Florida Keys Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Our guide on 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
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Old Town Key West

2 out of top 10 points of interest in this area

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Find hotels in Old Town Key West

Florida Keys Holiday

Our pick of the best Florida Keys Hotel Deals

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 NZ$688 per night from 20 July to 21 July
NZ$688
20 July - 21 July
includes taxes & fees
8/10 Very Good! (1,010 reviews)
"Great vacation. We will be returning soon!"

Reviewed on 9 Jul. 2025

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 NZ$440 per night from 13 Aug to 14 Aug
NZ$440
13 Aug - 14 Aug
includes taxes & fees
9/10 Wonderful! (1,130 reviews)
"Music was pathetic. They should improve that."

Reviewed on 11 Jul. 2025

Cheeca Lodge & Spa
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 NZ$550 per night from 23 July to 24 July
NZ$550
23 July - 24 July
includes taxes & fees
9/10 Wonderful! (1,484 reviews)
"Amenities were great"

Reviewed on 9 Jul. 2025

Chesapeake Beach Resort
See all 8,110 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

Duval Street

5/5(5 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(5 reviews)

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

Southernmost Point
Mallory Square

Mallory Square

4/5(3 reviews)

Enjoy the lively crowds, energetic performers and stunning sunset that make this city square the most popular meeting place in the evenings.

Mallory Square

What to do in Florida Keys

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

NZ$46
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

NZ$46
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

NZ$215
per traveller
Key West Day Trip & Glass Bottom-Boat Tour from Miami
See all activities in Florida Keys

Frequently asked questions

How much does a Florida Keys holiday 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 holiday 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 holiday?
Travellers 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 travelling 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 holiday goals, you'll find a package that's right for you.
Can I choose my airline with a Florida Keys Expedia holiday 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 holiday package?
Don't worry if you're rethinking your Florida Keys holiday 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 realise 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.