Historic Downtown Kissimmee vacation rentals

We found 38 vacation rentals — enter your dates for availability

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

  1. Family-Friendly Fun: Enjoy a variety of attractions that cater to all ages, perfect for family vacations.
  2. Charming Streets: Stroll through picturesque streets lined with unique shops and delightful restaurants.
  3. Cultural Experiences: Immerse yourself in vibrant local culture and arts centers that showcase the community’s creativity.
  4. Outdoor Adventures: Explore beautiful lakes and parks for outdoor activities and relaxation under the Florida sun.
  5. Variety of Accommodations: Choose from a range of vacation rentals, including cozy homes and spacious villas.

Popular types of accommodation around Historic Downtown Kissimmee

Planning a getaway to Historic Downtown Kissimmee? The excitement begins with selecting your perfect home away from home! Explore a variety of vacation rentals, from charming houses and spacious villas to cozy condos. Whether you're looking for downtown Kissimmee houses, apartment listings, or rentals nearby, you'll find a range of options to suit your needs and budget. Dive into our listings and discover the ideal base for your adventure!

  • Houses: These are the top choice for visitors seeking spacious accommodations, ideal for families or groups looking to enjoy a home-like atmosphere in Historic Downtown Kissimmee.
  • Villas: A popular option for those desiring luxurious amenities and private outdoor spaces, perfect for a relaxing getaway in Kissimmee.
  • Condos: A favored selection for travelers wanting convenient access to local attractions while enjoying the comforts of home.
  • Apartments: Great for solo travelers or couples, offering a cozy setting close to the action of Downtown Kissimmee.
  • Cottages: Charming and quaint, these accommodations provide a unique, cozy escape in a picturesque setting.**

Top attractions in and around Historic Downtown Kissimmee

Historic Downtown Kissimmee is perfect for family-oriented and entertainment-themed vacations. Visitors can explore a mix of attractions, including theme parks, beautiful lakes, and vibrant arts centers. The area offers a variety of points of interest catering to travelers seeking family fun, outdoor adventures, and cultural experiences, making it a delightful destination for all ages.

  1. SeaWorld® Orlando: A thrilling theme park that offers captivating marine life exhibits, exhilarating rides, and entertaining shows. With a focus on family fun, it provides an immersive experience that combines education and entertainment, making it a must-visit destination for visitors of all ages.
  2. Orange County Convention Center: A vibrant arts center that hosts various cultural events, exhibitions, and conferences. This venue is known for its impressive architecture and lively atmosphere, making it a hub for art enthusiasts and event-goers.
  3. Kissimmee Lakefront Park: A beautiful urban park located right in Historic Downtown Kissimmee, perfect for family outings. With scenic views, walking trails, and recreational activities, it offers a relaxing outdoor space that captures the essence of city life.

Things to do recommended for couples

Experience romance in Historic Downtown Kissimmee! Enjoy a fun round at Congo River Golf, savor a delightful meal at Pirate's Dinner Adventure, and feel the thrill of iFly Orlando. Each activity promises unforgettable moments together, surrounded by adventure and charm.

Things to do recommended for families

Your family will have a blast in Historic Downtown Kissimmee! Enjoy thrilling races at Kissimmee Go-Karts, dive into fun at Aquatica waterpark, and experience the excitement of sports at the ESPN Wide World of Sports Complex, all within a short drive from downtown.

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

When planning your trip, whether you're traveling with a group, family, pets, or looking for extended stays, be sure to prioritize your preferences with the right filters. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Historic Downtown Kissimmee with a group: Think about how many bedrooms you require, as well as any additional features like a complete kitchen or outdoor area for group activities. Thankfully, you can easily apply filters for these options and more on Vrbo.
  • Traveling to Historic Downtown Kissimmee with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can be very beneficial.
  • Taking your pets with you to Historic Downtown Kissimmee: For many families, a vacation wouldn't be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many pet-friendly properties come equipped with feeding bowls and beds, ensuring that both you and your pets feel comfortable and at home.
  • Planning for a long term stay visiting Historic Downtown Kissimmee: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the perfect 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 criteria as well.

Where to stay near Historic Downtown Kissimmee

Exploring Historic Downtown Kissimmee offers a delightful blend of family-friendly activities and vibrant local culture. Stroll through charming streets filled with unique shops and restaurants, and soak in the sunny Florida weather. Nearby neighborhoods provide opportunities for excursions and romantic getaways, making it a perfect destination for any traveler. Whether you're visiting the City of Kissimmee or simply enjoying the lively atmosphere, there's something for everyone in this enchanting locale.

  • Mill Run: Located 2 miles from Historic Downtown Kissimmee, Mill Run is a vibrant neighborhood perfect for families and outdoor enthusiasts. This area offers a blend of entertainment options, including a popular arena entertainment facility and nearby golf courses. Visitors can easily access local landmarks such as theme parks and stadiums, making it a great hub for adventure. Whether you're looking to enjoy a day at the resort or catch an exciting event, Mill Run provides a variety of experiences that cater to all ages.
  • Magic Landings: Situated 3 miles from Historic Downtown Kissimmee, Magic Landings is an engaging neighborhood known for its family-friendly atmosphere and outdoor activities. The area boasts an array of accessible venues, including a golf course and an arena entertainment facility. With its proximity to major attractions like stadiums and theme parks, Magic Landings is a fantastic destination for those seeking a mix of leisure and excitement. Enjoy a day filled with fun activities, and unwind at one of the local resorts after an adventure-filled day.
  • Venetian Bay Villages: Also located 3 miles from Historic Downtown Kissimmee, Venetian Bay Villages is a charming neighborhood that offers a blend of relaxation and entertainment. Families will love the accessible golf courses and resorts, making it an ideal spot for a getaway. Nearby attractions include theme parks and beautiful beaches, providing plenty of options for exploration. Whether you're interested in golfing or simply enjoying the picturesque surroundings, Venetian Bay Villages promises a delightful experience for all visitors.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, use our handy filters to search by price, location, and type of vacation rental. We're here to help you find the best options!

Unlock savings with One Key

When you book a qualifying Vrbo for your group getaway, you'll earn OneKeyCash™ on the full amount of your reservation. It's a great advantage to be the organizer! Sign up for our One Key rewards program to unlock exclusive member discounts and accumulate OneKeyCash™ on eligible stays. Join today and begin earning rewards!

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient platform for you to plan new trips, manage your existing travel arrangements, and keep track of your bookings. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/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.

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