Hotels in Historic Downtown Kissimmee

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Where to stay in Historic Downtown Kissimmee?

Properties are selected based on real traveler 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 traveler experience. Last updated on October 12, 2026.

A covered porch with wooden chairs and a ceiling fan.

A living room with a sofa, chairs, a coffee table, a TV, and a kitchen in the background.

A dining table set with red placemats, golden decorative bowls, and a fruit platter.

A building with a flat roof and a covered porch area.

1. Kapp and Kappy B&B

Historic Downtown Kissimmee

"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."

Judith

CNY953

CNY1,081 total

includes taxes & fees

Oct 13 - Oct 14

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

A spacious outdoor area with multiple white tables and planters, a central digital display, and a modern architectural design.

An outdoor dining area with round tables covered in foliage, surrounded by chairs, and a stone wall with plants.

A spacious lobby with a leather sofa, a bar area with stools, and a seating area with tables and chairs.

2. Embassy Suites by Hilton Orlando Lake Buena Vista South

8.7 km from Historic Downtown Kissimmee

Corrida

CNY734

CNY833 total

includes taxes & fees

Oct 18 - Oct 19

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

An outdoor patio area with wicker furniture, red accents, and palm trees.

A modern hotel lobby with seating areas, tables, and decorative wall panels.

A water play area with multiple fountains and colorful play structures.

3. Drury Plaza Hotel Orlando - Disney Springs Area

13.8 km from Historic Downtown Kissimmee

Paul

CNY1,223

CNY1,376 total

includes taxes & fees

Oct 25 - Oct 26

A multi-story hotel with a swimming pool, outdoor seating, and a landscaped area.

A hotel room with two beds, a desk, a chair, a window with a view of a theme park, and a bedside table with a phone and a clock.

A hotel room with a bed, a blue sofa, a bedside table with a lamp, a microwave, a coffee maker, and a framed abstract painting.

A coffee station with two coffee machines and a variety of coffee pods and cups.

4. Holiday Inn Express & Suites Orlando at SeaWorld by IHG

13.7 km from Historic Downtown Kissimmee

Osiris

CNY589

CNY663 total

includes taxes & fees

Oct 28 - Oct 29

A hotel with a large pool, palm trees, and a waterfall feature.

A bar area with a variety of seating options, including patterned chairs and stools, a bar counter with bottles, and a large mirror on the wall.

A hotel lobby with a reception desk, seating area, and a staircase leading to upper floors.

A spacious dining area with a long table set for a meal, surrounded by chairs.

5. Caribe Royale Orlando, WorldHotels Elite

11.1 km from Historic Downtown Kissimmee

Courtney

CNY1,265

CNY1,709 total

includes taxes & fees

Oct 30 - Oct 31

An outdoor patio area with seating, a bar, and a fire feature.

A swimming pool with lounge chairs and umbrellas, surrounded by a multi-story building with balconies.

A modern bar area with a long counter, bar stools, and a seating area with tables and chairs.

A hotel room with two beds, a desk, a chair, a lamp, and two paintings on the wall.

6. Hyatt House Orlando Airport

20.3 km from Historic Downtown Kissimmee

Carol

CNY803

CNY904 total

includes taxes & fees

Nov 3 - Nov 4

A hotel lobby with a long corridor, modern lighting, and large abstract wall art.

A modern living room with a grey sofa, round ottomans, a coffee table, and a dining area with chairs and a table.

7. Hyatt Regency Grand Cypress

14.3 km from Historic Downtown Kissimmee

carla

CNY1,078

CNY1,589 total

includes taxes & fees

Oct 28 - Oct 29

A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

An outdoor seating area with wicker furniture, a central wooden table, and a red brick wall with potted plants.

A hotel with a swimming pool, multiple parking spaces, and a view of the surrounding area.

A hotel room with a bed, a sofa, a coffee table, a TV, and a desk with a computer.

8. Seasons Florida Resort

7.2 km from Historic Downtown Kissimmee

Lina

CNY300

CNY341 total

includes taxes & fees

Oct 14 - Oct 15

A breakfast area with a counter displaying hard-boiled eggs, fruits, and muffins. There are two stools and a sign reading "TOP IT BREAKFAST".

A rooftop bar with round tables, a pool, and outdoor seating.

A pool table in a room with a mural of Orlando landmarks, a blue sofa with colorful cushions, and a bulletin board with local information.

9. Tru By Hilton Orlando Convention Center Area, FL

15.3 km from Historic Downtown Kissimmee

Tracey

CNY563

CNY634 total

includes taxes & fees

Oct 28 - Oct 29

An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

A spacious living room with a large window, a sofa set, a coffee table, and a television.

A view through a large window of a resort with a pool, palm trees, and a building in the background.

A hotel with multiple floors, a swimming pool, and palm trees.

