Title: Historic Seaport Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,948 Expedia.ca

[Historic Seaport Travel Guide](https://expedia.ca/Key-West-Historic-Seaport.dx553248635976383502)[Hotels in Historic Seaport](https://expedia.ca/Historic-Seaport-Key-West-Hotels.0-n553248635976383502-0.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)[Historic Seaport Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Seaport.d553248635976383502.Car-Rental-Guide)

![](https://images.trvl-media.com/place/501385/8fc21581-48e4-48a8-8cca-3cfabcd30450.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Historic Seaport 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 Seaport

Price found within the past 48 hours. Click for updated prices.

![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 $1,948

per person

Apr 26 - May 3

found 13 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.6/10 Exceptional! (1,002 reviews)

Everything was so clean.

Reviewed on Mar 1, 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 $2,951

per person

May 8 - May 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Bali bar was the best! Will stay again!

Reviewed on Mar 2, 2026

![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 $2,357

per person

Apr 20 - Apr 26

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Stayed there for 5 nights and it was very pleasant!

Reviewed on Mar 2, 2026

![Ella's Cottages - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/870000/863200/863188/deb4f031_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ella's Cottages - Key West Historic Inns

Old Town Key West

CA $2,981

per person

May 8 - May 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (390 reviews)

Dwight the front desk staff was awesome! So accommodating and friendly! The rooms were the perfect size and everything was walkable distance.

Reviewed on Feb 28, 2026

![Ridley House - Key West Historic Inns](https://images.trvl-media.com/lodging/5000000/4960000/4959000/4958964/34e7619a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ridley House - Key West Historic Inns

Key West Historic District

CA $2,975

per person

May 8 - May 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (845 reviews)

It was very loud- all night long. We asked staff about it and was told all the rooms are loud. The room was clean and the continental breakfast was nice.

Reviewed on Mar 2, 2026

## Where to stay in Historic Seaport

Find the best Historic Seaport areas and neighborhoods for the activities you enjoy most. [Learn more about Historic Seaport](https://expedia.ca/Key-West-Historic-Seaport.dx553248635976383502)

![Key West Historic District](https://images.trvl-media.com/place/553248635976481920/c3895c9f-e471-4c93-ac2e-85c99f8f8fec.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Old Town Key West

4 out of top 10 points of interest in this area

3.5/5(8 area reviews)

 Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area. 

[Find hotel + flight trips in Old Town Key West](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Old%20Town%20Key%20West&DestID=553248635976481920&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![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)

## Historic Seaport Hotel Deals

![Hyatt Centric Key West Resort and Spa](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL

Fully refundableReserve now, pay when you stay

CA $608

CA $780 total

Mar 22 - Mar 23

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

Clean room and beautiful grounds. Staff was very accommodating. Would definitely stay here again.

Reviewed on Feb 26, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=901&PinnedHotelID=901&HadPinnedHotel=true&regionId=553248635976383502)

![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Pier House Resort & Spa

1 Duval St Key West FL

Fully refundableReserve now, pay when you stay

CA $895

CA $1,099 total

Mar 6 - Mar 7

includes taxes & fees

9/10 Wonderful! (1,050 reviews)

It is a nice hotel, don't be fooled by the picture of the beach, it's not that big. The breakfast food was amazing, great service.

Reviewed on Mar 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=06%2F03%2F2026&endDate=07%2F03%2F2026&selected=19307&PinnedHotelID=19307&HadPinnedHotel=true&regionId=553248635976383502)

![NYAH Key West - Adults Only](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

NYAH Key West - Adults Only

420 Margaret Street Key West FL

Fully refundableReserve now, pay when you stay

CA $363

CA $470 total

Mar 4 - Mar 5

includes taxes & fees

8/10 Very Good! (1,004 reviews)

Yes

Reviewed on Mar 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=7500588&PinnedHotelID=7500588&HadPinnedHotel=true&regionId=553248635976383502)

[See all 2,752 properties in Historic Seaport](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&regionId=553248635976383502)

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 Seaport vacation package cost?

### How do I get a cheap travel package to Historic Seaport?

### Where should I stay in Historic Seaport?

### What are the top hotels in Historic Seaport?

### How far in advance should I book my Historic Seaport vacation?

### What does an Expedia Historic Seaport travel package include?

### What should I know before booking a Historic Seaport travel package?

### Can I choose my airline with a Historic Seaport Expedia vacation package?

### If I'm not able to travel, can I cancel my Historic Seaport vacation package?

### Discover the most popular places to visit in Historic Seaport

![Mallory Square which includes a sunset and a bay or harbor as well as a large group of people](https://images.trvl-media.com/place/501385/f076c469-e361-414e-8323-e71ccf56c947.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Mallory Square

4.5/5(148 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

[](https://expedia.ca/Mallory-Square-Key-West-Historic-District.d501385.Vacation-Attraction)

![Key West Shipwreck Museum featuring street scenes](https://images.trvl-media.com/place/6063545/ca5c72da-e4d8-405d-a89c-4f692670e34a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Key West Shipwreck Museum

4/5(13 reviews)

This interactive museum is home to unbelievable relics pulled from the bottom of the sea and a watchtower with views across the Gulf of Mexico.

[](https://expedia.ca/Key-West-Shipwreck-Museum-Key-West-Historic-District.d6063545.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)

![Friends cheers with cocktails on Key West cruise](https://mediaim.expedia.com/localexpert/587053/54666c36-0979-4755-bcfd-1df49670de5a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!

CA $73

per adult

**92%** of travellers recommend

[](https://expedia.ca/things-to-do/key-west-afternoon-at-the-reef-snorkeling-adventure-with-open-bar.a587053.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 $83

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)

[See all activities in Key West](https://expedia.ca/things-to-do/search?rid=553248635976383502)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.