11 Best Luxury Hotels in Key West, Florida

Turquoise waters, endless revelry, and free-spirited independence set Key West in Florida apart. Key West is the quintessence of a Floridian beach holiday, especially with the North Atlantic Ocean on one side and the Gulf of Mexico on the other. In fact, it’s much closer to Cuba than it’s to Miami! So, we were astounded by how many amazing stays we found on this island, which is the southernmost point of the continental US. Of them, the number of options for a luxury hotel in Key West, Florida, seems to be growing every year. Contrary to what we thought, Key West isn’t just a party town; its luxurious stays reflect its many personalities. What’s more, they cater to all kinds of travelers, whether you’re looking for a family vacation, a weekend with friends, or a romantic getaway, like us.

Don’t be fooled by the size of this island, though; there are endless indulgent options to choose where you want to put your feet up and be pampered. So, we’ve gone ahead and tackled the hard work of putting together the best of the lot. And no matter where you choose to stay, you’ll feel instant relaxation right from the time you set foot in them.

Winslow’s Bungalows – Key West Historic Inns

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We begin the list with what is part of the Key West Historic Inns collection, Winslow’s Bungalows. Staying here felt like having an upscale home in the heart of the island’s historic district, and the place is downright cool. This boutique resort, which occupies several historic homes, is named after Winslow Homer, who regularly vacationed in town during winter. The intimate setting, combined with the retro-chic decor and the hip vibe, made it the perfect place to indulge in a luxurious Key West vacation.

Despite there being a daily resort fee, it covered all the usual suspects, including towels at the three swimming pools and even a snorkel kit and mask for exploring the island’s marine life. The concierge was very helpful regarding everything, from suggesting the best snorkeling spots to making reservations at amazing restaurants. Even though there was no restaurant on the property, they served us a fantastic complimentary breakfast every morning. Moreover, the bar by the pool kept our thirst at bay, especially after a swim.

There might be as many as 85 rooms and suites here, but we never felt that we were at a hotel. Rather, we felt more like an esteemed guest in a private home. The rooms are less kitschy Florida and more Architectural Digest, with small fridges, plush beds, large TVs, and luxe bathrooms.

H2O Suites, Adults Only

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Best adults-only. We were looking for a luxurious adults-only stay in Key West, and the H2O Suites, Adults Only, suited us perfectly. The unabashedly upscale boutique hotel was breathtaking and luxurious in every aspect. It was a tranquil respite from the craziness and heat of the nearby Duvall Street.

What we liked about this hotel was its intimate and modern aesthetic. The courtyard filled with water features and lush tropical plants melted the hustle and bustle of the outside world. It had a spa-like feel, complete with a firepit that provided a nice and cozy feel in the evening. Aside from the fitness center, there was even a rooftop pool and bar where we could unwind. Bike hire, a complimentary happy hour, free welcome drinks, and a 24-hour front desk wrap up the amenities here.

Since we stayed in the premier luxury suite with a private pool, we had our own pool time whenever we wanted. We especially loved the added advantage of having a small private pool in our suite rather than fighting the crowds outside. Moreover, the front patio area with a little porch swing was perfect for enjoying coffee and reading.

The Gates Hotel Key West

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The Gates Hotel Key West is an upscale lifestyle hotel and one of the best stays for our getaway. This sun-soaked paradise might look like a motel but don’t be fooled by that. The gorgeous exterior opens to a lushly landscaped, well-designed interior with modern touches for the perfect vacation. Despite sitting slightly far from all the Duval Street action, staying here wasn’t inconvenient as the hotel ran shuttles until the wee hours. What could be better?

The moment we entered the property, we were greeted with welcome cocktails. Besides being pet-friendly, we loved many things about the hotel, starting with the gorgeous pool area. The large, L-shaped pool deck, with its daybeds, umbrellas, nautical paraphernalia, and the funky Rum Row bar, is easily the focal point here. After a swim, we’d lounge on the daybeds and order drinks from the bar. What’s more, the hotel even has a shared fitness center and a shared green space. But what’s special here is that the Rum Row pool bar has partnered with the first legal rum distillery in Key West and served prohibition-inspired drinks! Finally, the onsite food truck Blind Pigs serves excellent casual fare.

All elegant rooms and suites boasted luxe bathrooms with bespoke bath products, fridges, and TVs, with extras including pool views and coffee-making facilities. Besides being airy and spacious, the wooden floors, pops of blue, and sliding barn doors certainly radiated a Key West vibe.

The Marquesa Hotel

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We were in for a special stay at the Marquesa Hotel, an eggshell blue luxurious National Register of Historic Places property just off Duval Street. The boutique hotel is part of a collection of pastel-hued, Conch-style structures dating back to 1884.

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On the outside, the vibe is old Key West, complete with a tropical interior courtyard, pool, patio, and birds and butterflies everywhere. On the inside, it’s as swish as modern luxurious living gets for discerning travelers. The amenities are centered around the blissful pool deck, which has not one but two separate pools in a lush tropical garden setting. It was our favorite way to unwind on our holiday, and we returned here repeatedly. What’s more, there was also a fitness center and a hotel concierge who’d help us with everything from water excursions to moped/bike rentals. Despite there being just one dinner-serving restaurant, Café Marquesa, it’s a highly-rated and visited one. Nevertheless, they served us a delicious continental breakfast spread poolside, with pastries, fresh juices, coffee, and whatnot. 

