Properties are selected based on real traveller reviews and popularity among guests who’ve booked a night in Historic Downtown Kissimmee on Hotels.com. These Historic Downtown Kissimmee hotels consistently deliver on quality, location and traveller experience. Last updated on 14 September 2026.
"The location was perfect for us as my husband had surgery at HCA. Osceola Hospital. House is in a quiet neighborhood close to several restaurants. We did takeout and ate in the dining room. After dinner we sat on the wrap around porch and has a glass of wine to celebrate our anniversary. Tom Kapp made me breakfast the next morning and sat and had breakfast with me and visited. A short but lovely experience."
"The location was perfect for us as my husband had surgery at HCA. Osceola Hospital. House is in a quiet neighborhood close to several restaurants. We did takeout and ate in the dining room. After dinner we sat on the wrap around porch and has a glass of wine to celebrate our anniversary. Tom Kapp made me breakfast the next morning and sat and had breakfast with me and visited. A short but lovely experience."
"We were at the Rosen for a convention. EVERYONE from the hotel was amazing. We could not have had a better experience. Our room was immaculate. Will definitely stay there again!"
"We were at the Rosen for a convention. EVERYONE from the hotel was amazing. We could not have had a better experience. Our room was immaculate. Will definitely stay there again!"
"This hotel is amazing great location, Staff and Front desk are top of it class, I feel like Royal when at this property lots to do . Nice rooms, Beautiful views from the pool to the cabanas . Gym, laundry, meeting room for conferences, computer to use. You hav hammocks as well to relax. Breakfest included with your stay. I call it my 2nd home here. Thank for treating me like family. I will continue to stay here when I need a getaway fom home."
"This hotel is amazing great location, Staff and Front desk are top of it class, I feel like Royal when at this property lots to do . Nice rooms, Beautiful views from the pool to the cabanas . Gym, laundry, meeting room for conferences, computer to use. You hav hammocks as well to relax. Breakfest included with your stay. I call it my 2nd home here. Thank for treating me like family. I will continue to stay here when I need a getaway fom home."
"Very close to Disney Springs. We stayed here for one night before going on the Disney Cruise. Very clean, friendly staff, and next to a restaurant that was convenient. "
"Very close to Disney Springs. We stayed here for one night before going on the Disney Cruise. Very clean, friendly staff, and next to a restaurant that was convenient. "
"Convenient location to Orlando attractions. Continental breakfast was helpful but crowded. A little dinghy in the common areas and bed pillows. No frills but suites our travel purpose."
"Convenient location to Orlando attractions. Continental breakfast was helpful but crowded. A little dinghy in the common areas and bed pillows. No frills but suites our travel purpose."
"We really enjoyed our stay at the Buena Vista Orlando Suites. Very nice & spacious room and kept cleaned daily. Breakfast was good and the staff very inviting and helpful. From Robert in the front to the staff inside We enjoyed speaking with them especially Tammy . Truly a sweetheart .That goes for all on the floor , including the gentleman that came from behind the wall and changeout the trays. We truly recommend this hotel for anyone visiting Orlando . The best part it’s close to Disney...
"We really enjoyed our stay at the Buena Vista Orlando Suites. Very nice & spacious room and kept cleaned daily. Breakfast was good and the staff very inviting and helpful. From Robert in the front to the staff inside We enjoyed speaking with them especially Tammy . Truly a sweetheart .That goes for all on the floor , including the gentleman that came from behind the wall and changeout the trays. We truly recommend this hotel for anyone visiting Orlando . The best part it’s close to Disney...
"Super easy check in and out, hotel was nice for price and it was the perfect location close to a lot of things and in the middle of Orlando and Kissimmee "
"Super easy check in and out, hotel was nice for price and it was the perfect location close to a lot of things and in the middle of Orlando and Kissimmee "
"Easy free self parking , room was clean. Hotel it's close to the Florida mall.
I want to say thank you to Rose, front desk staff for giving the extra mile and be so humble and very friendly."
"Easy free self parking , room was clean. Hotel it's close to the Florida mall.
I want to say thank you to Rose, front desk staff for giving the extra mile and be so humble and very friendly."
