$384 12
$384 13	$397 14	$401 15	$420 16	$465 17	$479 18	$465 19
$450 20	$440 21	$447 22	$414 23	$446 24	$472 25	$484 26
$500 27	$494 28	$488 29	$498 30

July 2027

Su	Mo	Tu	We	Th	Fr	Sa
				$505 1	$616 2	$615 3
$613 4	$501 5	$446 6	$436 7	$478 8	$548 9	$545 10
$487 11	$461 12	$468 13	$477 14	$444 15	$498 16	$513 17
$409 18	$450 19	$441 20	$434 21	$440 22	$511 23	$501 24
$400 25	$350 26	$342 27	$371 28	$391 29	$433 30	$425 31

August 2027

Su	Mo	Tu	We	Th	Fr	Sa
$353 1	$318 2	$316 3	$322 4	$346 5	$359 6	$359 7
$316 8	$323 9	$310 10	$288 11	$302 12	$319 13	$305 14
$273 15	$259 16	$248 17	$248 18	$248 19	$268 20	$268 21
$238 22	$225 23	$216 24	$225 25	$233 26	$256 27	$256 28
$243 29	$192 30	$193 31

Swipe for Availability

Amenities 53

Air conditioning
Baking sheet
Bathtub
BBQ grill
Bed linens
Carbon monoxide detector
Cleaning Disinfection
Coffee maker
Dishes and silverware
Dishwasher
Downtown
Dryer
Enhanced cleaning practices
Essentials
Family/kid friendly
Fire extinguisher
Free parking on premises
Gym
Hair dryer
Hangers
Heating
High touch surfaces disinfected
Hot tub
Hot water
Indoor pool
Internet
Iron
Kettle
Kitchen
Long term stays allowed
Microwave
Oven
Patio or balcony
Private entrance
Refrigerator
Resort
Shampoo
Shower gel
Smoke detector
Stove
Suitable for children (2-12 years)
Suitable for infants (under 2 years)
Toaster
Towels provided
Town
TV
Washer
Wireless Internet
Communal pool
Game room
Outdoor pool
Private pool
Swimming pool

Reviews 5 (15)

nice spot. felt just like home... loved the resort 😉
Anonymous - Posted: 3/3/2026

We had such a wonderful stay at this location! The home was beautifully maintained and perfect for our family. There was plenty of space for everyone to relax comfortably, and it truly felt like a home away from home. The amenities were amazing and gave our family so much to enjoy throughout our stay. Everything was well-kept, convenient, and added a fun, relaxing element to our trip. The host was responsive, helpful, and made sure we had everything we needed. We really appreciated how smooth and easy the entire experience was from start to finish. Our family made great memories here, and we would absolutely stay at this location again. Highly recommend for families looking for a fun, comfortable home with fantastic resort amenities!
Anonymous - Posted: 2/28/2026

Thank you for sharing your experience with us! It brings us so much joy to hear that you and your family felt at home during your stay. We're glad you enjoyed the amenities and found them to enhance your trip. Creating a fun and relaxing environment for families is our top priority, and it’s wonderful to know that you made lasting memories here. Your kind words about our responsiveness mean a lot to us. We strive to make the entire process as smooth as possible, and it’s rewarding to hear that we succeeded. We would love to welcome you back anytime! Thank you for the high recommendation, and we look forward to hosting you again in the future.
Upstay staff

Posted: 3/5/2026

Will definitely use this host again!!!!
Anonymous - Posted: 2/9/2026

Thank you so much for your kind words, Sarah! It means a lot to us that you enjoyed your stay and are considering returning. We look forward to hosting you again in the future!
Upstay staff

Posted: 2/10/2026

We had an amazing stay at this home with my family! Everything was truly top tier from the beautiful, clean, and comfortable home to the warm hospitality of the host. They were very attentive, caring, and made sure we had everything we needed throughout our stay. The space felt like a true home away from home, and we created such wonderful memories there. I would highly recommend this place to anyone looking for comfort, peace, and excellent service. We will definitely be back! Stephen Collins
Anonymous - Posted: 2/7/2026

It brings us so much joy to hear that you and your family had an amazing stay! Creating a comfortable and welcoming environment is our top priority, and we're delighted that you felt at home during your time with us. Thank you for your kind words about our hospitality; we always strive to be attentive and ensure our guests have everything they need. We can't wait to welcome you back!
Upstay staff

Posted: 2/8/2026

My family loved our time at this beautiful, peaceful, and well decorated home !!!!! We will definitely recommend and stay there again !! For sure
Anonymous - Posted: 10/15/2025

