Kissimmee vacation rentals

We found 32,515 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Kissimmee by choosing from 1424 houses, 113 apartments, and other vacation rentals. Vacation homes provide the best amenities for you and your friends, family, or even pets, like WiFi and parking. At the end of the day, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Kissimmee

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Find out more about Kissimmee

Why visit Kissimmee

  • Theme Parks Galore: Kissimmee is your gateway to world-renowned theme parks, including Walt Disney World and Universal Studios, offering thrilling experiences for all ages.
  • Scenic Lakes: Enjoy outdoor adventures like fishing, boating, and picnicking at the beautiful lakes surrounding Kissimmee.
  • Family-Friendly Accommodations: Choose from a variety of vacation rentals, including spacious homes and villas, perfect for family stays.
  • Charming Local Vibe: Experience the warmth of Kissimmee’s friendly community and explore its charming neighborhoods.
  • Outdoor Adventures: Engage in a range of activities from airboat rides to hiking, making it a paradise for nature lovers.

Popular types of accommodation in Kissimmee

If you’re exploring vacation rentals in Kissimmee, you're in for a treat. Our most popular types of accommodations include houses, villas, and condos. Whether you're looking for a cozy house in Kissimmee or a spacious vacation home with a pool, we have options to suit every preference. Enjoy the comforts of home while being just minutes away from Orlando's attractions.

  • Houses: The top choice for travelers in Kissimmee, offering spacious and comfortable stays perfect for families or groups.
  • Villas: A luxurious option that provides ample amenities and private spaces for relaxation and entertainment.
  • Condos: Ideal for those seeking convenience and modern comforts, often located near attractions.
  • Apartments: A practical choice for shorter stays, offering essential amenities in a home-like setting.
  • Cottages: A quaint and charming option, perfect for a cozy getaway with a touch of homey warmth.**

Top attractions in and around Kissimmee

Kissimmee, Florida, offers a fantastic vacation experience suitable for families, business travelers, and entertainment enthusiasts alike. With an array of attractions including theme parks, amusement parks, and scenic lakes, there are plenty of options to explore. Whether you're seeking outdoor adventures, cultural experiences, or just some fun, Kissimmee has something for everyone to enjoy during their stay.

  • Universal Orlando Resort: A thrilling theme park just 13 miles from Kissimmee, offering exciting rides, immersive attractions, and beloved characters from movies. Perfect for family fun and entertainment, it promises unforgettable experiences for guests of all ages.
  • Orange County Convention Center: Located 10 miles away, this vibrant arts center hosts a variety of cultural events and exhibitions. It's an excellent spot for experiencing the local art scene and engaging in community events.
  • Kissimmee Lakefront Park: Situated within Kissimmee, this urban park features beautiful lakeside views, walking trails, and picnic areas, providing a relaxing outdoor space perfect for family outings and city vibes.

Things to do recommended for couples

Discover romance in Kissimmee with a round of mini-golf at Pirate's Island Adventure Golf, enjoy a delightful meal at Pirate's Dinner Adventure, or unwind with a wine tasting at True Blue Winery. Each experience offers a unique blend of fun and intimacy perfect for couples.

Things to do recommended for families

Experience family fun at Aquatica, a thrilling waterpark just 9 miles from Kissimmee. Enjoy sports at Austin-Tindall Regional Park, right in town, or embark on an adventure at Wonderworks, located 11 miles away. Each destination promises excitement and memorable moments for the whole family.

Things to do recommended for groups

In Kissimmee, groups can enjoy shopping and dining at Disney Springs™, just 9 miles away, or explore the vibrant atmosphere of Old Town. For those seeking outdoor fun, Mystic Dunes Golf Club offers a fantastic golfing experience in a beautiful setting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Kissimmee

If you’re traveling with a group, with family, bringing your pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Kissimmee with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Kissimmee with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, keeping in mind how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Kissimmee: For many families, a vacation wouldn’t feel right without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Kissimmee: If you're searching for vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Kissimmee

Kissimmee, Florida, is a vibrant destination perfect for family vacations and entertainment seekers alike. With its sunny weather and friendly atmosphere, you can explore family homes, charming vacation rentals, and beautiful fishing lakes. Nearby regions offer romantic excursions and a welcoming vibe, making it an ideal getaway for everyone. Whether you're looking for fun-filled adventures or a serene escape, Kissimmee has something for every traveler.