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Osceola County Clerk of the Court is worth a pic or two when discovering Historic Downtown Kissimmee. It's also full of great shops and restaurants, so you can spend the afternoon having a wander.
Kissimmee Civic Center is worth a pic or two when discovering Historic Downtown Kissimmee. It's also full of great shops and restaurants, so you can spend the afternoon having a wander.
If you're planning a bit of sightseeing, head to Monument of States – just one of the monuments in Historic Downtown Kissimmee. It's also full of great shops and restaurants, so you can spend the afternoon having a wander.
Historic Downtown Kissimmee is home to Violet's Venom Brewery, so why not stop by during your stay in Kissimmee? Kissimmee has other popular activities, such as ESPN Wide World of Sports Complex.
Historic Downtown Kissimmee is home to First United Methodist Church, so why not stop by during your stay in Kissimmee? It's also full of great shops and restaurants, so you can spend the afternoon having a wander.
The place is wonderful! The environment is friendly and welcoming, and the entire hotel feels brand new. Slept like a baby. Would happily leave a 5-star hotel review. Excellent choice for anyone seeking style and comfort.
Super comfortable beds, an excellent shower, and gorgeous decor. The team was kind and usually smiling. They seemed really interested in making the visit satisfying.
Breakfast was excellent and the staff are so attentive! Thanks to Alejandro and all the staff who made this...
The place is wonderful! The environment is friendly and welcoming, and the entire hotel feels brand new. Slept like a baby. Would happily leave a 5-star hotel review. Excellent choice for anyone seeking style and comfort.
Super comfortable beds, an excellent shower, and gorgeous decor. The team was kind and usually smiling. They seemed really interested in making the visit satisfying.
Breakfast was excellent and the staff are so attentive! Thanks to Alejandro and all the staff who made this...
Superb location and great pool bar area along with the stadium club bar, Will definitely be back 10 out of 10 (only small gripe $34 per day to self park my car)
Superb location and great pool bar area along with the stadium club bar, Will definitely be back 10 out of 10 (only small gripe $34 per day to self park my car)
Really enjoyed my stay at this hotel. The suite was perfect for my needs including a kitchen area, a living room, a nice balcony and even a washing machine and dryer. Even though the hotel is huge I didn’t feel it was during my stay. Based on the spacious pool areas it never felt crowded. The only downside to my stay was the barriers I felt were put in my way upon check in. I’d just arrived from the YK after a long flight and I was tired and just wanted to check in and go to my room to relax but...
Really enjoyed my stay at this hotel. The suite was perfect for my needs including a kitchen area, a living room, a nice balcony and even a washing machine and dryer. Even though the hotel is huge I didn’t feel it was during my stay. Based on the spacious pool areas it never felt crowded. The only downside to my stay was the barriers I felt were put in my way upon check in. I’d just arrived from the YK after a long flight and I was tired and just wanted to check in and go to my room to relax but...
Nice hotel with good amenities in a good location.
Good sized room with big screen TV
Breakfast is decent though the toaster has seen better days !
Would recommend
Nice hotel with good amenities in a good location.
Good sized room with big screen TV
Breakfast is decent though the toaster has seen better days !
Would recommend
Is Historic Downtown Kissimmee expensive to stay in?
You can find great hotels from £31 in Historic Downtown Kissimmee to suit a range of budgets. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Historic Downtown Kissimmee hotels?
Discover great deals on hotels in Historic Downtown Kissimmee with Hotels.com. Sign up for free to unlock member only prices and start earning rewards. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Historic Downtown Kissimmee hotels.
Can I receive a refund if I cancel my Historic Downtown Kissimmee hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Historic Downtown Kissimmee hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
What are some of the best pet-friendly hotels in Historic Downtown Kissimmee?
Travelling with your pet doesn't mean sacrificing a great hotel stay. In Historic Downtown Kissimmee, our travellers love:
To find more pet-friendly stays on Hotels.com, use the "Amenities" filter in your search and select "Pet friendly".
What are some of the top Historic Downtown Kissimmee hotels with free parking?
