Historic Downtown Kissimmee Vacation Packages 2026 from $280

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Your Historic Downtown Kissimmee Vacation

With a tailor-made vacation package to Historic Downtown Kissimmee, you can spend less time planning and more time simply enjoying this interesting neighborhood. From its shopping to its dining, there's plenty to discover here. When it's time to explore the sights, you'll find loads of top attractions nearby including Osceola Heritage Park, Kissimmee Lakefront Park and Silver Spurs Arena. Visit one, two or more during your trip to Historic Downtown Kissimmee. Expedia will help you turn your dream Historic Downtown Kissimmee vacation into reality, whatever your travel plans or budget.

The Latest Historic Downtown Kissimmee Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Westgate Towers Resort

Save 100% on your flight

$280

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.6/10 Excellent! (1,002 reviews)

Westgate Vacation Villas Resort

Save 100% on your flight

$283

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.2/10 Very Good! (2,028 reviews)

Todo

Reviewed on Aug 14, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

$362

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

7.8/10 Good! (564 reviews)

We decided to celebrate my birthday here. The pool closed around 8pm and the hot tub was included in that. Our tv didn’t work because if their WiFi. Our electrical portals didn’t work. The toilet was broken. Breakfast was an orange and a mini donut hole. This was NOT the way I wanted to experience Orlando for my birthday. The bed was comfortable but the pillows were flat. If you have a chance to book elsewhere, DO IT! Only perk?! Comfortable bed View No resort fee. And maybe that’s how they get you. I’d rather pay a resort fee if that meant getting my money’s worth. Zero stars! Never again

Reviewed on Aug 14, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$424

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.4/10 Very Good! (6,785 reviews)

The property was well maintained. Staff was great and extremely friendly/helpful. Cons- variety of food was limited. Rooms were nice but some of the details were not well painted. Light switches were old and dirty. Overall I would stay there again. They can improve on some of their character.

Reviewed on Aug 14, 2026

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$377

per person

Oct 10 - Oct 13

found 20 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

9/10 Wonderful! (1,304 reviews)

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

A traditional Japanese torii gate with a dragon sculpture in front, overlooking a calm lake with a distant view of a spherical building.

Bay Lake

4 out of top 10 points of interest in this area

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.

A theme park with a large rock formation, Old-Town sign, and various food and restaurant signs.

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

A golf course with sand bunkers, a water hazard, and a clubhouse in the background.

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.

A city skyline with modern buildings, a lake with swans, and a fountain.

Florida Center

2 out of top 10 points of interest in this area

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

A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

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.

Historic Downtown Kissimmee Hotel Deals

Rosen Inn Lake Buena Vista

8442 Palm Parkway Orlando FL

Fully refundableReserve now, pay when you stay

$62 nightly

$70 total

Aug 17 - Aug 18

Total with taxes and fees

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Fully refundable

$78 nightly

$88 total

Sep 1 - Sep 2

Total with taxes and fees

8.6/10 Excellent! (6,975 reviews)

"Nice"

Reviewed on Aug 14, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Fully refundableReserve now, pay when you stay

$123 nightly

$139 total

Sep 7 - Sep 8

Total with taxes and fees

See all 53,667 properties in Historic Downtown Kissimmee

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.

Stay near popular Historic Downtown Kissimmee attractions

Kissimmee Lakefront Park

8.4/10 (2,921 reviews)

Kissimmee Lakefront Park is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the entertainment choices in this family-friendly area.

See properties

Osceola County Clerk of the Court

8.8/10 (9 reviews)

After visiting Osceola County Clerk of the Court, make a plan to see the other sights and activities in Kissimmee. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

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Kissimmee Civic Center

7.2/10 (22 reviews)

Kissimmee Civic Center is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Discover the entertainment choices and shops in this family-friendly area.

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Bataan-Corregidor Memorial

8.2/10 (12 reviews)

You can find out about the history of Kissimmee when you stop by Bataan-Corregidor Memorial. Stroll along the lakeside or experience the entertainment choices in this family-friendly area.

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First United Methodist Church

6.4/10 (21 reviews)

After visiting First United Methodist Church, make a plan to see the other sights and activities in Kissimmee. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

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Violet's Venom Brewery

You can take time to visit Violet's Venom Brewery during your travels to Kissimmee. While you're in the area, find time to visit its shops.

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Monument of States

7.6/10 (17 reviews)

Learn about the local history of Kissimmee with a stop at Monument of States. Amble around this family-friendly area's lakeside or experience its entertainment choices.

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Things to do

Universal Orlando Resort Express Passes

$117

per traveler

80% of travellers recommend

Orlando: Polynesian Fire Luau with Dinner and Live Show

$75

per adult

92% of travellers recommend

Orlando: Jet Ski Rentals from Lake Buena Vista Area

$79

per adult

100% of travellers recommend

See all activities in Orlando

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Historic Downtown Kissimmee Vacations from $280

Book a Hotel + Flight or Car together to unlock savings

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Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Historic Downtown Kissimmee Vacation

The Latest Historic Downtown Kissimmee Vacation Packages

Westgate Towers Resort

Westgate Vacation Villas Resort

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Palace Hotel / Universal / I-Drive

Where to stay in Historic Downtown Kissimmee

Bay Lake

International Drive District

Reunion

Florida Center

Champions Gate

Historic Downtown Kissimmee Hotel Deals

Rosen Inn Lake Buena Vista

DoubleTree by Hilton at the Entrance to Universal Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Stay near popular Historic Downtown Kissimmee attractions

Kissimmee Lakefront Park

Osceola County Clerk of the Court

Kissimmee Civic Center

Bataan-Corregidor Memorial

First United Methodist Church

Violet's Venom Brewery

Monument of States

Things to do

Universal Orlando Resort Express Passes

Orlando: Polynesian Fire Luau with Dinner and Live Show

Orlando: Jet Ski Rentals from Lake Buena Vista Area