Downtown Key West Vacations from $620
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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.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,041, price is now $620 per person
$620
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
We booked for suite for night but the Tv was not connected, telephone was not working, phone never receive by front desk. I was so disappointed.
Reviewed on Dec 12, 2025
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,487, price is now $1,380 per person
$1,380
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.
Reviewed on Dec 12, 2025
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,057, price is now $629 per person
$629
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
The rooms are amazing, clean & well appointed. Also, Cheryl at the front desk was awesome. My husband recently had knee surgery & she took the time to make sure our room was in a convenient location.
Reviewed on Dec 12, 2025
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,954, price is now $1,179 per person
$1,179
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
Breakfast was served in a charming basket and included premium yogurt, OJ, cheese and nuts, bagels or croissants, coffee and small immunity elixirs. I spent some time around the pool and loved the music that was playing over the speakers. The staff was very friendly and the neighborhood was quiet despite being only a block away from Duval St.
Reviewed on Dec 13, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,569, price is now $967 per person
$967
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (831 reviews)
Staff was wonderful. Room was clean, lovely grounds. Didn’t want to leave!
Reviewed on Dec 12, 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
Old Town Key West
4 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.
Downtown Key West Hotel Deals
Heron House - Adult Only
512 Simonton St Key West FL
$169 nightly
The price is $190 total per night from Dec 14 to Dec 15
$190 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (1,141 reviews)
Clean room, very friendly staff, property is in a good location for walking to Duval Street.
Reviewed on Dec 10, 2025
Wicker Guesthouse
913 Duval Street Key West FL
$259 nightly
The price is $291 total per night from Dec 14 to Dec 15
$291 total
Dec 14 - Dec 15
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
cool place, good vibe, great view of the parades on Duval St
Reviewed on Dec 8, 2025
Duval House
815 Duval St Key West FL
$157 nightly
The price is $173 total per night from Dec 15 to Dec 16
$173 total
Dec 15 - Dec 16
Total with taxes and fees
9.4/10 Exceptional! (1,006 reviews)
Great spot only a 7/8 minute walk to either Mallory square and also a 7/8 minute walk to the southern most point and everything else is in between great location loved it will be back again
Reviewed on Dec 11, 2025
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.
Discover the most popular places to visit in Downtown Key West
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.
San Carlos Institute - Casa Cuba
4.5/5(22 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 seaside or experience its lively festivals.
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 seaside or discover the area's beautiful sunsets.
Things to do
Miami to Key West Day Trip with Activity Options
$35
per adult
82% of travellers recommend
Shipwreck Treasure Museum Tickets
$19
per adult
78% of travellers recommend
Sunset Dinner Cruise in Key West with Live Music & Unlimited Open Bar!
$81
per adult
88% of travellers recommend
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- Ernest Hemingway Home and Museum
- Duval Street
- Key West Lighthouse and Keeper's Quarters Museum
- Tennessee Williams Key West Exhibit
- Fort Zachary Taylor Historic State Park
- Visit Key West
- Saint Mary Star of the Sea
- South Beach
- City Zoo Gallery
- Bahama Village Vacations
- Old Town Key West Vacations
- San Carlos Institute - Casa Cuba
- Southernmost Point
- Jackson Square
- Key West Cemetery
- Key West Historic District Vacations
- Key West Butterfly and Nature Conservatory
- MLK Community Pool & Community Center
- The Kite House
- Donkey Milk House
- Florida Keys Eco - Discovery Center
- Oldest House Museum and Garden
- Harry S. Truman Little White House
- Red Barn Theater
- Curry Mansion Museum
- Florida Keys National Marine Sanctuary
- Romantic Vacation Packages Key West
- Simonton Beach
- Mel Fisher Maritime Museum
- Audubon House and Tropical Gardens
- Roy John-Karl Gallery
- Custom House Museum
- Visit Bahama Village
- Key West Museum of Art and History
- Visit Old Town Key West
- Sails To Rails Museum at Flagler Station
- Schooner Western Union
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.