Key West Vacations from $648

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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

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.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,056, price is now $648 per person
$648
per person
Mar 23 - Mar 26
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Great accommodations for a family

Reviewed on Jan 2, 2026

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was $1,616, price is now $807 per person
$807
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (831 reviews)
The room and pool area were clean and pleasant. Good hospitality from staff including bartenders Alejandro and Jefferson. Unfortunately, the room remained humid due to the bathroom connection to the rest of the unit (above door) and wall A/C unit. Biggest drawback is the roosters on property and next door which do their best to wake you up at 4:00 AM. I suggest ear plugs and/or other sleep aids.

Reviewed on Dec 29, 2025

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,582, price is now $793 per person
$793
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,044 reviews)
I loved the place, perfect location within walking distance, breakfast wasnt bad, hard boiled eggs, waffles bagels fruit pastry croissant yogurt coffee you can order 2 other egg dishes at an additional cost Winslow room was small but didn’t mind it as much as the bathroom being really small But we made it work and had a great time I would get a different room with a bigger bathroom

Reviewed on Jan 3, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,166, price is now $1,193 per person
$1,193
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.

Reviewed on Dec 12, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,197, price is now $738 per person
$738
per person
Mar 1 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Room was clean. A little wear and tear. Found the concierge to be very helpful. Ine of the front desk staff seemed a little unprofessional. Heard her scoffing at another customer's request. My family enjoyed the pool. It is large and heated. There are a lot of airplanes taking off and landing as the hotel is right next to the airport.

Reviewed on Jan 2, 2026

Don't see what you're looking for?
See all available trips from Phoenix to Key West
View all trips

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

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
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
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

What to do in Key West

Entertainer in character at the Shipwreck Treasure Museum in Key West

Shipwreck Treasure Museum Tickets

$19
per adult
78% of travellers recommend
Shipwreck Treasure Museum Tickets
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
Key West Half-Day Fishing Charter

Key West Half-Day Fishing Charter

$102
per adult
90% of travellers recommend
Key West Half-Day Fishing Charter
See all activities in Key West

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
$321 nightly
The price is $361 total per night from Jan 19 to Jan 20
$361 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (1,858 reviews)
The grounds are beautiful. Our room was a smaller room and it was nice but some things didn’t work properly. The toilet didn’t flush well, the shower head would turn on when filling the bathtub, tv would turn off randomly and the floors were dirty. Reasonably price in comparison to other places in ...

Reviewed on Jan 1, 2026

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Jan 5 to Jan 6
$329 total
Jan 5 - Jan 6
Total with taxes and fees
8/10 Very Good! (1,816 reviews)
The hotel is perfect for the price. Only disappointment was show service which might be due to the holiday season.

Reviewed on Jan 1, 2026

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$275 nightly
The price is $309 total per night from Jan 11 to Jan 12
$309 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,772 reviews)
Friendly staff

Reviewed on Jan 2, 2026

Oceans Edge Key West Resort, Hotel & Marina
See all 2,768 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.

Find the Best Key West Vacation Packages

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 (2 miles 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 25,800 in 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.

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

More vacations you might like

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 $648 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.

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.