Historic Downtown Kissimmee Vacations from $274

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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 Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $532, price is now $274 per person
$274
per person
Nov 14 - Nov 17
found 2 days ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,346 reviews)
I didn’t like about their room service and staff

Reviewed on Oct 9, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $2,277, price is now $949 per person
$949
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,360 reviews)
Over All It Was Great Me And My Kids Had Wonderful Time And Wanna Go Back

Reviewed on Oct 1, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $2,234, price is now $1,028 per person
$1,028
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,684 reviews)
Lo mejor. Me encantó súper recomendado.

Reviewed on Sep 30, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,371, price is now $687 per person
$687
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
8.8/10 Excellent! (486 reviews)
They messed up my reservation for our second and third days by putting my name incorrectly. I was called out of the pool in front of all the guests in the middle of the dayand made to go to the front desk. Only to find we had to scurry to pack our belongings and moved to another room. No fault of ours yet we were left to fend for ourselves. . It took 1 1/2 hours of prime day with our friends. It was humiliating and beyond inconvenient. We were compensated with 2 free drinks tickets. Judge for yourself if this was proper and professional.

Reviewed on Sep 28, 2025

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $716, price is now $361 per person
$361
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (1,001 reviews)
There was a very shady old looking red car parked outside our windows with loud music playing late into the night our last two nights

Reviewed on Aug 19, 2025

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
International Drive showing landscape views

International Drive District

1 out of top 10 points of interest in this area

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

Find hotels in International Drive District

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
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (3,628 reviews)
"Staff very helpful and friendly. They help get you to your cruise pick up and do it with a smile. Had a great stay. Very convenient and clean. Comfortable bed."

Reviewed on Oct 5, 2025

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Hyatt Regency Orlando International Airport
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (5,365 reviews)
"Rooms need to be cleaned better."

Reviewed on Oct 9, 2025

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Universal's Cabana Bay Beach Resort
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
9.2/10 Wonderful! (3,633 reviews)
"Nice area, lots to do, very cost effective compared to other resorts in area"

Reviewed on Oct 6, 2025

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Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 53,473 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Historic Downtown Kissimmee

Kissimmee Lakefront Park

Kissimmee Lakefront Park

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.

Kissimmee Lakefront Park

Osceola County Clerk of the Court

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.

Osceola County Clerk of the Court

Kissimmee Civic Center

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.

Kissimmee Civic Center

Things to do

Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$160
per traveler
84% of travellers recommend
Universal Orlando Resort Express Passes
Orlando: Chocolate Kingdom Factory Adventure Tour

Orlando: Chocolate Kingdom Factory Adventure Tour

$24
per adult
98% of travellers recommend
Orlando: Chocolate Kingdom Factory Adventure Tour
"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

$173
per adult
92% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
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.