Hotel Deals in Key West

Key West Guide

###A Weekend in Key West

In the 19th century, a large percentage of Key West’s residents were Bahamian immigrants known as “Conchs.” Today, the term is applied to anybody who’s born on this tiny but lively island off the coast of Florida. “Freshwater Conchs” are transplants who’ve lived here seven years or more. After experiencing Key West’s sunny beaches, warm temperatures, and fun-loving atmosphere, you might be tempted to make the move yourself (you certainly wouldn’t be the first). But it’s probably best to try it out for a weekend before calling the realtor. Here’s a suggested itinerary to get you started:

Day 1

Start your visit by getting to know Key West on the fun (though slightly cheesy) Conch Tour Train, a narrated, history-filled 90-minute ride on a yellow tram car. Then hit the beach. That’s why you’re here, isn’t it? Smathers Beach is a good choice—it’s a half-mile long and there are places to rent gear for windsurfing and jet-skiing. After a day in the sun, check out the famous Sloppy Joe’s Bar, a Key West staple that opened on the day Prohibition was repealed in 1933.

Day 2

In the mid-20th century, Key West became a favorite vacation spot for literary celebrities, including playwright Tennessee Williams, poet James Merrill, and novelist Ernest Hemingway. Be sure to plan a visit to the Ernest Hemingway Home & Museum, where the author lived for several years and wrote For Whom the Bell Tolls. Descendents of Hemingway’s six-toed cats still roam the property today. Later, spend the afternoon shopping on Duval Street, then party the night away at The Green Parrot, a bar that’s been around since 1880. Expect strong drinks and wildly uneven live music.

What to Eat

Two words for you: Cuban and seafood. Key West is only about 90 miles from Cuba, so it should come as no surprise that some of the best Cuban food in the United States can be found here. Wait in line with locals for marinated pork at El Siboney, then slurp down oysters and steamed beer shrimp at Alonzo’s Oyster Bar on Front Street.

Where to Stay

  • Marquesa Key Hotel: a small, award-winning boutique hotel in the heart of Key West’s historic district; it dates back to 1884
  • Casa Marina, A Waldorf Astoria Resort: Built in the 1920s, this luxury resort is listed on the National Register of Historic Places. The hotel has its own stretch of private beach near the shops on Duval Street.
  • La Te Da Hotel: a quaint and quiet B&B on the southern end of Duval Street; this hotel offers hearty breakfasts and a peaceful garden with a small pool
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Market PicksHotels Selected for Top Ratings and Value + 5% Groupon Bucks Credit

Get a 5% Groupon Bucks credit when you book a Market Pick hotel here.
Key West Marriott Beachside Hotel
Key West Marriott Beachside Hotel
Key West, Florida

5%

With a stay at Key West Marriott Beachside Hotel in Key West, you'll be on the waterfront and convenient to Key West Golf Club and Key West Art and Historical Society. This beach hotel is within close proximity of Key West Art and Historical Society and East Martello Museum and Gallery.

5% Credit

Palm Haven Restaurant
Palm Haven Restaurant
Key West, Florida

5%

With a stay at DoubleTree Resort by Hilton Grand Key - Key West in Key West, you'll be near the airport and convenient to East Martello Museum and Gallery and Key West Art and Historical Society. This eco-friendly resort is within close proximity of Robbie's and Key West Golf Club.

5% Credit

Sheraton Suites Key West
Sheraton Suites Key West
Key West, Florida

5%

With a stay at Sheraton Suites Key West in Key West, you'll be near the airport and minutes from Smathers Beach and close to Ernest Hemingway Home and Museum. This eco-friendly resort is within close proximity of Key West Art and Historical Society and East Martello Museum and Gallery.

5% Credit

Southernmost Beach
Southernmost Beach
Key West, Florida

5%

With a stay at Southernmost Hotel, you'll be centrally located in Key West, steps from Key West Butterfly and Nature Conservatory and South Beach. This eco-friendly hotel is within close proximity of Key West Lighthouse and Keeper's Quarters Museum and Ernest Hemingway Home and Museum.

5% Credit

The Reach, A Waldorf Astoria Resort
The Reach, A Waldorf Astoria Resort
Key West, Florida

5%

When you stay at The Reach, A Waldorf Astoria Resort in Key West, you'll be by the ocean and minutes from South Beach and Key West Butterfly and Nature Conservatory. This 4-star resort is within close proximity of Key West Lighthouse and Keeper's Quarters Museum and Ernest Hemingway Home and Museum.

5% Credit

Crowne Plaza Key West La Concha
Crowne Plaza Key West La Concha
Key West, Florida

5%

With a stay at Crowne Plaza La Concha Key West, you'll be centrally located in Key West, steps from San Carlos Institute - Casa Cuba and Key West Film Society. This hotel is within close proximity of Red Barn Theater and The Oldest House - Key West.

