Historic Downtown Kissimmee vacation rentals

We found 38 vacation rentals — enter your dates for availability

Discover a selection of 6 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

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.

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 dominate the rental scene, with about 27 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many come with private outdoor spaces, great for enjoying the warm Florida weather after a day of exploring local attractions. Additionally, several villas, apartments, and condos can be found, providing further options for travelers seeking different styles of accommodation.
Are there any beach house rentals in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, there are several beach house rentals available, offering visitors a unique way to experience this charming area. These vacation homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and cozy living areas. Many properties also include outdoor spaces such as patios or gardens, great for relaxing after exploring the nearby attractions. Located within a short drive from local points of interest like Lake Tohopekaliga and the vibrant shops and restaurants in downtown Kissimmee, these rentals provide a comfortable and convenient base for travelers. Find your rental near the beach in Historic Downtown Kissimmee.
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, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their meals conveniently. Many properties also feature coffee and tea makers for a quick morning pick-me-up. Onsite parking is a significant advantage, making it easy for travelers with vehicles to explore the area without hassle. Additionally, several rentals offer patios where guests can enjoy the warm Florida weather and relax outdoors. For those looking to maintain their fitness routine while away, some properties provide access to fitness facilities, ensuring a well-rounded stay.
Can I find family house rentals in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, families will find a variety of rental homes available, with about 13 options to choose from. This area is rich in charm and conveniently located near numerous attractions. Many of these properties feature spacious living rooms for family gatherings, fully equipped kitchens for preparing meals, and outdoor spaces superb for children to play in.

Visitors can enjoy easy access to nearby points of interest, including the vibrant Old Town entertainment complex, which offers dining, shopping, and amusement rides, as well as the scenic Lake Tohopekaliga, ideal for outdoor activities like fishing and picnicking.
Can I rent a vacation home with a pool or hot tub in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, there are plenty of vacation homes available for rent that feature both pools and hot tubs, with around 24 options to choose from. This charming area offers a mix of convenience and comfort, making it an ideal destination for travelers. Many of the rentals are equipped with private pools, spacious outdoor areas for relaxation, and hot tubs, superb for unwinding after a day of exploring the local attractions.

Travelers can expect amenities such as fully equipped kitchens, cozy living spaces, and proximity to local dining and shopping options. The historic charm of downtown also allows for easy access to nearby parks and recreational areas, providing a well-rounded vacation experience. Find your rental in Historic Downtown Kissimmee with a pool or a hot tub.
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.
Can I book pet-friendly vacation rentals in Historic Downtown Kissimmee?
Yes, you can find several pet-friendly vacation rentals in Historic Downtown Kissimmee. This area offers a charming blend of historic architecture and modern amenities, making it an appealing destination for travelers with pets. Many of these rentals typically feature spacious layouts, fully equipped kitchens, and outdoor spaces where pets can enjoy some fresh air.

The proximity to local parks and green spaces enhances the experience, with options such as the nearby Kissimmee Lakefront Park, which offers walking trails, picnic areas, and scenic views of the lake, superb for leisurely strolls with your furry companions. Additionally, the vibrant downtown area boasts various pet-friendly cafes and shops, ensuring that both you and your pet can enjoy your stay to the fullest.
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 to enjoy the pleasant weather and vibrant setting that Kissimmee has to offer. With temperatures typically ranging from the mid-50s to the low 80s Fahrenheit, visitors can comfortably explore the area's charming streets, local shops, and nearby attractions.

January stands out as the most popular month for travelers, making it an ideal time for those who thrive on lively social scenes and a plethora of activities. During this time, outdoor events and festivals abound, providing ample opportunities to immerse oneself in Kissimmee's culture and community. This is also a great time to enjoy the scenic beauty of the surrounding parks and lakes, superb for outdoor activities like hiking, biking, or simply enjoying a leisurely stroll.

For those seeking a more budget-friendly experience, November offers a quieter alternative. During this month, the crowds are thinner, allowing for a more relaxed exploration of the historic downtown area. Visitors can take advantage of lower rental prices while still enjoying the charming ambiance and local attractions.
Are there any remote work vacation rentals in Historic Downtown Kissimmee?
In Historic Downtown Kissimmee, there are numerous remote work vacation rentals available, with around 33 options to choose from. This area is well-suited for remote workers due to its vibrant setting and proximity to essential amenities. Many of these rentals offer dedicated workspaces, ensuring a comfortable and productive environment. Additionally, travelers can expect free Wi-Fi both in their rooms and in public areas, making it easy to stay connected.

The neighborhood is rich in history and charm, with plenty of dining and shopping options within walking distance. You can enjoy local cafes and restaurants that offer a superb break from work. The nearby Lake Tohopekaliga offers scenic views and recreational activities, providing a nice balance between work and leisure. 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, Florida, United States of America?
Historic Downtown Kissimmee is rich in charm and offers several attractions for visitors. The area features the Kissimmee Lakefront Park, which boasts scenic views of Lake Tohopekaliga, walking trails, and picnic spots, making it a great place for outdoor activities. The park is also home to a playground and a fishing pier, attracting families and nature enthusiasts alike.

Nearby, you can explore the vibrant local shops, antique stores, and restaurants along Main Street, which reflect the area's historical roots. The Osceola County Historical Society offers insights into the region's history, and the Kissimmee Historic District showcases beautiful architecture from the early 20th century.

Additionally, the area hosts various events and festivals throughout the year, providing a lively option for visitors looking to experience local culture.
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 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 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.
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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