Downtown Key West Vacations from $835
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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 $1,264, price is now $835 per person
$835
per person
May 31 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,020 reviews)
Rooms clean and spacious, pool nice. BUT, when they say "we are close to AIRPORT" what is NOT said is when i open my door to room i stare and hear jet engines. Are view is the AIRPORT RUNWAY!
I guess not wrong when close to airport.
If the property was farther away i would recommend.
Reviewed on Mar 19, 2026
Fitch Lodge - Key West Historic Inns
Key West Historic District
Price was $1,429, price is now $867 per person
$867
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (575 reviews)
Clean room, great staff, and a great experience.
Reviewed on Mar 19, 2026
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,481, price is now $1,614 per person
$1,614
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (536 reviews)
Love this place! Perfect location, nice rooms and cool bar with live music every night on site!
Reviewed on Mar 17, 2026
Oceans Edge Key West Resort, Hotel & Marina
Price was $1,775, price is now $1,222 per person
$1,222
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,825 reviews)
Nice property, nice rooms. Loved everything but our dining experience. Understaffed, undercooked meal and the service was lacking. Otherwise, it was a great stay
Reviewed on Mar 20, 2026
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Old Town Key West
Save 100% on your flight
Price was $3,511, price is now $2,504 per person
$2,504
per person
Jun 6 - Jun 13
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
No reviews
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(229 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
Duval House
815 Duval St Key West FL
$311 nightly
The price is $347 total per night from Mar 22 to Mar 23
$347 total
Mar 22 - Mar 23
Total with taxes and fees
9.4/10 Exceptional! (1,006 reviews)
Staff was wonderful very helpful. The gardens were beautiful. Very quiet and peaceful. Great location, easy access to all restaurants and shops and attractions.
Reviewed on Mar 19, 2026
The Cabana Inn Key West - Adults Only
413 Applerouth Lane Key West FL
Fully refundableReserve now, pay when you stay
$368 nightly
The price is $415 total per night from Mar 29 to Mar 30
$415 total
Mar 29 - Mar 30
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
The property has a beautiful pool, nice furniture around the pool and eating areas and beautiful plants on the property. The property is quiet and secluded but walkable to most every attraction. It is great!
Reviewed on Mar 19, 2026
Paradise Inn Key West - Adults Only
819 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
$390 nightly
The price is $439 total per night from Apr 19 to Apr 20
$439 total
Apr 19 - Apr 20
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
The Inn consisted of a number of buildings giving you a little more privacy. The rooms were large, including the bath. The grounds were lush with a lovely secluded pool in back. A nice breakfast buffet was included as well as a Happy Hour. Most everything was walkable and there were plenty of Ubers ...
Reviewed on Mar 18, 2026
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(1,710 reviews)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
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.
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 beautiful beaches or experience its lively festivals.
Things to do
Round-trip Transportation to Key West from Miami
$75
per adult
Miami to Key West Day Trip with Activity Options
$39
per adult
82% of travellers recommend
Shipwreck Treasure Museum Tickets
$19
per adult
78% of travellers recommend
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- Key West Vacations
- All inclusive Vacation Packages Key West
- 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.