Best Places to Stay in Key West and Things to Do - For Parrotheads (2023)

If you’re looking for the best places to stay in Key West, look no further. We all want to visit Key West and stay in the best accommodations with the coolest pools to experience the unique island atmosphere, the beautiful weather, and the crystal clear waters.

Most of all, when we hear the song Margaritaville, we don’t want to regret not making the trip down to this little slice of paradise. After all, you’ll be walking in the footsteps of Jimmy Buffett himself.


Jimmy Buffett-Style!

6 Reasons Why The Marker Is the Best
1. Gonna Put the World Away for a Minute
2. The Ocean Is My Only Medication
3. If Life Gives You Lemons, Make Margaritas
4. Waitress, I Need Two More Boat Drinks
5. Why Don’t We Get Drunk and Screw
6. I Want to Go Back, to the Islands
Best Places to Stay in Key West For Any Budget

While strolling through the Old Town, you’ll experience the magic that inspired the feel-good songs of Jimmy Buffett. It will most certainly become infectious in your mood. There’s little doubt why The Marker Key West has such a high percentage of repeat visitors—they are known for their fabulous outdoor bar and restaurant, posh accommodations, chill beach pool life, and the ability to get a little wild.

“Give me oysters and beer for dinner every day of the year,
And I’ll feel fine, I’ll feel fine.” – Jimmy Buffett

6 Reasons Why This Is the Best Place to Stay in Key West

Below are six reasons why The Marker Key West is one of the best places to stay in Key West on your next vacation—all inspired by Mr. Margartaville himself, Jimmy Buffet!

(Video) Jimmy Buffett Plays Surprise Key West Concert for 'Parrot Head' Fans

1. Gonna Put the World Away for a Minute

Best Places to Stay in Key West and Things to Do - For Parrotheads (1)

Driving down the Overseas Highway, you’ll begin to notice yourself unwind as you make your way closer to Key West. Considered one of the most scenic drives in the world, this 100-mile route over stunning turquoise blue and green waters should not be rushed. Some days you won’t have a choice as the traffic can get pretty treacherous.

Best Places to Stay in Key West and Things to Do - For Parrotheads (2)

Either way, kick back and relax as the highway hops from island to island. There’s little doubt that one of the joys of visiting the best Key West resorts is the drive down. Stay patient and trust the journey. Highlights along the way include Route 66-like roadside attractions, fresh-caught seafood restaurants, and breathtaking views. At this point, shirts are optional!

2. The Ocean Is My Only Medication

Yeah! You’ve made it to Key West. The first things you’ll notice are the palm tree-lined streets and the laidback atmosphere. Your first stop will probably be at your hotel located in the Old Town. This is also known as the historic district. It’s the western half of the island, where the central business district and the majority of tourist attractions are located.


We stayed at The Marker Waterfront Resort located at Mile Marker 0. We loved the location of this hotel. It sits along Key West’s historic seaport and is within walking distance of all of the best Key West resorts, bars, and restaurants. Our daily dose of medication included relaxing on our balcony and breathing in the fresh ocean air. No prescription is needed!

3. If Life Gives You Lemons, Make Margaritas

Most people will agree that The Marker Key West is best visited from March through May. During this time, it’s a bit more affordable than the more expensive winter months and the weather is warm and sunny.

Best Places to Stay in Key West and Things to Do - For Parrotheads (11)

Realistically, as long as you avoid the rainy season between August and October, you’ll probably have great weather. Otherwise, you might be forced to sit in a pub all day drinking margaritas.

But, as Jimmy Buffett advises, when life gives you lemons, make margaritas. To make you feel a little better, even on the sunniest of days in Key West, you may find yourself savoring some cool drinks at one of the iconic bars anyway.

4. Waitress, I Need Two More Boat Drinks

Best Places to Stay in Key West and Things to Do - For Parrotheads (12)

Life doesn’t get much better than hopping on a plane during a cold and dreary Midwest winter and escaping to the best Key West resorts.

(Video) Parrotheads relax at Key Lime Inn, Key West Florida

Duval Street

Best Places to Stay in Key West and Things to Do - For Parrotheads (13)

Did you know that a Midwest winter starts in October and ends sometime in May? The warm, tropical Key West air will rejuvenate your spirit and provide you with renewed energy.

