Florida Keys Vacations

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Where to stay in Florida Keys

Find the best Florida Keys areas and neighborhoods for the activities you enjoy most. Learn more about Florida Keys
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

Find the Best Florida Keys Vacation Packages

Florida Keys Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NT$4,527 per night from Aug 5 to Aug 6
NT$4,527
NT$6,779 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (1,486 reviews)
"Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept"

Reviewed on 2025/8/3

Chesapeake Beach Resort
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd, Marathon, FL
Fully refundableReserve now, pay when you stay
The price is NT$9,401 per night from Aug 17 to Aug 18
NT$9,401
NT$12,671 total
Aug 17 - Aug 18
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Our food at the Salt and Ash was the best meal we have ever had. It was so so good."

Reviewed on 2025/8/1

Hawks Cay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NT$5,965 per night from Aug 13 to Aug 14
NT$5,965
NT$8,734 total
Aug 13 - Aug 14
includes taxes & fees
9/10 Wonderful! (1,139 reviews)
"Restaurant options are great, they offer Italian, sushi, beachside dining and an American restaurant. There are also poolside versions of their regular American restaurant. The amenities are phenomenal, including pier fishing, bikes, games and various water sport activities. There are plenty of other ..."

Reviewed on 2025/8/2

Cheeca Lodge & Spa
See all 8,296 properties in Florida Keys
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.

Discover the most popular places to visit in Florida Keys

Duval Street featuring signage

Duval Street

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

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

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

Frequently asked questions

How much does a Florida Keys vacation package cost?
From just , you can tailor your Florida Keys package. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Florida Keys?
Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you dollars too. A Florida Keys vacation package makes it simple to arrange the perfect trip. With more than 550 airlines around the world to pick from, finding convenient flights that suit your busy schedule won't be an issue. On top of that, we've got over 1,000,000 hotel options globally to choose from. Now that's choice! Whatever your budget, Expedia can show you the world.
Where should I stay in Florida Keys?
If you want to explore popular attractions such as Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens, head for Key West. You might want to stay for a while to really get to know this buzzing city.
What are the top hotels in Florida Keys?
When it comes to properties in Key West, Margaritaville Beach House Key West and Southernmost Beach Resort are two fantastic options. If you're considering heading to Marathon, 24 North Hotel Key West and Faro Blanco Resort & Yacht Club will make you feel at home.
How far in advance should I book my Florida Keys vacation?
Travelers are normally able to browse international flights on Expedia within 12 months of departure. Booking at the last minute? With a little bit of luck, it's still possible to nab a cheaper ticket just weeks before your flight.
What does an Expedia Florida Keys travel package include?
That depends on what you're after. If you're traveling alone, you might decide to combine flights and hotels. Bringing the whole crew to Florida Keys? A travel package including rental cars, flights and hotels might be a better fit. Expedia gives you the freedom to customize your travel package.
What should I know before booking a Florida Keys travel package?
A package can be more affordable than separately booking everything you need for your trip. For example, bundle your flights, hotels and rental cars and save a tidy sum. No matter your vacation goals, you'll find a package that's right for you.
Can I choose my airline with a Florida Keys Expedia vacation package?
Yes, you can. We offer more than 550 partner airlines all over the world, so choose the carrier that's a good fit for your travel needs.
If I'm not able to travel, can I cancel my Florida Keys vacation package?
Don't worry if you're rethinking your Florida Keys vacation package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We realize life can occasionally throw a spanner in the travel works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.