Key West Vacations from $1,007

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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.
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,631, price is now $1,007 per person
$1,007
per person
Nov 12 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (220 reviews)
The Bishop Hotel is an amazing place to stay. They make you feel special from the moment you check-in. All of the staff are extremely friendly, helpful, and want you to have the best time. I really loved the security of the main door, no worry about anyone other than guests entering. The front desk has 24/7 coverage, great feature. Our room had a balcony, it was great to take a break and just relax and watch the day to day of Fleming St. Be sure to take your phone with you in case your balcony door is locked. Yes, it does happen. They are quick to rescue you. We were there in the off season, so it was a little quieter than normal, but we didn't mind. Highly recommend the Bishop, you won't be disappointed.

Reviewed on Aug 25, 2025

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $1,952, price is now $1,151 per person
$1,151
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Fantastic staff, always smiling. Great amenities, super clean, fantastic location.

Reviewed on Aug 25, 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,211, price is now $1,351 per person
$1,351
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (775 reviews)
it’s a great location but quiet. Love the free breakfast, pool and rooms! staff was great too!

Reviewed on Aug 23, 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 $2,269, price is now $1,436 per person
$1,436
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,006 reviews)
Beautiful property with several private pools. The front desk was very helpful in helping us get bikes delivered. They were always helping people and answering questions.The breakfast is perfect to get your day started. We will definitely return.

Reviewed on Aug 22, 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $2,882, price is now $1,827 per person
$1,827
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
It's a really nice property next to a marina. Quiet at night much livelier during the day. There is a shuttle from property to get to down town if you don't have a rental car. Rental car is needed and necessary in my opinion. The pool was great and there are three places to eat in the immediate area. Our first time here and we will be returning in the future.

Reviewed on Aug 25, 2025

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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
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
Southernmost Point featuring signage as well as a large group of people

Southernmost Point

4.5/5(3,182 reviews)

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

Southernmost Point
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

$27
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

$27
per adult
Full Day Trip in Key West from Miami
Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$40
per adult
92% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
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
$184 nightly
The price is $207 total per night from Aug 27 to Aug 28
$207 total
Aug 27 - Aug 28
Total with taxes and fees
8.4/10 Very Good! (1,483 reviews)
"Provided close access to all attractions in Key West."

Reviewed on Aug 25, 2025

Beachside Resort & Residences
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
$219 nightly
The price is $247 total per night from Sep 2 to Sep 3
$247 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (1,729 reviews)
"Excellent service"

Reviewed on Aug 25, 2025

Oceans Edge Key West Resort, Hotel & Marina
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
$132 nightly
The price is $149 total per night from Sep 2 to Sep 3
$149 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,073 reviews)
"Super quite and big beds"

Reviewed on Aug 24, 2025

Hilton Garden Inn Key West / The Keys Collection
See all 2,706 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.

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.

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Frequently asked questions

How much does a Key West vacation package cost?
Offering excellent value package deals from $1,007 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.