Florida Keys Holiday Packages

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Top Florida Keys holiday packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
Villas At Hawks Cay Resort
Hawks Cay Resort
Tranquility Bay Beachfront Hotel and Resort
Southernmost Beach Resort

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 AU$531 per night from 20 Apr to 21 Apr
AU$531
includes taxes & fees
20 Apr - 21 Apr
Reefhouse Resort & Marina: Family-friendly hotel with free parking and an outdoor pool. Located on the waterfront.
"This is our second trip to this property. It was great. We were awakened and dealt with a noisey neighbor the first night, but fortunately, the hotel was able to calm them down for the remainder of our stay. The staff and their crew were ready to do a great job. The charges to our credit card along ..."

Reviewed on 11 Apr. 2025

Reefhouse Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$442 per night from 29 Apr to 30 Apr
AU$442
includes taxes & fees
29 Apr - 30 Apr
Chesapeake Beach Resort: Pet-friendly hotel with 2 outdoor pools and a private beach. Located by the ocean.
"The property was clean and and everything was well maintained."

Reviewed on 12 Apr. 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 AU$588 per night from 27 Apr to 28 Apr
AU$588
includes taxes & fees
27 Apr - 28 Apr
Hawks Cay Resort: Family-friendly hotel with free WiFi and 5 outdoor pools. Located on the waterfront.
"Beautiful property, restaurants close too early for later eaters."

Reviewed on 8 Apr. 2025

Hawks Cay Resort
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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.