Deals on vacations and trips to Historic Downtown Kissimmee
Historic Downtown Kissimmee flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
Save 100% on your flight
Price was $384, price is now $182 per person
$182
per person
May 12 - May 15
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.
Extended Stay America Suites Orlando Conv Ctr Universal Blvd
International Drive District
Price was $861, price is now $268 per person
$268
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Westgate Vacation Villas Resort
Price was $729, price is now $327 per person
$327
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.
Westgate Cocoa Beach Resort
Price was $1,129, price is now $513 per person
$513
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Free water park access and an outdoor pool are featured at this smoke-free condo resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.
Westgate Towers Resort
Save 100% on your flight
Price was $734, price is now $350 per person
$350
per person
Mar 23 - Mar 28
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Top Historic Downtown Kissimmee hotels deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
$131 nightly
The price is $148 total per night
$148 total
Mar 9 - Mar 10
Total with taxes and fees
This smoke-free condo resort features 3 restaurants, 6 outdoor pools, and 10 outdoor tennis courts. There's fun for all ages with a free kid's club and mini golf, and barbecue grills are available on site. Enjoy the 8 hot tubs and perks like free WiFi.
Pool
Hot Tub
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$218 nightly
The price is $245 total per night
$245 total
Feb 22 - Feb 23
Total with taxes and fees
Free water park access, 3 restaurants, and 6 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Enjoy the 2 hot tubs and perks like free WiFi.
Pool
Hot Tub
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
$106 nightly
The price is $119 total per night
$119 total
Mar 11 - Mar 12
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Pool
Hot Tub
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $174 total per night
$174 total
Mar 2 - Mar 3
Total with taxes and fees
This smoke-free hotel features 2 restaurants, 2 outdoor pools, and 2 hot tubs. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a theme park shuttle.
Pool
Hot Tub
DoubleTree by Hilton Hotel Orlando at SeaWorld
10100 International Drive Orlando FL
$115 nightly
The price is $129 total per night
$129 total
Mar 8 - Mar 9
Total with taxes and fees
This smoke-free resort features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.
Vacation Village Orlando, Celebration
2975 Arabian Nights Blvd Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
$117 nightly
The price is $132 total per night
$132 total
Mar 8 - Mar 9
Total with taxes and fees
7 outdoor pools, 7 hot tubs, and a gym are all featured at this smoke-free condo. Bring the family and enjoy the children's pool, playground, and arcade/game room. WiFi in public areas is free.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Historic Downtown Kissimmee
View all propertiesLowest 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.
Popular places to visit
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.
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.
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.
Frequently asked questions
Photos of local treasures
Browse Historic Downtown Kissimmee vacation photos for more inspiration