If you're travelling by car, make your life easier by booking a Historic Downtown Kissimmee hotel with free parking. Our travellers like:
Kapp and Kappy B&B: A bed & breakfast with an average guest rating of 9.8 out of 10
Is it worth staying in Historic Downtown Kissimmee?
You're spoilt for choice with 84 hotels in the area so it's easy to find your perfect somewhere. Basing yourself in Historic Downtown Kissimmee makes it easy to explore Kissimmee, including the areas of Lake Berkley and Bellavida.
Find out more about Historic Downtown Kissimmee
Where Enchantment Meets Heritage: Discover the Allure of Historic Downtown Kissimmee
Historic Downtown Kissimmee is a charming blend of rich history and vibrant culture, inviting visitors to stroll along its picturesque streets. The heart of the area is Kissimmee Main Street, lined with unique shops, delightful eateries, and historic buildings that whisper tales of yesteryear. Don’t miss the iconic Welcome Gate, a gateway to the area's heritage. With its proximity to lush lakes and theme parks, this destination offers a perfect balance of relaxation and excitement. Experience local festivals, art events, and the warm embrace of a community steeped in tradition – Historic Downtown Kissimmee is a treasure waiting to be explored.
Discover great hotels in Historic Downtown Kissimmee
Historic Downtown Kissimmee offers a variety of hotel accommodations, from quaint inns to modern hotels, all within easy reach of local attractions. This area is known for its welcoming atmosphere, making it a great choice for a memorable vacation stay, with plenty of options to suit different budgets. Here are some of the best hotels in Historic Downtown Kissimmee that our travellers love:
Lambert Innopens in new window: This inviting 2.5-star hotel provides a comfortable retreat for leisure travellers looking for convenience and entertainment. With amenities such as a flatscreen television, cable television, and a welcoming atmosphere, it ensures a pleasant stay. Guests have appreciated the engaging entertainment options available, making it a great choice for those seeking a relaxing getaway with easy access to local attractions.
Budget Inn Eastopens in new window: This 2.0-star hotel offers a charming experience for those who relish exploring the nearby attractions, including theme parks and local amenities. With a focus on comfort, it provides essential entertainment options like a television. Visitors have enjoyed the convenient location, which is complemented by accessible services such as a laundromat and proximity to various transport links. This hotel caters perfectly to travellers seeking a delightful base for their adventures.
Flamingo Innopens in new window: This 2.5-star motel presents a relaxed atmosphere with essential amenities for leisure travellers. With entertainment options that include a television, cable television, and premium television channels, it serves as a comfortable spot for unwinding after a day of exploration. Guests have highlighted the motel's inviting environment, making it an excellent choice for those desiring simplicity and ease during their stay in Kissimmee.
Top locations to stay in Historic Downtown Kissimmee
Staying in Historic Downtown Kissimmee places you near SeaWorld® Orlando, Orange County Convention Center, and Disney's Animal Kingdom® Theme Park. SeaWorld® offers thrilling entertainment and festivals, while the Convention Center hosts diverse events. Disney's Animal Kingdom® is ideal for family adventures and immersive experiences. For first-time visitors, staying near Disney's Animal Kingdom® is best, given its unique attractions and iconic status.
Near SeaWorld® Orlandoopens in new window: Staying close to SeaWorld® Orlando means you'll have easy access to thrilling aquatic shows and marine experiences. This vibrant area offers a sunny atmosphere perfect for family-friendly adventures, with plenty of entertainment options, cultural attractions, and shopping venues nearby. Enjoy the lively festivals and take a leisurely stroll around the picturesque lake while soaking up the excitement of the theme park.
Near Orange County Convention Centeropens in new window: If you're looking for a bustling hub of activity, staying near the Orange County Convention Center is a top choice. This area is known for hosting a variety of festivals and events and boasts a rich entertainment scene. You’ll find a great mix of shopping and cultural attractions that will keep you engaged, alongside beautiful outdoor spaces perfect for relaxing after a busy day.