Best Places to Stay in Key West and Things to Do - For Parrotheads (14)

You’ll be able to get a taste of the Caribbean without having to leave the States.

Best Places to Stay in Key West and Things to Do - For Parrotheads (15)

Get your bearings by strolling down Duval Street. This is the perfect opportunity to grab a drink or peruse places to entertain yourself later.

Best Places to Stay in Key West and Things to Do - For Parrotheads (16)

There’s no need to make recommendations here. If something looks appetizing and/or popular, it will be like that. The area is so small that it’s easy to find exactly whatever you’re searching for.

Best Places to Stay in Key West and Things to Do - For Parrotheads (17)

With that in mind, there’s no better place to celebrate your trip and kick off the night than Mallory Square at sunset. Honestly, I don’t want to ruin the experience for you. Just go. Afterward, head out to dinner, preferably somewhere that provides outdoor dining.

Conclude the evening by stopping at a bar (or every bar) until you reach your hotel. Hint: It’s probably a good time to call it a night if you say, “Waitress, I need two more boat drinks in a slurred voice.”

(Video) The Conch Shack - Key West, Florida

5. Why Don’t We Get Drunk and Screw

Best Places to Stay in Key West and Things to Do - For Parrotheads (18)

Believe it or not, Key West can be quite a romantic place, especially at The Marker Key West. Sure, the town has a bad reputation for public drunkenness, wild pub crawls, public nudity, young spring breakers, old spring breakers, homeless people, and all of the above walking around barefoot.

Fun Activities to Ignite the Romance

But, if you spend your days doing whatever it is that tickles your pickle or ruffles your truffles, you’re sure to have a romantic time. Here are some ways to ignite the romance:

Best Places to Stay in Key West and Things to Do - For Parrotheads (19)

After a fun and charming day full of these romantic activities you might hear these seven sweet words—why don’t we get drunk and screw?

6. I Want to Go Back, to the Islands

You know you’re in paradise when you wake up to palms swaying in the warm, tropical breezes. Key West is a special place to visit, unlike anywhere we’ve ever been. While Jimmy Buffett may no longer be considered a local in Key West, his legend and character continue to live on.

Best Places to Stay in Key West and Things to Do - For Parrotheads (20)

If for whatever reason, you’re unable to visit Key West, remember living life like a Jimmy Buffett song has nothing to do with where you spend your vacation and has everything to do with your attitude or philosophy on life. In his own words, “I’m growing older, but not up.” Either way, I know that “I want to go back, to the island.”

Best Places to Stay in Key West

Key West is known for being one of the most expensive destinations in the US. Unfortunately, no matter what type of accommodation you decide on, it’s going to feel expensive. We’d suggest you pick from one of the options below.

(Video) Florida Keys Key West Parrot Head Meeting of the Minds

Budget: Duval Gardens (great location) or Knowles House B&B (happy hour)
Mid-Range: Douglas House (relaxing) or Avalon Bed and Breakfast (on Duval St.)
Luxury: The Marker Key West (fun resort vibes) or Santa Maria Suites Resort (all-suite villas)
Honeymoon or Special Occasion: H2O Suites- Adults Only (private pools)

Check out the highlights of our trip to Key West below!

Best Places to Stay in Key West and Things to Do - For Parrotheads (21)


What should I not miss in Key West? ›

Don't miss the two pink flamingos in the wading pool.
  • Key West Cemetery. Photo courtesy of Dale M. ...
  • Key West Lighthouse Museum. Old Town. ...
  • The Ernest Hemingway Home & Museum. Old Town. ...
  • Harry S. ...
  • Conch Tour Train. ...
  • Florida Keys Eco-Discovery Center. ...
  • Mallory Square Sunset Celebration. ...
  • Dry Tortugas National Park.

What area of Key West is most popular? ›

The 8 Best Neighborhoods in Key West for Tourists
  • Duval Street.
  • Downtown/Historic Seaport.
  • Heart of Old Town.
  • Casa Marina.
  • Bahama Village.
  • Truman Annex.
  • New Town.
  • Sunset Key.
4 Oct 2022

How many days is good to spend in Key West? ›

Key West is worth a day trip, but the more time you have, the better! You could easily spend a week in Key West, but 3-4 days is optimal if you want to do it all and still have time to relax.