10. Wyndham Grand Orlando Resort Bonnet Creek

14.5 km from Historic Downtown Kissimmee

Jennifer

CNY830

CNY1,250 total

includes taxes & fees

Oct 29 - Oct 30

A modern hotel with "La Quinta" signage, featuring a prominent entrance and a covered outdoor area.

A modern kitchen with dark wood cabinets, stainless steel appliances, and pendant lighting.

A hotel room with two beds, a desk, and a large window offering a view of buildings and greenery.

A modern gym with treadmills, exercise mats, and a fitness display.

11. La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

12.7 km from Historic Downtown Kissimmee

"The staff was friendly and professional quite helpful when inquiring about places to shop. The hotel is beautiful. The breakfast was good. They had great water pressure and air conditioning work great in the Florida heat. The parking can be challenging if you spend the entire day at the theme parks however you will find a place even if all the spaces are taken. (curbside around the property) it works."

Sherry

CNY596

CNY671 total

includes taxes & fees

Oct 20 - Oct 21

A modern restaurant with multiple dining tables and chairs, a bar area, and a television mounted on the wall.

A hot tub with a waterfall mural, a metal ladder, and a tiled floor.

A modern lounge area with a sofa set, ottomans, and a small table.

A modern hotel room with a large white bathtub, a neatly made bed, and a small bedside table with a lamp.

12. Wingate by Wyndham - Orlando International Airport

21.1 km from Historic Downtown Kissimmee

Lydia

CNY596

CNY671 total

includes taxes & fees

Oct 14 - Oct 15

A hotel with a central entrance, palm trees, and a clear sky.

A multi-story hotel with a swimming pool surrounded by palm trees and greenery.

A hotel room with two beds, a large window with curtains, an air conditioning unit, and a bedside table with a lamp.

A hotel room with a bed, a sofa, a coffee table, and a desk. There are three framed pictures on the wall.

13. Comfort Suites Maingate East

11.3 km from Historic Downtown Kissimmee

Wendy

CNY503

CNY571 total

includes taxes & fees

Nov 2 - Nov 3

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

A lobby with a central seating area, wooden ceiling, and patterned carpet.

A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.

A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.

14. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

23 km from Historic Downtown Kissimmee

Cory

CNY506

CNY570 total

includes taxes & fees

Oct 28 - Oct 29

An aerial view of a resort with multiple swimming pools, landscaped gardens, and outdoor seating areas.

A spacious hotel lobby with a central staircase, multiple seating areas, and large windows offering views of the outdoor area.

A large hotel with multiple floors, surrounded by a well-maintained golf course and a lake.

A large hotel with multiple towers, a well-maintained lawn, and a reflective water body in front.

15. Rosen Shingle Creek

14.9 km from Historic Downtown Kissimmee

nithin

CNY798

CNY897 total

includes taxes & fees

Oct 18 - Oct 19

A swimming pool with people in the water, including a person in a green and red inflatable ring.

A hotel sign with "BUENA VISTA SUITES" and a building with multiple floors and windows.

A modern restaurant with a curved counter, multiple seating areas, and a variety of appliances and decor.

A hotel room with two beds, a desk with a chair, a television, and large abstract paintings on the wall.

16. Buena Vista Suites Orlando

11.2 km from Historic Downtown Kissimmee

"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...

Constantinos

CNY809

CNY1,084 total

includes taxes & fees

Oct 25 - Oct 26

A modern dining area with a large table, chairs, and a coffee station.

A market area with shelves stocked with snacks, beverages, and packaged goods.

A modern hotel building with a prominent 'avid' sign, multiple windows, and a covered entrance area.

A hotel room with a glass shower enclosure, two beds, a desk with a chair, and a large abstract painting on the wall.

17. avid hotel Orlando International Airport by IHG

19.3 km from Historic Downtown Kissimmee

YU-CHIN

CNY676

CNY760 total

includes taxes & fees

Nov 2 - Nov 3

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.

A hotel pool area with lounge chairs, a fire pit, and a large pool.

A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.

18. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

22.9 km from Historic Downtown Kissimmee

Rachael

CNY575

CNY646 total

includes taxes & fees

Oct 29 - Oct 30

A modern lobby with a checkered carpet, seating area, and a reception desk.

A hotel room with a large bed, a desk, a chair, and a wall-mounted lamp.

A modern lobby with seating areas, a patterned pillar, and hanging light fixtures.

A self-service beverage area with refrigerated drink dispensers, snack shelves, and a water cooler.

19. Holiday Inn Express Orlando International Airport by IHG

19 km from Historic Downtown Kissimmee

William

CNY677

CNY762 total

includes taxes & fees

Oct 13 - Oct 14

A hotel room with a large bed, a sofa, a small table, and a TV.

A lobby with two patterned armchairs, a central coffee table, and three framed artworks on the wall.

A modern hotel with a covered entrance, palm trees, and a clear sky.

A modern hotel room with a blue accent wall, a large bed, a sofa, a small table, and a TV.

