This culture and arts hub in Key West Historic District comes recommended by travelers, so be sure to put it on your to-do list. Don't stop there, though. There are a lot more spots ready for you to check out after San Carlos Institute - Casa Cuba. Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens, and Mallory Square are not far away.

Plan a trip to see San Carlos Institute - Casa Cuba

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Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$617

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.6/10 Exceptional! (1,016 reviews)

Staff was friendly and very helpful.

Reviewed on Oct 15, 2025

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

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$2,203

per person

Dec 28 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,005 reviews)

Our room was clean and comfortable. The AC kept us cool. The staff was very friendly and helpful.

Reviewed on Oct 15, 2025

Oceans Edge Key West Resort, Hotel & Marina

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$2,318

per person

Dec 28 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

I love that our room over looked the marina and part of the ocean. The sunset was also beautiful from our room

Reviewed on Oct 15, 2025

Browse tours and tickets to explore San Carlos Institute - Casa Cuba

Tours & day trips

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Key West Express Day Trip from Miami

Free cancellation available

Wildlife & nature

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Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Free cancellation available

History & culture

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Key West Day Trip & Glass Bottom-Boat Tour from Miami

Free cancellation available

Private & custom tours

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Dry Tortugas National Park Day Trip by Luxury Private Boat

Free cancellation available

Food, drink & nightlife

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Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Free cancellation available

Popular places to visit

Jackson Square

You can learn about the history of Key West with a stop at Jackson Square. Stroll along the seaside or discover the area's beautiful sunsets.

Duval Street

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

Oldest House Museum and Garden

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

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.