Do I need jeans in Key West? ›

Locals live in shorts. Unless, of course, there's a cold snap which typically happens in the fall months. Add a pair of jeans, sweater, and tennis shoes to your stacks of shorts and T-shirts to be safe. Winter in Key West is comfortable, with an average high of 75°F and average low of 65°F.

What is the best month to go to Key West? ›

The best time to visit Key West is between March and May. The winter crowds will taper off, the hotel rates become reasonable and the weather is remarkably similar to winter's blissful 70s and 80s. Speaking of winter – that season is the island's busiest and priciest.

What is the best side to stay on in Key West? ›

If you want to be in the heart of things, the best area to stay in Key West is the downtown area. Here, you'll be within easy walking distance of Duval Street, giving you plenty of options for drinking and dining, as well as some excellent shopping.

What is the name of the famous street in Key West? ›

World-famous Duval Street is known as the party epicenter of Key West and is the island's “main drag.” Running north and south, the thoroughfare is lined with bars, pubs, outdoor cafes, shops, galleries, restaurants, and celebrated attractions. It is also where you'll find our waterfront Key West hotel.

How many days do you need in the Keys? ›

5-7 days is perfect for a Florida Keys Road Trip, so many things to do. (and there's also a National Park bonus!) Florida Keys tours range from snorkeling to seeing dolphins in the wild. Dry Tortugas is one of the best things to do in all of the Florida Keys.

What is the cheapest month to go to Key West? ›

Go during the off season, roughly June to November. (September and November are the cheapest of all.) Shop around for accommodations and compromise on amenities or location. Seek out affordable, casual restaurants.

Is staying in Key West Worth It? ›

Is Key West worth visiting? If you're looking for a multi-purpose destination - lively nightlife, exceptional water-sports, Old Town atmosphere, plus plenty of literary and political history - then quirky Key West should suit you down to the ground.

Do you need a car in Key West? ›

You don't really need a car in Key West unless you're planning to do a lot of shopping or are heading out to multiple far-fetched points in the Keys. The island is only four miles long and about one mile wide, so almost everything is located within walking distance.

Can you walk with alcohol in Key West? ›

No alcohol, please. The Florida Keys & Key West do enforce open container laws that prohibit open containers of alcohol on most public beaches, parks and streets; including world-famous Duval Street.

Can you walk on the street with alcohol in Key West? ›

A common misperception is that open containers of alcohol are permitted in Key West city limits. While in fact, the opposite is true. The Key West Municipal Code, § 18-87 prohibits open containers of alcoholic beverages in public.

What is the dress code for Key West? ›

The unofficial dress code in Key West is very casual, so you shouldn't worry about trying to fit those high heels in your suitcase. If you want to dress it down even more, go for it! A nicer pair of shorts or jeans won't make you feel out of place either.

How many days are enough for the Florida Keys? ›

While it's always ideal to spend more time in any destination, I recommend staying for at least four days in the Florida Keys, if not longer. To accomplish many things to do in the Florida Keys, you'll need a solid five days.

What months are hurricane season in Key West? ›

The Atlantic hurricane season formally begins June 1 and ends November 30. Historically, the chances of hurricane activity are greater between August 15 and October 15. Can I travel to the Florida Keys during hurricane season? Absolutely.

What are the rainy months in Key West? ›

The rainy season occurs from May through October, when visitors should expect lots of showers and thunderstorms, particularly in the mornings. June through November is the hurricane season, with September being the most likely time for severe tropical storms to hit.

Which part of Key West is best for families? ›

Southernmost Beach Resort, Key West

Located, as its name suggests, at the very south end of the Florida Keys in Key West, the charming 4-star Southernmost Beach Resort is another great choice for those traveling as a family.

What is the difference between Old Town and New Town Key West? ›

The area of Key West that is called New Town is the part of the island that is located east of Old Town. Unlike if you stay in the Historic District, you don't have most attractions on your front step if you stay at Key West hotels in New Town.

