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

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is NZ$797 per night from 12 Apr to 13 Apr
NZ$797
12 Apr - 13 Apr
includes taxes & fees
Stay at this luxury hotel in Key Largo. Enjoy free parking, a full-service spa and 3 restaurants. Our guests praise the pool and the helpful staff in their reviews. ...
The hotel property is beautiful and large. Plenty of sitting and walking areas. Kids can swim, snorkel, play in the sand, fish, basketball, tennis, sit by the fire etc. the rooms, however, are expensive and very small. Thankfully we didn't spend much time in them with all the great outdoor space. ...

Reviewed on 16 Mar 2026

Opens in a new windowReefhouse Resort & Marina
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$1,261 per night from 12 Apr to 13 Apr
NZ$1,261
12 Apr - 13 Apr
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window

Reviewed on 12 Mar 2026

Opens in a new windowCheeca Lodge & Spa
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is NZ$411 per night from 12 Apr to 13 Apr
NZ$411
12 Apr - 13 Apr
includes taxes & fees
Stay at this hotel in Key Largo. Enjoy free Wi-Fi, a marina and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Amazing

Reviewed on 16 Mar 2026

Opens in a new windowWaterside Suites & Marina
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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.