Historic Downtown Kissimmee Vacations from $379

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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.
Parkway International Resort

Parkway International Resort

3 out of 5
Save 100% on your flight
Price was $625, price is now $379 per person
$379
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
9.4/10 Exceptional! (2,394 reviews)
Clean rooms, spacious, friendly staff

Reviewed on Jun 21, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Save 100% on your flight
Price was $911, price is now $472 per person
$472
per person
Aug 13 - Aug 20
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
7.8/10 Good! (507 reviews)
It was okay. They charged me with $250 as security deposit which I didn’t get back yet.

Reviewed on Jun 16, 2026

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 $880, price is now $501 per person
$501
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (6,626 reviews)
We were traveling with another family our room was great very clean. Their's was disgusting they had to go to the front desk and get another room it was so bad. Some of the staff were very helpful and friendly some weren't. Definitely worth upgrading the room. We had the 2 bedroom with a full kitchen and laundry in the room. Huge tub in the master bathroom.

Reviewed on Jun 22, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,872, price is now $1,076 per person
$1,076
per person
Sep 2 - Sep 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (1,009 reviews)
The cottage was wonderful. Stocked with everything you need just bring your food, drink and toilet paper! The cottage we stayed at was a perfect location just 5 minute walk to the amazing pool complex. The resort is great. Planning on going back soon.

Reviewed on Jun 20, 2026

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Save 100% on your flight
Price was $900, price is now $538 per person
$538
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,567 reviews)
Very nice and peaceful place for a vacation

Reviewed on Jun 22, 2026

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 District

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.

Find hotels in International Drive District

Historic Downtown Kissimmee Hotel Deals

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
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $152 total per night from Jul 14 to Jul 15
$152 total
Jul 14 - Jul 15
Total with taxes and fees
9.2/10 Wonderful! (5,863 reviews)
"Muy buen lugar !"

Reviewed on Jun 22, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
$228 nightly
The price is $257 total per night from Jun 24 to Jun 25
$257 total
Jun 24 - Jun 25
Total with taxes and fees
8/10 Very Good! (10,259 reviews)
"Was t what I was expecting. Smaller in person. The resort isn’t as big as the picture suggests"

Reviewed on Jun 23, 2026

The Grove Resort & Water Park Orlando
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
$141 nightly
The price is $159 total per night from Jun 25 to Jun 26
$159 total
Jun 25 - Jun 26
Total with taxes and fees
9/10 Wonderful! (7,034 reviews)
"Great for families and kids"

Reviewed on Jun 23, 2026

Universal's Cabana Bay Beach Resort
See all 51,890 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 Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad

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

Monument of States

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.

Monument of States

Things to do

Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$213
per traveler
80% of travellers recommend
Universal Orlando Resort Express Passes
Orlando: Polynesian Fire Luau with Dinner and Live Show

Orlando: Polynesian Fire Luau with Dinner and Live Show

$75
per adult
92% of travellers recommend
Orlando: Polynesian Fire Luau with Dinner and Live Show
Orlando: Jet Ski Rentals from Lake Buena Vista Area

Orlando: Jet Ski Rentals from Lake Buena Vista Area

$79
per traveler
100% of travellers recommend
Orlando: Jet Ski Rentals from Lake Buena Vista Area
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.