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 $593, price is now $338 per person
$338
per person
Aug 3 - Aug 7
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 mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
Save 100% on your flight
Price was $1,147, price is now $614 per person
$614
per person
Jul 22 - Jul 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
Price was $897, price is now $487 per person
$487
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Save 100% on your flight
Price was $1,820, price is now $1,024 per person
$1,024
per person
Jul 23 - Jul 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.
Seasons Florida Resort
Save 100% on your flight
Price was $727, price is now $417 per person
$417
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.
Top Historic Downtown Kissimmee hotels deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $134 total per night
$134 total
Jun 9 - Jun 10
Total with taxes and fees
This smoke-free aparthotel 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
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $224 total per night
$224 total
May 20 - May 21
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.
Pool
Free WiFi
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$214 nightly
The price is $241 total per night
$241 total
May 21 - May 22
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
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Free Cancellation
Reserve now, pay when you stay
$150 nightly
The price is $169 total per night
$169 total
May 19 - May 20
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
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
7400 Canada Ave Orlando FL
Free Cancellation
$85 nightly
The price is $96 total per night
$96 total
May 21 - May 22
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Enjoy the 24-hour gym and free buffet breakfast each morning.
Pool
Hot Tub
Universal's Endless Summer Resort - Dockside Inn and Suites
7125 Universal Boulevard Orlando FL
Free Cancellation
Reserve now, pay when you stay
$146 nightly
The price is $164 total per night
$164 total
May 20 - May 21
Total with taxes and fees
This smoke-free hotel features 2 outdoor pools, a gym, and a restaurant. Bring the family and enjoy the children's pool, early theme park entry, and arcade/game room. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.
Pool
Free WiFi
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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
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 entertainment choices 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 entertainment choices and shops in this family-friendly area.
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