Florida Keys Holiday Packages

Save when you book Florida Keys package deals

Choose two or more items and save on your trip:

Book your Florida Keys holiday

Holidays To Florida Keys

The Florida Keys are a strip of islands at the southernmost point of Florida.

Once you pay a visit to this—the only living reef in the continental U.S.--you'll enjoy its endless blue waters, postcard-perfect sunsets and wild habitats. A Florida Keys holiday might include stops in Key Largo, the island village of Islamorada, Big Pine Key, Sugarloaf, and the iconic Key West. But these popular spots are just the tip of the proverbial reef as the Keys is a land of many adventures—and some paths are more travelled than others.

Things to do

Kick off your Florida Keys holidays in mainland Florida. If you land at Orlando International Airport, snag one of our Orlando car hire deals and start cruising in style. You'll cruise down the Overseas Highway, a 182-kilometre bridge that crosses islets of coral and limestone. Exit for attractions along the way: Explore the boardwalk in Key Largo, visit the Theatre of the Sea in Islamorada, and feed the deer in Big Pine Key (these tiny antlered creatures are exclusive to the Keys). You might hike the trails in Sugarloaf or Marathon and take a picnic for the beach. If you proceed to Key West, take a tour of the Ernest Hemingway House and the neighbouring Audubon House to learn some island history.

Shopping, dining & nightlife

"It's five o'clock somewhere" is a mantra throughout the Keys. Restaurants are open all hours to serve local seafood (conch chowder is a favourite) and a multitude of ethnic fare. Cuban, Caribbean, Thai and Japanese eateries are popular spots for tourists and locals alike. You'll also find plenty of American pubs that offer up the infamous "cheeseburger in paradise," in tribute to the endearing Jimmy Buffet song (he's a frequent visitor to Key West).

Florida Keys holiday packages provide heaps of places to shop at, so keep that credit card ready. Stop in Key Largo or Sugarloaf to pick out some flip-flops or a new bathing suit and stock up on seashells. Commerce is liveliest close to mainland and in the lower Keys you'll find major retailers in these areas alongside independent small businesses that sell clothing, botanicals and other goods. If you love art, visit the local galleries. Find a print you just have to have? They’ll pack and ship your masterpieces back home to you.

Florida Keys packages aren’t complete without time spent on the water. Check out local evening escapes like schooner rides, wine tastings, and party cruises where you can sing and celebrate on the water. For late-night thrills, visit Key West where the Duvall Street party never ends—note that some of the bars are clothing-optional. In others, you can dance on the tables and raise a toast when the roosters crow (which is often, as many chickens live in the streets).

What's next?

Whether you’re ready to snag one of our Florida Keys deals or just want to spoil your family with Orlando holiday packages, Wotif has your back. Book your getaway today and head for sunny Florida tomorrow!

Top Florida Keys hotels

Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is NZ$543 per night from 15 Jan to 16 Jan
NZ$543
includes taxes & fees
15 Jan - 16 Jan 2025
Stay at this 3.5-star beach hotel in Key Largo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the bar in our reviews. ...
"Beautiful"

Reviewed on 18 Dec. 2024

Reefhouse Resort & Marina
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2.5 out of 5
527 Caribbean Drive, Key Largo, FL
The price is NZ$228 per night from 6 Jan to 7 Jan
NZ$228
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this hotel in Key Largo. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
"Very friendly"

Reviewed on 14 Dec. 2024

Marina Del Mar Resort and Marina
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$769 per night from 25 Dec to 26 Dec
NZ$769
includes taxes & fees
25 Dec - 26 Dec
Book a stay at this beach hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
"I loved everything about this property. Tomas at the front desk was extremely nice, which I greatly appreciate these days with service industry standards changing. Also, I wish these properties would never do room charge, I've never been charged the correct amount at the end of the start regardless ..."

Reviewed on 15 Dec. 2024

Hawks Cay Resort
Don't see what you're looking for?
See all available properties in Florida Keys
View all properties
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.