Cute Houseboat In New Town Key West Yacht
It doesnt get any more Florida Keys than this! This boat is moored in New Town but you can take it anywhere you want around the city. Want to travel further afield? You can also hire an experienced Captain to take you on day trips around other Keys. Its powered mostly using solar energy, making it a great choice for more environmentally-conscious travellers.
Casa Marina Where To Stay In Key West On The Beach
The Casa Marina subdistrict is located on the southern side of the island, immediately to the southwest of Bahama Village. It is named after the luxury resort in the neighborhood that was founded by Henry Flagler in the late 19th century.
The area is known for its private beach and outdoor swimming pools. Often considered somewhat of a playground for the rich and famous, it is a fabulous choice for those who want a beach vacation with a stylish atmosphere and arent worried about spending big to pay for it.
At either end of the beach, beautiful piers jut out into the ocean. This allows you to stroll along, enjoying serene views while surrounded by nothing but water.
Attractions like a water sports company provides rentals for those looking to hit the waves and have some fun. Meanwhile, a sand artist creating sculptures to request on the beach offers a slightly more relaxing activity for those seeking a slower pace.
Then, no matter how you choose to spend your days, a great choice of bars and restaurants allows everyone to kick back and relax with some fine food and drink of an evening.
When you combine that with the shops and other facilities that are within close proximity, Casa Marina becomes one of the best spots on the island for those seeking a truly relaxing vacation.
Stay In Casa Marina If you arent worried about money you want to relax on a private beach you are interested in water sports or sand sculptures you want a good choice of bars and restaurants.
Casa Marina Key West A Waldorf Astoria Resort
Although its a little farther from Mallory Square than some of the other resorts on this list , the Casa Marina Key West, A Waldorf Astoria Resort, more than makes up for this fact with its large beach.
Around 1,100 feet from end to end, this private beach is the star attraction at this Mediterranean-style resort. In addition to offering a great place to relax, its also the center of water-based activities like sea kayaking and jet skiing .
The fun doesnt stop at the beach, either. Other activities and amenities include lounging around the two outdoor swimming pools, getting pampered at the full-service spa, or enjoying a meal in the on-site steakhouse .
A variety of room options are also available. Popular choices are the loft-rooms, which feature additional living space, pull-out sofas, and furnished balconies.
Address: 1500 Reynolds Street, Key West, Florida
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S From A Beautiful Beach
This 186-room, 3-story hotel is located across the street from Smathers Beach and the unbelievably blue waters of the Atlantic Ocean, near the quirkiness and historic sights of Old Town. Explore the culture, nightlife, and water activities on the most famous of the Florida Keys and return back to the quiet casual luxury of your premium guest room oasis. Relax in a poolside cabana, paddleboard in the ocean, or gather around our fire pit in the evening with a frozen concoction. Everything you need to enjoy your island vacation is waiting for you at Margaritaville Beach House Key West.
Frequently Asked Questions About Key West

What is the best location to stay in Key West?
If you are visiting Key West for the first time, Duval Street, Old Town is the best place to stay on the island with its proximity to main landmarks, shops, and bars. Santa Maria Suites and Duval Gardens are the best hotels here.
What is the best area to stay in the Florida Keys?
Southwestern parts of Florida Key that make up the Old Town are the best area where you will find great places to stay and good restaurants and bars. Key West is the most popular destination for visitors to the keys.
Is it expensive to stay in Key West?
Due to its location and high tourist demand Key West is an expensive city. Just to give you an idea, you should approximately budget around $300+ per day on average including accommodation.
How many days should you stay in Key West?
To enjoy beaches, restaurants and the main attractions in Key West I would recommend you to stay at least 3 or 4 days.
What is the best month to go to Key West?
Thanks to great weather and low humidity, is the peak season for Key West. If you want to save on hotel prices you can visit Key West between June and November.
It is time for me to say goodbye to you, travelers. I hope that this blog post helped you to find your ideal place to stay in Key West and you have already started the countdown for your trip. In this post, I talked about the best areas to stay in Key West with hotels from luxury to budget as well as Airbnbs in each neighborhood.
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Things To See And Do In Old Town:
- Duval Street isnt the only nightlife in the city. Hit up some local favorites in this tour of Key Wests alternative bars and clubs.
- Key West is home to the Southernmost Point in the Continental United States you can take a guided tour of the best attractions in the area on this experience.
- Famous writer Ernest Hemingway spent his late years in the Caribbean. Check out his Key West residence and learn more about his work at his former house.
- The Key West Butterfly and Nature Conservatory has a huge selection of native insect life perfect for a family day out on the odd bad weather day.
