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Florida Keys Flight + Hotel packages

Florida Keys Hotels

See all 368 Hotels in Florida Keys
24 North Hotel Key West

24 North Hotel Key West

3820 North Roosevelt Boulevard, Key West
4.0 out of 5.0
4.1 out of 5 (30 reviews)

Situated near the airport, this hotel is 2.2 mi (3.6 km) from Key West Harbour.

$220

$220
Southernmost Beach Resort

Southernmost Beach Resort

1319 Duval Street, Key West
4.0 out of 5.0
4.5 out of 5 (180 reviews)

This Key West historical district hotel is 2 blocks from Southernmost Point. Ernest Hemingway Home and Museum, and Key West Lighthouse and Keeper's Quarters ...

$239

$239
The Inn at Key West

The Inn at Key West

3420 N Roosevelt Blvd, Key West
3.5 out of 5.0
4.0 out of 5 (32 reviews)

Located within minutes of Old Town, the Ernest Hemingway Home & Museum, Mallory Square, Duval Street shops, restaurants, and nightlife.

$139

$139
Parrot Key Hotel & Resort

Parrot Key Hotel & Resort

2801 N Roosevelt Blvd, Key West
4.0 out of 5.0
4.0 out of 5 (181 reviews)

Situated on the waterfront, this romantic resort is within 3 mi (5 km) of Smathers Beach, Ernest Hemingway Home and Museum, and Audubon House and Tropical Gardens. ...

$134

$134
Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

2400 N Roosevelt Blvd, Key West
2.5 out of 5.0
3.8 out of 5 (108 reviews)

A 3-minute drive from Key West Airport and 10 minutes from Old Town, Fairfield Inn and Suites by Marriott Key West offers easy access to attractions like Duval ...

$139

$139
Lime Tree Bay Resort

Lime Tree Bay Resort

68500 Overseas Hwy, Long Key
3.5 out of 5.0
3.8 out of 5 (23 reviews)

This waterfront resort sits on 1/4 mile of tropical waterfront in the heart of the Florida Keys. Close to Long Key State Park and Dolphin Research Center.

$109

$109
Islander Resort, a Guy Harvey Outpost

Islander Resort, a Guy Harvey Outpost

82100 Overseas Highway, Islamorada
3.0 out of 5.0
3.9 out of 5 (72 reviews)

Nestled on the beach, this Islamorada resort is within 1 mi (2 km) of Hurricane Monument and History of Diving Museum. Windley Key Fossil Reef Geological State ...

$159

$159
Best Western Key Ambassador Resort Inn

Best Western Key Ambassador Resort Inn

3755 S Roosevelt Blvd, Key West
2.5 out of 5.0
4.3 out of 5 (9 reviews)

Located on the Atlantic side of Island and just minutes from the Key West Art Society and Historical Downtown. Nearby points of interest include Smathers Beach, ...

$170

$170
Casa Marina, A Waldorf Astoria Resort

Casa Marina, A Waldorf Astoria Resort

1500 Reynolds Street, Key West
4.0 out of 5.0
4.2 out of 5 (237 reviews)

Looking out over the Straits of Florida towards Cuba, this upscale resort places guests a 3-minute drive from downtown Key West. The Ernest Hemingway Home & ...

$247

$247
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd, Key West
3.5 out of 5.0
4.1 out of 5 (147 reviews)

Located on the quieter side of Key West, this tropical-style resort offers complimentary scheduled shuttle service to Duval Street as well as shuttle service ...

$124

$124
Map

Experience Your Best Florida Keys Vacation

Cross the Overseas Highway to the distant Florida Keys and the symbolism is hard to miss: you're not leaving the country, but then again, you are. From top to bottom, the Keys offer something magically removed and unlike any other US beach vacation.

With everything from sunken treasures in Key Largo and family-friendly exploration in Marathon to trophy fishing in Islamorado and pub-studded Key West, this is a place of must-see and must-do.

Ready to design your own Florida Keys vacation? Start with this Orbitz insider guide for our favorite things to do, best times to go and insider gems.

Best time to take a vacation to Florida Keys

Spring break, pleasant weather, festivals or cheap rates -- your Florida Keys vacation is as easy as good timing.

For a perfectly balmy winter or spring break vacation, visit the Keys from December to May for temperatures in the low 80s. It's popular time to visit but the swelling, energetic scene is exactly the draw, especially for those heading to wild Key West.

Visit June through October for the lowest rates and fewer crowds when humidity and regular rainfall are the norm. Celebrate Key West's annual Hemingway Festival in July with readings, a fishing tournament and a look-a-like contest.

Insider tips for Florida Keys travel

Full Moon Party at Pierre's Restaurant (Islamorada)

Every time there's a full moon, this seaside restaurant throws a huge beach party, complete with fireworks, tiki bars, a Reggae band, stilt walkers, fireblowers, acrobats, face painters and more.

Jetpack water sports

Strap on a jet pack and unleash your inner James Bond. Tethered to an unmanned water craft, this thrilling new water sport sets you into flight to turn, hover and cruise 30 feet over the water.

Beach at Fort Zachary Taylor Historic State Park (Key West)

Follow locals to this pristine beach with Australian pines and vibrant reefs.

Mrs. Mac's Kitchen (Key Largo)

Belly up to this quirky roadside diner for delish homemade grub. Swing by for champagne breakfast, or join the lunch/dinner crowd for hogfish and the famed Key Lime Freeze.

Scooner Wharf Bar (Key West)

Hang with boaters and locals, catch live acts from magicians to musicians and feast on fresh seafood.

* Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.