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.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
per person
Aug. 7 - Aug. 11
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
8.8/10 Excellent! (433 reviews)
Beautiful historic Key West Inn one block off of Duval. Quiet, great location, small bar with an excellent breakfast. Eric the bartender had great recommendations for restaurants and Pilar Rum.

Reviewed on May 28, 2024

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
per person
Aug. 7 - Aug. 11
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
8.8/10 Excellent! (1,002 reviews)
Amazing! Will definitely be going back!

Reviewed on May 28, 2024

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
per person
Aug. 7 - Aug. 11
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
7.8/10 Good! (1,594 reviews)
Ibis Bay Resort was phenomenal. From the great hospitality from Claudine and the bartender to the peaceful room upgrade. Initially we weren’t sure what this place would entail. To our surprise everything met our expectation and more. We will be coming back. If you see a bad review on here take it lightly…because this place is great for rest and relaxation from high strung lifestyles.

Reviewed on May 28, 2024

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Old Town Key West
Save 100% on your flight
per person
Aug. 10 - Aug. 17
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
6.6/10 (1,002 reviews)
Very nice place to stay

Reviewed on May 30, 2024

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Key West Historic District
Save 100% on your flight
per person
Aug. 7 - Aug. 11
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,002 reviews)
The pool is was quiet and beautiful. Very relaxing. Our room was clean but the toilet kept not filling up with water. Also one staff member acted very annoyed by any request we had.

Reviewed on May 16, 2024

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
Audubon House and Tropical Gardens featuring a house

Key West Historic District

4 out of top 10 points of interest in this area
4.5/5(156 area reviews)

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.

Find hotel + flight trips in Key West Historic District

Downtown Key West Hotel Deals

Heron House - Adult Only
Heron House - Adult Only
3.5 out of 5
512 Simonton St, Key West, FL
The price is CA $218 per night from Jun. 3 to Jun. 4
CA $218
CA $286 total
includes taxes & fees
Jun 3 - Jun 4
9/10 Wonderful! (1,068 reviews)
"Perfect for a quick getaway with many friendly returning guests. Well kept and clean."

Reviewed on May 28, 2024

Heron House - Adult Only
Duval House
Duval House
3 out of 5
815 Duval St, Key West, FL
The price is CA $190 per night from Jun. 3 to Jun. 4
CA $190
CA $243 total
includes taxes & fees
Jun 3 - Jun 4
9.2/10 Wonderful! (1,000 reviews)
"This place is amazing and I will be back...staff is amazing."

Reviewed on May 27, 2024

Duval House
Wicker Guesthouse
Wicker Guesthouse
3.5 out of 5
913 Duval Street, Key West, FL
The price is CA $287 per night from Jun. 2 to Jun. 3
CA $287
CA $323 total
includes taxes & fees
Jun 2 - Jun 3
8.2/10 Very Good! (1,002 reviews)
"It was great for the location, very close to shopping, bars, restaurants"

Reviewed on May 28, 2024

Wicker Guesthouse
See all 2,670 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.

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All Inclusive Vacations

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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 $1,081. 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.

Discover the most popular places to visit in Downtown Key West

Image for Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Ernest Hemingway Home and Museum
Image for San Carlos Institute - Casa Cuba

San Carlos Institute - Casa Cuba

You can enjoy some culture when you stop by San Carlos Institute - Casa Cuba in Key West. Stroll along the beautiful beaches or seek out the biking trails.

San Carlos Institute - Casa Cuba
Image for Jackson Square

Jackson Square

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.

Jackson Square

Things to do

Image for Jimmy Buffett Tour

Jimmy Buffett Tour

CA $107
Per adult
100% of travellers recommend
Jimmy Buffett Tour
Image for Key West Craft Cocktail Crawl

Key West Craft Cocktail Crawl

CA $127
Per adult
96% of travellers recommend
Key West Craft Cocktail Crawl
Image for Miami: Key West day trip with optional boating activities

Miami: Key West day trip with optional boating activities

CA $161
Per adult
Miami: Key West day trip with optional boating activities
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.