A street sign reading "Welcome to Kissimmee, Florida" with a mural of horses on a building.

Search Hotels with a Bar in Historic Downtown Kissimmee

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Historic Downtown Kissimmee Hotels with a Bar

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Historic Downtown Kissimmee hotels with a bar

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

1. Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
4.0 star property
13.8 km from Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (6,227 reviews)
"The free hot breakfast the kickback food and drinks were so worth the stay."
United States
Komal
The price is ₹16,521
₹18,586 total
includes taxes & fees
25 Nov - 26 Nov
Drury Plaza Hotel Orlando - Disney Springs Area
An aerial view of a resort with a winding pool, sun loungers, and palm trees.

2. Hilton Orlando Buena Vista Palace - Disney Springs® Area

Hilton Orlando Buena Vista Palace - Disney Springs® Area
4.0 star property
14.1 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (2,084 reviews)
"Was really nice and convenient walk to Disney springs"
United States
Elisabeth
The price is ₹14,447
₹20,634 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Orlando Buena Vista Palace - Disney Springs® Area
A spacious lobby with a reception desk, seating area, and a decorative flower arrangement.

3. Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
8.7 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (1,671 reviews)
"Room was clean, breakfast was delicious, and the location was great!"
United States
Kaitlyn
The price is ₹11,219
₹12,733 total
includes taxes & fees
8 Nov - 9 Nov
Embassy Suites by Hilton Orlando Lake Buena Vista South
Pool

4. Hyatt Regency Grand Cypress

Hyatt Regency Grand Cypress
4.0 star property
14.3 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (2,404 reviews)
"Great hotel!"
United States
Christine
The price is ₹14,433
₹21,579 total
includes taxes & fees
22 Nov - 23 Nov
Hyatt Regency Grand Cypress
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
23 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (5,700 reviews)
"Great location, breakfast, clean, and very nice and helpful staff!"
United States
Robert
The price is ₹7,183
₹8,081 total
includes taxes & fees
24 Nov - 25 Nov
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

6. Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite
4.5 star property
11.1 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (5,339 reviews)
"Perfect family resort."
United States
Omid
The price is ₹16,522
₹22,647 total
includes taxes & fees
22 Nov - 23 Nov
Caribe Royale Orlando, WorldHotels Elite
A nighttime pool area with multiple pools, palm trees, and a dining setup.

7. Hilton Orlando Lake Buena Vista - Disney Springs® Area

Hilton Orlando Lake Buena Vista - Disney Springs® Area
4.0 star property
13.5 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (1,778 reviews)
"Excellent location, near Disney springs, a great walkable space."
United States
Kristi
The price is ₹12,833
₹18,818 total
includes taxes & fees
18 Nov - 19 Nov
Hilton Orlando Lake Buena Vista - Disney Springs® Area
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

8. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
22.9 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (6,242 reviews)
"Fantastic hotel, loved every minute of our stay!"
United States
Melissa
The price is ₹9,266
₹10,424 total
includes taxes & fees
24 Nov - 25 Nov
Home2 Suites by Hilton Orlando at Flamingo Crossings
An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

9. Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
4.0 star property
14.5 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3,178 reviews)
"Great experience, will definitely stay here in the future!"
United States
Oscar
The price is ₹14,357
₹20,638 total
includes taxes & fees
15 Nov - 16 Nov
Wyndham Grand Orlando Resort Bonnet Creek
A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

10. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
18.3 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (6,333 reviews)
"Good location and perfect for families!"
United States
Mayrah
The price is ₹2,259
₹6,766 total
includes taxes & fees
4 Nov - 5 Nov
Kompose Boutique Resort at Theme Parks
A large hotel with multiple floors, a central courtyard, and a reflective water feature.

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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
22.9 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (2,310 reviews)
"We were very pleased with our stay here. The location, the rooms and breakfast were great!"
United States
Michael
The price is ₹8,878
₹9,988 total
includes taxes & fees
29 Nov - 30 Nov
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A rooftop bar with round tables, a pool, and outdoor seating.

12. Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL
3.5 star property
15.3 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (4,230 reviews)
"Loved our stay!"
United States
Talore
The price is ₹7,990
₹8,989 total
includes taxes & fees
25 Nov - 26 Nov
Tru By Hilton Orlando Convention Center Area, FL
A hotel courtyard with outdoor seating, palm trees, and a chessboard.

13. Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village
3.0 star property
13.2 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (1,938 reviews)
"Great breakfast, friendly staff!"
United States
Kara
The price is ₹7,027
₹8,440 total
includes taxes & fees
15 Nov - 16 Nov
Fairfield Inn & Suites Lake Buena Vista in Marriott Village
A hotel atrium with a central fountain, palm trees, and a circular seating area.

14. Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport
4.0 star property
18.2 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (4,597 reviews)
"Great place to stay"
United States
frank
The price is ₹20,795
₹23,395 total
includes taxes & fees
23 Nov - 24 Nov
Hyatt Regency Orlando International Airport
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

15. Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista
3.5 star property
13.7 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (6,274 reviews)
"Awesome place to stay"
United States
Yotuel
The price is ₹5,400
₹6,075 total
includes taxes & fees
16 Nov - 17 Nov
Rosen Inn Lake Buena Vista
A large hotel with multiple towers, a well-maintained lawn, and a reflective water body in front.

16. Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
14.9 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (4,995 reviews)
"Great staff, location, resort was amazing"
United States
Dominic
The price is ₹10,187
₹11,460 total
includes taxes & fees
24 Nov - 25 Nov
Rosen Shingle Creek
A modern lobby with a reception desk, seating area, and a view of the city.

17. AC Hotel by Marriott Orlando Lake Buena Vista

AC Hotel by Marriott Orlando Lake Buena Vista
3.5 star property
13.6 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (2,022 reviews)
"Everything was excellent, the AC in the room, the cleanliness and the comfort of the bed."
United States
Cristina
The price is ₹11,300
₹12,712 total
includes taxes & fees
3 Nov - 4 Nov
AC Hotel by Marriott Orlando Lake Buena Vista
A modern hotel with a glass facade, palm trees, and a sign reading "DoubleTree by Hilton."

18. DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport
4.0 star property
21 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (2,734 reviews)
"Clean room, great area for food and nice pool."
United States
Lizette
The price is ₹8,574
₹9,646 total
includes taxes & fees
22 Nov - 23 Nov
DoubleTree by Hilton Orlando Airport
An outdoor patio area with seating, a bar, and a fire feature.

19. Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
20.3 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (2,848 reviews)
"Great place to stay."
United States
CHRIS
The price is ₹13,104
₹14,742 total
includes taxes & fees
22 Nov - 23 Nov
Hyatt House Orlando Airport
A hotel pool area with a water slide, palm trees, and a bridge.

20. Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
9.2 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3,742 reviews)
"clean room, helpful staff, and great breakfast."
United States
Wilfredo
The price is ₹4,027
₹6,726 total
includes taxes & fees
23 Nov - 24 Nov
Radisson Hotel Orlando Lake Buena Vista South
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.
View all properties

Top Historic Downtown Kissimmee Hotel Reviews

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Have visited multiple times and enjoyed each and every time."
Peter 5-night trip
Posted less than an hour ago
Westgate Lakes Resort & Spa Universal Studios Area

Frequently asked questions

Searching for hotels with bars in Historic Downtown Kissimmee?
Historic Downtown Kissimmee offers 81 hotels and other lodging options to choose from, and likely many will have a bar where you can enjoy an evening cocktail after exploring the city. While you're in the area, consider a visit to Disney Springs™ and ESPN Wide World of Sports Complex.
What are the best hotels with bars in Historic Downtown Kissimmee?
Below are some of top hotels with bars in and around Historic Downtown Kissimmee: Hyatt Regency Orlando International Airport: Hotel with 2 restaurants. Enjoy the bar, free WiFi and breakfast. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel with 3 restaurants. Enjoy the 2 poolside bars, free WiFi and 6 outdoor pools. Marriott's Grande Vista: Aparthotel with 3 restaurants. Enjoy the 2 poolside bars, free WiFi and 4 outdoor pools. The Grove Resort & Water Park Orlando: Resort with 3 restaurants. Enjoy the 3 poolside bars, free WiFi and 6 outdoor pools. Universal's Cabana Bay Beach Resort: Hotel with 2 restaurants. Enjoy the 2 poolside bars, free WiFi and 2 outdoor pools.
What is there to do in Historic Downtown Kissimmee?
Absorb the local culture in the area by visiting ESPN Wide World of Sports Complex, then unwind with a refreshing drink. Other places to see include Kissimmee Civic Center and Lake Tohopekaliga. Historic Downtown Kissimmee is recognised for its array of shops.
How can I get to Historic Downtown Kissimmee and around the area?
You might want to make the most of these transportation choices in and around Historic Downtown Kissimmee: Fly into Kissimmee, FL (ISM-Kissimmee Gateway), which is located 1.9 mi (3 km) away. You can also search for flights into Orlando International Airport (MCO), which is 11.2 mi (18 km) away.

Explore a world of travel with Expedia