Historic Downtown Kissimmee vacation rentals

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Discover a selection of 63 homes and other vacation rentals in Historic Downtown Kissimmee that are perfect for your trip. 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 is accessible or non-smoking.

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Find out more about Historic Downtown Kissimmee

Find out more about Historic Downtown Kissimmee

Why visit Historic Downtown Kissimmee

  • Family-friendly activities: Enjoy a range of attractions suitable for all ages, from theme parks to outdoor adventures.
  • Charming neighborhoods: Explore local neighborhoods for an authentic taste of Kissimmee's vibrant culture.
  • Diverse accommodations: Choose from a variety of vacation rentals, including cozy apartments and private homes.
  • Rich history: Discover the unique historical significance that enriches the atmosphere of downtown Kissimmee.
  • Outdoor experiences: Take advantage of nearby lakes and parks for relaxation and recreational activities.

Popular types of accommodation around Historic Downtown Kissimmee

Historic Downtown Kissimmee offers a diverse selection of vacation rentals, perfect for any traveler. Choose from houses, villas, and condos that cater to your needs. Whether you're searching for Kissimmee apartments, downtown Kissimmee apartments for rent, or cozy studio apartments, you'll find the ideal accommodation to enhance your stay. Discover the charm and convenience of this vibrant area while enjoying the comfort of your home away from home.

  • Houses: The top choice for visitors in Historic Downtown Kissimmee, offering spacious accommodations ideal for families or groups.
  • Villas: A close second, these luxurious properties provide a blend of comfort and style for a relaxing getaway.
  • Condos: Popular for their convenience and amenities, condos are a great option for couples or small families.
  • Apartments: A practical choice, perfect for travelers seeking a home-like atmosphere during their stay.
  • Cottages: Charming and cozy, cottages offer a quaint retreat in the heart of Kissimmee.**

Top attractions in and around Historic Downtown Kissimmee

Historic Downtown Kissimmee is perfect for family vacations and entertainment seekers alike. Visitors can enjoy nearby theme parks, lakes, and amusement parks, offering a mix of outdoor and cultural experiences. Explore the charm of the area and discover local neighborhoods for an authentic taste of Kissimmee. Make the most of your trip by diving into the vibrant attractions this historic downtown has to offer.

  • Universal Orlando Resort: A thrilling theme park 13 miles from Historic Downtown Kissimmee, offering exciting rides, shows, and attractions based on popular movies. It's a family-friendly destination where visitors can immerse themselves in the magic of entertainment.
  • Orange County Convention Center: Located 10 miles away, this vibrant arts center showcases a variety of cultural events, exhibitions, and performances, making it a hub for art enthusiasts and community gatherings.
  • Kissimmee Lakefront Park: Situated within Historic Downtown Kissimmee, this urban park features scenic views of the lake, walking trails, and playgrounds, creating a perfect space for families to enjoy the outdoors and city ambiance.

Things to do recommended for couples

Get ready for a romantic getaway in Historic Downtown Kissimmee. Enjoy a fun round of mini-golf at Pirate's Island Adventure Golf, savor a delightful dinner at Pirate's Dinner Adventure, and experience the thrill of indoor skydiving at iFly Orlando. Perfect for couples seeking adventure and romance.

Things to do recommended for families

Families visiting Historic Downtown Kissimmee can splash around at Aquatica waterpark, enjoy thrilling sports at ESPN Wide World of Sports Complex, and explore the fun-filled Wonderworks arcade. These attractions promise adventure and excitement for all ages within a short drive.

Things to do recommended for groups

Group travelers in Historic Downtown Kissimmee can enjoy shopping at Disney Springs™, only 9 miles away, experience the lively atmosphere at Old Town, 7 miles away, and immerse themselves in a captivating show at Medieval Times, just 4 miles away, for a memorable local adventure.

*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 around Historic Downtown Kissimmee

When traveling with a group, family, pets, or planning for extended stays, it's important to prioritize your preferences when searching. Here are some helpful booking tips for using Vrbo.

