Florida Keys Holidays

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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

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$439 per night from 15 Jan to 16 Jan
NZ$439
15 Jan - 16 Jan
includes taxes & fees
9.2/10 Wonderful! (1,602 reviews)
Great little place on highway 1 in Islamorada. Renovated, clean great bathrooms, balconies, 2 heated pools and a jacuzzi, wonderful breakfast excellent and friendly staff and a welcome champagne drink 😃. Wait did i forget to mention amazing ocean views with ample beach chairs and umbrellas. They ...

Reviewed on 26 Dec 2025

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 NZ$542 per night from 4 Jan to 5 Jan
NZ$542
4 Jan - 5 Jan
includes taxes & fees
8/10 Very Good! (1,002 reviews)
Room was clean and spacious. Bathroom door was difficult to close/slide. There was no hook to hand the cloths. Toiletries were good. Resort has lot of facilities/amenities. Cafe and restaurant have limited vegetarian options.

Reviewed on 25 Dec 2025

Hawks Cay Resort
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard Marathon FL
Fully refundableReserve now, pay when you stay
The price is NZ$710 per night from 12 Jan to 13 Jan
NZ$710
12 Jan - 13 Jan
includes taxes & fees
9/10 Wonderful! (1,069 reviews)
Beautiful property, staff are very friendly

Reviewed on 20 Dec 2025

Isla Bella Beach Resort & Spa
See all 8,426 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
South Beach which includes a beach and a coastal town as well as a large group of people

Florida Keys Beaches

5/5(1 review)

Why not spend a lazy afternoon at Florida Keys Beaches during your trip to Long Beach Estates?

Florida Keys Beaches
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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

NZ$77
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
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$47
per adult
90% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

NZ$99
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
See all activities in Florida Keys

Frequently asked questions

Can I cancel my flight booking to Florida Keys due to COVID-19?
If you've yet to book your tickets, read the terms and conditions of the airfare you're considering. If you've already reserved your flight to Florida Keys, make use of our Customer Service Portal. The information here will help determine which COVID-19 policies apply to your booking and guide you with the next steps.
What's the best way to find cheap flights to Florida Keys that have flexible change policies?
We understand that things can change from one minute to the next, so booking a flexible ticket with Expedia is a sensible idea. Just tick the "No change fee" box directly under the "Flexible change policies" filter. Your low-cost, flexible flight to Florida Keys is just a few clicks away.
What are some of the general tips for travellers to Florida Keys during the COVID-19 outbreak?
The COVID-19 pandemic has brought about dramatic changes to the way we travel. If you're planning an escape to Florida Keys, the following tips will help you navigate these new rules and challenges:
  • Research what, if any, rules or restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so be sure to check before you lock something in.
  • When you pass through airport screening, keep your face mask on. You will be asked to briefly lower it for identification purposes. Anyone refusing to wear a mask may be fined and denied entry.
  • Avoid handing your boarding pass directly to a TSA employee. Instead, position the pass on the reader and then hold it up to allow the agent to visually inspect it.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag for screening.
  • Put any personal items (phone, wallet and keys) in your carry-on rather than a bin to minimize handling during screening.
  • Separate any food you have for X-ray screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to Florida Keys?
Delta is a leading airline servicing Florida Keys. Search for airfares to Key West Intl. Airport (EYW) and you'll have 191 Delta flights each month to pick from.
How can I find cheap tickets to Florida Keys?
An effective strategy for scoring cheap airfares is to be flexible with your travel dates. Begin with searching for your flight to Florida Keys, then click on the "flexible dates" box to see prices for nearby days. Another helpful hint? Book well in advance. To give you an idea of fares, was the best price for a flight to Florida Keys in the last seven days.
How much is a flight to Florida Keys?
The cost of a round-trip journey to Florida Keys in the last seven days ranged between and . If you were travelling one way from (), you could have gotten a great deal from only .
What are the most popular airports to fly into in Florida Keys?
Start planning your Florida Keys escape by securing one of the 1119 flights each month to Key West Intl. Airport (EYW). This is the region's main entry point.
When is the cheapest time to fly to Florida Keys?
Jet off on a Tuesday to boost your odds of picking up the cheapest deal to Florida Keys. Mondays are usually the second most affordable day to depart. Saturday is normally the most expensive day to fly anywhere.
How much is a plane ticket to Florida Keys?
In the last seven days, ticket prices to Florida Keys varied from to .
Which airlines with flights to Florida Keys employ COVID-19 cleanliness policies?
As passengers begin travelling once again, most reputable airlines have introduced social distancing and other important measures to help lessen the spread of COVID-19. Here are some of them:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • Frontier Airlines - this airline is known for electrostatic cleaning and conducting passenger temperature checks.

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