  • Orlando: Orlando is a bustling metropolis and a key highlight for travelers visiting Kissimmee. Known for its vibrant family-friendly atmosphere, it offers an array of entertainment-themed experiences and outdoor adventures. Visitors can explore world-famous theme parks like Walt Disney World and Universal Studios, or indulge in shopping at popular malls and outlets. Orlando is also home to stunning arts centers and beautiful parks, making it a perfect destination for those seeking a mix of relaxation and excitement. Don't miss the iconic landmarks such as the Orlando Science Center and the picturesque Lake Eola Park.
  • Four Corners: Four Corners is a charming village located near Kissimmee, ideal for families and outdoor enthusiasts. This community offers easy access to exciting resorts and pristine golf courses, making it a great spot for both relaxation and recreation. With its proximity to major theme parks and sports stadiums, Four Corners provides a unique blend of entertainment and leisure activities. Whether you're hitting the greens or enjoying a family outing at nearby attractions, Four Corners is a welcoming retreat for all types of travelers.
  • Windsor Hills: Windsor Hills is a delightful neighborhood situated around Kissimmee, renowned for its family-oriented atmosphere and entertainment options. This community features luxurious resorts, shopping areas, and excellent golf facilities, catering to visitors looking for fun and relaxation. Windsor Hills is conveniently located near popular theme parks and sports venues, making it easy to experience the best that the area has to offer. Families can enjoy the vibrant community pools and playgrounds, while adults can explore local dining and shopping hotspots.

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to significant savings. Also, extending your stay can often result in better deals. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow your search by price, location, and type of vacation rental.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer truly has its perks. Enroll in our One Key rewards program to enjoy exclusive savings for members and earn OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is designed to help you easily create new trips, manage your plans, and keep track of your bookings. Your saved or booked properties are conveniently organized into categories: Potential, Upcoming, or Current Trips. To discover all the features of Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore Kissimmee from vacation home rentals

Set just south of Orlando in Florida's Osceola County, Kissimmee's population has doubled twice since Walt Disney World opened nearby in 1971. Once a rural outpost where citrus groves and cattle ranches flourished, the city has maintained a sense of the past with a historic downtown, antique shops, and vintage amusement parks. Its sunny weather and wetlands make it a destination for anyone seeking warm temps, whether you prefer a weekend relaxing poolside or a more vigorous outdoor adventure. Its family attractions and close proximity to Disney make it a draw for the young and the young-at-heart.

Historic sites near Kissimmee vacation homes

Kissimmee has numerous historic sites and museums to explore during your trip. Vacation rentals are available near fascinating places like the Museum of Military History, a museum with military relics, photographs, and personal stories, and Osceola County Welcome Center and History Museum, a local history museum with dioramas and interactive exhibits of the county’s history. You can also visit the Monument of the States, a mid-century monument with stones sourced from the 50 states to celebrate American unity.

Places to visit near Kissimmee vacation rentals

Don't list the attractions in Kissimmee out loud to your kids. The excitement might be too much for them. Luckily, the amusements on offer are fun for grown-ups, too. Green Meadows Farm is a peaceful countryside getaway where you can pet the animals, milk a cow, and have a picnic on the grass. Gatorland is a theme park with a playful, vintage feel. There are live animal shows and plenty of alligators in its breeding marsh, and you can buy hot dogs to feed them. Fun Spot America features old-time carnival rides and go-kart tracks.

Activities near Kissimmee vacation homes

Kissimmee's historic downtown is the center of commercial life and offers a mix of family-owned businesses, shops, and restaurants. Consider a Kissimmee vacation rental within walking distance of Main Street, where you can enjoy breakfast at an outdoor cafe before deciding how you'll take in the surrounding wetland wilderness. Eco-tours via horseback, zipline, or airboat are just a few of your options. You'll likely have the chance to spot alligators, black bears, and dozens of bird species. Nighttime helicopter tours over the city provide a unique thrill, as the region's theme park lights twinkle below.

Best time to travel to Kissimmee vacation homes

You don't have to worry about the cold in Kissimmee, even in winter. January temperatures average in the 70s, and skies are typically sunny. The city is crowded during the Christmas holiday but otherwise peaceful, and you might score a Kissimmee vacation rental at a low rate. Spring weather is mild, with highs between the 60s and 80s, and rental prices are still low. Summer is the busy season and also the hottest, so look for lodging with air-conditioning. Temperature-wise, autumn is as lovely as spring, but it's also the height of hurricane season, so check local forecasts.

Blow a kiss to a bald eagle from your Kissimmee kayak

Set on the headwaters of the Everglades, the largest subtropical wilderness in the U.S., and on the northern border of Lake Tohopekaliga, your Kissimmee vacation rental is surrounded by wetlands and animal habitats. Many of these are protected in Nature Conservancy's Disney Wilderness Preserve, 15 miles south of Kissimmee. It's an 11,500-acre home to gopher tortoises, bald eagles, and sandhill cranes. The Shingle Creek Regional Park is another natural wonder, this one right in the city itself, with rivers for kayaking and canoeing, and nature trails for spotting birds.

How to get to and around Kissimmee

The nearest airport is in Orlando Intl. Airport (MCO), located 11.4 mi (18.3 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Kissimmee, FL (ISM-Kissimmee Gateway), which is 1.8 mi (2.9 km) away.

