Historic Downtown Kissimmee Vacations from $287

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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.
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
International Drive District
Save 100% on your flight
Price was $651, price is now $287 per person
$287
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
16/10 Exceptional! (3,666 reviews)
EVERYTHING WAS Great BUT THEY DO NEED BETTER BREAKFAST

Reviewed on Nov 25, 2025

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,017, price is now $387 per person
$387
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18/10 Exceptional! (1,681 reviews)
From the minute we checked in and Michelle greeted us, we knew we picked the right spot! Since it’s quiet season, they were able to upgrade our room to double balcony oceanfront. It felt like we were right over the beach! Very clean rooms and facilities. We were visiting my nephew who goes to school at DSC and the valet guys were so accommodating, allowing us to leave the car out front for a few hours here and there without charging us the parking fee. Sore isl shout out to Dom from valet. The pool area was great and we loved the tiki bar (shout out to Doug the bartender!) he even gave me a special drink for my bday!!! They give s’mores kits at night to use at the pool side fire pits too! When we come back to visit, we will definitely rebook at the Shores!!!

Reviewed on Nov 16, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $839, price is now $362 per person
$362
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
16.4/10 Exceptional! (5,482 reviews)
All of the above, Ladies, Gents and everyone inbetween understand this is the right place. The right choice, hands down and outright stellar for each and every thing you can judge.

Reviewed on Nov 24, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $759, price is now $361 per person
$361
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.6/10 Exceptional! (1,085 reviews)
Yes room was very nice and staff was super polite and helpful

Reviewed on Nov 22, 2025

Parkway International Resort

Parkway International Resort

3 out of 5
Price was $963, price is now $459 per person
$459
per person
Jan 27 - Feb 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
19.2/10 Exceptional! (2,052 reviews)
personnel was fabulous. Kind, courteous and very helpful The room was very clean, just a little musty.

Reviewed on Nov 23, 2025

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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

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
$133 nightly
The price is $150 total per night from Dec 1 to Dec 2
$150 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (5,603 reviews)
Have stayed here several times with the family. Super convenient to City Walk and the parks!

Reviewed on Nov 23, 2025

Universal's Cabana Bay Beach Resort
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
$67 nightly
The price is $76 total per night from Dec 14 to Dec 15
$76 total
Dec 14 - Dec 15
Total with taxes and fees
8.4/10 Very Good! (5,324 reviews)
Na

Reviewed on Nov 25, 2025

Rosen Inn at Pointe Orlando
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
$89 nightly
The price is $101 total per night from Dec 15 to Dec 16
$101 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (6,884 reviews)
Room was clean and staff were nice and willing to help.

Reviewed on Nov 23, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 54,017 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

4/5(12 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 lively festivals in this family-friendly area.

Kissimmee Lakefront Park

Osceola County Clerk of the Court

5/5(1 review)

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 lively festivals and shops in this family-friendly area.

Kissimmee Civic Center

Things to do

Aquatica Orlando

Aquatica Orlando

$45
per traveler
82% of travellers recommend
Aquatica Orlando
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
Florida: 90 Minute Everglades Cruise

Florida: 90 Minute Everglades Cruise

$50
per adult
100% of travellers recommend
Florida: 90 Minute Everglades Cruise
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.