  • Traveling to Historic Downtown Kissimmee with a group: Think about how many bedrooms you'll require, as well as any amenities you might want, like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Historic Downtown Kissimmee with young kids: Traveling with little ones can be tough. It's important to prioritize their comfort and safety, along with age-appropriate features like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Historic Downtown Kissimmee: For many, a family vacation isn’t truly complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Historic Downtown Kissimmee: If you’re in search of vacation rentals offering discounts 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Historic Downtown Kissimmee

Historic Downtown Kissimmee offers a vibrant mix of family-friendly activities and charming excursions, perfect for an unforgettable vacation. Visitors can explore lively neighborhoods filled with entertainment and relaxation, all under the sunny Florida skies. With nearby areas to discover and a variety of accommodations, including cozy apartments for rent, Kissimmee is an ideal destination for romantic getaways, business trips, or family fun. Experience the unique atmosphere and rich history that make this city truly special.

  • Orlando: Orlando, a bustling metropolis, is the heartbeat of Central Florida and a well-known family vacation destination. With its world-renowned theme parks, including Walt Disney World and Universal Studios, visitors can immerse themselves in thrilling rides and magical experiences. The city also boasts vibrant shopping areas, diverse dining options, and a rich arts scene, making it ideal for entertainment lovers. Don't forget to explore the beautiful parks and outdoor spaces that offer a refreshing escape from the excitement of the attractions.
  • Kissimmee: Kissimmee is a charming city located adjacent to Historic Downtown Kissimmee, offering a blend of family-friendly activities and entertainment options. With its proximity to major theme parks and shopping centers, visitors can easily access a variety of attractions, including the famed Old Town entertainment district. Kissimmee is also known for its beautiful lakes and outdoor adventures, perfect for those seeking a balance of relaxation and excitement. Whether you're dining at local eateries or enjoying a day at a nearby resort, Kissimmee is a delightful destination for all.
  • Mill Run: Mill Run is a peaceful neighborhood just a couple of miles from Historic Downtown Kissimmee, offering a family-oriented atmosphere with plenty of outdoor activities. This area features resorts, an entertainment arena, and golf courses, making it a great spot for both relaxation and recreation. Visitors can easily access nearby theme parks and stadiums, ensuring a fun-filled vacation. The community's friendly vibe and outdoor spaces provide an excellent backdrop for creating lasting memories with loved ones.

Best time to go to Historic Downtown Kissimmee

If you're planning a trip to Historic Downtown Kissimmee, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.6°F (15.9°C)Light RainMostly SunnyAverageAverage
February64.4°F (18.0°C)Light RainMostly SunnySlightly HighSlightly Low
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
April72.7°F (22.6°C)Light RainMostly SunnyAverageAverage
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageSlightly High
July82.4°F (28.0°C)Moderate RainMostly SunnySlightly HighSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageAverage
September80.4°F (26.9°C)Moderate RainMostly SunnySlightly LowSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowSlightly Low
November68.5°F (20.3°C)Light RainMostly SunnySlightly LowAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? Being flexible with your travel dates can help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Plan your group getaway by booking an eligible Vrbo, and you'll earn OneKeyCash on your reservation. Being the planner has its perks. When you join our travel rewards program, One Key, you'll gain immediate access to member discounts and the opportunity to earn and redeem OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy and organized way to plan your journeys. You can create new trips, resume planning from where you left off, or manage your existing itineraries all in one place. Your saved or booked properties will be neatly sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, vacation houses are the most popular type of rental accommodation, with about 26 available throughout the area. These houses often feature spacious interiors with multiple bedrooms, fully equipped kitchens, and private outdoor spaces, making them ideal for families or groups looking for a comfortable home base. Additionally, several villas, apartments, and condos can be found, providing travelers with a variety of options to suit different preferences. Many of these properties are located near local attractions, restaurants, and parks, allowing guests to easily explore the vibrant downtown atmosphere.
Are there any beach house rentals in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, there are about 12 beach house vacation rentals available. These properties are often located near the vibrant downtown area, providing easy access to local shops, restaurants, and attractions. Most beach houses feature amenities that include spacious living areas, fully equipped kitchens, and outdoor spaces for dining and relaxation. Some may also offer private pools or direct access to nearby parks, making them suitable for families or groups looking to enjoy a comfortable stay in a lively setting.
How much does it cost to rent a vacation home in Historic Downtown Kissimmee?
Prices for vacation rentals in Historic Downtown 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 Historic Downtown 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 Historic Downtown Kissimmee vacation house rentals?
You can find great discounts on house rentals in Historic Downtown 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.
What are popular rental amenities in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, travelers can expect a variety of popular rental amenities that enhance their stay. Many vacation rentals feature fully equipped kitchens, allowing guests to prepare meals at their convenience. A significant number of properties also include private pools, with some offering heated options for year-round enjoyment. Additionally, outdoor patios are common, providing a great space to relax and unwind after exploring nearby attractions.
Are there any family house rentals in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, there are around 12 family-friendly house rentals available, making it a great choice for families looking for a memorable getaway. This charming area features spacious homes with amenities such as large living rooms, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and adults can relax. Many properties also offer conveniences like Wi-Fi and air conditioning to ensure a comfortable stay.

