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 Towers Resort
Save 100% on your flight
Price was $497, price is now $257 per person
$257
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Westgate Vacation Villas Resort
Price was $2,328, price is now $728 per person
$728
per person
Apr 30 - May 7
found 1 day ago
Roundtrip non-stop 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.
Extended Stay America Suites Orlando Conv Ctr Universal Blvd
International Drive District
Price was $843, price is now $264 per person
$264
per person
May 8 - May 10
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 Cocoa Beach Resort
Price was $1,129, price is now $513 per person
$513
per person
Apr 12 - Apr 15
found 5 hours 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 Town Center Resort
Save 100% on your flight
Price was $760, price is now $372 per person
$372
per person
Apr 25 - Apr 30
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.
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 hotel 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
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $123 total per night
$123 total
Mar 8 - Mar 9
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
$157 nightly
The price is $177 total per night
$177 total
Mar 4 - Mar 5
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
$117 nightly
The price is $131 total per night
$131 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.
Pool
Pet friendly
Vacation Village Orlando, Celebration
2975 Arabian Nights Blvd Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $124 total per night
$124 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
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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
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 entertainment choices in this family-friendly area.
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 lively festivals in this family-friendly area.
Violet's Venom Brewery
You can take time to visit Violet's Venom Brewery during your travels to Kissimmee. While you're in the area, find time to visit its shops.
Frequently asked questions
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