
Downtown Key West Vacation Packages
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Top Holiday Package Deals in Downtown Key West
Price found within the past 48 hours. Click for updated prices.



Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
per person
May 17 - May 24
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Key West (EYW)
9.8/10 Exceptional! (1,002 reviews)
A lovely, quaint motel in the heart of it all. The staff was OUTSTANDING. Super clean rooms and pool area. Will definitely stay again!
Reviewed on Mar. 27, 2025

Fitch Lodge - Key West Historic Inns
Key West Historic District
per person
May 17 - May 24
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Key West (EYW)
8.8/10 Excellent! (421 reviews)
Fitch Lodge is a great property somewhat away from the crowds and noise of Key West but still close enough to be easily accessible to most of the city’s attractions, shopping and dining. The pool is small but we didn’t even use it other than to relax by with our complimentary afternoon cocktail. Very relaxing visit to KW!
Reviewed on Mar. 25, 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

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.
Downtown Key West Hotel Deals

Duval House
815 Duval St, Key West, FL
The price is CA $312 per night from Apr. 2 to Apr. 3
CA $312
CA $382 total
includes taxes & fees
Apr 2 - Apr 3
9.2/10 Wonderful! (1,001 reviews)
"It was very cool"
Reviewed on Mar. 26, 2025

Heron House - Adult Only
512 Simonton St, Key West, FL
The price is CA $242 per night from Apr. 3 to Apr. 4
CA $242
CA $315 total
includes taxes & fees
Apr 3 - Apr 4
9/10 Wonderful! (1,065 reviews)
"The location is perfect."
Reviewed on Mar. 26, 2025

Paradise Inn Key West - Adults Only
819 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $457 per night from Mar. 31 to Apr. 1
CA $457
CA $578 total
includes taxes & fees
Mar 31 - Apr 1
9/10 Wonderful! (1,002 reviews)
"The Paradise Inn is an absolutely wonderful place to stay. It is very conveniently located in the center of old town Key West making walking to all events and locations very easy. The staff are very friendly and the morning breakfast buffet is fantastic. The pool and hot tub are just the right size ..."
Reviewed on Mar. 26, 2025
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
Discover the most popular places to visit in Downtown Key West

Ernest Hemingway Home and Museum
4.5/5(77 reviews)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Jackson Square
4.5/5(4 reviews)
You can learn about the history of Key West with a stop at Jackson Square. Stroll along the beautiful beaches or discover the area's beautiful sunsets.
Things to do

MIAMI: Key West Day Trip with Boating Options
CA $111
per adult

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
CA $142
per adult
76% of travellers recommend

The Dark Side of Key West Adults Only Walking Tour
CA $50
per adult
100% of travellers recommend
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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.