If you're traveling by train, the main station is Kissimmee Station. Consider catching the metro at Tupperware Station or Poinciana Station to see more of the city.

Couple's retreat in Kissimmee vacation homes

Couples will find plenty of romantic experiences and locations in Kissimmee. Vacation homes are available near places like Lake Tohopekaliga, a huge fishing lake with wildlife viewing, airboat rides, and swimming, and Kissimmee Lakefront Park, a waterside park with walking paths and fishing areas. You’ll also enjoy Main Gate Flea Market, an indoor flea market with booths selling clothing, accessories, and other goods.

Frequently asked questions

What is the best area to stay in Kissimmee when booking a vacation rental?
When planning a vacation rental in Kissimmee, Florida, one of the best areas to consider is the Kissimmee Historic District. This charming neighborhood offers a delightful blend of old Florida charm and modern amenities. Staying here gives you easy access to local attractions like the scenic Lake Tohopekaliga, which is great for fishing, boating, and picnicking. Additionally, the district is home to unique shops, cafes, and the vibrant weekly farmer's market, providing a taste of local culture.

Another fantastic option is the Kissimmee Gateway area, which is conveniently located near major highways and provides quick access to the world-renowned theme parks. This area boasts a variety of vacation rentals, making it a popular choice for families and groups. Nearby, you can explore the thrilling attractions of Walt Disney World Resort and Universal Studios, ensuring that your days are filled with excitement and adventure.

If you prefer a more resort-style experience, consider the Formosa Gardens neighborhood. This area features upscale vacation rentals with access to community amenities like pools and clubhouses.
How much does it cost to rent a vacation home in Kissimmee?
Prices for vacation rentals in Kissimmee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Kissimmee to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Kissimmee vacation house rentals?
You can find great discounts on house rentals in Kissimmee on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Kissimmee?
For renting a beach house in Kissimmee, Florida, travelers should consider properties near Lake Tohopekaliga, which offers a scenic waterfront experience. This area features vacation homes with lake access, providing opportunities for fishing and boating. Many of these rentals come equipped with private docks, outdoor grills, and spacious decks, superb for enjoying the Florida sunshine and beautiful sunsets.

Additionally, the community around the nearby Kissimmee Lakefront Park is ideal for those looking to enjoy both nature and recreation. Rentals in this area often include amenities like swimming pools, game rooms, and fully equipped kitchens, suiting families or groups seeking a relaxing getaway. The park itself offers walking trails, picnic areas, and playgrounds, enhancing the family-friendly atmosphere.

While Kissimmee is not directly on the ocean, its proximity to nearby beaches, such as those in Cocoa Beach or the Atlantic Coast, makes it a convenient base for day trips. Travelers can find properties that offer easy access to major highways leading to these coastal areas, ensuring a blend of lakefront relaxation and beach adventures. Find your rental near the beach in Kissimmee.
Are there any houseboat rentals in Kissimmee?
In Kissimmee, travelers can find a selection of houseboat rentals available for a unique vacation experience. These houseboats are typically located near popular attractions such as Lake Tohopekaliga, where guests can enjoy beautiful views and access to various water activities. Most houseboats come equipped with essential amenities, including kitchens for meal preparation, living areas for relaxation, and outdoor decks for soaking up the sun or enjoying evening sunsets. This option allows visitors to immerse themselves in the natural surroundings while still being close to the excitement of nearby theme parks and entertainment venues.
What is the most popular type of vacation rental accomodation in Kissimmee?
In Kissimmee, vacation houses are the most popular type of rental accommodation, with around 12,198 available across the area. These homes are often situated in family-friendly neighborhoods and are designed to cater to large groups or families. Most vacation houses feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for longer stays. Many also come with private pools, outdoor patios, and game rooms for entertainment, allowing guests to relax and enjoy their time together.

Villas are another popular option, with about 3,357 available, offering luxury amenities such as private pools, hot tubs, and gourmet kitchens, often located near major attractions like Walt Disney World and Universal Studios. Condos, apartments, and cottages are available as well, providing additional choices for travelers seeking smaller accommodations.
Are there any family house rentals in Kissimmee?
In Kissimmee, Florida, there are numerous family-friendly house rentals available, with around 14,378 options to choose from. This area is renowned for its proximity to major attractions such as Walt Disney World, Universal Studios, and SeaWorld, making it a great spot for families looking to create lasting memories.

Visitors can find homes in neighborhoods like Windsor Hills and Emerald Island, where many properties feature spacious layouts, private pools, and fully equipped kitchens ideal for family meals. Additionally, game rooms and entertainment areas are common in these rentals, providing fun activities for all ages after a day of exploring the parks.

