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Key West Flight + Hotel Packages

Key West Flight + Hotel Packages - 3 Nights

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Key West Flight + Hotel Packages - 6 - 7 Nights

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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Top Key West Hotels Deals

See all 619 Hotels in Key West
Southernmost Beach Resort

Southernmost Beach Resort

1319 Duval Street, Key West
4.5 out of 5.0
4.3 out of 5 (53 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 ...

$344

$344
24 North Hotel Key West

24 North Hotel Key West

3820 North Roosevelt Boulevard, Key West
4.5 out of 5.0
3.9 out of 5 (23 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 ...

$254

$254
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West
4.5 out of 5.0
4.9 out of 5 (10 reviews)

Located in Stock Island, this hotel is 0.2 mi (0.4 km) from Key West Harbour and within 3 mi (5 km) of Robbie's and Key West Golf Club. Ernest Hemingway Home ...

$269

$269
Best Western Key Ambassador Resort Inn

Best Western Key Ambassador Resort Inn

3755 S Roosevelt Blvd, Key West
3.0 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, ...

$239

$239
Fairfield Inn & Suites by Marriott Key West, Keys Collection

Fairfield Inn & Suites by Marriott Key West, Keys Collection

3852 North Roosevelt Boulevard, Key West
3.5 out of 5.0
4.2 out of 5 (15 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 ...

$269

$269
The Gates Hotel Key West

The Gates Hotel Key West

3824 N Roosevelt Blvd, Key West
4.5 out of 5.0
4.2 out of 5 (20 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 ...

$263

$263
Ibis Bay Beach Resort

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd, Key West
3.0 out of 5.0
3.7 out of 5 (36 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 ...

$279

$279
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd, Key West
4.0 out of 5.0
4.2 out of 5 (103 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 ...

$278

$278
Hilton Garden Inn Key West,The Keys Collection

Hilton Garden Inn Key West,The Keys Collection

3850 N Roosevelt Blvd, Key West
4.0 out of 5.0
4.5 out of 5 (2 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 ...

$237

$237
Seashell Motel & Key West Hostel

Seashell Motel & Key West Hostel

718 South Street, Key West
2.0 out of 5.0
2.0 out of 5 (3 reviews)

Located in the heart of Key West, this hostel is within a 15-minute walk of South Beach and Ernest Hemingway Home and Museum. Audubon House and Tropical Gardens ...

$148

$148