20. Hyatt Place Orlando / I-Drive / Convention Center

17.2 km from Historic Downtown Kissimmee

Joy Routzahn

CNY562

CNY632 total

includes taxes & fees

Oct 18 - Oct 19

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Our prices for hotels in Historic Downtown Kissimmee are cheapest in February

Top landmarks in Historic Downtown Kissimmee

Kissimmee Lakefront Park

8.4/10 (2,921 reviews)

Kissimmee Lakefront Park is worth a pic or two when discovering Historic Downtown Kissimmee.

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Kissimmee Civic Center

7.2/10 (22 reviews)

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.

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Osceola County Clerk of the Court

8.8/10 (9 reviews)

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.

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Violet's Venom Brewery

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.

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Monument of States

7.6/10 (17 reviews)

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.

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Bataan-Corregidor Memorial

8.2/10 (12 reviews)

If you're planning a bit of sightseeing head to Bataan-Corregidor Memorial— just one of the monuments in Historic Downtown Kissimmee.

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First United Methodist Church

6.4/10 (21 reviews)

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.

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Check out reviews of Historic Downtown Kissimmee hotels guests love

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

10/10 Excellent

"The stay was absolutely wonderful! The location was near all of the theme parks, the hotel was clean with a friendly staff and the breakfast buffet was delicious with many options. Definitely recommend!"

Holiday Inn Resort Orlando Suites - Waterpark by IHG

8/10 Good

"Lots of unexpected hidden fees. Like having to pay each night for parking among other things."

Marriott's Grande Vista

10/10 Excellent

"Huge property with lots of pool options! Staff was able to switch our rooms when our first room had an odor. The room we stayed in was great and comfortable!"

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent

"Great hotel with wonderful amenities and pool. Food was great and the staff were wonderful. Be quick booking the bus to the parks or you will miss out. The foodcourt area was not open at all the 4 nights we were there but maybe it was low season (late Sept). There are plenty of restaurant options on site and in 2-5 mins walk and a gas station across the road well stocked with other holiday necessities. This was good value for money and our kids loved it. Not great coffee though."

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"It was was much bigger and much better than we imagined."

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"Vraiment bien, navette facile, location d’auto sur place, restaurants et etc. Il manquait seulement un petit congélateur dans les chambres pour les ice pack 🙂"

The Grove Resort & Water Park Orlando

10/10 Excellent

"Very clean room, and rooms look well maintained"

Universal's Cabana Bay Beach Resort

10/10 Excellent

"Loved the Place"

DoubleTree by Hilton Orlando Theme Park Resort

10/10 Excellent

"I has a excellent time at the Double Tree."

Frequently asked questions

Is Historic Downtown Kissimmee expensive to stay in?

You can find great hotels from CNY341 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?

Traveling with your pet doesn't mean sacrificing a great hotel stay. In Historic Downtown Kissimmee, our travelers love:

Kapp and Kappy B&B has an average guest rating of 9.8 out of 10. 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 traveling by car, make your life easier by booking a Historic Downtown Kissimmee hotel with free parking. Our travelers 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 82 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 neighborhoods of Lake Berkley and Hunters Creek.

Find out more about Historic Downtown Kissimmee

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Book Hotels in Historic Downtown Kissimmee on Hotels.com

Hotels in Historic Downtown Kissimmee

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Historic Downtown Kissimmee?

1. Kapp and Kappy B&B

2. Embassy Suites by Hilton Orlando Lake Buena Vista South

3. Drury Plaza Hotel Orlando - Disney Springs Area

4. Holiday Inn Express & Suites Orlando at SeaWorld by IHG

5. Caribe Royale Orlando, WorldHotels Elite

6. Hyatt House Orlando Airport

7. Hyatt Regency Grand Cypress

8. Seasons Florida Resort

9. Tru By Hilton Orlando Convention Center Area, FL

10. Wyndham Grand Orlando Resort Bonnet Creek

11. La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

12. Wingate by Wyndham - Orlando International Airport

13. Comfort Suites Maingate East

14. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

15. Rosen Shingle Creek

16. Buena Vista Suites Orlando

17. avid hotel Orlando International Airport by IHG

18. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

19. Holiday Inn Express Orlando International Airport by IHG

20. Hyatt Place Orlando / I-Drive / Convention Center

Price trends for hotels in Historic Downtown Kissimmee

Typical weather for Kissimmee

Top landmarks in Historic Downtown Kissimmee

Kissimmee Lakefront Park

Kissimmee Civic Center

Osceola County Clerk of the Court

Violet's Venom Brewery

Monument of States

Bataan-Corregidor Memorial

First United Methodist Church

Check out reviews of Historic Downtown Kissimmee hotels guests love

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Marriott's Grande Vista

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Universal's Endless Summer Resort - Dockside Inn and Suites

The Grove Resort & Water Park Orlando

Universal's Cabana Bay Beach Resort

DoubleTree by Hilton Orlando Theme Park Resort

Frequently asked questions

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