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.
Palazzo Lakeside Hotel
Price was $489, price is now $172 per person
$172
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip 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.
Residence Inn by Marriott Daytona Beach Oceanfront
Price was $1,423, price is now $542 per person
$542
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 Cocoa Beach Resort
Price was $2,184, price is now $993 per person
$993
per person
Mar 9 - Mar 13
found 1 day ago
Roundtrip non-stop 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 Vacation Villas Resort
Save 100% on your flight
Price was $652, price is now $304 per person
$304
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 Palace Hotel / Universal / I-Drive
International Drive District
Price was $985, price is now $462 per person
$462
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.
Top Historic Downtown Kissimmee hotels deals
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
Dec 15 - Dec 16
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 at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
Free Cancellation
$98 nightly
The price is $110 total per night
$110 total
Dec 15 - Dec 16
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
Avanti International Resort
8738 International Dr Orlando FL
$89 nightly
The price is $100 total per night
$100 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Bring the family and enjoy the children's pool, free theme park shuttle, and arcade/game room. Enjoy the gym and perks like free WiFi.
Pool
Hot Tub
La Quinta Inn & Suites by Wyndham Orlando Airport North
7160 N Frontage Rd Orlando FL
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $89 total per night
$89 total
Dec 17 - Dec 18
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and free continental breakfast each morning.
Pool
Hot Tub
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $125 total per night
$125 total
Jan 4 - Jan 5, 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
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$188 nightly
The price is $212 total per night
$212 total
Dec 14 - Dec 15
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
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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 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 lively festivals and shops in this family-friendly area.
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