Old Town Key West Vacations from $1,166

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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 Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$1,166
per person
Dec 13 - Dec 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (563 reviews)
Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

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

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

Old Town Key West
Save 100% on your flight
$5,908
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip 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

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$2,225
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
$2,076
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned.

Reviewed on Oct 12, 2026

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Key West Historic District
Save 100% on your flight
$2,344
per person
Dec 20 - Dec 27
found 19 hours ago
Roundtrip flight included
New York (NYC) to Key West (EYW)
2/10 (1 review)
The listing says this property is “on beach property,” but it is not on the beach or even close to a beach, which was very misleading. While we were staying there, the pool was also resurfaced. We were told that it was a “last-minute” discovery that the pool needed to be closed, but this significantly affected our stay. We also had trouble getting ahold of anyone when we had questions or concerns. Calls to the management/maintenance contact went unanswered, and no one returned our calls. Another issue was the condition of the balconies. We were on one of the lower floors, and whenever the guests above us used their deck, dirt and sand would fall down onto ours while we were sitting outside. It made it very unpleasant to actually use the outdoor space. Overall, the property description was misleading, the unexpected pool closure was disappointing, communication was poor, and the balcony situation made the stay less enjoyable than expected.

Reviewed on Sep 12, 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.

A two-story house with green shutters and a wooden balcony.

Key West Historic District

2 out of top 10 points of interest in this area

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

New Town

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Fort East Martello Museum and Gallery.

A sunset over the ocean with scattered clouds.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.

A pier with people dining under umbrellas, a sailboat in the distance, and a sunset over the water.

Historic Seaport

Many of the best parts of the southern portion of Florida are rolled into one location. Enjoy your time experiencing attractions in this historic area.

Old Town Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$239 nightly
$269 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (3,621 reviews)
"We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned."

Reviewed on Oct 12, 2026

Southernmost Beach Resort and Guesthouses
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$276 nightly
$310 total
Oct 25 - Oct 26
Total with taxes and fees
8.4/10 Very Good! (966 reviews)
"Will not return again poor service room was dirty"

Reviewed on Oct 13, 2026

Casa Marina Key West, Curio Collection by Hilton
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

525 United Street Key West FL
$159 nightly
$179 total
Oct 14 - Oct 15
Total with taxes and fees
The Southernmost Inn - Adults Only
See all 1,282 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.

Stay near popular Old Town Key West attractions

A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
See properties
A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

Ernest Hemingway Home and Museum

9.2/10 (8,543 reviews)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
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A wooden sign with information about South Beach, Key West, Florida, including public beach status, restaurant hours, and beach chair rental.

South Beach

8.4/10 (5,461 reviews)
Head to the southernmost beach of the continental United States to relax and swim in the waters where famous writer Tennessee Williams once took his daily swim.
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A beach sign with rules and hours for Clarence S. Hughes Memorial Beach.

Clarence S. Higgs Memorial Beach Park

8.4/10 (4,659 reviews)
Pay your respects at an impressive African burial site, explore landscaped gardens or snorkel with the family at this oceanfront beach park.
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A building with a sign reading "The Key West Butterfly & Nature Conservatory".

Key West Butterfly and Nature Conservatory

9.2/10 (1,711 reviews)
With about 60 species of butterfly, an indoor waterfall and a tropical rainforest, this nature conservatory is one of the most popular attractions in Key West.
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A historical marker for The Little White House, built in 1890, used by American Navy officers, and listed on the National Register of Historic Places in 1974.

Harry S. Truman Little White House

9.0/10 (995 reviews)
Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.
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A white lighthouse with a black top, surrounded by lush greenery and residential buildings.

Key West Lighthouse and Keeper's Quarters Museum

8.6/10 (548 reviews)
Climb to the top of this historic lighthouse for unparalleled photo opportunities and then visit the former home of Key West’s lighthouse keepers.
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An aquarium exhibit with fish tanks and informational displays.

Florida Keys Eco - Discovery Center

8.8/10 (128 reviews)
Learn about the area’s important marine ecology at this comprehensive attraction that addresses global environmental concerns, interesting for visitors of all ages.
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Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

$59
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

$79
per adult
98% of travellers recommend
Sunset Sail in Key West with Beverages Included
See all activities in Key West

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.