Downtown Key West Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Plan, book, travel with confidence
Better together
Save up to CA $775 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Holiday Package Deals in Downtown Key West
Price found within the past 48 hours. Click for updated prices.
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
per person
Jul. 17 - Jul. 23
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
8.8/10 Excellent! (1,007 reviews)
Has its own beach, just walk downstairs, no driving or Uber required, No charge for umbrellas, beach chairs or towels. A bar, casual and formal dining right on the premises. Walkable to everything on Duval St. Has parking right there.
Reviewed on Jun. 13, 2024
Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
per person
Aug. 26 - Sep. 2
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
7.8/10 Good! (1,572 reviews)
Ibis Bay Resort es un verdadero paraíso tropical. Con su ubicación pintoresca y sus servicios de primera clase, ofrece a los huéspedes una experiencia inolvidable. Desde relajarse en sus playas de arena blanca hasta disfrutar de emocionantes actividades acuáticas, hay algo para todos los gustos. Además, su atención al detalle y su ambiente acogedor hacen que cada visita se sienta como un verdadero escape. Sin duda, es un destino que vale la pena explorar para unas vacaciones inolvidables.
Reviewed on Jun. 10, 2024
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Save 100% on your flight
per person
Aug. 26 - Sep. 2
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
6.6/10 (1,006 reviews)
Besides they never cleaned our room but once in 5 days after calling/asking and running out of everything. They were happy to bring stuff but not clean was strange but would definitely stay here again. amazing place/resort. Love the adult pool.
Reviewed on Jun. 8, 2024
Winslow's Bungalows - Key West Historic Inns
Key West Historic District
Save 100% on your flight
per person
Aug. 26 - Sep. 2
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9/10 Wonderful! (727 reviews)
The bungalows and property are amazing and have very beautifully landscaped gardens. Great private bungalows nestled into a scenic tropical paradise. We also used the swimming pool every midday after touring numerous beaches, historic sites, and restaurants. It's perfectly located in the middle of Old Town where all the fun starts. You can Uber anywhere for around 10 dollars and they are only minutes away when requested. The only negative is the cleaning service was hit or miss, so request maid service every day. The staff is very helpful and quick to rectify any needs or issues.
Reviewed on Jun. 10, 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
Key West Historic District
4 out of top 10 points of interest in this area
4.5/5(156 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.
Downtown Key West Hotel Deals
Heron House - Adult Only
512 Simonton St, Key West, FL
The price is CA $196 per night from Jun. 16 to Jun. 17
CA $196
CA $261 total
includes taxes & fees
Jun 16 - Jun 17
9/10 Wonderful! (1,079 reviews)
"Great location to see the sights of Key West. Relaxing pool was a plus!"
Reviewed on Jun. 10, 2024
Duval House
815 Duval St, Key West, FL
The price is CA $177 per night from Jun. 18 to Jun. 19
CA $177
CA $229 total
includes taxes & fees
Jun 18 - Jun 19
9.2/10 Wonderful! (1,013 reviews)
Perfect Location!
"The Duval House was the perfect location for all things Key West. It is a quaint property with a B&B feel. The property is beautiful and well maintained! The daily breakfasts and coffee service were excellent! The only issue we had was regulating the room temperature due to the window a/c unit. We ..."
Reviewed on Jun. 10, 2024
The Cabana Inn Key West - Adults Only
413 Applerouth Lane, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jun. 19 to Jun. 20
CA $212
CA $301 total
includes taxes & fees
Jun 19 - Jun 20
8.6/10 Excellent! (1,008 reviews)
"Patrick was wonderful."
Reviewed on Jun. 7, 2024
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
Frequently asked questions
Discover the most popular places to visit in Downtown Key West
Ernest Hemingway Home and Museum
4.5/5(77 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(4 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.
San Carlos Institute - Casa Cuba
5/5(1 review)
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.
Things to do
Miami: Key West day trip with optional boating activities
CA $161
Per adult
The Ghosts of Key West Walking Tour
CA $34
Per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.