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.
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was CA $1,806, price is now CA $1,317 per person
CA $1,317
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.8/10 Exceptional! (1,002 reviews)
Breakfasts were great and they had a very good selection of drinks at the bar.

Reviewed on Apr 9, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $3,390, price is now CA $2,375 per person
CA $2,375
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (542 reviews)
Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!

Reviewed on Apr 5, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Price was CA $4,925, price is now CA $3,700 per person
CA $3,700
per person
Jul 2 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (354 reviews)
Location was great. Near most of Key West Attractions. Parked the car and walked everywhere.

Reviewed on Apr 14, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $1,910, price is now CA $1,450 per person
CA $1,450
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.4/10 Exceptional! (1,030 reviews)
Was not told that housekeeping needs to be requested one day in advance. Also that dirty towels were to be left outside not on the bathroom floor thatwas litature that was left in room.

Reviewed on Apr 17, 2026

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5
Price was CA $3,636, price is now CA $2,770 per person
CA $2,770
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.4/10 Exceptional! (3 reviews)
Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .

Reviewed on Mar 26, 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
Old Town Key West

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 hotels in Old Town Key West

Historic Seaport Hotel Deals

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $657 per night from Apr 26 to Apr 27
CA $657
CA $831 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (1,083 reviews)
We loved the location and the rooms. But my favorite was the beds!! OMG i slept so great on these beds. When i got home i called them to find out the manufacturer and model because I'm going to order the same bed for my house lol. Great time highly recommend Key west and the Pier House Resort

Reviewed on Apr 17, 2026

Pier House Resort & Spa
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
420 Margaret Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from May 12 to May 13
CA $197
CA $284 total
May 12 - May 13
includes taxes & fees
8/10 Very Good! (1,000 reviews)
The sunset was gorgeous. But the Caribbean Chicken was waaaay too spicy to eat. Plus we paid $20 a piece extra to get high shelf liquor in our drinks and it was watered down and not the quality of the bottle.

Reviewed on Apr 15, 2026

NYAH Key West - Adults Only
Heron House Court - Adult Only

Heron House Court - Adult Only

3 out of 5
412 Frances St Key West FL
The price is CA $229 per night from Apr 19 to Apr 20
CA $229
CA $305 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Loved this place really recommend it

Reviewed on Apr 15, 2026

Heron House Court - Adult Only
See all 2,738 properties in Historic Seaport
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Historic Seaport vacation package cost?
Our Historic Seaport vacation packages, which begin at just CA $1,317, are the easiest way to save. Handpick your preferred flights, hotels and rental cars to create your perfect trip.
How do I get a cheap travel package to Historic Seaport?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Choose a combination that suits you and see your savings pile up. Of course, a package deal is never a one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 properties globally, which lets you customize your Historic Seaport adventure.
Where should I stay in Historic Seaport?
Take the leg work out of sightseeing by staying just around the corner from Historic Seaport's fantastic attractions. Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens are two which top many visitors' bucket lists.
What are the top hotels in Historic Seaport?
Curry House and Ocean Key Resort - A Noble House Resort are among the most well-known properties in Historic Seaport. Why not take a look at the amenities and facilities at each and then decide?
How far in advance should I book my Historic Seaport vacation?
While not all air carriers release ticket prices early, you can usually compare international airfares on Expedia up to a year in advance. This is when you'll nab some incredible deals. If you're purchasing tickets last minute, you may still be in luck. Sometimes the cheapest prices become available just weeks prior to departure.
What does an Expedia Historic Seaport travel package include?
With Expedia, you can choose any combination of flights, car rentals and hotels to build your ideal Historic Seaport package. Once you've made your booking, you can add on the fun things like activities and tours. Remember — the more you bundle, the greater the savings!
What should I know before booking a Historic Seaport travel package?
So many places to wander around, so many things to see and do. With a travel package, you'll be able to cross more of them off your list. Bundle your flights, hotels and rental cars and get ready to save.
Can I choose my airline with a Historic Seaport Expedia vacation package?
With a vacation package, you're the boss. Whether you're looking to fly to Historic Seaport in coach or business class, simply pick from the available airline options. Expedia has access to more than 550 partner airlines all over the world.
If I'm not able to travel, can I cancel my Historic Seaport vacation package?
Don't worry if you're rethinking your Historic Seaport vacation package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We know your circumstances can suddenly change, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.

Discover the most popular places to visit in Historic Seaport

Mallory Square

Mallory Square

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.

Mallory Square
Key West Shipwreck Museum

Key West Shipwreck Museum

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.

Key West Shipwreck Museum

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $59
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $77
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Kayak the mangrove tidal creeks

Key West Mangrove Kayak Eco Tour

CA $110
per adult
100% of travellers recommend
Key West Mangrove Kayak Eco Tour
See all activities in Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.