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 $927, price is now $221 per person
$221
per person
Jan 4 - Jan 9
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 $1,903, price is now $631 per person
$631
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 Palace Hotel / Universal / I-Drive
International Drive District
Price was $1,327, price is now $458 per person
$458
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip 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.
The Delaney Hotel
South Orange
Price was $1,325, price is now $561 per person
$561
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a snack bar/deli are also offered.
Florida Hotel & Conference Center in the Florida Mall
Price was $970, price is now $411 per person
$411
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This traditional aparthotel includes 3 restaurants, an outdoor pool, and a gym. Bring the family and enjoy the free theme park shuttle and kid-friendly dining. Enjoy the hot tub and perks like 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
Nov 18 - Nov 19
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.
Rosen Inn at Pointe Orlando
9000 International Drive Orlando FL
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $76 total per night
$76 total
Dec 18 - Dec 19
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.
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr, Orlando, FL
$99 nightly
The price is $112 total per night
$112 total
Dec 9 - Dec 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.
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
Nov 24 - Nov 25
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.
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
Nov 23 - Nov 24
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.
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$189 nightly
The price is $213 total per night
$213 total
Nov 18 - Nov 19
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.
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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 lively festivals 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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