Which side of Key West has better beaches? ›

Most of the top beaches in Key West are located on its southern shore, with the majority clustered along a stretch of water only a little over a mile in length. Key West's largest beach, Smathers Beach, is an exception.

What food is Key West famous? ›

Conch, pronounced “konk,” is the queen of all foods in Key West and was a staple food of early settlers. You've probably seen the pretty shell of the sea snail used for decorations but it's the meat that sends seafood aficionados across the globe into a spin.

What drink is Key West famous for? ›

Rum Runner @ Island Dogs

Created in the 1950s at the Tiki Bar of Holiday Isle in Islamorada, the rum runner is the quintessential cocktail of the Florida Keys.

What dessert is Key West known for? ›

Key lime pie and Key West go hand in hand. While there are plenty of delicious varieties of this creamy, tart dessert, there are also a lot of other sweet treats to tempt your taste buds at restaurants, bakeries and ice cream shops across the island.

What is sloppy joes in Key West known for? ›

Sloppy Joe's has three complementary divisions: food, beverage, and retail store. The bar offers generous drinks, live music and dancing. The quality of the entertainment, showcased on the huge stage facing Duval Street, is exceptional–and ranges from rollicking bluegrass to raucous rock.

What celebrities own homes in Key West? ›

  • 1) Hemingway House. Ernest Hemingway fell in love with both the natural beauty of the island and the atmosphere at Hog's Breath Saloon. ...
  • 2) Margaritaville Flagship Restaurant. ...
  • 3) Robert Frost Cottage. ...
  • 4) Truman Little White House. ...
  • 5) Audubon House. ...
  • 6) Key West Memorial Sculpture Gardens. ...
  • 7) Jimmy Buffett - Shrimp Boat Studio.

Why are there no beaches in the Keys? ›

The Keys don't have wide sandy beaches because the coral reefs we enjoy as snorkelers and scuba divers prevent the erosion and sand from building up along the shore. So while the beaches aren't what make the Keys special, there are still some pretty special beaches in the Keys.

Which key has the nicest beach? ›

  • Cannon Beach: Key Largo.
  • Far Beach: Key Largo.
  • Founders Park Beach: Islamorada.
  • Sombrero Beach: Marathon.
  • Curry Hammock State Park Beach: Marathon.
  • Calusa Beach: Big Pine Key.
  • Loggerhead Beach: Big Pine Key.
  • Fort Zachary Beach: Key West.
22 Aug 2022

Which key has the clearest water? ›

Fort Zachary Taylor Park Beach, Key West

Fort Zachary Taylor Historic State Park is a National Historic Landmark that offers some of the clearest blue waters for snorkeling and diving in Key West.

What is the prettiest Florida Key? ›

While Key Largo is undoubtedly the prettiest of all the Florida Keys, it's also one that's home to plenty of activities for the avid beachgoer.

What is the best time of year to visit the Florida Keys? ›

Best time to visit the Florida Keys for great weather and events. If you want great weather, aim to plan your trip during the dry season between December and March. Hurricane season has been and gone, the temperature is pleasant and the mugginess is bearable.

What is the most famous Florida Key? ›

Key West. Easily the most famous of the Florida Keys, there's a reason why Key West is the most popular destination in the Keys.

What is the easiest way to get around Key West? ›

The best way to get around Key West is on foot. Mopeds and bicycles are also popular, though mopeds can be dangerous. Taxis are available on the street, as well as in front of the Key West International Airport (EYW) in the middle of the island.

How do visitors get around in Key West? ›

Key West transportation ranges from taxis, shuttles and car rentals to bicycles, scooters and your own two feet. Duval Street and the Old Town area are very walkable. Setting off on foot is a great way to visit the shops, cafes, art galleries and unique buildings and architecture of this tropical Florida Keys location.

What is the best way to get around the Keys? ›

Here are some of the best ways to get around Key West.
  1. Take the Old Town Trolley Tour. ...
  2. Tour the City on a Bike. ...
  3. Hop in an Electric Car. ...
  4. Rent a Car. ...
  5. Cruise around by Boat. ...
  6. Call a Cab or Limo Service.

