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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 151 Hotels in Key West
24 North Hotel Key West

24 North Hotel Key West

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

Situated in Key West, this hotel is 0.7 mi (1.2 km) from Key West Tropical Forest and Botanical Garden and within 3 mi (5 km) of Key West Art and Historical ...

$110

$110
Casa Marina Resort - A Waldorf Astoria Resort

Casa Marina Resort - 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 & ...

$229

$229
Parrot Key Hotel & Resort

Parrot Key Hotel & Resort

2801 N Roosevelt Blvd, Key West
4.0 out of 5.0
4.0 out of 5 (29 reviews)

Situated on the waterfront, this romantic resort is within 3 mi (5 km) of The Unitarian Universalist Fellowship of Key West, Ernest Hemingway Home and Museum, ...

$143

$143
Fairfield Inn and Suites Key West

Fairfield Inn and Suites Key West

2400 N Roosevelt Blvd, Key West
2.5 out of 5.0
3.6 out of 5 (34 reviews)

A 3-minute drive from Key West Airport and 10 minutes from Old Town, Fairfield Inn and Suites Key West offers easy access to attractions like Duval Street, Mallory ...

$139

$139
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 ...

$134

$134
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
The Inn at Key West

The Inn at Key West

3420 N Roosevelt Blvd, Key West
3.5 out of 5.0
3.9 out of 5 (31 reviews)

Located within minutes of Old Town, the Ernest Hemingway Home & Museum, Mallory Square, Duval Street shops, restaurants, and nightlife.

$122

$122
Southernmost Beach Resort

Southernmost Beach Resort

508 South St, Key West
4.0 out of 5.0
4.4 out of 5 (51 reviews)

This Key West historical district hotel is 2 blocks from Southernmost Point. Ernest Hemingway Home and Museum, and Key West Lighthouse and Keeper's Quarters ...

$179

$179
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd, Key West
3.5 out of 5.0
4.2 out of 5 (102 reviews)

Located on the quieter side of Key West, this tropical-style resort offers complimentary scheduled shuttle service to Duval Street as well as shuttle service ...

$124

$124