Title: Old Town Key West Vacation Packages & Trips 2025 from $577 | Expedia.ca [Hotels in Old Town Key West](https://expedia.ca/Old-Town-Key-West-Key-West-Hotels.0-n553248635976481920-0.Travel-Guide-Filter-Hotels)[Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Old Town Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Key-West.d553248635976481920.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635976481920/c3895c9f-e471-4c93-ac2e-85c99f8f8fec.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Old Town Key West 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 Old Town Key West Price found within the past 48 hours. Click for updated prices. ![Fitch Lodge - Key West Historic Inns](https://images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/76c68788_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fitch Lodge - Key West Historic Inns Key West Historic District CA $1,024 per person Nov 22 - Nov 26 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Key West (EYW) 8.8/10 Excellent! (484 reviews) Property has a very cozy feel Very nice lobby area breakfast was cute and fun. Parking is very limited. Flash flooding made it a tad bit difficult to reach out room. Reviewed on Aug 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-26/?FromAirport=DTW&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1397643&paandie=true&dealMarker=v-7qfSU6EOWLM_kTp7q12Bnj0sMRfWu1EJMLWU6r-59ludlJ41otG_jDnIc_5Uor) ![Lighthouse Hotel - Key West Historic Inns](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/2155599f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lighthouse Hotel - Key West Historic Inns Old Town Key West CA $1,135 per person Nov 22 - Nov 26 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Key West (EYW) 9/10 Wonderful! (791 reviews) The property was very green, with large plantings and hedged areas. Our room turned out to be a two bedroom cottage with it's own back porch. Everything was stylish and clean. The property is close to dining and the Hemingway House (across the street). Duval Street is only 1 block away with dining, drinking and shows! I have stayed here before and will stay again. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-26/?FromAirport=DTW&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1171079&paandie=true&dealMarker=MBaOCROZU75TrgN8IlJuy4MyUzVuzHa_39sNt7bd3icRDEbr-P0g4wusxOlgJuXV) ![Ridley House - Key West Historic Inns](https://images.trvl-media.com/lodging/5000000/4960000/4959000/4958964/e470d82d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ridley House - Key West Historic Inns Key West Historic District CA $1,325 per person Nov 22 - Nov 26 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Key West (EYW) 9.2/10 Wonderful! (819 reviews) Everything was amazing. we arrived early and in a rain storm my two kids and I were soaked head to toe and the water even entered our luggage. they let us check in early got us en upgrade to. amazing staff and perfect spot close to all in Key West Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-26/?FromAirport=DTW&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4958964&paandie=true&dealMarker=v-7qfSU6EOWLM_kTp7q12Bnj0sMRfWu1EJMLWU6r-58TfSryfwSABANCSF2Zx3Hs) ![The Key West Hotel](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/bc64cbf7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Key West Hotel Key West Historic District CA $3,412 per person Nov 22 - Nov 26 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Key West (EYW) 9.2/10 Wonderful! (496 reviews) My wife and I have come to KeyWest for years, this by far the nicest and affordable with great music and staff. It's our new go to place! Reviewed on Oct 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-26/?FromAirport=DTW&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8657021&paandie=true&dealMarker=v-7qfSU6EOWLM_kTp7q12GBAadamI1-64veadKVP0m5R1SwgQpmYWmUPr8NwzUgp) ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Windward Pointe, Key West CA $1,122 per person Nov 22 - Nov 26 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Key West (EYW) 9.6/10 Exceptional! (1,016 reviews) Family friendly.. amenities Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-26/?FromAirport=DTW&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=868697&paandie=true&dealMarker=v-7qfSU6EOWLM_kTp7q12Bnj0sMRfWu1EJMLWU6r-59H3eoUTkcvUJgtjTW6COSM) ## Where to stay in Old Town Key West Find the best Old Town Key West areas and neighborhoods for the activities you enjoy most. [Learn more about Old Town Key West](https://expedia.ca/Key-West-Old-Town-Key-West.dx553248635976481920) ![Smathers Beach which includes windsurfing, a beach and tropical scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63797-Florida-Keys.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Beachside 1 out of top 10 points of interest in this area When in Beachside, you can plan a visit to Duval Street and Smathers Beach, some noteworthy sights in the nearby area. [Find hotel + flight trips in Beachside](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Beachside&DestID=864982244484468736&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/339000/339914-Audubon-House-And-Tropical-Gardens.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Key West Historic District 2 out of top 10 points of interest in this area 4.5/5(156 area reviews) Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district. [Find hotel + flight trips in Key West Historic District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Key%20West%20Historic%20District&DestID=6281809&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63795-Florida-Keys.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Key West If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing. [Find hotel + flight trips in Downtown Key West](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Key%20West&DestID=553248635976470405&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://mediaim.expedia.com/destination/9/1fcb30338150b9f6e4b06a071a60583e.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### New Town 4/5(16 area reviews) Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden. [Find hotel + flight trips in New Town](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=New%20Town&DestID=553248635976480351&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Key West Butterfly and Nature Conservatory showing flowers, animals and zoo animals](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63942-Key-West-Butterfly-And-Nature-Conservatory.