Kissimmee also offers easy access to local amenities, including shopping centers and restaurants, ensuring that families have everything they need within reach. See all family-friendly rentals in Kissimmee.
Can I rent a vacation home with a pool or hot tub in Kissimmee?
In Kissimmee, there are a vast number of vacation homes available for rent that feature pools and hot tubs, with around 17,440 options to choose from. This popular destination near Orlando is renowned for its proximity to theme parks, making it ideal for families and groups seeking a fun getaway. Neighborhoods such as Windsor Hills and Storey Lake are particularly popular for their vacation rentals, offering resort-style amenities.

Travelers can expect many desirable features in these homes, including private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens that facilitate family meals. Many properties also include game rooms, home theaters, and easy access to community amenities like clubhouses, fitness centers, and playgrounds, ensuring a well-rounded vacation experience. Find your rental in Kissimmee with a pool or a hot tub.
Can I find long-stay vacation rentals in Kissimmee?
A long-stay vacation rental in Kissimmee is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Kissimmee?
In Kissimmee, travelers will find a wide selection of over 3,000 pet-friendly house rentals, making it an ideal destination for those looking to vacation with their furry friends. Many of these rentals are situated in close proximity to popular attractions such as Walt Disney World and Universal Studios, ensuring convenience for families and groups. Expect amenities like private pools, fully equipped kitchens, and spacious living areas, which enhance the comfort of your stay.

The neighborhood surrounding Lake Tohopekaliga offers beautiful views and opportunities for outdoor activities, including dog-friendly parks where pets can enjoy some fresh air. Additionally, the nearby Shingle Creek Regional Park features trails that are superb for leisurely walks with your pet, providing a nice escape into nature without straying too far from your accommodations. See all pet-friendly rentals in Kissimmee.
Are there any remote work vacation rentals in Kissimmee?
In Kissimmee, there is a substantial selection of remote work vacation rentals available, with around 17,478 options for travelers. This area is well-suited for those who need to blend work and leisure, as many properties come equipped with essential amenities such as Wi-Fi, dedicated office spaces, and comfortable workstations. You can expect features like desks, ergonomic chairs, and in some cases, even computer monitors to facilitate productivity during your stay.

Kissimmee is conveniently located near popular attractions like Walt Disney World and Universal Studios, offering plenty of opportunities to unwind after work. The neighborhood includes a mix of modern condos and spacious homes, often with amenities like pools, game rooms, and outdoor areas, making it an ideal environment for families or professionals seeking a balance of work and play. Additionally, many rentals provide access to business centers and meeting rooms, ensuring ample resources are available for any remote work needs. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Kissimmee vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Kissimmee with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Kissimmee?
In Kissimmee, popular rental amenities cater to families and groups looking for a comfortable stay. Most vacation rentals come equipped with WiFi, allowing guests to stay connected during their trip. Kitchens are standard, providing the convenience of preparing meals at home. Many properties feature private pools, with a significant number also offering heated pools, ensuring a pleasant swimming experience year-round.
When is the best time to visit Kissimmee for a vacation rental?
The best time to visit Kissimmee for a vacation rental is during the peak season from June to August, particularly in July when the area comes alive with vibrant energy. This summer period is great for families and adventure seekers looking to enjoy the world-famous theme parks, outdoor activities, and abundant sunshine that Kissimmee has to offer.

During these months, expect warm temperatures ranging from the mid-70s to the low 90s Fahrenheit, providing ideal conditions for exploring attractions like Walt Disney World and Universal Studios. The long daylight hours also make it convenient for sightseeing and enjoying outdoor adventures, such as airboat rides in the nearby wetlands or leisurely strolls through local parks and nature reserves.

For those who prefer a quieter experience and are looking for better value, October is an excellent time to visit. The weather remains pleasantly warm, with temperatures typically in the mid-70s to low 80s Fahrenheit, and the crowds are significantly reduced.
How early should I book a Kissimmee vacation rental?
Book your Kissimmee vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Kissimmee?
In Kissimmee, visitors can enjoy a variety of attractions that cater to different interests. The area is renowned for its proximity to major theme parks, with Walt Disney World Resort just a short drive away, offering iconic attractions such as Magic Kingdom and Epcot. Vacation rentals in Kissimmee often provide convenient access to these parks, making it an ideal base for families.

For those interested in outdoor activities, Lake Tohopekaliga is a beautiful spot for fishing, boating, and wildlife viewing, and properties nearby often feature scenic lake views and easy access to recreational facilities. Additionally, the Old Town entertainment district in Kissimmee is lively, with shops, restaurants, and amusement rides, creating a fun atmosphere for visitors.

The nearby Kissimmee Prairie Preserve State Park offers breathtaking natural landscapes and opportunities for stargazing, making it superb for nature enthusiasts.
Can I change or cancel my Kissimmee home rental booking on Vrbo?
To find Kissimmee vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Kissimmee vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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