Name: The Southernmost Inn - Adults Only
Price range: $246 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.

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,702

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,006 reviews)

Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto

Reviewed on Oct 20, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,861

per person

Dec 6 - Dec 11

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

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

Save 100% on your flight

$4,112

per person

Jan 21 - Jan 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

10/10 Exceptional! (1 review)

Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West

Save 100% on your flight

$3,727

per person

Jan 10 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

10/10 Exceptional! (3 reviews)

Loved it

Reviewed on Mar 20, 2026

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Old Town Key West

$2,177

per person

Jan 21 - Jan 26

found 17 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

9.8/10 Exceptional! (9 reviews)

Absolutely loved the Privacy and that we were right next to Cuban Coffee Queen! This is a nice little place to stay with great privacy. It was clean, had the little things, like Q-Tips! Will definitely stay there next year!

Reviewed on Aug 27, 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

$306 nightly

$344 total

Nov 15 - Nov 16

Total with taxes and fees

8.4/10 Very Good! (996 reviews)

"Beautiful property with private beach."

Reviewed on Oct 30, 2026

The Southernmost Inn - Adults Only

525 United Street Key West FL

Fully refundableReserve now, pay when you stay

$219 nightly

$246 total

Nov 2 - Nov 3

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.