Downtown Key West Vacations from $1,088

Book a Hotel + Flight or Car together to unlock savings

Your Downtown Key West Vacation

Our Downtown Key West vacation packages are a time-saving and convenient way to arrange and book your next escape. Experience the magic of this unique neighborhood without the bother of planning everything yourself. Your trip to Downtown Key West wouldn't be complete without stopping by big-name attractions nearby such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Don't just imagine it — make it a reality! Book your ideal Downtown Key West vacation with Expedia and get to where you're going your way.

The Latest Downtown Key West Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

Key West Historic District
$1,088
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (960 reviews)
My husband and I loved our stay at Ridley house. The property is beautiful and well maintained and our room was a nice size with a comfortable bed. We were served a breakfast spread every morning with plenty of food choices. The manager Angel was so helpful and knowledgeable, and he asked us every time he saw us if we needed anything. I don't remember the person's name who filled in for him, but she helped us set up rentals and a sandbar sunset cruise. We used the pool every day, to soak up some sun before heading out for the day. Duval street was an easy two blocks away.

Reviewed on Oct 13, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$1,800
per person
Nov 22 - Nov 27
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

Coconut Beach Resort

Coconut Beach Resort

Old Town Key West
Save 100% on your flight
$1,455
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (226 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$2,424
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
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
$5,699
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Where to stay in Downtown Key West

Find the best Downtown Key West areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Key West
A white building with shutters, palm trees, and a lawn.

Old Town Key West

4 out of top 10 points of interest in this area

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

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.

Downtown Key West Hotel Deals

Duval House

Duval House

815 Duval St Key West FL
$191 nightly
$212 total
Oct 25 - Oct 26
Total with taxes and fees
Duval House
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

819 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
$168 nightly
$189 total
Oct 26 - Oct 27
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"Place was great, clean, and reasonable. Beware the roosters at 6am but that might be the entire city of Key West Old Town"

Reviewed on Oct 13, 2026

Paradise Inn Key West - Adults Only
Wicker Guesthouse

Wicker Guesthouse

913 Duval Street Key West FL
$229 nightly
$258 total
Oct 25 - Oct 26
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Location was great"

Reviewed on Oct 15, 2026

Wicker Guesthouse
See all 2,721 properties in Downtown 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 Downtown Key West attractions

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
The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

Jackson Square

8.8/10 (110 reviews)
You can learn about the history of Key West with a stop at Jackson Square. Stroll along the seaside or discover the area's beautiful sunsets.
See properties
A historic building with ornate architecture, a balcony, and a coat of arms.

San Carlos Institute - Casa Cuba

8.6/10 (34 reviews)
You can spend an afternoon exploring the galleries in San Carlos Institute - Casa Cuba during your trip to Key West. Stroll along the area's beautiful beaches or experience its lively festivals.
See properties

Tennessee Williams Key West Exhibit

9.0/10 (2 reviews)
You can spend an afternoon studying the exhibits at Tennessee Williams Key West Exhibit during your travels in Key West. Wander the seaside and beautiful beaches in the area.
See properties

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

Explore a world of travel with Expedia

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