Key West Vacations from $1,021

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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.

The Latest Key West Vacation Packages

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
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,010 reviews)
Want to be sure to recognize the consierge service with Jeremy. He was great and hooked up a refresher dive course and reef dive very easily.

Reviewed on Mar 24, 2025

Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

4 out of 5
New Town
Save 100% on your flight
per person
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,710 reviews)
The Havana Cabana was a fun place to stay with great amenities. The pool is beautiful and it was so easy to get downtown with the shuttle. Definitely recommend.

Reviewed on Mar 26, 2025

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,623 reviews)
Premises beautiful Staff and food excellent

Reviewed on Mar 24, 2025

Douglas House

Douglas House

3 out of 5
Old Town Key West
Save 100% on your flight
per person
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (44 reviews)
Staff was friendly and helpful. Great location

Reviewed on Mar 26, 2025

Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays

Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays

3 out of 5
Old Town Key West
Save 100% on your flight
per person
May 3 - May 10
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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

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.

Find hotels in Old Town Key West

Find the Best Key West Vacation Packages

Key West Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Population
25,800
Max Temp Winter
75ºF
Max Temp Summer
85ºF
Top Sights
Smathers Beach, Fort Zachary Taylor Historic State Park and South Beach

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 $353 per night from Mar 31 to Apr 1
$353
includes taxes & fees
$314 per night
Mar 31 - Apr 1
8.2/10 Very Good! (1,024 reviews)
"It was amazing!"

Reviewed on Mar 23, 2025

Beachside Resort & Residences
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is $497 per night from Mar 30 to Mar 31
$497
includes taxes & fees
$442 per night
Mar 30 - Mar 31
8.6/10 Excellent! (2,352 reviews)
"This place has everything you could ask for at a tropical resort."

Reviewed on Mar 25, 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 $428 per night from Mar 31 to Apr 1
$428
includes taxes & fees
$380 per night
Mar 31 - Apr 1
8.6/10 Excellent! (1,705 reviews)
"From the time we arrived, the staff members were very accommodating"

Reviewed on Mar 25, 2025

Margaritaville Beach House 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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Key West vacation package cost?
Offering excellent value package deals from $1,021 on Expedia, you’ll be pleasantly surprised at how much a vacation to Key West costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Key West?
You can typically find lower prices and greater availability in August, September and October. Check out our cheap Key West vacation packages and you could get some great off-season deals.
How many days is enough for Key West?
Key West vacations can be as short or long as you like, but to get a real feel for this place, we reckon 3 days is about right. In this timeframe, you can visit major attractions like South Beach and Clarence S. Higgs Memorial Beach Park and track down some underrated gems. Don’t forget to visit cool neighborhoods such as Old Town Key West and Historic Seaport either. If you plan wisely, you can even take a day trip from Key West too.
Is it worth booking a vacation package to Key West?
It’s easy to see why a Key West vacation is on the to-do list of many travelers. Leading attractions like Ernest Hemingway Home and Museum are just the beginning of what you can explore here.
How to find the best Key West package deals?
Bagging a cheap Key West package deal is a breeze with Expedia. Once you’ve entered your preferred dates and destination under our “Packages” tab, set your budget, add a couple of filters and browse what’s available. You can personalize your search by “Area,” “Amenities,” “Property type” and more. Sort the results by “Price: low to high” to view the most wallet-friendly Key West package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Key West vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You’ll usually land a better deal than booking each component separately. And you’ll still have the freedom to create a personalized Key West vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Key West?
If you’re considering a spur-of-the-moment Key West trip, browse our last-minute deals that can be booked up to one week before you take off. Don’t want to leave things to the last minute? You can score terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Key West?

  1. Choose when to get away: Check your calendar and get your bags packed. Your favorite time of year and the type of activities available will also help you decide when to visit Key West.
  2. Budget wisely: As well as the cost of your hotel, you should consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that could arise during your trip to Key West.
  3. Organize your Key West getaway with Expedia’s trip planning tool: Look for and book hotels and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Key West together.
  4. Determine how many days away: Start by compiling a list of the activities and attractions you’d like to experience in Key West. Then, estimate how long you’ll need for each, as well as any travel time.
  5. Combine your airfare and accommodations: Once you’ve nailed down your trip dates and duration, book the right Key West vacation package for you.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to see and do. Check out some of the incredible things to do in Key West and reserve your tickets early to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Key West vacation packages?
If you’re like us, you love jet-setting around the world but don’t love the big price tag that can sometimes come with it. That’s why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Key West trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.

Discover the most popular places to visit in Key West

Duval Street featuring signage

Duval Street

4.5/5(3,475 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
Smathers Beach showing a luxury hotel or resort, tropical scenes and a beach

Smathers Beach

4/5(1,151 reviews)

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

Smathers Beach
Mallory Square which includes a sunset and a bay or harbor as well as a large group of people

Mallory Square

4.5/5(3,096 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

$49
per adult
80% 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

$49
per adult
Full Day Trip in Key West from Miami
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

$99
per adult
76% of travellers recommend
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
See all activities in Key West

Explore a world of travel with Expedia

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