Best Hotels In Key West
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Key Wests high-low vibes extend to its lodging. Yes, you can tuck away in a bungalow on a private island with a butler, but you can also tuck in to a cozy suite in a historic home with gardens ringed by palm trees and a rowdy pool scene. Theres something for everyone here, and the islands iconic status as a tourist hot spot means that both the rooms and the service can compete with other, larger markets. No matter where you stay, from the moment you arrive, youll feel an instant wave of relaxation. No matter what you’re after, our editors’ guide to Key West’s best hotels will help you find it. Read on for a definitive list.
Click the link to read our complete Key West guide.
All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.
Another Key West icon, Pier House made its name in the ’70s as a haven for the creative set. Today, it’s a sprawling resort right on the water, with plenty of activities, an excellent spa, and great dining options . Some rooms are a bit dated in their decorthere’s still a surprising amount of rattan herebut suites have patios or balconies, making them ideal for enjoying a Key West sunset. Beds and amenities are nice, too. Pier House is in the middle of it all, but once you’re facing the ocean, you’ll forget all about the hullabaloo on Duval Street.
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Sheraton Suites Key West
This 4-star hotel is an oceanfront island escape from the real world.
All the suites come complete with a full kitchenette and a full dining area. Only some suits boast flat-screen TVs and balconies with amazing ocean views.
If the two of you are fans of water sports, there is amazing water sport activities on offer, a minutes walk from the hotel at Smathers Beach, one of the very best beache and most romantic places in Key West.
Couples who prefer a slower paced holiday may prefer to relax by the hotels elaborate lagoon-style pool.
If you dont feel like going out, there are numerous restaurants at the hotel to enjoy. Drifters Cove is one of the more popular spots with Caribbean style meals as well as a few more traditional dishes. Shipwreck Restaurant is another popular option for seafood.
Foodies will be happy to know that there is also great restaurants nearby the hotel including The Flaming Buoy Filet Co., an American restaurant in a groovy tropical setting or the Salute!
To stay fit after dining at these wonderful restaurants, you can drop by the hotels fitness centre that prides itself on having top notch weight lifting and cardio equipment.
Want to explore Duval Street too? Take the hotels complimentary shuttle to go on an adventure downtown. You might even like to get some shopping in.
Click here to book your stay.
Old Town Best Place To Stay In Key West For Your First Time
Key West Historic District, also known locally as the Old Town, is where the city first began. This is where you will find the most iconic architecture in the city, as well as the bulk of local attractions. First-time visitors will get a good understanding of everything on offer, as well as a vast selection of excursions to take them elsewhere along the Keys.
The Old Town is also the best-connected part of the city. It sits literally in the centre of Key West, so you can easily reach all of the other neighbourhoods mentioned in this guide on foot. This is perfect for those that dont have access to a car.
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Key West Best Area To Stay In Florida Keys For Nightlife
- COOLEST thing to do in Key West Relax on the beach or enjoy some water sports at the Fort Zachary Taylor Historic State Park
- BEST place to visit in Key West Visit the Ernest Hemingway Home and Museum to learn about the islands most famous resident
Youve probably heard of Key West, most people have. This island is at the southernmost tip of the Keys and was built on the back of cigar-making, as well as money taken from shipwrecks. As a result of this history, the island is filled with beautiful mansions and cottages in white and pastel colors, but its still a laidback and relaxing area to visit.
The city is welcoming to everyone, offering everything from expensive restaurants to hidden dive bars. This is what makes staying in Key West ideal when youre deciding where to go in the Florida Keys for nightlife.
Historic Seaport Best Place In Key West For Water Sports
Located immediately to the east of Mallory Square and north of Duval Streel, Key Wests historic seaport is the busiest part of the entire city. Multiple marinas are full of stunning yachts and vessels, while the Key West Express ferry service takes passengers on voyages across the Gulf Of Mexico.
You also have a collection of companies offering tours on fishing boats or private hires, allowing you to get out and spend some time on the water. Theres even a water sports company, where you can take part in activities such as windsurfing, parasailing, snorkelling, and even catamaran cruises.
Around the historic seaport, numerous bars, restaurants, and coffee shops provide you with places to enjoy a drink or meal, while watching the boats bob up and down on the waves. Perhaps the most famous is the Schooner Wharf Bar, which is known for its live music and New Years Eve festivities.
With some of the most scenic views in Key West and convenient access to the most popular areas, the historic seaport is a great choice for anyone who wants a relaxing break, where they have access to everything the island has to offer.
However, with so much going on, it is an area that gets remarkably busy. This means you may need to book in advance and be aware of issues like limited parking and large crowds.
