Key West Historic District Vacations

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Your Key West Historic District Vacation

Reserving a Key West Historic District vacation package is a superb way to get to know this neighborhood. From its hot spots to its lesser-known delights, there's plenty to discover. Start your trip to Key West Historic District by checking out nearby attractions such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. No matter your travel plans or budget, booking your perfect Key West Historic District vacation has never been easier with Expedia.

The Latest Key West Historic District Vacation Packages

Prices and availability subject to change. Additional terms may apply.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Jun 27 - Jul 1
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Jun 9 - Jun 12
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (1,012 reviews)
Staff is wonderful and the food and drinks were great. Highly recommend.

Reviewed on Apr 24, 2024

Ocean Villas of Deerfield

Ocean Villas of Deerfield

2.5 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,007 reviews)
Ms. Debbie keeps this place in great condition! Our villa was extremely clean and efficient for our 5 day stay! Close and walkable to beach, shops, and restaurants!!! We had a relaxing and enjoyable stay in Deerfield! Ms. Debbie is all about her business, so if she comes across a little too forward, just remember what it takes to run a tight ship and keep it that way! This place gets 5 ⭐️. I can't brag enough about the cleanliness of the rooms!!! We will be back!!

Reviewed on Apr 24, 2024

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Jun 18 - Jun 22
Roundtrip flight included
Newark (EWR) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
We stayed one night to catch a cruise ship. The desk manager was so nice. We were very early, so we only expected to check our luggage and walk around , but he found us a room to go ahead and check in right away. We loved the art deco hotel, and later found out it was in the movie "Birdcage," Our room was comfortable and quiet.

Reviewed on Apr 21, 2024

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Jun 7 - Jun 11
Roundtrip flight included
New York (JFK) to Miami (MIA)
8.2/10 Very Good! (635 reviews)
Hotel staff are friendly and helpful. Staff offered to store one's luggage as check out is at 11:00AM. Breakfast is served at a sister hotel a few blocks away on Ocean Drive. There is water, tea and coffee available throughout the day. My concerns about my stay related to the temperature of the room which was too cold and one could not adjust thermostat, which was on the wall, but it did nothing to affect the overall temperature of the room. Added to that, the maximum temperature for the hot water was much too low, although there was very hot water in the sink but did not transfer to the shower. The television in the room was difficult to operate with the remote and we could not figure out how to change the channel on the cable. The YouTube option was a functional substitute.

Reviewed on Apr 4, 2024

Where to stay in Key West Historic District

Find the best Key West Historic District areas and neighborhoods for the activities you enjoy most. Learn more about Key West Historic District
Key West Historic District

Old Town Key West

2 out of top 10 points of interest in this area
4.5/5(226 area reviews)

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.

Find hotel + flight trips in Old Town Key West

Key West Historic District Hotel Deals

Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $359 per night from Apr 28 to Apr 29
$359
$467 total
includes taxes & fees
Apr 28 - Apr 29
8.2/10 Very Good! (1,779 reviews)
"We had the best time! The staff is amazing, the property is clean and well maintained and the rooms are up to date and modern!"

Reviewed on Apr 20, 2024

Southernmost Beach Resort
Heron House - Adult Only
Heron House - Adult Only
3.5 out of 5
512 Simonton St, Key West, FL
The price is $179 per night from Apr 28 to Apr 29
$179
$221 total
includes taxes & fees
Apr 28 - Apr 29
9/10 Wonderful! (1,041 reviews)
"Heron House was a great find for us. The location was excellent and the rooms and property overall are outstanding."

Reviewed on Apr 24, 2024

Heron House - Adult Only
Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns
4 out of 5
725 Truman Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $370 per night from May 14 to May 15
$370
$458 total
includes taxes & fees
May 14 - May 15
8.8/10 Excellent! (642 reviews)
"Cute place, great staff."

Reviewed on Apr 23, 2024

Winslow's Bungalows - Key West Historic Inns
See all 1,721 properties in Key West Historic District
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 Key West Historic District vacation package cost?
Less than you might think — from a low $440, actually! By combining flights, hotels and car rentals into a custom-built vacation package, your Key West Historic District escape is just a few clicks away.
How do I get a cheap travel package to Key West Historic District?
Book everything in the one place with our Key West Historic District vacation packages. We have deals on flights, hotels, tours and more that’ll keep your pocketbook happy and adventurous side satisfied. And, with more than 550 airlines and 1,000,000 hotel options throughout the world to choose from, you’ll have the flexibility to mix and match as you want.
Where should I stay in Key West Historic District?
Travelers come from far and wide to experience Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens in Key West Historic District. Book yourself a room within a stone’s throw of these must-see attractions to make sightseeing easy.
What are the top hotels in Key West Historic District?
Secure a room at Southernmost Retreat: 2 Blocks From Duval In Old Town. It’s one of the area’s most sought-after hotels. Another top option in Key West Historic District is Walk to Duval Waterfront Marina View 2-Bed Galleon + Beach + Sunset Tiki Bar.
How far in advance should I book my Key West Historic District vacation?
Savvy travelers book early. Air carriers typically release flights up to 12 months ahead of departure, and this is an excellent opportunity to pick up some of the lowest prices. Just been told you need to take some vacation time next week? Don’t fret. Expedia are never short of fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Key West Historic District travel package include?
Hotels, flights and a cool set of wheels for your road trip adventures. Simply select your preferred bundle and get access to incredible deals. Once you’ve made your booking, add on a few sightseeing tours and watch your savings stack up. When it comes to creating your Key West Historic District break, you’re in control!
What should I know before booking a Key West Historic District travel package?
You’ll enjoy amazing savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything together will make your trip planning easier. So why waste time or money? Whether you’re putting together a ritzy romantic getaway or a budget solo adventure, check out our vacation packages today.
Can I choose my airline with a Key West Historic District Expedia vacation package?
Yes, and with more than 550 airlines to select from across the globe, you have loads of choice. Look through the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Key West Historic District vacation package?
If your vacation plans in Key West Historic District have changed, it’s a relief to know that it’s possible to cancel your booking. If your booking was made less than 24 hours ago, you may be eligible for a refund. If your booking is older than that, your hotel, airline or car rental company may charge fees. To learn more, check our Customer Service Portal.

Discover the most popular places to visit in Key West Historic District

Image for Duval Street

Duval Street

4.5/5(3,475 reviews)

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

Duval Street
Image for Mallory Square

Mallory Square

4.5/5(3,096 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

Mallory Square
Image for Southernmost Point

Southernmost Point

4.5/5(3,182 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point

Things to do

Image for Morning Reef Snorkel With Unlimited Mimosas & Breakfast

Morning Reef Snorkel With Unlimited Mimosas & Breakfast

$46
Per adult
90% of travellers recommend
Morning Reef Snorkel With Unlimited Mimosas & Breakfast
Image for Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

$163
Per adult
84% of travellers recommend
Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail
Image for Guided Jet Ski Tour in Key West

Guided Jet Ski Tour in Key West

$183
Per adult
94% of travellers recommend
Guided Jet Ski Tour in Key West
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.