Title: Historic Downtown Kissimmee Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $494 Expedia.ca [Historic Downtown Kissimmee Travel Guide](https://expedia.ca/Orlando-Historic-Downtown-Kissimmee.dx800089)[Hotels in Historic Downtown Kissimmee](https://expedia.ca/Historic-Downtown-Kissimmee-Orlando-Hotels.0-n800089-0.Travel-Guide-Filter-Hotels)[Flights to Orlando](https://expedia.ca/Cheap-Flights-To-Orlando.d178294.Travel-Guide-Flights)[Things to do in Orlando](https://expedia.ca/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities)[Historic Downtown Kissimmee Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Downtown-Kissimmee.d800089.Car-Rental-Guide) ![](https://images.trvl-media.com/place/800089/8e7bf26c-0611-47cb-b22d-aa4a7ff10dda.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Historic Downtown Kissimmee Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Holiday Package Deals in Historic Downtown Kissimmee Price found within the past 48 hours. Click for updated prices. ![Westgate Towers Resort](https://images.trvl-media.com/lodging/1000000/180000/170900/170878/bd08ea58_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Towers Resort CA $494 per person Apr 9 - Apr 14 found 22 hours ago Roundtrip non-stop flight included Montreal (YUL) to Orlando (MCO) 8.6/10 Excellent! (1,002 reviews) Always clean and very cozy my favorite place to stay Reviewed on Feb 2, 2026 ![Palazzo Lakeside Hotel](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/de0795f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palazzo Lakeside Hotel CA $826 per person Mar 8 - Mar 15 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Orlando (MCO) 8.2/10 Very Good! (5,145 reviews) Clean room. Comfortable beds/pillows. Reviewed on Feb 4, 2026 ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Lakes Resort & Spa Universal Studios Area CA $673 per person Apr 22 - Apr 27 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Orlando (MCO) 8.2/10 Very Good! (5,482 reviews) It was such a great peaceful place Mr Brian showed us to are building and then took to the room showed us how amazing it was he was such a delightful man. I will be back again!! Reviewed on Feb 4, 2026 ![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/410a3d83_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Town Center Resort CA $793 per person Mar 8 - Mar 15 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Orlando (MCO) 8/10 Very Good! (1,367 reviews) Room was amazing, all though the jacuzzi jets were dirty so once i turned them on the water got really gross. They need to do better at cleaning. I was certainly disappointed because i got the room for the jacuzzi and didn’t get to use it because it was filthy. Reviewed on Feb 5, 2026 ![The Shores Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/15800/15752/b7ce5af2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shores Resort & Spa CA $676 per person Apr 22 - Apr 27 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Orlando (MCO) 9/10 Wonderful! (1,681 reviews) Great experience. Friendly staff. Room was amazing with a huge balcony. Reviewed on Feb 3, 2026 ## Where to stay in Historic Downtown Kissimmee Find the best Historic Downtown Kissimmee areas and neighborhoods for the activities you enjoy most. [Learn more about Historic Downtown Kissimmee](https://expedia.ca/Orlando-Historic-Downtown-Kissimmee.dx800089) ![International Drive showing landscape views](https://images.trvl-media.com/place/6034244/0464e66f-0125-4dd1-98af-a6abd0723a03.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### International Drive District Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions. [Find hotel + flight trips in International Drive District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=International%20Drive%20District&DestID=6034244&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![EyeEm Custom Shoots Q4 2018](https://images.trvl-media.com/place/6034611/b5337a03-4529-4792-ad22-c3362778c5b1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Bay Lake 4 out of top 10 points of interest in this area 4.5/5(195 area reviews) Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses. [Find hotel + flight trips in Bay Lake](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Bay%20Lake&DestID=6034611&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Champions Gate Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area. [Find hotel + flight trips in Champions Gate](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Champions%20Gate&DestID=6070422&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Central business district in Orlando city, is the 23rd largest metropolitan area in the United States of America.](https://images.trvl-media.com/place/553248635976479235/984ca81f-6338-43c3-9ca1-16234d9a8ef5.