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Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney

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Welcome to Retro Retreat at Windsor Hills! Minutes from the Magic!
WINDSOR HILLS RESORT Complimentary amenities! Waterpark! Jacuzzi! Pools!
Second floor MICKEY SUITE Twin size beds • Charging hub • Smart TV
Private kitchen
Interior

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6133.8 sq m

Popular amenities

  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View map
Kissimmee, FL
  • Place, Mystic Dunes Golf Club
    ‪19 min walk‬
  • Place, Bonanza Golf & Gifts
    ‪3 min drive‬
  • Place, Walt Disney World® Resort
    ‪6 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪34 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Magic Suite- First floor Bedroom

1 Double Sofa Bed

Mickey Suite- Second floor Bedroom

2 Single Beds

Owner's Suite- Second floor King Bedroom

1 King Bed

2 bathrooms

Magic Suite Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Mickey Suite Bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Owner's Suite Bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Dining area

About this property

Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney

2 Miles from Walt Disney World | Retro-Themed Vacation Rental | Private Plunge Pool

Step back in time to the nostalgic charm of the 1950s in this unique two-story retro-themed townhome—modern comfort meets vintage flair! Located just 2 miles from Disney and moments from other major Orlando attractions, it’s the perfect stay for magical memory-making.

Take a quick stroll to the community’s resort-style pool, waterslides, and clubhouse—all just steps from your door.

Whether you’re mixing work and fun, planning park-hopping adventures, or seeking a simple escape from the everyday, Retro Retreat is ready to welcome you.

Welcome to Retro Retreat at Windsor Hills!

FEATURES THAT DELIGHT OUR GUESTS

2 miles from Walt Disney World

16 miles to Universal Studios Florida

12 miles to SeaWorld Orlando

Ground floor bedroom with en-suite bathroom

Kitchen fully equipped with essential cooking items

Smart lock for seamless check-in

Complimentary on-site parking for two vehicles

GOOD TO KNOW

Families are warmly welcomed: Highchair, pack-and-play, and a wagon included.

Ideal for extended stays and snowbirds in a gated community

Remote workers enjoy high-speed Wi-Fi, fitness center, ATM, and Cyber Café access

DETAILS AND AMENITIES

KITCHEN: Stocked with utensils, pots, pans, coffee maker, dishwasher, and appliances to support home-cooked meals.
LAUNDRY: Full-size washer and dryer included.
LIVING/DINING AREA: Spacious layout with dining table and breakfast ledge for 8 guests, plus a large Smart TV.

BEDROOMS:
Second Floor

Owner Suite: King bed, USB headboard charging, reading lights, Smart TV, private bath

Mickey Suite: Twin beds, Smart TV, reading lights

First Floor

Magic Suite: Flex room with Queen sleeper sofa, desk, office chair, Smart TV, and access to full bath

TECH & ENTERTAINMENT:

Fast Wi-Fi (239 Mbps)

Smart TVs in every room

OUTDOORS:

Private lanai with a plunge pool

PARKING:
Two vehicles allowed. One in the driveway, the other in designated nearby resort spots. First come, first served.

COMMUNITY AMENITIES:

Resort pool, hot tub, and splash area

Fitness center, tennis, basketball, volleyball, ping pong, mini golf

Game room, movie theater, marketplace & grill, ATM

Playground and recreation park

SECURITY:
Safe, gated community with 24/7 manned security. Guest registration required with driver’s license presented at arrival.

EXTRAS & NOTES

Optional pool heat: $40/night, set to 86°F from 8 AM–10 PM (note: heating time may vary based on weather)

Weekly lawn and pool maintenance expected during stays

Kid-friendly board games available on request

Special occasion? Balloon bouquets, cakes, cupcakes, and gift baskets available—just ask!

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Starting a wash load of towels is always appreciated! Leave beds unmade
All trash must be bagged (13 gal) placed inside the bench & latched closed. Overflow must be brought to a resort trash compactor.
Log out of any streaming channels on the TVs.
Failure to complete these may result in a negative review from the host.
Picture of valid driver’s license, or government issued ID, is required for the issuance of SmartLock code. The ID needs to match the account holder.
Complete/sign the following documents: Guest Name list, with the full names of all guests, adults and children + Full House Rules + Guest Agreement.
On account of negative hosting experiences, the owner is now only accepting booking requests from guests with prior host reviews.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Long-term renters welcome
This property uses eco-friendly cleaning products
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

This property does not have any lifts
A car is recommended for transport to and from this property

About the area

Kissimmee

Located in Windsor Hills, a neighbourhood in Kissimmee, this holiday home is near theme parks and on a lake. Old Town and Flamingo Crossings Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Hollywood Studios®. Travelling with kids? Don't miss Disney's Blizzard Beach Water Park and Disney's Animal Kingdom® Theme Park. Discover the area's water adventures with fishing and swimming nearby, or enjoy the great outdoors with ecotours and cycling.
View more Holiday homes in OrlandoOpens in a new window
Map
Kissimmee, FL