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Uptown - Upper Duval 4.5/5(3 area reviews) If you're spending some time in Uptown - Upper Duval, Duval Street and Key West Butterfly and Nature Conservatory are top sights worth seeing. [Find hotel + flight trips in Uptown - Upper Duval](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Uptown%20-%20Upper%20Duval&DestID=553248635976473524&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Old Town Key West Hotel Deals ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Southernmost Beach Resort and Guesthouses 1319 Duval Street, Key West, FL Fully refundable CA $236 CA $360 total Oct 29 - Oct 30 includes taxes & fees 8.6/10 Excellent! (2,766 reviews) "I loved the variety of restaurants and the location. It was perfect for my daughter and I, we will be back! Thank you 🤗" Reviewed on Oct 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=29%2F10%2F2025&endDate=30%2F10%2F2025&selected=863329&PinnedHotelID=863329&HadPinnedHotel=true®ionId=553248635976481920) ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Casa Marina Key West, Curio Collection by Hilton 1500 Reynolds Street, Key West, FL Fully refundableReserve now, pay when you stay CA $245 CA $359 total Oct 15 - Oct 16 includes taxes & fees 8.2/10 Very Good! (384 reviews) "The property was very pretty. Loved that it is on the beach. There was an elevator that was down so we had to use another one that I think was the staff elevator. It wouldn’t open the one time we used it for several minutes. The inside was very hot as it was not air conditioned. It was kind of scary, ..." Reviewed on Oct 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F10%2F2025&endDate=16%2F10%2F2025&selected=12346&PinnedHotelID=12346&HadPinnedHotel=true®ionId=553248635976481920) ![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Reach Key West, Curio Collection by Hilton 1435 Simonton Street, Key West, FL Fully refundableReserve now, pay when you stay CA $252 CA $367 total Oct 15 - Oct 16 includes taxes & fees 8.4/10 Very Good! (1,002 reviews) "The receptionists were very friendly and helpful and 4 Marlins was food exquisite !" Reviewed on Oct 3, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F10%2F2025&endDate=16%2F10%2F2025&selected=457821&PinnedHotelID=457821&HadPinnedHotel=true®ionId=553248635976481920) [See all 1,335 properties in Old Town Key West](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F10%2F2025&endDate=10%2F10%2F2025®ionId=553248635976481920) 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 an Old Town Key West vacation package cost? > Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Old Town Key West from just CA $1,024. And the more you bundle, the more money you save. The vacation of your dreams has never been so affordable. ### How do I get a cheap travel package to Old Town Key West? > One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got everything you need. Select a combination that best suits you and watch your savings grow. Of course, a travel package is never one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 hotel options around the globe, which lets you customize your Old Town Key West getaway. ### Where should I stay in Old Town Key West? > A trip to Old Town Key West isn't complete without stopping by Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Book a hotel as close as possible for quick access to these awesome attractions. ### What are the top hotels in Old Town Key West? > Secure a room at [Southernmost Retreat: 2 Blocks From Duval In Old Town](https://www.expedia.ca/Key-West-Hotels-Southernmost-Retreat-2-Blocks-From-Duval-In-Old-Town.h67446229.Hotel-Information). It's one of this area's most in-demand properties. Another top-rated option in Old Town Key West is [Curry House](https://www.expedia.ca/Key-West-Hotels-Curry-House.h9355435.Hotel-Information). ### How far in advance should I book my Old Town Key West vacation? > Smart travelers often book as early as possible. You can generally look up international fares on Expedia up to a year before your intended flight. If you're purchasing tickets last minute, don't despair. Budget prices occasionally become available just weeks prior to departure. ### What does an Expedia Old Town Key West travel package include? > Hotels, car rentals and flights — we bring you the very best deals. All you have to do is pick and choose your favorite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to create an awesome Old Town Key West vacation. ### What should I know before booking an Old Town Key West travel package? > A package can be cheaper than separately booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save big. Whatever your vacation goals are, there's sure to be a package within your budget. ### Can I choose my airline with an Old Town Key West Expedia vacation package? > Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you. ### If I'm not able to travel, can I cancel my Old Town Key West vacation package? > You can. We realize life doesn't always go to plan, so we're here to help if you have to make changes to your Old Town Key West vacation package. You may be able to amend or cancel your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) for more information. Also, be sure to check your itinerary for the finer details on change fees. ### Discover the most popular places to visit in Old Town Key West ![Southernmost Point](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498010-southernmost-point.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Southernmost Point Snap a memorable photograph from the edge of North America at this monumental landmark. [](https://expedia.ca/Southernmost-Point-Old-Town-Key-West.d501380.Vacation-Attraction) ![South Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497910-south-beach-fm.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### South Beach The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town. [](https://expedia.ca/South-Beach-Old-Town-Key-West.d6246827.Vacation-Attraction) ![Higgs Beach which includes a beach and tropical scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63798-Florida-Keys.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Clarence S. Higgs Memorial Beach Park Pay your respects at an impressive African burial site, explore landscaped gardens or snorkel with the family at this oceanfront beach park. [](https://expedia.ca/Clarence-S-Higgs-Memorial-Beach-Park-Old-Town-Key-West.d6246822.Vacation-Attraction) ### Things to do ![Aerial view of people snorkeling in Key West](https://mediaim.expedia.com/localexpert/585220/33764975-3db8-4de6-a174-18e4cf9a40c6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast CA $69 per adult **92%** of travellers recommend [](https://expedia.ca/things-to-do/key-west-morning-snorkel-adventure-with-bottomless-mimosas-breakfast.a585220.activity-details) ![12 hours Day at Key West With Boat Tour and Snorkeling](https://mediaim.expedia.com/localexpert/599857/aefdb7f1-206a-4531-bc6a-78614e1a0f10.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar CA $38 per adult **80%** of travellers recommend [](https://expedia.ca/things-to-do/day-trip-to-paradise-from-miami-key-west-tour-with-snorkeling.a599857.activity-details) ![Aboard the trolley in Key West](https://mediaim.expedia.com/localexpert/191537/2dd77e4c-4c5c-4b3c-954d-bfd0d44bd289.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Historic Key West Old Town Trolley Hop-On Hop-Off Tour CA $77 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/historic-key-west-old-town-trolley-hop-on-hop-off-tour.a191537.activity-details) [See all activities in Key West](https://expedia.ca/things-to-do/search?rid=553248635976481920) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.