It’s wonderful to hear that you and your family enjoyed your stay at our home! We take great pride in creating a peaceful and beautifully decorated space for our guests. Knowing that you would recommend us and plan to return truly makes our efforts worthwhile. We can’t wait to welcome you back for another memorable visit!
Upstay staff

Posted: 10/16/2025

Our stay was perfect, the house is wonderful, super clean and the decor is super cozy, the games room is perfect and we had a lot of fun with karaoke, Luciana was super attentive and always answered all our questions and our check in was super smooth and the location is also great, there are several restaurants around and a supermarket and close to the Disney parks, 5 stars, we will definitely come back again.
Anonymous - Posted: 8/18/2025

We’re thrilled to hear that you had a perfect stay! It’s wonderful to know that you enjoyed the cozy decor and had a blast in the games room with karaoke. We always strive to provide a smooth check-in experience and are glad that Luciana was able to assist you throughout your stay. The location is indeed a great advantage, and we’re happy you found it convenient for dining and visiting the Disney parks. We can’t wait to welcome you back for another fantastic visit!
Upstay staff

Posted: 8/25/2025

Great location and amenities
Anonymous - Posted: 8/11/2025

Thank you, Cayla! We're thrilled to hear that you enjoyed the great location and amenities during your stay with us. We strive to provide a comfortable and convenient experience for all our guests, and your feedback means a lot to us. We hope to welcome you back to Upstay in Clermont soon!
Upstay staff

Posted: 9/11/2025

The home was perfect! Lots of space to play in the arcade for the kids while we watched a movie on the big screen. Bedrooms were SO COMFORTABLE! Kids had plenty to do and the resort was only one street over. Lazy River was fun and my youngest really enjoyed the splash pad part, while my oldest played in the indoor arcade. The resort recently open so they are super strict so expect to hear lifeguard whistles the entire time.
Anonymous - Posted: 8/3/2025

Thank you so much for your wonderful review! We’re thrilled to hear the home was perfect for your family, and that the kids enjoyed the arcade and splash pad while you relaxed. It’s great that the bedrooms were so comfortable and that the nearby resort added to your fun experience. Thanks for the helpful note about the lifeguard whistles—it's important for future guests to know. We’d love to host you again anytime! Warm regards, Luciana – Co-Host
Upstay staff

Posted: 8/9/2025

Everything was amazing! Our family loved relaxing in the pool and movie room. Spacious rooms perfect to enjoy well needed family time.
Anonymous - Posted: 8/2/2025

Thank you so much for your kind words! We’re so happy to hear your family enjoyed relaxing in the pool and movie room. It’s wonderful that the spacious rooms helped you all enjoy some well-needed family time. We’d love to host you again anytime! Warm regards, Luciana – Co-Host
Upstay staff

Posted: 8/9/2025

Truly amazing , place was spotless great layout comfortable beds the host was very accommodating quick to response the family loved every second there
Anonymous - Posted: 7/8/2025

We’re thrilled to hear that you had such an amazing stay! It’s wonderful to know that you found the place spotless and enjoyed the layout and comfort of the beds. We always strive to be accommodating and responsive, so it’s great to see that reflected in your experience. Thank you for sharing your positive feedback, and we hope to welcome you and your family back again soon!
Upstay staff

Posted: 9/11/2025

very clean and nice place. Will definitely stay again:)
Anonymous - Posted: 6/16/2025

Thank you, Shirley! We're so glad you enjoyed the clean and cozy space. We'd be happy to welcome you back anytime—hope to see you again soon!
Upstay staff

Posted: 7/10/2025

Great place to stay!
Anonymous - Posted: 5/5/2025

Thanks Tiffany! We’re so happy to hear you enjoyed your stay and found our home great. Hope to host you again in the future!
Upstay staff

Posted: 6/11/2025

Loved the place.
Anonymous - Posted: 4/8/2025

We're glad to hear you loved the place. It was an honor hosting you, Leslie. We look forward to having you again in the future!
Upstay staff

Posted: 5/1/2025

very great stay, close to everything! the home is beautiful and roomy, the pool is wonderful i couldn’t recommend it more!! amazing stay
Anonymous - Posted: 3/16/2025

It was a pleasure hosting you, Kaitlyn! We're so glad you had a great stay and enjoyed the space. We'll continue to do our best to provide a comfortable experience and look forward to hosting you again!
Upstay staff

Posted: 5/1/2025

Highly recommend and the host are very responsive. I wrote them at 4am they wrote back promptly
Anonymous - Posted: 3/9/2025

Thanks again for choosing to stay with us, Majiah! We're so glad you enjoyed your stay and would love to host you again anytime!
Upstay staff

Posted: 5/1/2025

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