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.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Key West (EYW)
9.8/10 Exceptional! (1,002 reviews)
This was our first time to stay at Orchid Key Inn but it won’t be our last! We loved the location, the staff was helpful, the pool was great!

Reviewed on Jul. 5, 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
Great Breakfast and Happy Hour! Wonderful Staff!

Reviewed on Jul. 4, 2025

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Old Town Key West
per person
Aug 28 - Sep 1
found 7 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.2/10 Very Good! (193 reviews)
Lovely hotel, rooms clean and spacious, staff very friendly. We would stay again.

Reviewed on Jul. 4, 2025

Aquaria House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock

2 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 22
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
No reviews
Spindrift House by Brightwild Huge Pool Dock

Spindrift House by Brightwild Huge Pool Dock

2 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 22
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
No reviews

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

3 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

Key West Beach Vacation

Unwind on the shore while you watch the sunlight glistening across the water during your Key West vacation. If you're hoping for an unforgettable beach experience, a trip to Key West will definitely deliver. There's a good chance you've heard of Smathers Beach (3 kilometres away). We suggest staying in accommodations close by. However, many sightseers also opt for Key West packages that are closer to South Beach or Boca Chica Nude Beach, two other excellent nearby options.

Things You Should Know About Key West

  • Escape the daily grind at one of our Key West beach hotels. The sweet sound of lapping water and seagulls cawing far above are just a couple of clicks away.
  • If you're searching for lots of room to spread out and relax, Key West private vacation homes are a great choice. After a much-needed family getaway or a few nights escape with that special someone? Grand Maloney Hotel and The Capitana Key West will fit the bill.
  • With a population of approximately 65,532 cm Key West, you're sure to find some friendly locals who are happy to share their sightseeing tips. For more handy hints, check out our Key West things to do page.

Ready to book your vacation to Key West?

 

Choose your dates

Key West Hotel Deals

Beachside Resort & Residences
Beachside Resort & Residences
3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Jul 8 to Jul 9
CA $202
CA $296 total
Jul 8 - Jul 9
includes taxes & fees
8.4/10 Very Good! (1,282 reviews)
"The Front desk Ms.Amanda and Mr.Joseph was excellent. The Shuttle drivers were very good. The Room was good."

Reviewed on Jul. 2, 2025

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses
Southernmost Beach Resort and Guesthouses
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $271 per night from Aug 4 to Aug 5
CA $271
CA $396 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,601 reviews)
"Beautiful Property!"

Reviewed on Jul. 3, 2025

Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection
3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 3 to Aug 4
CA $151
CA $208 total
Aug 3 - Aug 4
includes taxes & fees
7.6/10 Good! (1,040 reviews)
"love it"

Reviewed on Jul. 2, 2025

Hilton Garden Inn Key West / The Keys Collection
See all 2,745 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

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
Southernmost Point

Southernmost Point

4/5(160 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point
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

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 $38
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

CA $38
per adult
Full Day Trip in Key West from Miami
Key West Day Trip & Glass Bottom-Boat Tour from Miami

Key West Day Trip & Glass Bottom-Boat Tour from Miami

CA $177
per traveller
Key West Day Trip & Glass Bottom-Boat Tour from Miami
See all activities in Key West

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 $1,324 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.