What's nearby

  • Mystic Dunes Golf Club - 19 min walk - 1.7 km
  • Bonanza Golf & Gifts - 3 min drive - 3.1 km
  • Walt Disney World® Resort - 6 min drive - 5.1 km
  • Disney's Animal Kingdom® Theme Park - 8 min drive - 4.8 km
  • Disney Springs™ - 12 min drive - 14.1 km

Getting around

  • Kissimmee Station - 27 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 23 min drive

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Del Taco - ‬3 min drive
  • ‪Osaka Bay Buffet - ‬3 min drive
  • ‪Sickies Garage Burgers & Brews - ‬4 min drive

Frequently asked questions

Does Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney?

As of 27 March 2026, prices found for a 1-night stay for 2 adults at Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney on 22 June 2026 start from NZ$369, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney pet-friendly?

No, pets are not allowed at this property.

How much is parking at Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney?

On-site parking is available at the property.

What time is check-in at Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney?

Check-in begins at 4:00 PM.

What time is check-out at Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney?

Checkout is at 10:00 AM.

Where is Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney located?

This family-friendly Kissimmee holiday home is located on a lake, within 3 mi (5 km) of Mystic Dunes Golf Club and Walt Disney World® Resort. Island H2O Live! and Jack Nicklaus Course are also within 3 miles (5 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 32 out of 33 reviews
Rating 8 - Good. 0 out of 33 reviews
Rating 6 - Okay. 0 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 1 out of 33 reviews

9.6/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Megan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

In town for Sports

Great location to ESPN WWS and parks!
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

Natasha L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tranquil

My family and I enjoyed our stay at the Retro Retreat. The kids loved the waterpark and pool. Mommy enjoyed the piña coladas.Management was excellent. They went above and beyond to help me with a last minute reservation issue. I am grateful for their assistance.
Stayed 2 nights in Mar 2025
Verified

10/10 Excellent

amy j.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay at Retro Retreat

Retro retreat was exactly as advertised. Super cute and clean condo, extremely close to Disney. My kids enjoyed having their own pool and also had fun at the community pool, which is an easy walk from the condo. I would definitely recommend this condo to anyone looking for a place to stay near Orlando.
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Kelly H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation home

Great vacation home. Owner was very responsive. Water park was awesome. House is not baby/toddler proof but the additional amenities for little kids were a plus. Location was quick and easy to Disney & Sea World. Park in the neighborhood was great too.
Stayed 6 nights in Feb 2023
Verified

10/10 Excellent

Naomi O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property close to Disney

We had a wonderful stay in Windsor Hills. The property was lovely, well proportioned for a family of 4, and with all the facilities you need. The estate is secure and close to the parks, Disney is 10-15 minutes drive. The host was very welcoming and responsive. Highly recommended.
Stayed 13 nights in Dec 2022
Verified

10/10 Excellent

Allison K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls week perfection!

The house itself was exactly as described! Rita was very responsive and communicated well. Great location. The teens loved it as much as the moms!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Jessica M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location

We rented from Rita for my daughters birthday trip to Orlando. We were 10-15 minutes away from Disney parks, sea world and around the corner from Walmart and other stores and restaurants. Rita was a perfect host and helped us with our stay and surprising my daughter with balloons when we arrived. The pool was perfect and the house was so cute!
Stayed 4 nights in Nov 2020
Verified

10/10 Excellent

Andrea M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect!

We have stayed in other properties inside Windsor Hills before so we knew we already loved the location. This property was great! Super clean, looked exactly liked the pictures posted! The pool was very refreshing! Kitchen was well stocked although we didn’t cook anything. The retro theme was super cool and we will definitely consider staying there again!
Stayed 7 nights in Aug 2020
Verified

10/10 Excellent

Eric L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Perfect Home for our Family

We've stayed at Windsor Hills previously and love the neighborhood, but this home was a notch above other rentals. You could tell that the owners took care of the property, furniture, and furnished it for renters to have a great vacation. The property was very clean and perfect for us. It was well equipped with everything we needed. We had two children with so it was great that the rental was equiped with quality a pack-and-play, high chair, and baby gates. We loved our time here and would love to stay again in the future.
Stayed 11 nights in May 2021
Verified

10/10 Excellent

Carrie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful place

This property is decorated so cute! It has all the conveniences of home, and very close to shops and restaurants. The process to enter the front gates is a bit aggravating so make sure to add everyone who will come visit to the list. We really like this property and the pool was a great added benefit! Rita is great to work with and responds quickly to all needs! Thank you so much for having us, we can’t wait to come back next year!!
Stayed 4 nights in Apr 2021
Verified

