Historic Seaport Vacations from $781
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Your Historic Seaport Vacation
Make travel planning hassle-free by creating a vacation package to Historic Seaport. We'll look after the minutiae, so you can concentrate on soaking up everything this neighborhood can offer. Can't wait to head out and see the sights during your trip to Historic Seaport? Be sure to check out nearby attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia can put your plans into action. Book your ultimate Historic Seaport vacation now.
The Latest Historic Seaport Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,180, price is now $781 per person
$781
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,006 reviews)
Was an amazing experience. The staff was lovely ......my only complaint was the roosters but thats a Key West thing lol strongly reccomend and will be returning
Reviewed on Aug 31, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,596, price is now $841 per person
$841
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (779 reviews)
it’s a great location but quiet. Love the free breakfast, pool and rooms! staff was great too!
Reviewed on Aug 23, 2025
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,546, price is now $918 per person
$918
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,011 reviews)
We enjoyed our stay for the most part. Convenient location and not super busy. The weather closed the pools a few times. The shower was Hot, didn't go cooler which was preferred since we stayed at the end of summer. It was calm and we walked down to the ocean to watch the sunrise.
Reviewed on Aug 30, 2025
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,191, price is now $791 per person
$791
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,729 reviews)
In general, I enjoyed my stay at Ocean Edge Resort. The room was clean and comfortable with a nice view of the ocean and the Marina. The property in general looks beautiful with an island vibe touch and it’s really pleasant to walk around. The staff at the front desk were friendly and polite. My only complaint is the restaurant. Extremely overpriced for the poor quality of the breakfast offered and the terrible customer service. The only thing I can save is the key lime pie. My advice, if you are looking for a nice place to stay in Key West, this is a lovely option, just don’t go to the restaurant.
Reviewed on Aug 31, 2025
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,430, price is now $951 per person
$951
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,008 reviews)
Absolutely beautiful 2 beds 2 bath village. We really enjoyed. Clean, comfortable. Loved the doble shower bathroom.
We definitely come back and will recommend this hotel to anyone.
Thank you Cheryl for let us feel to welcoming at the check in.
Reviewed on Aug 29, 2025
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
3 out of top 10 points of interest in this area
4.5/5(226 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
Hyatt Centric Key West Resort and Spa
601 Front St, Key West, FL
Fully refundableReserve now, pay when you stay
$232 nightly
The price is $261 total per night from Sep 7 to Sep 8
$261 total
Sep 7 - Sep 8
Total with taxes and fees
Pier House Resort & Spa
1 Duval St, Key West, FL
Fully refundableReserve now, pay when you stay
$387 nightly
The price is $435 total per night from Sep 1 to Sep 2
$435 total
Sep 1 - Sep 2
Total with taxes and fees
The Marker Key West Harbor Resort
200 William Street, Key West, FL
Fully refundableReserve now, pay when you stay
$233 nightly
The price is $262 total per night from Sep 3 to Sep 4
$262 total
Sep 3 - Sep 4
Total with taxes and fees
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.
Discover the most popular places to visit in Historic Seaport
Mallory Square
4.5/5(3,096 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.
Audubon House and Tropical Gardens
4.5/5(291 reviews)
Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.
Key West Shipwreck Museum
4/5(324 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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$40
per adult
92% of travellers recommend
Half-Day Key West's Ultimate Sandbar Adventure with Mangrove Kayak Tour
$126
per adult
98% of travellers recommend
Key West's All-Inclusive Combo With Jetski, Parasail, Snorkeling & Lunch
$161
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.