Name: The Southernmost Inn - Adults Only
Price range: $235 total

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Your Old Town Key West Vacation

Organizing your next exciting getaway just got a whole lot easier with a vacation package to Old Town Key West. Take in the best this neighborhood has to offer while making precious memories you'll replay for years. Some leading nearby attractions to check out during your trip to Old Town Key West include Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia will help put your plans into action. Book your ideal Old Town Key West vacation now.

The Latest Old Town Key West Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

$800

per person

Jan 9 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,001 reviews)

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,237

per person

Nov 29 - Dec 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (564 reviews)

Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!

Reviewed on Oct 29, 2026

Pier House Resort & Spa

Key West Historic District

$1,783

per person

Jan 9 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,363 reviews)

The Marker Key West Harbor Resort

Key West Historic District

$1,308

per person

Jan 9 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,033 reviews)

needs to be refurbished

Reviewed on Oct 27, 2026

Ridley House - Key West Historic Inns

Key West Historic District

$866

per person

Jan 9 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (969 reviews)

Was a great location. Wonderful staff. Breakfast was great! Was nice to have the pool to cool off in the afternoons.

Reviewed on Oct 29, 2026

Where to stay in Old Town Key West

Find the best Old Town Key West areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Key West

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

Old Town Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$263 nightly

$296 total

Nov 15 - Nov 16

Total with taxes and fees

8.6/10 Excellent! (3,660 reviews)

"The entire stay was perfect! See you next year!!"

Reviewed on Oct 29, 2026

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Fully refundableReserve now, pay when you stay

$307 nightly

$345 total

Nov 15 - Nov 16

Total with taxes and fees

8.4/10 Very Good! (995 reviews)

"Amazing time spent at the Casa. We will be back."

Reviewed on Oct 29, 2026

The Southernmost Inn - Adults Only

525 United Street Key West FL

Fully refundableReserve now, pay when you stay

$209 nightly

$235 total

Oct 30 - Oct 31

Total with taxes and fees

See all 1,284 properties in Old Town Key West

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.