Downtown Key West Vacations

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Your Downtown Key West Vacation

Our Downtown Key West vacation packages are a fast and practical way to plan and book your next break. Discover the true character of this unique neighborhood without the pressure of organizing everything yourself. Some top nearby attractions to check out during your trip to Downtown Key West include Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Whatever your travel goals or budget, booking your dream Downtown Key West vacation has never been easier with Expedia.

The Latest Downtown Key West Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
per person
Aug 5 - Aug 11
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
7.8/10 Good! (1,595 reviews)
The hotel is quite nice. Apart from Duval's heavy crowd and easy transportation to it. Very nice complex, excellent for kids. Amazing lobby. The only remark I would do is room's bathroom size. Nevertheless, it is a great place and a great option.

Reviewed on May 12, 2024

Beachside Resort & Residences

Beachside Resort & Residences

4 out of 5
Save 100% on your flight
per person
Aug 5 - Aug 11
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.4/10 Very Good! (1,002 reviews)
Everything was perfect. I don’t say that lightly. It was not busy season so that could have made a difference. Every meal I ate was fresh, hot and delicious. I will definitely be back!! Everyone was extremely polite and helpful.

Reviewed on May 13, 2024

Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Key West Historic District
Save 100% on your flight
per person
Aug 5 - Aug 11
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (668 reviews)
Place is pretty run down which is crazy considering how much they charge per night. Super close to the fun part of Key West. Never got check in details so was confused when we got there and had no info. Lucky for us someone answered the phone and got us in quickly which was very nice.

Reviewed on May 10, 2024

H2O Suites - Adults Only

H2O Suites - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jun 21 - Jun 24
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (477 reviews)
Very nice and helpful staff

Reviewed on May 15, 2024

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Key West Historic District
Save 100% on your flight
per person
Aug 5 - Aug 11
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
The property is clean and well maintained. There is a wonderful bar on sight with awesome bartenders. Its close to everything on duval and if you are going to key west give this place a try

Reviewed on May 15, 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(4,033 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 $152 per night from May 19 to May 20
$152
$196 total
includes taxes & fees
May 19 - May 20
9/10 Wonderful! (1,060 reviews)
"We had broken blinds on our door that I had to cover with a washcloth for privacy. They should’ve been replaced along with the broken blinds on our window. Also, one ceiling fan could only operate on low…. A higher speed and it would vibrate to the point of concern. Having said that, we very much ..."

Reviewed on May 13, 2024

Heron House - Adult Only
Duval House
Duval House
3 out of 5
815 Duval St, Key West, FL
The price is $169 per night from May 23 to May 24
$169
$212 total
includes taxes & fees
May 23 - May 24
9.2/10 Wonderful! (982 reviews)
"Beautiful gardens, great staff, comfortable room and location."

Reviewed on May 7, 2024

Duval House
Wicker Guesthouse
Wicker Guesthouse
3.5 out of 5
913 Duval Street, Key West, FL
The price is $229 per night from May 21 to May 22
$229
$258 total
includes taxes & fees
May 21 - May 22
8.2/10 Very Good! (969 reviews)
"This was an awesome place, the spot I found was actually for them. The area was on the main strip and would reserve the same place again the next time I go back down there."

Reviewed on May 13, 2024

Wicker Guesthouse
See all 2,683 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

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 $984. 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

4.5/5(1,707 reviews)

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

4.5/5(22 reviews)

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

4.5/5(81 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.

Jackson Square

Things to do

Image for Jimmy Buffett Tour

Jimmy Buffett Tour

$79
Per adult
100% of travellers recommend
Jimmy Buffett Tour
Image for Key West Craft Cocktail Crawl with Food Pairings

Key West Craft Cocktail Crawl with Food Pairings

$94
Per adult
96% of travellers recommend
Key West Craft Cocktail Crawl with Food Pairings
Image for The Ghosts of Key West Walking Tour

The Ghosts of Key West Walking Tour

$25
Per adult
100% of travellers recommend
The Ghosts of Key West Walking Tour
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.