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Key West Vacations

Key West vacations let you soak up the Florida sun while enjoying history, quirky local charm, and a dynamic social scene. A big bonus? Flip-flops count as formal wear here!

Major Attractions

There are several must-visit Key West attractions. The Ernest Hemingway Home and Museum (look for the estate's famed polydactyl cats) and the Harry S Truman Little White House, where the former President wintered, are historical gems. The Southernmost Point buoy on the corner of South and Whitehead streets is a great photo opportunity, and the Key West Butterfly and Nature Conservancy is a crowd-pleaser for all ages.

Key West is fairly easy to navigate; bike rentals are one way to get around. Still, many visitors discover it's helpful to line up car rentals in Key West. You may wish to cross the Seven Mile Bridge and check out Marathon Key. If you're visiting in a hotter month, you'll appreciate being able to hop into an air-conditioned rental car rather than pedaling from spot to spot.

Festivals and Events

Your Key West visit will definitely correspond with one favorite local event: The Key West Sunset Festival, held nightly at Mallory Square. The Key West Fishing Tournament runs from April through November; submit proof of your catch and receive a certificate and possibly a prize. Speaking of seafood, celebrate the beginning of lobster season in early August during Key West Lobsterfest. Unquestionably, the most anticipated annual event is Fantasy Fest, held the last weekend in October. It's like Mardi Gras, island style. Regardless of when you visit, concierges at Key West hotels can give you a rundown of what's on the calendar during the week or weekend of your visit.

Browse Travelocity's Key West packages and save up to $537 when you book your hotel and flight at the same time. Why not rent or charter a sailboat with the money you'll save on Key West vacation packages?

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Key West Flight + Hotel packages

Top Key West Hotels Deals

See all 200 Hotels in Key West
Ibis Bay Beach Resort

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd, Key West
2.5 out of 5.0
3.7 out of 5 (35 reviews)

The white-sand beach of Ibis Bay Beach Resort is a 5-minute drive from downtown Key West. Both the Ernest Hemingway Home & Museum and Southernmost Point are ...

$138

$138
Best Western Key Ambassador Resort Inn

Best Western Key Ambassador Resort Inn

3755 S Roosevelt Blvd, Key West
2.5 out of 5.0
4.0 out of 5 (6 reviews)

Located on the Atlantic side of Island and just minutes from the Key West Art Society and Historical Downtown. Nearby points of interest include Smathers Beach, ...

$170

$170
Hilton Garden Inn Key West,The Keys Collection

Hilton Garden Inn Key West,The Keys Collection

3850 N Roosevelt Blvd, Key West
3.5 out of 5.0
5.0 out of 5 (1 reviews)

Located in the heart of Key West, this hotel is 1.1 mi (1.7 km) from Key West Golf Club and within 3 mi (5 km) of Key West Art and Historical Society and Smathers ...

$139

$139
Casa Marina, A Waldorf Astoria Resort

Casa Marina, A Waldorf Astoria Resort

1500 Reynolds Street, Key West
4.0 out of 5.0
4.1 out of 5 (148 reviews)

Looking out over the Straits of Florida towards Cuba, this upscale resort places guests a 3-minute drive from downtown Key West. The Ernest Hemingway Home & ...

$259

$259
The Southernmost Inn-Adults Only

The Southernmost Inn-Adults Only

525 United Street, Key West
2.5 out of 5.0
4.6 out of 5 (83 reviews)

Located in Key West Historic District, this hotel is within a 10-minute walk of Key West Butterfly and Nature Conservatory and Ernest Hemingway Home and Museum. ...

$98

$98
Fairfield Inn & Suites by Marriott Key West, Keys Collection

Fairfield Inn & Suites by Marriott Key West, Keys Collection

3852 North Roosevelt Boulevard, Key West
3.0 out of 5.0
4.2 out of 5 (14 reviews)

Located in the heart of Key West, this hotel is 1.1 mi (1.8 km) from Key West Golf Club and within 3 mi (5 km) of Key West Art and Historical Society and Smathers ...

$139

$139
24 North Hotel Key West

24 North Hotel Key West

3820 North Roosevelt Boulevard, Key West
4.0 out of 5.0
4.0 out of 5 (22 reviews)

Situated near the airport, this hotel is 2.2 mi (3.6 km) from Key West Harbour and within 6 mi (10 km) of Key West Lighthouse and Keeper's Quarters Museum and ...

$115

$115
La Concha Hotel & Spa

La Concha Hotel & Spa

430 Duval St, Key West
4.0 out of 5.0
4.2 out of 5 (113 reviews)

Located in Key West Historic District, this spa hotel is steps from San Carlos Institute - Casa Cuba, Oldest House Museum and Garden, and Red Barn Theater. Key ...

$170

$170
Silver Palms Inn

Silver Palms Inn

830 Truman Ave, Key West
3.5 out of 5.0
3.8 out of 5 (12 reviews)

Silver Palms Inn is a half-mile from the Ernest Hemingway House and Museum and Key West Lighthouse, and 3 blocks from Duval Street. Mallory Square is a 3-minute ...

$139

$139
The Gates Hotel Key West

The Gates Hotel Key West

3824 N Roosevelt Blvd, Key West
4.0 out of 5.0
4.2 out of 5 (17 reviews)

Situated at the northern tip of Key West, this hotel is within 2 miles (3.2 kilometers) of Smathers Beach and the airport and is minutes away from Earnest Hemingway ...

$134

$134