5% Credit

Cafe Marquesa
Cafe Marquesa
Key West, Florida

5%

Welcome to Key West's finest small hotel set in the center of the historic district. A compound of four buildings set around a lush interior garden and two swimming pools, the Marquesa offers a quiet retreat for those wanting luxury and privacy. The transformation from 1884 conch houses to beautifully restored rooms and suites with marble baths and all amenities has brought the Marquesa many awards, including being named the 1 Hotel in Florida in Travel and Leisure Magazine's Top 100 and 1 on Tripadvisor. Our location is perfect for exploring Key West just one block from Duval Street, four blocks from Mallory Square and the Gulf of Mexico, and a mile from the Atlantic Ocean. A car is not necessary it is all within walking distance. We do, however, offer free off street parking if you drive to Key West. Our guest rooms will enchant you. They are immaculate, light and airy, equipped with all amenities to make you feel at home only more pampered. In the evening your bed will be turned down, fresh towels put in place, a Godiva chocolate on your pillow to savor. In the morning, for a nominal charge, we will bring a continental breakfast to your room or serve it to you in our poolside garden with the sounds of a sparkling fountain and trickling waterfall in the background. If you must stay in touch, we offer two DSL computer workstations for guests and WIFI throughout the property for those with equipped laptops. Sorry, pets are not accepted. ALL GUEST ROOMS ARE SMOKE FREE. CHILDREN Children 14 and older are welcome. No children under the age of 14 are permitted.

5% Credit

Westin
Westin
Key West, Florida

5%

With a stay at Sunset Key Guest Cottages, A Westin Resort in Key West, you'll be in the historical district and minutes from Key West Museum of Art and History and Audubon House and Tropical Gardens. This 4-star resort is within close proximity of Custom House Museum and A Key Encounter.

5% Credit

The Banyan Resort
The Banyan Resort
Key West, Florida

5%

With a stay at The Banyan Resort in Key West, you'll be on the Strip and minutes from Key West Film Society and Audubon House and Tropical Gardens. This eco-friendly resort is within close proximity of Red Barn Theater and The Oldest House - Key West.

5% Credit

Pier House
Pier House
Key West, Florida

5%

With a stay at Pier House Resort & Caribbean Spa, you'll be centrally located in Key West, steps from Ripley's Believe It or Not and Pirate Soul Museum. This 4-star hotel is within close proximity of Key West Shipwreck Museum and Key West Aquarium.

5% Credit

The Ocean Key Resort & Spa
The Ocean Key Resort & Spa
Key West, Florida

5%

With a stay at Ocean Key Resort - A Noble House Resort in Key West, you'll be on the riverwalk and minutes from Ripley's Believe It or Not and Audubon House and Tropical Gardens. This 4-star resort is within close proximity of Key West Shipwreck Museum and Key West Aquarium.

5% Credit

Best Western Key Ambassador Resort Inn
Best Western Key Ambassador Resort Inn
Key West, Florida

5%

When you stay at Best Western Key Ambassador Resort Inn in Key West, you'll be on the waterfront and minutes from East Martello Museum and Gallery and Key West Art and Historical Society. This resort is within close proximity of Robbie's and Key West Harbour.

5% Credit

Little Palm Island
Little Palm Island
Little Torch Key, Florida

5%

When you stay at Little Palm Island Resort & Spa - A Noble House Resort in Little Torch Key (Coupon Bight Aquatic Preserve), you'll be within the region of Bahia Honda State Park and Beach.

5% Credit

Parrot Key Hotel and Resort
Parrot Key Hotel and Resort
Key West, Florida

5%

When you stay at Parrot Key Hotel & Resort in Key West, you'll be on the waterfront and close to Smathers Beach and Ernest Hemingway Home and Museum. This 4-star resort is within close proximity of East Martello Museum and Gallery and Higgs Beach.

5% Credit

Banana Cabana Restaurant
Banana Cabana Restaurant
Marathon, Florida

5%

Located in Marathon, Banana Bay Resort & Marina - Marathon is by the sea and minutes from Sombrero Beach and Crane Point Museum and Nature Center. This hotel is within close proximity of The Turtle Hospital and Pigeon Key Foundation.

5% Credit

Paradise Inn
Paradise Inn
Key West, Florida

5%

A stay at Paradise Inn places you in the heart of Key West, walking distance from Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. This romantic hotel is within close proximity of San Carlos Institute - Casa Cuba and Jackson Square.

5% Credit

Courtyard Key West Waterfront
Courtyard Key West Waterfront
Key West, Florida

5%

With a stay at Courtyard by Marriott Key West Waterfront in Key West, you'll be close to Smathers Beach and Ernest Hemingway Home and Museum. This hotel is within close proximity of East Martello Museum and Gallery and Key West Golf Club.

