Title: Old Town Key West Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $934 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.

![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Vacation Club at Beach House, Key West

CA $934

per person

Apr 27 - Apr 30

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

This place is amazing! The property is beautiful and quiet. The pool area was clean and well cared for. Our room was spacious, very clean and had everything we needed. The staff was kind and always helpful. We would definitely go back.

Reviewed on Feb 5, 2026

![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 $4,081

per person

Apr 9 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!

Reviewed on Jan 28, 2026

![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 $1,465

per person

Apr 9 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.6/10 Exceptional! (1,002 reviews)

Said there was beach There is no beach Our initial flight was cancelled we re-rebooked for two days later The hotel would not refund the 2 nights We will reach out again to Expedia but hotel is. also very difficult to reach a live person

Reviewed on Feb 5, 2026

![The Gardens Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/424c57d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Gardens Hotel

Old Town Key West

CA $2,162

per person

Apr 9 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

Wonderful all around!

Reviewed on Jan 25, 2026

![Bishop Hotel Key West](https://images.trvl-media.com/lodging/104000000/103380000/103373900/103373822/976e1cc5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bishop Hotel Key West

Old Town Key West

CA $2,291

per person

Apr 18 - Apr 25

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.8/10 Exceptional! (291 reviews)

This was a fantastic hotel. Warm like a home with all the amenities you could want. Staff were friendly, often going above and beyond. Breakfast was lovely and the pools were outstanding. Ivan the hotel cat was a great touch. The room was clean and very comfortable. We’d stay here again!

Reviewed on Feb 4, 2026

## 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)

![Audubon House and Tropical Gardens featuring a house](https://images.trvl-media.com/place/6068599/e22dc889-0174-435e-9d9b-302d362fd045.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)

![Duval Street](https://images.trvl-media.com/place/6068616/ac9e1424-8949-4483-8a12-9063d1511aa2.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)

![Wide aerial panorama of Key West, Florida](https://images.trvl-media.com/place/553248635976480351/87477fd8-e61c-4ccb-8f10-57f3d82227dc.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 Fort East Martello Museum and Gallery. 

[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)

![Sunset on Carnival Cruise in Key West.](https://images.trvl-media.com/place/1187/48023594-76b8-4930-a4a9-06a0f12911a4.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)

![Mallory Square showing a sunset and general coastal views as well as a small group of people](https://images.trvl-media.com/place/501385/8fc21581-48e4-48a8-8cca-3cfabcd30450.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Historic Seaport

 While visiting Historic Seaport, you might make a stop by sights like Duval Street and Key West Historic Seaport. 

[Find hotel + flight trips in Historic Seaport](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Historic%20Seaport&DestID=553248635976383502&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 $637

CA $817 total

Feb 8 - Feb 9

includes taxes & fees

8.6/10 Excellent! (3,045 reviews)

Room was nice. The sink was clogged.

Reviewed on Jan 31, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=863329&PinnedHotelID=863329&HadPinnedHotel=true&regionId=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 $636

CA $808 total

Feb 8 - Feb 9

includes taxes & fees

8.2/10 Very Good! (525 reviews)

Beautiful beach- gorgeous hotel-top level service - love everything about it!

Reviewed on Feb 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=12346&PinnedHotelID=12346&HadPinnedHotel=true&regionId=553248635976481920)

![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

Fully refundableReserve now, pay when you stay

CA $639

CA $788 total

Feb 8 - Feb 9

includes taxes & fees

9.2/10 Wonderful! (1,145 reviews)

Room was clean ,location off main street and porch were quaint and perfect atmosphere for the key west flavor.Atmosphere was more than genuine.

Reviewed on Feb 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=529611&PinnedHotelID=529611&HadPinnedHotel=true&regionId=553248635976481920)

[See all 1,350 properties in Old Town Key West](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F02%2F2026&endDate=08%2F02%2F2026&regionId=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?

### How do I get a cheap travel package to Old Town Key West?

### Where should I stay in Old Town Key West?

### What are the top hotels in Old Town Key West?

### How far in advance should I book my Old Town Key West vacation?

### What does an Expedia Old Town Key West travel package include?

### What should I know before booking an Old Town Key West travel package?

### Can I choose my airline with an Old Town Key West Expedia vacation package?

### If I'm not able to travel, can I cancel my Old Town Key West vacation package?

### Discover the most popular places to visit in Old Town Key West

![Southernmost Point featuring signage as well as a large group of people](https://images.trvl-media.com/place/501380/97e2b26c-38ce-483b-b59e-7a017404ab35.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 featuring a sandy beach and general coastal views as well as a small group of people](https://images.trvl-media.com/place/6246827/42d13a3e-a933-4e9f-b857-cde9f4314a24.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://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.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 $62

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/key-west-morning-snorkel-adventure-with-bottomless-mimosas-breakfast.a585220.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 $85

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/historic-key-west-old-town-trolley-hop-on-hop-off-tour.a191537.activity-details)

![Commotion on the Ocean Sunset Sail](https://mediaim.expedia.com/localexpert/191563/7e4be692-c00e-461c-919c-2a29890f9b88.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Key West Sunset Sail with Live Music, Drinks and Appetizers!

CA $111

per adult

**92%** of travellers recommend

[](https://expedia.ca/things-to-do/key-west-sunset-sail-with-live-music.a191563.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.