Key West Vacation Packages

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Your Key West Vacation

Lock in a Key West vacation package and focus on what counts — enjoying yourself. There's no more travel planning headaches, just a lot more free time to savor what's special about this captivating city, such as its beaches and relaxed vibe. If a sightseeing tour is on the agenda during your trip to Key West, look around well-known attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Whoever you're taking a break with and whatever you plan to spend, your dream Key West vacation is just clicks away with Expedia.

Top Key West Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
per person
Jul. 18 - Jul. 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Key West (EYW)
9.4/10 Exceptional! (1,010 reviews)
A very nice place to stay. Grounds were lovely

Reviewed on Apr. 30, 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Save 100% on your flight
per person
Jul. 21 - Jul. 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.2/10 Wonderful! (762 reviews)
Really liked the location of the property and quiet area.

Reviewed on Apr. 29, 2025

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul. 21 - Jul. 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
We stayed at this hotel during our trip to Key West and overall had a great experience. The room had everything we needed and even more — it was clean, cozy, and thoughtfully prepared. The atmosphere was welcoming, and the service was excellent; the staff were friendly and always ready to help. The only downside was breakfast. I ordered avocado toast, but the bread was badly burnt, which really took away from the dish. Hopefully, it was just a one-time issue. Aside from that, it’s a lovely hotel, and I would happily stay here again!

Reviewed on Apr. 30, 2025

The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jun. 13 - Jun. 18
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.6/10 Exceptional! (1,001 reviews)
This is sooo cute, clean and convenient. Was able to bike to Mallory square at sunset. Then able to hit Duvall Street on the way home. Manager is so nice and incredibly helpful. Definitely will stay here again

Reviewed on Apr. 23, 2025

Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
Old Town Key West
per person
Jul. 21 - Jul. 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
8.6/10 Excellent! (2,353 reviews)
Piscina the water ins’t clear

Reviewed on Apr. 30, 2025

Where to stay in Key West

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

Old Town Key West

4 out of top 10 points of interest in this area
3.5/5(8 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

Gold Coast Beach Vacation

Take a break from the stresses of everyday life and relax on your Gold Coast vacation. There's nothing more invigorating than the smell of salty sea air and the sound of waves crashing onto the shore. Organize your trip to Gold Coast the quick and easy way by locking in one of our Gold Coast packages. Many travelers decide to spend their nights close to Golden Beach, a must-see just 0.2 miles (0.3 km) from the city center.

Ready to book your vacation to Key West?

 

Choose your dates

Key West 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 CA $395 per night from May 20 to May 21
CA $395
CA $537 total
includes taxes & fees
May 20 - May 21
8.6/10 Excellent! (2,452 reviews)
"Great place to stay. Has it all. 3 pools, beach and more."

Reviewed on Apr. 29, 2025

Southernmost Beach Resort
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $331 per night from May 18 to May 19
CA $331
CA $460 total
includes taxes & fees
May 18 - May 19
8.6/10 Excellent! (1,709 reviews)
"Had a great time thanks"

Reviewed on Apr. 29, 2025

Margaritaville Beach House Key West
Fairfield Inn and Suites by Marriott Key West
Fairfield Inn and Suites by Marriott Key West
3 out of 5
2400 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Jun. 1 to Jun. 2
CA $252
CA $323 total
includes taxes & fees
Jun 1 - Jun 2
7.8/10 Good! (1,095 reviews)
"I was very excited about visiting this property and hanging out by the pool. However, we weren’t impressed with the friendliness of the staff who drove the shuttle and the pool bartender who closed the bar early with my husband standing there ready to order drinks during Spring Break week. The housekeeping ..."

Reviewed on Apr. 20, 2025

Fairfield Inn and Suites by Marriott Key West
See all 2,810 properties in 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Key West vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,381 on Expedia. But how much your vacation to Key West costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Key West?
August, September and October are the best times to look for cheap Key West vacation packages. Travelling in quieter months means you can usually find reduced prices on accommodations and flights.
How many days is enough for Key West?
With about 3 days, you’ll have plenty of time to enjoy popular neighbourhoods such as Key West Historic District and Old Town Key West during your Key West vacation. Be sure to also add Southernmost Point and Ernest Hemingway Home and Museum to your list of must-sees. Up for some more adventures? Consider venturing outside of Key West on day trips and tours.
Is it worth booking a vacation package to Key West?
Key West is a good vacation destination with attractions like Smathers Beach among the many things to keep you busy. Whether you’re travelling with the family or getting away with friends, a Key West vacation promises fun for everyone.
How to find the best Key West package deals?
Use Expedia’s filters to help you find some fabulous Key West package deals. When you start your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your trip for midweek, or search for Key West package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it’s usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Key West vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can tailor your Key West getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Key West?
If you’re planning an impromptu Key West getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Key West?

  1. Pick your travel dates: The things you want to do in Key West and your preferred season will help you decide when to get away.
  2. Budget wisely: As well as the price of your accommodations, you should consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Key West.
  3. Work out your trip length: Consider how much time you’d like to spend discovering Key West. Plan your itinerary so you can get to all the attractions and experiences you’re interested in at a leisurely pace.
  4. Bundle your airfare and accommodations: Once you’ve nailed down your dates and duration, book the ideal Key West vacation package for you.

Discover the most popular places to visit in Key West

Duval Street

Duval Street

4.5/5(161 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
Mallory Square

Mallory Square

4.5/5(148 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
Smathers Beach which includes a luxury hotel or resort, tropical scenes and a beach

Smathers Beach

4/5(56 reviews)

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

Smathers Beach

What to do in Key West

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

CA $68
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

CA $107
per adult
MIAMI: Key West Day Trip with Boating Options
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

CA $68
per adult
Full Day Trip in Key West from Miami
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.