Historic Downtown Kissimmee, FL

Orlando

A street sign reading "Welcome to Kissimmee, Florida" with a mural of horses on a building.
A yellow vintage car driving down a brick-paved street lined with a black metal fence and green benches.
A lighthouse by a calm lake, surrounded by trees and a grassy area.
A green-roofed building with a covered porch, surrounded by trees and a well-maintained lawn.
A castle-like structure with the words "Medieval Times" on the top.

Stay in Historic Downtown Kissimmee for family fun, local history, and a mix of outdoor and indoor activities.

Historic Downtown Kissimmee is an ideal destination for family and entertainment travelers. You can enjoy outdoor activities at Kissimmee Lakefront Park or attend events at the Kissimmee Civic Center. For a unique experience, visit the Osceola County Clerk of the Court, which showcases local history. Nearby, explore Violet's Venom Brewery for a taste of local brews, or catch a show at Medieval Times. If you're looking for aquatic fun, the Bob Makinson Aquatic Center and Skate Reflections arcade provide entertainment options, while the Blue Lake trail offers a chance to enjoy nature.

While you're in Historic Downtown Kissimmee, visit some of its nearby neighborhoods. Saint Cloud is known for family and outdoor experiences, featuring Royal St. Cloud Links and Lakefront Park. Another nearby area, Kissimmee, offers family and entertainment experiences with attractions like the Silver Spurs Arena and Old Town shopping mall. Additionally, Celebration provides its own charm, with the Celebration Golf Club and various parks for local leisure activities. Each of these nearby areas adds to the overall appeal of your visit.

The best time to visit Historic Downtown Kissimmee is generally from May to August when the weather is warm and mostly dry. This period can be sunny, providing a pleasant atmosphere for outdoor activities. However, July to September marks the wetter months, which may influence your plans. Demand for accommodations tends to stay steady throughout the year, with slightly busier periods in March and June to July. If you prefer a quieter experience, consider visiting between October and December when the crowds are lighter.


Stay near popular Historic Downtown Kissimmee attractions

Things to do


Historic Downtown Kissimmee Hotel Deals

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
$215 nightly
The price is $242 total per night from Nov 23 to Nov 24
$242 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
Hyatt Regency Orlando International Airport
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
$118 nightly
The price is $133 total per night from Dec 2 to Dec 3
$133 total
Dec 2 - Dec 3
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista Orlando FL
$96 nightly
The price is $108 total per night from Dec 2 to Dec 3
$108 total
Dec 2 - Dec 3
Total with taxes and fees
Book a stay at this spa aparthotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Marriott's Grande Vista
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
$93 nightly
The price is $104 total per night from Nov 23 to Nov 24
$104 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.6/10 Excellent! (7,209 reviews)
"Great location , clean , I will stay here again."

Reviewed on Nov 11, 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
9500 Turkey Lake Rd Orlando FL
$116 nightly
The price is $131 total per night from Nov 12 to Nov 13
$131 total
Nov 12 - Nov 13
Total with taxes and fees
Book a stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.4/10 Very Good! (7,350 reviews)
"Everything about westgate was perfect especially the restaurant on the property the food was so good!!!"

Reviewed on Nov 11, 2026

Westgate Lakes Resort & Spa Universal Studios Area
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
$222 nightly
The price is $250 total per night from Dec 7 to Dec 8
$250 total
Dec 7 - Dec 8
Total with taxes and fees
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
8.2/10 Very Good! (10,954 reviews)
"This was my family’s 4th time staying here while visiting theme parks. The location is about a 15 minute drive to Disney. The property is always always always clean! The lazy river area is perfect for a day of lounging. We also love the outdoor bar area. It is such an incredible value. Not to mention, ..."

Reviewed on Nov 11, 2026

The Grove Resort & Water Park Orlando
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.

Where to stay in Historic Downtown Kissimmee

Find the best Historic Downtown Kissimmee areas and neighborhoods for the activities you enjoy most. Learn more about Historic Downtown Kissimmee
Learn more about Historic Downtown Kissimmee

Bay Lake

A noteworthy feature of Bay Lake is its exciting theme parks. While you're in town, be sure to stop and check out Epcot® and Walt Disney World® Resort.

International Drive District

Visitors to International Drive District rave about its breathtaking beach views, exciting theme parks, and popular shops. You might also want to make some time to see Orange County Convention Center or Orange County Convention Center North while you're exploring the neighborhood.

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

Reunion

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.



Historic Downtown Kissimmee, FL

Choose one or more items to build your trip:

Explore a world of travel with Expedia