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Florida Center 2 out of top 10 points of interest in this area While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida. [Find hotel + flight trips in Florida Center](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Florida%20Center&DestID=553248635976479235&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Downtown Orlando](https://images.trvl-media.com/place/800087/456c7527-7a8a-4ea3-8793-151017f3c5da.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Orlando 3.5/5(17 area reviews) Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation. [Find hotel + flight trips in Downtown Orlando](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Orlando&DestID=800087&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Historic Downtown Kissimmee Hotel Deals ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 8800 Vistana Centre Dr Orlando FL CA $157 CA $177 total Feb 25 - Feb 26 includes taxes & fees 9.2/10 Wonderful! (4,489 reviews) The condo was clean. The staff was friendly. The beds were comfortable and the coffee bar was great. Thank you so much. Reviewed on Feb 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&selected=23110&PinnedHotelID=23110&HadPinnedHotel=true®ionId=800089) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rosen Inn at Pointe Orlando 9000 International Drive Orlando FL Fully refundableReserve now, pay when you stay CA $101 CA $114 total Feb 21 - Feb 22 includes taxes & fees 8.4/10 Very Good! (5,659 reviews) Everything was fine except they now charge for parking. I've stayed at this location 3 times total. Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=8892&PinnedHotelID=8892&HadPinnedHotel=true®ionId=800089) ![The Grove Resort & Water Park Orlando](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Grove Resort & Water Park Orlando 14501 Grove Resort Avenue Winter Garden FL Fully refundableReserve now, pay when you stay CA $231 CA $335 total Feb 22 - Feb 23 includes taxes & fees 8/10 Very Good! (8,987 reviews) room was clean staff where excellent unlike going to other hotels to pick my daughter up from cheer they where rude… security was courteous and well manner not rude… there pools and hot tubs where clean. great please stay at Reviewed on Jan 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=4691657&PinnedHotelID=4691657&HadPinnedHotel=true®ionId=800089) [See all 53,987 properties in Historic Downtown Kissimmee](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=06%2F02%2F2026&endDate=07%2F02%2F2026®ionId=800089) Lowest 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Historic Downtown Kissimmee vacation package cost? ### How do I get a cheap travel package to Historic Downtown Kissimmee? ### Where should I stay in Historic Downtown Kissimmee? ### What are the top hotels in Historic Downtown Kissimmee? ### How far in advance should I book my Historic Downtown Kissimmee vacation? ### What does an Expedia Historic Downtown Kissimmee travel package include? ### What should I know before booking a Historic Downtown Kissimmee travel package? ### Can I choose my airline with a Historic Downtown Kissimmee Expedia vacation package? ### If I'm not able to travel, can I cancel my Historic Downtown Kissimmee vacation package? ### Discover the most popular places to visit in Historic Downtown Kissimmee ![Kissimmee Lakefront Park Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad](https://images.trvl-media.com/place/6177922/9a4f15a9-e553-4437-8074-85ea3cba5d75.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.ca/Kissimmee-Lakefront-Park-Historic-Downtown-Kissimmee.d6177922.Vacation-Attraction) #### First United Methodist Church After visiting First United Methodist Church, make a plan to see the other sights and activities in Kissimmee. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants. [](https://expedia.ca/First-United-Methodist-Church-Historic-Downtown-Kissimmee.d553248621532654171.Vacation-Attraction) ### Things to do ![Universal Orlando Resort Theme Park Tickets](https://mediaim.expedia.com/localexpert/449578/292355e4-a5b6-4251-bddb-ccea0177846f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Universal Orlando Resort Theme Park Tickets (US & Canada) CA $209 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/universal-orlando-resort-theme-park-tickets-us-canada.a449578.activity-details) ![Aquatica Orlando](https://mediaim.expedia.com/localexpert/407892/33b09fce-abbf-446b-bce5-738d4c15128d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Aquatica Orlando CA $73 per traveller **84%** of travellers recommend [](https://expedia.ca/things-to-do/aquatica-orlando.a407892.activity-details) ![Florida: 90 Minute Everglades Cruise](https://mediaim.expedia.com/localexpert/47891876/33dc2687-1323-4f4f-83b1-a21a4a724609.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Florida: 90 Minute Everglades Cruise CA $76 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/florida-90-minute-everglades-cruise.a47891876.activity-details) [See all activities in Orlando](https://expedia.ca/things-to-do/search?rid=800089) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.