Upstay Family Home w Cinema Pool BBQ Clermont
Family dining area seating 8 guests
Open-layout living room with smart TV and high speed internet
Safari Lion King themed Movie Theater
5 Bedroom home exterior and driveway
Presented by Upstay
Windsor Island Resort Lazy River
Furnished outdoor patio area
Safari Lion King themed Movie Theater and Games room
Safari Lion King themed Movie Theater and Games room with pool table
Safari Lion King themed Games room
Living room with modern furnishings
Open-layout living room with smart TV and high speed internet
Family dining area seating 8 guests
Kitchen with centered island and bar stools
Chef's kitchen with modern silver appliances
Kitchen Island with hanging ceiling lights
Contemporary Kitchen with centered island
Staircase leading upstairs
Shuffleboard games table
King Bedroom with en-suite bathroom
King Bedroom with en-suite bathroom and smart TV
En-suite bathroom with double vanity
En-suite bathroom with standing shower
Queen bedroom with shared en-suite bathroom
Queen bedroom with shared en-suite bathroom
Shared en-suite bathroom
Second queen bedroom with smart TV
Second queen bedroom with smart TV
Mickey Mouse themed twin bedroom with single beds
Mickey Mouse themed bedroom with smart TV
Full bathroom with vanity, shower and hairdryer
Hogwarts themed bunk bedroom with full beds
Hogwarts themed bunk bedroom with full beds
Hogwarts themed bunk bedroom with full beds
Hogwarts themed bunk bedroom
En-suite bathroom with standing shower
In-home laundry facilities
Windsor Island Resort water slides
Lazy Water Slide at Windsor Island Resort
Outdoor fire pit at Windsor Island Resort
Children's Splash play area at Windsor Island Resort
Hot tub at Windsor Island Resort
Fitness Center at Windsor Island Resort
Games room at Windsor Island Resort
Outdoor pool area with sun loungers at Windsor Island Resort
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House - Rating 5 (15)

Upstay Family Home w Cinema Pool BBQ Clermont

Bedroom 5 bedrooms
Bathroom 4 baths
Guests 12 guests
Pets Not Allowed Pets Not Allowed
  • Location: Orlando, Florida
  • Type: House
  • View: Downtown
Location Location
Description 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 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
Available
Unavailable
Check-In
Check-Out
August 2026
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$130 23 $133 24 $130 25 $130 26 $130 27 28 29
30 $130 31          
September 2026
Su Mo Tu We Th Fr Sa
    $130 1 $130 2 3 4 5
6 $157 7 8 9 10 11 12
13 14 15 16 17 $227 18 $219 19
20 21 22 23 $193 24 25 26
$157 27 $158 28 $142 29 $151 30      
October 2026
Su Mo Tu We Th Fr Sa
        $164 1 $218 2 $218 3
$177 4 $165 5 $180 6 $183 7 $197 8 $265 9 $271 10
$264 11 $231 12 $231 13 $232 14 $232 15 $273 16 $248 17
$200 18 $188 19 20 21 22 $257 23 $245 24
$192 25 $177 26 $173 27 $182 28 $211 29 $244 30 $248 31
November 2026
Su Mo Tu We Th Fr Sa
$194 1 $170 2 $211 3 $180 4 $215 5 $242 6 $253 7
$224 8 $176 9 $230 10 $233 11 $239 12 $245 13 $263 14
$210 15 $193 16 $203 17 $189 18 $210 19 20 21
22 $330 23 $331 24 $445 25 $456 26 $445 27 $428 28
$242 29 $218 30          
December 2026
Su Mo Tu We Th Fr Sa
    $196 1 $182 2 $192 3 $253 4 $243 5
$218 6 $199 7 $196 8 $193 9 $232 10 $263 11 $268 12
$226 13 $215 14 $220 15 $200 16 $242 17 $358 18 $466 19
$571 20 $637 21 $638 22 $701 23 $703 24 $686 25 $705 26
$757 27 $750 28 $736 29 $697 30 $696 31    
January 2027
Su Mo Tu We Th Fr Sa
          $666 1 $664 2
$308 3 $248 4 $229 5 $203 6 $207 7 $262 8 $278 9
$218 10 $194 11 $188 12 $194 13 $203 14 $271 15 $288 16
$278 17 $265 18 $235 19 $212 20 $220 21 $243 22 $252 23
$235 24 $222 25 $240 26 $225 27 $245 28 $255 29 $259 30
$235 31            
February 2027
Su Mo Tu We Th Fr Sa
  $227 1 $222 2 $235 3 $254 4 $267 5 $282 6
$255 7 $266 8 $264 9 $279 10 $298 11 $402 12 $439 13
$465 14 $329 15 $303 16 $302 17 $317 18 $370 19 $341 20
$299 21 $295 22 $288 23 $291 24 $306 25 $353 26 $344 27
$310 28            
March 2027
Su Mo Tu We Th Fr Sa
  $315 1 $288 2 $277 3 $306 4 $427 5 $441 6
$394 7 $439 8 $471 9 $461 10 $409 11 $520 12 $520 13
$498 14 $505 15 $518 16 $531 17 $549 18 $573 19 $552 20
$536 21 $432 22 $490 23 $495 24 $511 25 $581 26 $575 27
$558 28 $486 29 $454 30 $453 31      
April 2027
Su Mo Tu We Th Fr Sa
        $529 1 $545 2 $457 3
$413 4 $376 5 $357 6 $363 7 $432 8 $458 9 $419 10
$404 11 $286 12 $429 13 $431 14 $443 15 $444 16 $359 17
$304 18 $494 19 $498 20 $497 21 $489 22 $498 23 $498 24
$492 25 $490 26 $485 27 $479 28 $492 29 $493 30  
May 2027
Su Mo Tu We Th Fr Sa
            $321 1
$324 2 $349 3 $346 4 $340 5 $340 6 $333 7 $328 8
$313 9 $315 10 $310 11 $308 12 $299 13 $322 14 $299 15
$272 16 $244 17 $241 18 $406 19 $406 20 $406 21 $321 22
$273 23 $258 24 $246 25 $260 26 $284 27 $376 28 $376 29
$366 30 $268 31          
June 2027
Su Mo Tu We Th Fr Sa
    $310 1 $323 2 $323 3 $333 4 $337 5
$330 6 $357 7 $372 8 $359 9 $362 10 $389 11 $384 12
$384 13 $384 14 $374 15 $374 16 $393 17 $440 18 $423 19
$413 20 $421 21 $433 22 $411 23 $442 24 $473 25 $480 26
$506 27 $500 28 $500 29 $482 30      
July 2027
Su Mo Tu We Th Fr Sa
        $485 1 $599 2 $598 3
$616 4 $425 5 $425 6 $426 7 $457 8 $512 9 $494 10
$385 11 $339 12 $341 13 $351 14 $402 15 $467 16 $483 17
$416 18 $442 19 $443 20 $439 21 $450 22 $519 23 $500 24
$403 25 $375 26 $341 27 $347 28 $389 29 $427 30 $423 31
Swipe Swipe for Availability
Amenities 53 Amenities
  • 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 Rating 5 (15) Reviews
Rating 5
nice spot. felt just like home... loved the resort 😉
Anonymous - Posted: 3/3/2026
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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
Rating 5
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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