Plan a trip to see Key West Historic Seaport

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Bay Breeze Premium Apartments By Eskape Collection

$451

per person

Feb 6 - Feb 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (189 reviews)

Will be nice if the hotel can think about what a new hotel guest will be going through. They will usually drive up to the hotel and look for parking. Then they will look into how to check-in and how to get to their room. It will be nice to mention in the welcome text to fill out the registration and the credit card authorization, AND also mention if we have a vehicle, what shall we do. Also will be helpful if the text will let us know the office in the building will be closed on Saturdays (and Sundays?) We were trying to figure all these out while carrying our luggages under strong winds, lucky it didn't rain. Will also be helpful to text us that we need to submit those 2 forms, then we will receive our gate and door codes. Restroom didn't smell fresh. Other than the aforementioned, the stay was good.

Reviewed on Oct 27, 2025

Hawks Cay Resort

$648

per person

Jan 29 - Feb 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Amazing for young families! Heading back again!

Reviewed on Nov 29, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$898

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (56 reviews)

Gorgeous hotel, great pool and private beach.

Reviewed on Dec 3, 2025

Browse tours and tickets to explore Key West Historic Seaport

Tours & day trips

See all 174 activities

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

History & culture

See all 58 activities

Key West Conch Tour Train

Free cancellation available

Wildlife & nature

See all 49 activities

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Free cancellation available

Private & custom tours

See all 35 activities

Dry Tortugas National Park Day Trip by Luxury Private Boat

Free cancellation available

Adventure & outdoor

See all 19 activities

Key West Half-Day Fishing Charter

Free cancellation available

Popular places to visit

22 room mansion all decked out for Valentine’s Day. Home to Florida’s 1st millionaire.

Curry Mansion Museum

You can spend time studying the exhibits at Curry Mansion Museum during your trip to Key West. Stroll along the area's seaside or experience its lively festivals.

Oldest House Museum and Garden

4.5/5(8 reviews)

With its period décor and vintage documents, South Florida’s oldest house provides an impression of life in the Florida Keys archipelago in the 19th century

The Kite House

Enjoy an outing to The Kite House during your stay in Key West. Wander the seaside or discover the area's beautiful sunsets.

Mallory Dock

4.5/5(1,061 reviews)

You can search for that perfect souvenir at Mallory Dock during your visit to Key West. Wander the area's seaside or simply enjoy one of its lively bars.