Visitors can explore the vibrant local culture, with attractions like the Kissimmee Lakefront Park and the historic district, which is filled with shops and dining options. Additionally, the proximity to theme parks like Walt Disney World and Universal Studios makes this locale especially appealing for families seeking both relaxation and adventure.
Can I rent a vacation home with a pool or hot tub in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, travelers can find a variety of vacation homes available for rent that feature pools and hot tubs, with around 23 options to choose from. This charming area is known for its proximity to local attractions and vibrant community atmosphere. Many of the properties come equipped with private pools, hot tubs, and spacious outdoor areas ideal for relaxation and entertainment.

In addition to these amenities, guests can expect well-appointed interiors, often including full kitchens for home-cooked meals, cozy living spaces, and easy access to nearby restaurants and shops.
Are there any Historic Downtown Kissimmee vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Historic Downtown 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.
Are there pet-friendly vacation rentals in Historic Downtown Kissimmee?
Yes, you can book pet-friendly vacation rentals in Historic Downtown Kissimmee. This vibrant area offers several vacation rentals that cater to pet owners, providing a welcoming environment for your furry friends. Many of these rentals come equipped with essential amenities such as full kitchens, comfortable living spaces, and outdoor areas where pets can enjoy some fresh air.

The neighborhood is conveniently located near various parks and recreational areas, making it easy to take your pets for walks or playtime. Nearby parks typically feature open spaces and walking trails suitable for pets, adding to the overall appeal of staying in this historic area.
Can I find long-stay vacation rentals in Historic Downtown Kissimmee?
A long-stay vacation rental in Historic Downtown 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.
When is the best time to visit Historic Downtown Kissimmee for a vacation rental?
The best time to visit Historic Downtown Kissimmee for a vacation rental is during the peak season from January to March. This period is particularly popular among travelers seeking a warm escape, as temperatures typically range from the mid-50s to the low 80s Fahrenheit, making it ideal for outdoor activities and exploring the vibrant downtown area.

During these months, visitors can enjoy various attractions, including the nearby theme parks and the charming shops and restaurants lining the historic streets. January stands out as the most popular month, with many events and festivities taking place, providing a lively atmosphere superb for those looking to immerse themselves in the local culture.

If you're looking for a more budget-friendly option, consider visiting in November. This quieter time of year offers comfortable weather and the chance to explore Kissimmee's outdoor spaces without the crowds. You can enjoy leisurely walks along Lake Tohopekaliga and take in the beautiful scenery at a more relaxed pace.

Ultimately, your choice depends on whether you prefer the vibrant energy of the peak season or the tranquil charm of the shoulder months.
Are there any remote work vacation rentals in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, travelers will find a variety of remote work-friendly vacation rentals, with around 31 options available. This vibrant area offers a blend of historical charm and modern amenities, making it an ideal setting for those looking to balance work and leisure. Many of these accommodations are equipped with essential remote work amenities, including high-speed Wi-Fi, dedicated office spaces, desks, and comfortable chairs, providing a conducive environment for productivity. Some properties may even feature computer monitors to enhance the remote work experience.

Additionally, guests can enjoy the local attractions, such as the Kissimmee Lakefront Park, which offers beautiful views and recreational activities just a short distance away. The area is also rich in dining options and shops, adding convenience for longer stays. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Historic Downtown Kissimmee vacation rental?
Book your Historic Downtown 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 Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, visitors can enjoy a variety of attractions that showcase the area's charm and history. The vibrant Main Street is lined with quaint shops, local eateries, and cafes, making it a great spot for leisurely strolls. The Kissimmee Lakefront Park offers scenic views of Lake Tohopekaliga and features walking trails, picnic areas, and a playground, superb for families. Additionally, the nearby Osceola County Historical Society offers insights into the local heritage with its museum and historic buildings. The area also hosts various community events throughout the year, enhancing the lively atmosphere.
Can I change or cancel my Historic Downtown Kissimmee home rental booking on Vrbo?
To find Historic Downtown 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Historic Downtown 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.

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