Best places to stay in Historic Seaport:
> > CHECK BEST HOTELS NEAR HISTORIC SEAPORT < <
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Duval Street Where To Stay In Key West For The First Time
Duval Street in Key West is the most popular street on the island and has an incredibly colorful vibe. Located at the center of the Old Town, this district is within walking distance to Downtown Key West as well. Offering many shops, bars, restaurants, and museums and its proximity to main attractions makes Duval Street a perfect area to stay in Key West for first-timers.
You can easily discover Duval Street on foot but if you dont feel like walking, you may earn some time by taking The Duval Loop free shuttle which runs on the main street. Start your sightseeing by going to Ernest Hemingway Home and Museum and continue your stroll to Historic Seaport while checking out the beautiful cafes and quirky shops on the way.
If you are into nightlife, you will want to check out popular bars in Duval Street at night. It offers one of the best night scenes in Key West. Doesnt it already sound exciting?
Here you will find many accommodation options for all budgets. Since it is a popular and touristy district I highly recommend you make a booking in advance. I am going to give the top 4 accommodations to stay in Key West but if you want more options you can check out the best Airbnbs in Key West as well. Also, if you are planning to continue your trip in Miami you might wanna read where to stay in Miami!
Oceans Edge Resort & Marina Key West

Billing itself as the city’s newest and biggest luxury vacation destination, Oceans Edge Resort & Marina Key West offers guests no end of fun things to do. The resort boasts six swimming pools and plenty of waterfront activities, including one free hour of paddleboard and kayak usage.
Numerous outdoor adventures and outings can also be organized by resort staff, including exciting fishing excursions, snorkeling, guided Jet Ski tours, bike rentals, dinner cruises, and even airplane rides over the Keys. The resort also has a marina. A must-do while staying here is enjoying an alfresco gourmet meal in the charming waterside restaurant.
Guests have a wide choice when it comes to accommodations. Perfect for couples, the romantic ocean-view king rooms come with their own private balconies, while a much bigger two-bedroom suite is ideal for larger groups of friends or family members. Highlights of these larger, nearly 1,000-square-foot, six-person units include en-suite bathrooms, a separate living area with a pullout couch, plus an expansive private balcony with table and chairs.
Address: 5950 Peninsular Ave, Key West, Florida
Accommodation: Oceans Edge Resort & Marina Key West
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Modern Home In New Town Sea Glass Cay
This Florida Keys Airbnb sits on the boundary between Old Town and New Town, so youre actually within walking distance of both areas. The home itself has a calm oceanic vibe to it, with enough space for up to eight people. The huge pool area is surrounded by luscious plant life, and there is a breakfast bar nearby where you can take in the morning air.
Book Luxury Vacation Homes In Key West
Key West is one of the most popular places for luxury rentals in the Florida Keys. One of its highlights is The Ernest Hemingway Home and Museum, which is the former residence of the famous author. You could also visit the landmark for the southernmost point in the continental U.S. or check out Duval Street, a thrilling area filled with unique shops, waterfront dining, and lively bars. For more shopping, Mallory Square is a plaza with boutiques and shops offering a variety of goods and souvenirs. Key West also features an abundance of outdoor activities, such as surfing, diving, snorkeling, hiking, biking, and nature walks to see native wildlife.
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Things To See And Do In Smathers Beach:
Cucumber Key Photography
- The Artisan Market in Casa Marina is a must-visit attraction where you can pick up local cuisine and souvenirs.
- Smathers Beach itself offers a peaceful spot to soak up the sun, snorkel and enjoy the Caribbean breeze.
- Scooters Direct mostly sell scooters, but you can also hire them for a unique way to explore the city.
Best Luxury Airbnb In Islamorada: Beachfront Cottage
This luxury offering has 2 bedrooms and 2 bathrooms, suitable for up to 5 guests. Its also in the best neighborhood in the Florida Keys if you want to be close to the beach and the town. Situated in a gated community, this Airbnb has a private infinity pool. In addition, youll enjoy your own private beach and dock during your stay. Its also considered to be one of the best Airbnbs in all of Florida.
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Lower Duval Best Area In Key West For Nightlife
Key West is the best place to stay in the Florida Keys for nightlife, and Lower Duval is where youll find it! The entirety of Duval Street is within the Historic District, but in many ways, it is a neighbourhood in its own right. Upper Duval provides a more peaceful location thats still close to the action.
Lower Duval is also home to some of the best shopping boutiques on the Keys. Youll also find some great restaurants and cafés dotted around the area. In many ways, this is the citys entertainment district.