Florida Keys Holiday Packages

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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

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 AU$290 per night from 24 Sept to 25 Sept
AU$290
24 Sept - 25 Sept
includes taxes & fees
Chesapeake Beach Resort: Pet-friendly hotel with free breakfast and free WiFi. Located by the ocean.
Relaxation 😌
"Such a relaxing and fun spot. Enjoyed snorkeling every day at sunrise and sunset 😍 Can't wait for my next stay 🤗"

Reviewed on 15 Sept 2025

Opens in a new windowChesapeake Beach Resort
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$417 per night from 23 Sept to 24 Sept
AU$417
23 Sept - 24 Sept
includes taxes & fees
Reefhouse Resort & Marina: Family-friendly hotel with free parking and an outdoor pool. Located near the bay.
"The hotel definitely has that classic, old-Florida Keys charm, which I understand is part of the concept and appeal. That said, I think some of the facilities could be improved while still keeping the same “style.” The beds, for example, were not the most comfortable. On the positive side, the location ..."

Reviewed on 15 Sept 2025

Opens in a new windowReefhouse Resort & Marina
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 AU$256 per night from 1 Oct to 2 Oct
AU$256
1 Oct - 2 Oct
includes taxes & fees
Cheeca Lodge & Spa: Luxury resort with free valet parking and 3 outdoor pools. Guests love the helpful staff!
"Beautiful and relaxing hotel!!"

Reviewed on 18 Sept 2025

Opens in a new windowCheeca Lodge & Spa
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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.