Downtown Key West Vacations from $817

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Your Downtown Key West Vacation

Our Downtown Key West vacation packages are a time-saving and convenient way to arrange and book your next escape. Experience the magic of this unique neighborhood without the bother of planning everything yourself. Your trip to Downtown Key West wouldn't be complete without stopping by big-name attractions nearby such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Don't just imagine it — make it a reality! Book your ideal Downtown Key West vacation with Expedia and get to where you're going your way.

The Latest Downtown Key West Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,668 reviews)
I really loved the whole experience from beginning to end! The receptionist are awesome and very pleasant to speak to all the staff are very pleasant and we really really enjoyed our stay

Reviewed on Jul 29, 2025

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Great place, huge rooms, 2 bathrooms, washer and dryer, screened in porch. Covered parking. Pool and games for lids. We had a great time.

Reviewed on Jul 29, 2025

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
We have fallen in love with this place !!! Never had been here, came to Orchid Key for our anniversary weekend and are hooked. Local motel, quaint, clean, retro, friendly and amazing location. We have already rebooked ♥️

Reviewed on Jul 28, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Stayed with my husband and 3 kids. The room was very spacious. The balcony was gorgeous overlooking the pool and the ocean. We all agreed for our next family trip we will stay here again. It was very close to the marina where we rented our boat. The island is fairly small so we didn’t feel we missed out by not staying on Duval street, especially with kids. I really appreciated the washer and dryer so we didn’t have to bring home wet bathing suits. The pool area has a volleyball area and outdoor games. Totally worth it to stay here with family.

Reviewed on Jul 27, 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
Beautiful with excellent customer service. I very much enjoyed being here and didnt want to leave

Reviewed on Jul 27, 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
Key West Historic District

Old Town Key West

3 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 hotels in Old Town Key West

Downtown Key West Hotel Deals

Duval House

Duval House

3 out of 5
815 Duval St, Key West, FL
$131 nightly
The price is $144 total per night from Aug 10 to Aug 11
$144 total
Aug 10 - Aug 11
Total includes taxes and fees
9.4/10 Exceptional! (1,015 reviews)
"Perfect location, beautiful grounds and great staff. Will be booking again"

Reviewed on Jul 26, 2025

Duval House
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
512 Truman Ave, Key West, FL
$170 nightly
The price is $192 total per night from Aug 5 to Aug 6
$192 total
Aug 5 - Aug 6
Total includes taxes and fees
9.8/10 Exceptional! (1,008 reviews)
"Beautiful with excellent customer service. I very much enjoyed being here and didnt want to leave"

Reviewed on Jul 27, 2025

Almond Tree Inn Hotel - Adults Only
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane, Key West, FL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $148 total per night from Aug 4 to Aug 5
$148 total
Aug 4 - Aug 5
Total includes taxes and fees
8.8/10 Excellent! (1,014 reviews)
"Would 10/10 recommend"

Reviewed on Jul 27, 2025

The Cabana Inn Key West - Adults Only
See all 2,778 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Downtown Key West

Ernest Hemingway Home and Museum featuring heritage elements and a house

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
Jackson Square featuring heritage architecture and an administrative buidling

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
San Carlos Institute - Casa Cuba

San Carlos Institute - Casa Cuba

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.

San Carlos Institute - Casa Cuba

Things to do

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

$99
per adult
74% of travellers recommend
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
The Dark Side of Key West Adults Only Walking Tour

The Dark Side of Key West Adults Only Walking Tour

$35
per adult
The Dark Side of Key West Adults Only Walking Tour
Guided Night Kayak Adventure Tour in Luminous Lagoon

Guided Night Kayak Adventure Tour in Luminous Lagoon

$85
per adult
74% of travellers recommend
Guided Night Kayak Adventure Tour in Luminous Lagoon
See all activities in Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.