How much it costs the fairy to go to Key West? ›

Round Trip - Full Fare
Adults (13-61 years Old)$185.00
Seniors (62+ Years Old)$175.00
Juniors (5-12 Years Old)$135.00
Children (4 and Younger)$85.00

What is the coldest month in the Keys? ›

Average Temperature in Florida Keys

The cool season lasts for 3.0 months, from December 7 to March 6, with an average daily high temperature below 77°F. The coldest month of the year in Florida Keys is January, with an average low of 66°F and high of 74°F.

Is 2 nights enough in Key West? ›

Is 2 days enough in Key West? 2 full days or 2 nights in Key West are perfect for city explorers. You can visit the main attractions or landmarks of Key West Historic District and check off the Truman House, Hemingway House, food tour, Key West Cemetery and spend time at the Duval Street.

What is difference between Key Largo and Key West? ›

For instance, Key West is known for its shopping, nightlife, and bustling streets whereas Key Largo is the ideal destination for a more relaxing and laid-back stay. You'll need to ask yourself what sorts of activities you want to try while in Florida. History buffs are going to want to head to Key West.

Is it better to stay in Key Largo or Islamorada? ›

For those wishing for a more laidback, small-town vibe, Islamorada is the way to go; and for those wanting a more bustling, high-energy spot, Key Largo is where it's at. Either way, travelers will find a fantastic vacation destination that showcases the best of the beautiful Florida Keys.

Can you see Cuba from Key West? ›

“ The problem is that the earth, being round, curves and Cuba, which is about 90 miles from Key West, falls below the horizon when you look towards it from Key West. It means that regardless of how great your eyesight is, and how clear the day is, there is no way you can see Cuba from anywhere in Key West.

Is there a free trolley in Key West? ›

This FREE hop-on hop-off bus service runs from the City's Park and Ride on Grinnell Street, along Caroline Street, right on Simonton Street, around Front Street, up the length of Whitehead, through Truman Waterfront, then returns down the length of Simonton to Fleming.

Can you Uber in Key West? ›

Ride to and from Key West Airport with Uber. Instead of waiting for the EYW shuttle or taxi, you can request a ride directly in the app and be on your way.

Can you walk around Key West island? ›

One of the best things about Key West is you can walk just about everywhere. Don't bring your car - leave it at home! We rode the bus to our hotel and got a good view of the island before we arrived at our lodging. Once you are in Key West, you can walk to Mallory Square, Sunset Pier, and Duval Street.

What is Key West most known for? ›

Key West, the southernmost point in the United States, is famous for watersports, lively nightlife, beaches, historic sites and its pastel, conch-style architechture.

Can you walk around with open containers in Key West? ›

A common misperception is that open containers of alcohol are permitted in Key West city limits. While in fact, the opposite is true. The Key West Municipal Code, § 18-87 prohibits open containers of alcoholic beverages in public.

What is the cheapest time to visit Key West? ›

Visit Key West in the off-season

The fall (September–November) is the low season in Key West, and room rates can drop by 50 percent or more. The hot, storm-prone summer months also see lower prices, and you'll find decent discounts in April and May after the winter crowds thin out.

What should I buy in Key West Florida? ›

10 Best Souvenirs to Buy in Florida Keys
  • Key West Cigars.
  • Cuban coffee.
  • Local shells.
  • Artisan jewelry.
  • Handmade sandals.
  • Blown glass.
  • Fishing gear.
  • Native foods.

What time do they stop serving alcohol in Key West Florida? ›

Generally speaking, alcohol is not allowed to be sold in Florida between midnight and 7 A.M.

Can you drink tap water in Key West? ›

The FKAA treated water is pumped 130 miles from Florida City to Key West, supplying water to the entire Florida Keys. The water provided to customers in the Florida Keys is continuously monitored and tested to ensure the water quality is consistent, safe, and meets all federal and state drinking water standards.

Can you drink on sidewalks Key West? ›

Additionally, public consumption of alcohol is not acceptable. You can be cited for consuming alcohol or possessing alcohol on streets, sidewalks, in parking lots or on beaches throughout the state. An open container can be an open bottle or can, flask, cup, or glass containing any amount of alcohol.


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