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.
CoCo Key Hotel and Water Resort
International Drive District
Save 100% on your flight
Price was $602, price is now $286 per person
$286
per person
Feb 20 - Feb 25
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Free water park access, 4 restaurants, and 3 outdoor pools are all featured at this traditional hotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy perks like a free theme park shuttle.
Palazzo Lakeside Hotel
Price was $1,138, price is now $289 per person
$289
per person
Feb 20 - Feb 25
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
The Shores Resort & Spa
Price was $814, price is now $333 per person
$333
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and complimentary bicycles are available on site. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Residence Inn by Marriott Daytona Beach Oceanfront
Price was $1,494, price is now $649 per person
$649
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free buffet breakfast each morning.
Westgate Town Center Resort
Save 100% on your flight
Price was $711, price is now $321 per person
$321
per person
Feb 22 - Feb 27
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 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
DoubleTree by Hilton Hotel Orlando at SeaWorld
10100 International Drive Orlando FL
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $119 total per night
$119 total
Jan 3 - Jan 4, 2026
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
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Free Cancellation
Reserve now, pay when you stay
$133 nightly
The price is $150 total per night
$150 total
Jan 6 - Jan 7, 2026
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
Wyndham I-Drive Avanti Resort & Conference Center
6515 International Drive Orlando FL
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $90 total per night
$90 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the outdoor pool and perks like free self parking.
Pool
Hot Tub
Rosen Inn at Pointe Orlando
9000 International Drive Orlando FL
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $82 total per night
$82 total
Dec 25 - Dec 26
Total with taxes and fees
This hotel features 3 outdoor pools, a gym, and a restaurant. Bring the family and enjoy the free theme park shuttle, playground, and kid-friendly dining. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi.
Pool
Pet friendly
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $110 total per night
$110 total
Jan 11 - Jan 12, 2026
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
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
$111 nightly
The price is $125 total per night
$125 total
Jan 8 - Jan 9, 2026
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
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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.
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.
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