Historic Downtown Kissimmee Vacations from $191

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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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $984, price is now $191 per person
$191
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,171 reviews)
Gould be a good idea to provided some info how to open the gate

Reviewed on Aug 24, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,230, price is now $475 per person
$475
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,002 reviews)
This was a good time!

Reviewed on Aug 23, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $837, price is now $341 per person
$341
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,254 reviews)
I didn't like the pools, the pictures i saw online wasn't what I actually saw in person. I was disappointed. There were no many entertainments at the facility

Reviewed on Aug 25, 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $550, price is now $253 per person
$253
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (3,048 reviews)
You get what you pay for! Location was great, property was clean and quiet. Cleaning services should be done daily. Rooms need renovation. Would stay again.

Reviewed on Aug 25, 2025

ette hotel

ette hotel

5 out of 5
Price was $1,175, price is now $556 per person
$556
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on Aug 11, 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

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
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Sep 10 to Sep 11
$104 total
Sep 10 - Sep 11
Total with taxes and fees
8.2/10 Very Good! (6,552 reviews)
"."

Reviewed on Aug 23, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $98 total per night from Sep 16 to Sep 17
$98 total
Sep 16 - Sep 17
Total with taxes and fees
8.8/10 Excellent! (2,925 reviews)
"Excellent place great customer service and Beautiful room clean, spacious, overall excellent quality love the pool. Would recommend it also definitely going again.."

Reviewed on Aug 24, 2025

Marriott's Grande Vista
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
$142 nightly
The price is $160 total per night from Sep 3 to Sep 4
$160 total
Sep 3 - Sep 4
Total with taxes and fees
8.8/10 Excellent! (5,147 reviews)
"One day delay Frontier cancelled a flight had to cram everything in 2.5 days already had attractions car booked caused me extra money out of pocket Will be call Expedia for some sort of compensation"

Reviewed on Aug 23, 2025

Universal's Cabana Bay Beach Resort
See all 52,351 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.
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All Inclusive Vacations
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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 lively festivals 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 lively festivals 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

Perfect spot to park in the shade next to the sandy beach in St. Cloud. Care for a swim?

Kissimmee and St. Cloud Beach Tour on All Electric Trike (4 hrs.)

$71
per adult
Kissimmee and St. Cloud Beach Tour on All Electric Trike (4 hrs.)
Electric Mountain Bike parked in front of the sandy beach at St. Cloud Lakefront Park.

Experience Wild Florida Nature Up Close on Electric Bike (2 hrs.)

$49
per adult
100% of travellers recommend
Experience Wild Florida Nature Up Close on Electric Bike (2 hrs.)
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$149
per traveler
84% of travellers recommend
Universal Orlando Resort Express Passes
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.