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.
Southernmost House - Adult Exclusive
Old Town Key West
CA $1,518
per person
Sep 25 - Sep 28
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We had a great time at the Southernmost House. The staff was extremely kind, helpful, and friendly. The food at the bar that we had for breakfast and lunch was fantastic. The house was charming, and while it needs some updating, the staff is actively working to improve the property. We always had a place to park our golf cart and any issue we had was solved quickly. The location was great and we would definitely stay there again.
Reviewed on Aug 20, 2026
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.
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.
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 Key West Tropical Forest and Botanical Garden.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Historic Seaport
While visiting Historic Seaport, you might make a stop by sights like Duval Street and Florida Keys Beaches.
Downtown Key West Hotel Deals
Heron House - Adult Only
512 Simonton St Key West FL
CA $135
CA $197 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (1,170 reviews)
"Very nice place, friendly staff, great location."
Reviewed on Aug 22, 2026
Duval House
815 Duval St Key West FL
CA $140
CA $187 total
Aug 31 - Sep 1
includes taxes & fees
9.6/10 Exceptional! (1,093 reviews)
"Staff was attentive and friendly"
Reviewed on Aug 22, 2026
Wicker Guesthouse
913 Duval Street Key West FL
CA $240
CA $270 total
Sep 14 - Sep 15
includes taxes & fees
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 a Downtown Key West vacation package cost?
Chart your own course with our Downtown Key West vacation packages, which start from a low CA $1,518. Handpick the hotels and flights that fit your travel plans. Then, add on one or two enriching experiences to round off your unique getaway.
How do I get a cheap travel package to Downtown Key West?
Our Downtown Key West vacation packages offer plenty of savings for the savvy explorer. For the best deal, simply bundle your flights, hotels and activities into a convenient package. But impressive bargains are just the beginning of your next amazing adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 hotel options all over the world to pick from. Whatever your style or budget, there's a vacation package here just for you.
Where should I stay in Downtown Key West?
A trip to Downtown Key West has to include Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Book a hotel right nearby for quick access to these impressive sights.
What are the top hotels in Downtown Key West?
If it's your first visit to Downtown Key West, reserve a room at Maya's Secret Treasure @ Duval Private Pool And Balcony Over Duval + Last Key or Southernmost Retreat: 2 Blocks From Duval In Old Town. Both hotels offer comfy beds and are favorites with lots of travelers.
How far in advance should I book my Downtown Key West vacation?
Savvy travelers will likely want to book as early as possible. You can normally browse through international fares on Expedia up to 12 months before your flight. If you're purchasing tickets last minute, don't worry. Cheap prices occasionally become available just weeks before departure dates.
What does an Expedia Downtown Key West travel package include?
Choose from a combination of hotels, rental cars and flights. Once you've made your booking, you can add some experiences and activities. Want to pick your fare class? That's easily done too. The choice is all yours when it comes to putting together your ideal Downtown Key West escape.
What should I know before booking a Downtown Key West travel package?
Whether it's relaxation or adventure you're seeking, a Downtown Key West vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your accommodations with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Downtown Key West Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the freedom to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Downtown Key West vacation package?
It's hard to predict what the future holds, so it's good to know that you can change or cancel your Downtown Key West vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
Stay near popular Downtown Key West attractions
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.
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 beautiful beaches or discover the area's beautiful sunsets.
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.
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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $63
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $78
per adult
88% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
CA $85
per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.