Old Town Key West Vacation Packages

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Top Holiday Package Deals in Old Town Key West

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
CA $2,693
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (564 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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
Save 100% on your flight
CA $5,395
per person
Dec 27 - Jan 3
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
Our stay at the Southern Most was great! The location is perfect and the staff was wonderful. The beach, the pool the rooms were spotless and the staff couldn’t have been any nicer. Highly recommended.

Reviewed on Oct 26, 2026

Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West
Save 100% on your flight
CA $6,497
per person
Jan 11 - Jan 18
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
10/10 Exceptional! (3 reviews)
Loved it

Reviewed on Mar 20, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
CA $5,175
per person
Dec 27 - Jan 3
found 24 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
staff was super friendly and accomodating

Reviewed on Oct 22, 2026

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

CA $4,155
per person
Dec 30 - Jan 6
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (3 reviews)
Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .

Reviewed on Mar 26, 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

While visiting Historic Seaport, you might make a stop by sights like Duval Street and Florida Keys Beaches.

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
CA $166
CA $293 total
Oct 28 - Oct 29
includes taxes & fees
8.6/10 Excellent! (3,650 reviews)
"Our stay at the Southern Most was great! The location is perfect and the staff was wonderful. The beach, the pool the rooms were spotless and the staff couldn’t have been any nicer. Highly recommended."

Reviewed on Oct 26, 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
CA $344
CA $482 total
Nov 2 - Nov 3
includes taxes & fees
8.4/10 Very good! (990 reviews)
"Great hotel and conveniently located in Key West! We truly enjoyed our time there"

Reviewed on Oct 25, 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
Fully refundableReserve now, pay when you stay
CA $162
CA $246 total
Oct 27 - Oct 28
includes taxes & fees
8.4/10 Very good! (1,455 reviews)
"This is a small, boutique type inn. There are steep steps to the second and third floors so if you have heavy luggage, be careful. The continental breakfast was pretty good, you can make your own waffles. The “happy hour “ was cheese, nuts, some stale crackers and wine. Great location on the ..."

Reviewed on Oct 26, 2026

The Southernmost Inn - Adults Only
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.

Frequently asked questions

How much does an Old Town Key West vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Old Town Key West from just CA $2,693. And the more you bundle, the more money you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Old Town Key West?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got everything you need. Select a combination that best suits you and watch your savings grow. Of course, a travel package is never one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 hotel options around the globe, which lets you customize your Old Town Key West getaway.
Where should I stay in Old Town Key West?
A trip to Old Town Key West isn't complete without stopping by Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Book a hotel as close as possible for quick access to these awesome attractions.
What are the top hotels in Old Town Key West?
Secure a room at Southernmost Retreat: 2 Blocks From Duval In Old Town. It's one of this area's most in-demand properties. Another top-rated option in Old Town Key West is Curry House.
How far in advance should I book my Old Town Key West vacation?
Smart travelers often book as early as possible. You can generally look up international fares on Expedia up to a year before your intended flight. If you're purchasing tickets last minute, don't despair. Budget prices occasionally become available just weeks prior to departure.
What does an Expedia Old Town Key West travel package include?
Hotels, car rentals and flights — we bring you the very best deals. All you have to do is pick and choose your favorite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to create an awesome Old Town Key West vacation.
What should I know before booking an Old Town Key West travel package?
A package can be cheaper than separately booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save big. Whatever your vacation goals are, there's sure to be a package within your budget.
Can I choose my airline with an Old Town Key West Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Old Town Key West vacation package?
You can. We realize life doesn't always go to plan, so we're here to help if you have to make changes to your Old Town Key West vacation package. You may be able to amend or cancel your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

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.
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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.
See properties
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)
The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.
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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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $79
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $83
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
See all activities in Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.