Near Disney's Animal Kingdom® Theme Parkopens in new window: Being near Disney's Animal Kingdom® Theme Park immerses you in a world of wildlife and adventure, with unique experiences that connect you to nature. The surrounding area is equally vibrant, with plenty of opportunities for shopping and cultural attractions. Plus, the enchanting atmosphere of the theme park provides a magical backdrop for your stay.
Things to do near Historic Downtown Kissimmee
Historic Downtown Kissimmee is a delightful blend of charming streets lined with historic buildings and vibrant community life. Stroll through local shops, savour delightful eateries, and enjoy lively festivals. With scenic lakes nearby, indulge in outdoor activities like boating or picnicking, while the arts scene offers theatre and live performances for a memorable experience.
Walt Disney World® Resortopens in new window – Step into a world of magic at this iconic theme park, where you can explore enchanting lands, meet beloved characters, and enjoy thrilling rides. With a stunning array of attractions and entertainment options, there’s something for everyone in the family to experience, from exhilarating roller coasters to charming parades.
Universal Studios Floridaopens in new window – Experience the excitement of the movies at Universal Studios Florida. This theme park brings your favourite films to life with immersive rides and shows. Don’t miss the chance to enter the world of blockbuster hits and enjoy interactive attractions that will keep you on the edge of your seat.
Universal Orlando Resortopens in new window – Discover a larger-than-life adventure at Universal Orlando Resort, where you can enjoy a mix of thrilling rides and entertainment. With themed areas that transport you to different worlds, this resort offers endless fun, from heart-pounding attractions to leisurely strolls through beautifully designed landscapes.
Magic Kingdom® Parkopens in new window – Visit the enchanting Magic Kingdom® Park, where fairy tales come alive. Wander through charming lands, enjoy classic attractions, and witness spectacular fireworks that light up the night sky. This park is a dream come true for families looking to create unforgettable memories together.
4 tips for savvy savings when booking a hotel in Historic Downtown Kissimmee
Book for the cheapest times: The most affordable time to visit Historic Downtown Kissimmee is during August, September, and November, when hotel prices are typically lower. To truly appreciate the area's key landmarks, cultural attractions, and historical sites, it's advisable to plan for at least a 4 to 5-day stay. This budget-friendly duration allows for ample exploration of the local festivals, sunny weather, and various entertainment options, including theatres and shopping. With the possibility that prices could drop during these months, it’s a great value for money for those looking to enjoy sports, birdwatching, and the scenic lakes in the region.
Look for last-minute deals on Hotels.com: To explore last-minute deals to Historic Downtown Kissimmee, you may start by visiting the Dealsopens in new window or Last-Minute Dealsopens in new window sections on Hotels.com, where you could find discounted rates on nearby hotels as your travel date approaches. Enabling email alerts or push notifications can keep you informed about flash sales and special promotions, helping you seize potential savings. Additionally, the Smart Shoppingopens in new window tool available via the app allows you to compare hotel prices and amenities, increasing your chances of finding the best options. With these resources, you’re more likely to be notified of any price drops or room availability for a spontaneous getaway.
Be flexible with dates: Prices can fluctuate based on factors such as the hotel's location, star rating, and the time of year, so being flexible with your dates may help you save on your stay at a hotel in Historic Downtown Kissimmee. For those seeking a distinctive experience, boutique hotels can provide a more personalised touch and potentially better value. When you book through Hotels.com, we will inform you whether the price for your chosen dates is above or below the average. If the price is on the higher side, we can recommend more affordable dates, which could help you secure a better deal.
Consider your location: Opting for accommodation near key attractions or city centres can provide convenience, yet it often comes with elevated costs. For more budget-friendly options, you might consider hotels located in less central areas or neighbourhoods, striking a balance between price and accessibility to the sites you wish to visit. Independent hotels situated further afield usually tend to be more affordable and can offer a more authentic experience.
Best time to go to Historic Downtown Kissimmee
Historic Downtown Kissimmee has a varied climate due to its size, so the best time to visit depends on the region and your preferences for weather and crowds. The peak travel months to visit Historic Downtown Kissimmee are March, July, and December, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by no to moderate rainfall. In contrast, May, September, and October are ideal if you're looking for a calmer vacation, marked by light to moderate rainfall and mostly sunny conditions.