10/10 Excellent

Candace b.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing vacation home

If I could give a 10 star I would. We have stayed in the Kissimmee/Orlando area for the past 4 years and this was our favorite place to stay. It was an easy booking process thanks to Rita. Communication with her was great even once we were there. The townhome was fantastic and it was so clean and well taken care of. The pool patio was nice and clean so we enjoyed it. We absolutely loved the on site water park, it was a hit! It’s so close to Disney so we enjoyed all our Disney adventures. Great home and great location. We had the best time! We will definitely be rebooking this spot next year. Thanks for an amazing vacation rental!!
Stayed 4 nights in May 2024
Verified

10/10 Excellent

Anthony S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best Part of the Trip!

This property saved our trip! We took our first trip to Disney and did a poor job planning. We went with a 9 year old and a 10 month old. It was hot, the baby was tired and the days were often cut short at the parks because of it. The house, pool and water park saved our trip. By the 3rd day my 9 year old was asking to stay at the pool all day instead of waiting in 2 hour long lines in the heat. We will only stay here next time we come back!
Stayed 8 nights in Jun 2022
Verified

10/10 Excellent

Clara B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A perfect family getaway!

I loved every single moment of this experience. I rented this villa for 7 nights with my husband, two kids (9 and 4) and my mom. First of all, Rita Maria's communication was top notch. She answered any question I had prior to the trip, and she even answered messages at 11:00 at night! Prompt and truthful in all over her responses. She never made me feel silly for answering minute questions. Now, onto the property. It was spectacular! There were no neighbors behind us, so it felt private. The pictures did not do it justice. The retro feel was so fun! We were excited looking at everything because it was so uniquely decorated. We each had our own bedroom and bathroom, so I cannot even begin to tell you how convenient that was! We all took turns taking a hot bath in the master bath since it had a deep tub. Every room had a tv, so there was no fighting about who gets to watch what. And the pool! My goodness, we felt absolutely no need to go to the main pool by the community building when we had one of our own! Every morning my mom would get up, make a cup of coffee, and sit by the pool. The kids couldn't wait to jump in! Also, it's 5ft deep. So if you don't have a swimmer in your family, bring floaties. They have a pool cleaner who is scheduled to come around and vaccum and chlorinize (is that a word?) the pool. You will have to buy your own supplies, and that was fine with us. Don't go to the Walmart. You won't make it out alive. Take a left on Irlo Bronson and there is a Target down there. Not only was this a gated community (super safe!), but it's the closest gated community to Disney parks. We were at the parks in a blink of an eye. And when you have eager kids, and me too, you are ready to get there fast! I've been telling everyone about this place, and I already have people asking "where did you find it?" I'll be singing Retro Retreat's praises to anything with a pulse. Thank you so much for an enjoyable and memorable stay!
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

Amanda T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice property close to Disney

Very convenient and nice amenities!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Judi B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

New to renting but all went well and close to parks.
Stayed 3 nights in Oct 2022
Verified

10/10 Excellent

Alissa M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great weekend spot

Thank you for a great stay. Very close to Disney.
Stayed 3 nights in Sep 2022
Verified

10/10 Excellent

Steven M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved it.

The house is very well decorated and we loved the location. Its a very secure gated community that felt very safe. About 15min drive to Disney depending on traffic. We used the pool almost every day and the community pool area is very nice as well though we didn't feel the need to use it much with out own pool. Communication with Rita was easy and she was very nice to deal with. We'd definitely stay here again.
Stayed 11 nights in Jul 2022
Verified

10/10 Excellent

Amy O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Retro Retreat was Rockin’!

Rita Marie’s property is amazing! The decor is spot on… so cute and detail oriented. We enjoyed having space, privacy and the private pool. The community pool and waterpark were perfect for a rest day in between the parks. We usually stay on Disney grounds, yet the ease of driving and this location lead us to believe we will definitely be back! Thank you!
Stayed 4 nights in Aug 2022
Verified

10/10 Excellent

Kristi M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay for Disney trips!

This is our third time staying in the Windsor Hills complex, and this was the best property we have stayed at so far. The host was responsive and helpful, the condo was clean and cozy, the amenities were perfect for our stay. It’s a short drive to the parks and everything else you need is close by, too. Having access to the big pool as well as our own small pool was nice for the hot days. A really lovey property for families with kids. We would definitely stay here again!
Stayed 4 nights in Jun 2022
Verified

10/10 Excellent

Andrea W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing vacation home

We had a wonderful experience. The host was very pleasant to deal with. The home was cozy and very clean. Great location with amenities and lots within only a few minutes driving distance. The villa has a little water park which is great as well. Our family had a fantastic time!
Stayed 7 nights in May 2022
Verified

10/10 Excellent

Jamie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Disney stay

We have been coming to Disney for years with family. We have stayed at most of the Disney resorts at least once and will now always stay here.
Stayed 3 nights in Mar 2022
Verified

10/10 Excellent

brittany s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The best!

