Historic Downtown Kissimmee Vacations

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Your Historic Downtown Kissimmee Vacation

From its shopping to its dining, there's a lot to love about Historic Downtown Kissimmee. Book a Historic Downtown Kissimmee vacation package and prepare to experience the delights of this neighborhood. Kick off your trip to Historic Downtown Kissimmee with a visit to nearby attractions such as Osceola Heritage Park, Silver Spurs Arena and 192 Flea Market. Whatever your travel plans or budget, booking a perfect Historic Downtown Kissimmee vacation is quick and easy with Expedia.

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
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip flight included
Newark (EWR) to Orlando (MCO)
8/10 Very Good! (4,010 reviews)
It is a beautiful property and seems to be renovated recently.

Reviewed on Jun 7, 2024

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
Save 100% on your flight
per person
Jul 16 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Orlando (MCO)
8.4/10 Very Good! (1,000 reviews)
Nice stay but there is housekeeping

Reviewed on May 30, 2024

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Florida Center
per person
Aug 21 - Aug 28
found 7 hours ago
Roundtrip flight included
Newark (EWR) to Orlando (MCO)
7/10 Good! (2,439 reviews)
The rooms are very outdated and didn’t feel clean. There were several abandoned buildings around the property and it felt extremely unsafe once the sun set. Stated a continental breakfast would be available but that was only hard boiled eggs, toast, and a two types of cereal.

Reviewed on Jun 5, 2024

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
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip flight included
Newark (EWR) to Orlando (MCO)
8.2/10 Very Good! (836 reviews)
Great value, con no elevator so unless you are in first floor not the best choice (alternatively not the most attentive staff to help check in / check out)

Reviewed on Jun 5, 2024

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Newark (EWR) to Orlando (MCO)
7.8/10 Good! (3,697 reviews)
They had a host that was very welcoming and helpful throughout the stay. Do not do the free breakfast unless you want 90 minute time share presentation

Reviewed on Jun 6, 2024

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
Downtown Orlando

Downtown Orlando

4/5(769 area reviews)

Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation.

Find hotel + flight trips in Downtown Orlando

Historic Downtown Kissimmee Hotel Deals

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
The price is $199 per night from Jun 10 to Jun 11
$199
$274 total
includes taxes & fees
Jun 10 - Jun 11
8.2/10 Very Good! (5,501 reviews)
"Loved it!"

Reviewed on Jun 4, 2024

The Grove Resort & Water Park Orlando
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
3.5 out of 5
14500 Continental Gateway, Orlando, FL
Fully refundable
The price is $86 per night from Jun 10 to Jun 11
$86
$145 total
includes taxes & fees
Jun 10 - Jun 11
6.4/10 (5,539 reviews)
"The staffs are great and responses are quick. I had to kill a cockroache in the kids bedroom and there were anta in the kitchen. The room we had was by the pool so the music was really loud, cannot nap or sleep before 9pm. The cleanliness is good. The kids pool has poop so we didn't get to enjoy ..."

Reviewed on Jun 6, 2024

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Universal's Endless Summer Resort - Dockside Inn and Suites
Universal's Endless Summer Resort - Dockside Inn and Suites
3 out of 5
7125 Universal Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is $188 per night from Jun 9 to Jun 10
$188
$212 total
includes taxes & fees
Jun 9 - Jun 10
9/10 Wonderful! (5,200 reviews)
"Loved the food. The staff were very friendly. Pool was great."

Reviewed on Jun 5, 2024

Universal's Endless Summer Resort - Dockside Inn and Suites
See all 52,648 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Historic Downtown Kissimmee vacation package cost?
Custom build your Historic Downtown Kissimmee package from an affordable $342. Pick from any combination of rental cars, flights and hotels to create the trip you’ve been dreaming about. Don’t forget to add on some activities and experiences!
How do I get a cheap travel package to Historic Downtown Kissimmee?
Bundle your hotels and flights with Expedia to save big bucks on your next trip. With more than 550 airlines and 1,000,000 properties across the world, your Historic Downtown Kissimmee vacation package can be customized exactly to suit your travel style. With all that extra money, why not throw in one or two fun tours and experiences? It’s an easy way to unlock even more savings. Your dream vacation in Historic Downtown Kissimmee is much closer than you thought!
Where should I stay in Historic Downtown Kissimmee?
Stay somewhere within a stone’s throw of ChampionsGate Golf Club. This fantastic attraction is in the thick of the action and on the must-do lists of many tourists.
What are the top hotels in Historic Downtown Kissimmee?
Storey Lake Ihr 2022 and 4 Bedrooms Villa - Storey Lake are two of the most sought-after properties in Historic Downtown Kissimmee. Why not check out the facilities and rates at each and then make up your mind?
How far in advance should I book my Historic Downtown Kissimmee vacation?
Get rewarded with the widest variety and the cheapest prices by booking your trip to Historic Downtown Kissimmee nice and early. Air carriers generally publish flights anywhere up to a year before departure, so secure your spot as soon as you can. Having said that, Expedia is dedicated to providing you with the best bargains around, so there’s never a bad time to book your dream vacation!
What does an Expedia Historic Downtown Kissimmee travel package include?
That depends on what you’re after. If you’re traveling alone, you might decide to combine hotels and flights. Bringing the whole crew to Historic Downtown Kissimmee? A travel package that includes hotels, flights and rental cars might suit you better. Expedia gives you the freedom and flexibility to tailor-make your travel package.
What should I know before booking a Historic Downtown Kissimmee travel package?
So many places to go, so many things to do. With a package, you’ll be able to tick more of them off your list. Combine your hotels, flights and rental cars and enjoy big savings.
Can I choose my airline with a Historic Downtown Kissimmee Expedia vacation package?
Yes, you’re in charge. Expedia has access to more than 550 airlines globally, so you can tailor your Historic Downtown Kissimmee adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Historic Downtown Kissimmee vacation package?
If your travel plans in Historic Downtown Kissimmee have been upended, it’s good to know that it is possible to amend or cancel your booking. If you made your booking less than 24 hours ago, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. For more details, visit our Customer Service Portal.

Discover the most popular places to visit in Historic Downtown Kissimmee

Image for Kissimmee Lakefront Park

Kissimmee Lakefront Park

4/5(12 reviews)

Explore the great outdoors at Kissimmee Lakefront Park, a lovely green space in Kissimmee. Amble around this family-friendly area's lakeside or experience its entertainment choices.

Kissimmee Lakefront Park
Image for Osceola County Clerk of the Court

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
Image for Kissimmee Civic Center

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

Image for 90 Minute Pontoon Cruise in Florida

90 Minute Pontoon Cruise in Florida

$70
Per adult
90 Minute Pontoon Cruise in Florida
Image for 2 Hour Eco Tour

2 Hour Eco Tour

$70
Per adult
2 Hour Eco Tour
Image for Florida: 90 Minute Everglades Cruise

Florida: 90 Minute Everglades Cruise

$55
Per adult
Florida: 90 Minute Everglades Cruise
See all activities in Orlando

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