Florida Keys Holiday Packages

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Top Florida Keys holiday packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
The Grand Guesthouse
Winslow's Bungalows - Key West Historic Inns
Lighthouse Hotel - Key West Historic Inns
1 Hotel South Beach

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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

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard, MM 47, Marathon, FL
Fully refundableReserve now, pay when you stay
The price is AU$811 per night from 23 Feb to 24 Feb
AU$811
includes taxes & fees
23 Feb - 24 Feb
Isla Bella Beach Resort & Spa: Luxury hotel with free WiFi and 5 outdoor pools. Located near the bay.
"Everyone was so nice and it was so romantic"

Reviewed on 18 Feb. 2025

Isla Bella Beach Resort & Spa
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is AU$944 per night from 26 Feb to 27 Feb
AU$944
includes taxes & fees
26 Feb - 27 Feb
Baker's Cay Resort Key Largo, Curio Collection by Hilton: Family-friendly resort with 2 outdoor pools and 2 restaurants. Located by the ocean.
"Our favorite place to stay in Key Largo. Staff is amazing and the food is awesome - try the Snapper at Calusa (restaurant at resort)."

Reviewed on 16 Feb. 2025

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2.5 out of 5
527 Caribbean Drive, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is AU$354 per night from 23 Feb to 24 Feb
AU$354
includes taxes & fees
23 Feb - 24 Feb
Marina Del Mar Resort and Marina: Pet-friendly hotel with free WiFi and free parking. Located on the waterfront.
"This was a beautiful property. It is older probably could use a little updating very good value walkable to two restaurants, beautiful pool however the pool is not heated, but we didn’t need the heat so we lucked out. I would highly recommend it again."

Reviewed on 18 Feb. 2025

Marina Del Mar Resort and Marina
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