We have stayed a few times now at Windsor area and from now on we will always check to see if this rental is available first. It was perfect! So clean, so quiet, great communication, helpful and even go above and beyond after our visit when we forgot an item. Can’t wait to come back!
Stayed 3 nights in Feb 2022
Verified

10/10 Excellent

Jennifer D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location and home

We stayed here for 8 nights over Thanksgiving break. Communication with property owner was top notch. The home was very clean. I read prior reviews so packed dish detergent, laundry detergent, and trash bags. We did Instacart and used Publix. Amazing!!!! We only cooked a few meals but the kitchen had everything we needed. I did forget pan spray on my order so that was a big oops on my part and we went out to dinner instead that day. The beds were comfy. We loved having three bathrooms since we had two teens. I did see that the house had lots of supplies for younger children so for those with little ones, this would be a good spot too. The weather was crazy when we were there, in the 40s one night and 70s another. So we only used the pool one day but it was a perfect size to just hang out and float. Since it did get cold and we only used one of the twin beds we used some of the blankets from that bed. The family enjoyed the living room space and TV after a long day at the parks. The proximity to Disney was fantastic and only a 25 min drive to Universal. The theme of the house was cute and vibrant at the same time. It made it feel like a cool vacation home. We loved our stay and would stay here again without hesitation. Hopefully in warmer months so we can enjoy the community pool area as it looks like a lot of fun! Oh and the wifi worked great for when my husband did some work while everyone else slept, so if you need a working vaca, it’s a great spot!
Stayed 8 nights in Nov 2021
Verified

10/10 Excellent

Yasmin v.

Liked: Cleanliness, check-in, communication, location, listing accuracy

PERFECT PLACE

I just want to express my gratitude to Rita for making our trip more pleasant and easy than we thought, we have had bad experiences with other places but definitely Rita's place is perfect super clean, a safe neighborhood, close to everything, the decoration excellent. the resort staff super friendly and very helpful as well as the host rita she solved any request or question in munutes. Like the host, we the guests must take care of and leave the property in the same way that we found it so that everyone can continue to have a wonderful experience ....
Stayed 3 nights in Nov 2021
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place

Really enjoyed the stay. We liked the retro decor. We would stay there again. Very clean and the pool was outstanding. The owner was very helpful when checking in.
Stayed 14 nights in Oct 2021

About the host

Hosted by Rita Maria

Host profile image
I don’t just design vacation rentals—I imagine birthday candles being blown out, little ones skipping off to Disney, and stories that become family lore. That’s the lens I bring to every home I host.

Before founding Property ReImagined LLC, I spent over 15 years as a lead designer for Royal Caribbean—crafting guest spaces that blended comfort, luxury, and connection across their global fleet. That experience taught me how to anticipate needs, elevate details, and deliver joy on a world-class stage.

Now I bring that same standard to land—curating family-friendly vacation homes near Walt Disney World that are warm, whimsical, and exceptionally managed.

Because behind every reservation is a real story—and it’s my joy to help shape it.

💫 Our Hosting Philosophy

✨ Magical Hospitality
We believe little things aren’t little. From surprise welcome touches to themed spaces made for celebration—we’re here to add a sprinkle of pixie dust to your stay.

✨ Clean, Safe & Thoughtfully Prepared
Every home is cleaned, staged, and inspected by licensed professionals. We prepare each space with care—so all you need to do is relax.

✨ Guest-First, Always
If something’s off, we want to know. We resolve issues with speed, empathy, and integrity—because your peace of mind is part of the experience.

✨ Designed for Real-Life Magic
Our homes are made for connection: shared meals, poolside laughs, milestone moments, and late-night talks that last long after checkout.

✨ Built on Respect & Integrity
We honor the trust of our guests, our neighbors, and the owners who partner with us. That means clear policies, fair practices, and high standards—every time.

Whether you're visiting Orlando for the theme parks, a milestone celebration, or a long-overdue family reunion—thank you for letting us be part of your story. Welcome home. 🏡✨

Warmly,
Rita Maria ✨Curator of Magical Stays

Why they chose this property

Windsor Hills is an unmatched VACATION RENTAL HOME COMMUNITY

What makes this property unique

1950's theme. Private splash pool with no neighbors peeking over your fence. Unique Design. Each room comes with its own en-suite full bathroom, so there is no need to share bathrooms.
Did we mention we are located 2 miles from 🎠 Disney World ®️ and offer themed rooms.

Languages:

English, French, Spanish, Portuguese

Premier Host

They consistently provide great experiences for their guests
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