5% Credit

La Mer And Dewey House
La Mer And Dewey House
Key West, Florida

5%

These splendid representations of turn of the century architecture serve as a perfect romantic getaway. Located in the heart of Old Town and overlooking the beach ocean and lush gardens each unique room opens to a tropical paradise. All of the recently renovated luxury guest rooms have a private bath and king queen or two double beds. Complimentary Continental Breakfast and Afternoon Tea with 24 hour latte service are provided along with morning newspaper and turn down service.

5% Credit

Key Lime Inn
Key Lime Inn
Key West, Florida

5%

KEY LIME INN IS LOCATED IN THE CENTER OF KEY WESTS HISTORICDISTRICT JUST TWO BLOCKS FROM DUVAL STREET. AAA APPROVED 3DIAMOND RATING LARGE POOL CONVENIENT PARKING WIRELESSINTERNET CONTINENTAL BREAKFAST.

5% Credit

Hilton Key Largo Resort
Hilton Key Largo Resort
Key Largo, Florida

5%

Located in Key Largo, Hilton Key Largo Resort is by the sea and close to Bluefin Rock Harbor Marina and Dolphins Plus. This beach resort is within the vicinity of Florida Keys Wild Bird Center and Dolphin Cove.

5% Credit

Marriott Key Largo Bay Beach Resort
Marriott Key Largo Bay Beach Resort
Key Largo, Florida

5%

With a stay at Key Largo Bay Marriott Beach Resort in Key Largo, you'll be on the waterfront and close to MarineLab Undersea Laboratory and Dolphin Cove. This beach hotel is within close proximity of John Pennekamp Coral Reef State Park and Christ of the Deep.

5% Credit

Holiday Inn Key Largo
Holiday Inn Key Largo
Key Largo, Florida

5%

With a stay at Holiday Inn Key Largo in Key Largo, you'll be close to Dolphins Plus and Bluefin Rock Harbor Marina. This eco-friendly hotel is within close proximity of Dolphin Cove and John Pennekamp Coral Reef State Park.

5% Credit

Pelican Cove Resort
Pelican Cove Resort
Islamorada, Florida

5%

When you stay at Pelican Cove Resort & Marina in Islamorada, you'll be on the waterfront and convenient to Theater of the Sea on Islamorada and History of Diving Museum. This beach hotel is within the vicinity of Hurricane Monument and Bud n' Mary's Dive Center.

5% Credit

Courtyard Key Largo
Courtyard Key Largo
Key Largo, Florida

5%

Located in Key Largo, Courtyard by Marriott Key Largo is on the waterfront and close to Dolphins Plus and Dolphin Cove. This eco-friendly resort is within close proximity of John Pennekamp Coral Reef State Park and Bluefin Rock Harbor Marina.

5% Credit

The Moorings Village Islamorada
The Moorings Village Islamorada
Islamorada, Florida

5%

With a stay at The Moorings Village and Spa in Islamorada, you'll be on the beach and minutes from Hurricane Monument, and close to History of Diving Museum. This beach property is within the vicinity of Bud n' Mary's Dive Center and Theater of the Sea on Islamorada.

5% Credit

Chesapeake Beach Resort
Chesapeake Beach Resort
Islamorada, Florida

5%

When you stay at Chesapeake Beach Resort in Islamorada, you'll be by the ocean and convenient to History of Diving Museum and Theater of the Sea on Islamorada. This beach resort is within the vicinity of Hurricane Monument and Bud n' Mary's Dive Center.

5% Credit

Bayside Inn Key Largo
Bayside Inn Key Largo
Key Largo, Florida

5%

There’s no shortage of tropical charm at Bayside Inn Key Largo, which lies along the western coast of Florida’s northernmost Key. Here, you’ll find swaying palm trees, white-sand beaches, and spectacular sunsets. Take in your fill of ocean views from the heated waterfront pool or a pair of wooden piers that jut out into the turquoise waters of Buttonwood Sound. The hotel also rents kayaks and fishing poles—fishing is allowed from either pier.

5% Credit

Hilton Marco Island Beach Resort & Spa
Hilton Marco Island Beach Resort & Spa
Marco Island, Florida

5%

With a stay at Hilton Marco Island Beach Resort and Spa in Marco Island (Gulf Coast Visitor Center Everglades), you'll be close to Marco Town Center Mall. This 4-star hotel is within the region of Collier Seminole State Park and Flamingo Island Course - Lely Resort.

5% Credit

Marriott's Crystal Shores
Marriott's Crystal Shores
Marco Island, Florida

5%

With a stay at Marriott's Crystal Shores in Marco Island (Gulf Coast Visitor Center Everglades), you'll be close to Marco Town Center Mall. This 4-star hotel is within the region of Collier Seminole State Park and Flamingo Island Course - Lely Resort.

5% Credit

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