Historic Seaport Vacation Packages
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Top Holiday Package Deals in Historic Seaport
Price found within the past 48 hours. Click for updated prices.
The Marker Key West Harbor Resort
Key West Historic District
Price was CA $2,563, price is now CA $1,867 per person
CA $1,867
per person
May 24 - May 30
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
I appreciated the affiliation with Southern Most; being able to use their parking when on the other side of the island. Close proximity to major restaurants and Docks. The Marker has a great breakfast menu and friendly, helpful staff!
Reviewed on Apr 15, 2026
Hyatt Vacation Club at Windward Pointe, Key West
Price was CA $3,008, price is now CA $1,928 per person
CA $1,928
per person
May 24 - May 30
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Key West (EYW)
9.4/10 Exceptional! (1,030 reviews)
Very nice room with all amenities
Reviewed on Apr 16, 2026
Hyatt Vacation Club at Beach House, Key West
Price was CA $2,966, price is now CA $1,922 per person
CA $1,922
per person
May 24 - May 30
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Key West (EYW)
9.4/10 Exceptional! (1,017 reviews)
Great property. Rooms spacious. Pool beautiful. Only minus is it is a ways from the property to my Key West proper, with Uber and Lyft expensive to get there.
Reviewed on Apr 17, 2026
The Key West Hotel
Key West Historic District
Price was CA $4,512, price is now CA $3,252 per person
CA $3,252
per person
Jul 2 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Old Town Key West
Price was CA $3,125, price is now CA $2,273 per person
CA $2,273
per person
May 20 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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
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
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.
Historic Seaport Hotel Deals
Pier House Resort & Spa
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
NYAH Key West - Adults Only
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
Heron House Court - Adult Only
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
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.
Frequently asked questions
Discover the most popular places to visit in Historic Seaport
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.
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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $59
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $77
per adult
88% of travellers recommend
Key West Mangrove Kayak Eco Tour
CA $110
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.