“In a sea of amazing historic modern hotels, the Marquesa was extra-special. We were treated like royalty, and loved every minute of it!”

WOW Travel

We loved that the rooms were housed in two separate structures: one in Key West-style cottages and the other in a newer building at the sister hotel, Marquesa 414, diagonally across the street. Between them, all 44 rooms and suites boasted chic touches like super-cozy tribes, modern bathrooms with Gilchrist & Soames bath products, and plush linens. They also have mini-fridges and a snack tray with a selection of (payable) drinks.

Havana Cabana at Key West

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We immersed ourselves in the good vibes of Key West at Havana Cabana at Key West. This was a beautiful spot for a chilled-out Florida Keys vacation. We found everything we wanted, from art and great music to mojitos, to enjoy and have a good time. Authentic Key West style and modern elegance were the overarching themes at this hotel. The rooms were spacious yet cozy and airy and bright. At the same time, they were flush with mod-cons, including huge-screen HDTVs, coffee machines, fridges, and bespoke bath products. Our premium king room offered superb views of the Gulf of Mexico and a patio where we could enjoy a cup of coffee or a glass of wine.

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The amenities at this resort were top-notch, too, especially the outdoor freeform lagoon-like pool with zero-entry access, plush daybeds, umbrellas, and poolside service. It’s set amidst rock waterfalls and lush landscaping, making it our favorite spot on the property. Besides the onsite hot tub, there was also a restaurant on the property, free Wi-Fi, free parking, and even a free airport shuttle. Did we mention that the Florida Keys Overseas Heritage Trail was right outside the property, fronting the water? Yes!

Ocean Key Resort & Spa

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We have two words and only two words why you should stay at the Ocean Key Resort & Spa: Sunset Pier. It’s “the” place for watching sunsets in the Keys, and this resort looks right out to it. So, the classic Key West combination of sunsets on the pier and slushy frozen drinks was right outside our door. What could be better?

This Tommy Bahama-esque has a plethora of amenities, starting with the absolutely gorgeous sea-facing pool. After a long and languorous swim, the plush daybeds, poolside cocktails, and snacks awaited us. Besides the poolside bar and grill of Liquid, the other all-day restaurant is Hot Tin Roof, where more sunsets awaited us. When we wanted to unwind, we’d head to the amazing SpaTerre, where massages and treatments influenced by Balinese rituals completely rejuvenated and revitalized us.

We loved the rooms and suites, with their colorful rugs, striped fabrics, cheery floral surfaces, and pastel-hued walls that gave off an elegant tropical island vibe. Moreover, the balconies looked out to Duval Street or the Gulf of Mexico, and we obviously took a sea-facing one. Our oceanfront king suite even had alfresco furniture, where the staff would deliver a hearty breakfast spread every day.

Hyatt Centric Key West Resort & Spa

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Best sea-facing hotel. The main selling point of the harborfront Hyatt Centric Key West Resort & Spa is that one can see Key West’s swoon-worthy and famous sunset views from everywhere in the hotel! Tucked on the island’s western edge, this Hyatt property is close to Duval Street, Old Town, the marina, and the beach, making it the perfect all-around base for exploring the best of Key West.

We loved the tropical vibe of this hotel, which boasts classic Key West architecture and a pond with a caged parrot and small turtles. The front desk team made our check-in a very smooth affair, while the concierge was instrumental in booking some excellent tours and even arranging bike, scooter, or boat rentals. In fact, they even had a two-hour bike service for exploring the island. The harbor-front swimming pool was, undoubtedly, our favorite, after which we headed to the full-service Jala Spa for a massage and body treatment. A restaurant, pool bar, and grill satisfied our cravings and hunger pangs. Finally, we decided to end the day by watching the gorgeous sunset at the beach. After all, the Florida Keys, specifically Key West, is one of the world’s most spectacular sunset locations.

All elegant and bright rooms and suites here have fridges, cable TVs, plush beds, and private balconies with wonderful views. The remodeled oversized bathrooms are a huge plus point.

Santa Maria Suites Resort

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Best location. It’ll be odd to call the Santa Maria Suites Resort a hidden gem, considering it sits on a prominent corner just off Duval Street. That said, a concrete facade and lush landscaping keep this luxurious expanse well-secluded from the world outside. This all-suite hotel was perfect for us as we wanted to stay in the heart of the town but also unwind in tranquility.

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We loved a lot of things about this tranquil oasis, starting with the attentive staff, who were ready to pamper us silly with their outstanding hospitality and friendliness. We loved that there were not one but two heated outdoor freeform pools here where we could swim in and lounge. What’s more, we could sip on cocktails and nibble on snacks at our loungers surrounded by gardens. Besides free onsite parking, the full-service concierge took care of all our whims and fancies, from sunset boat rides to restaurant reservations. The long list of extras here includes happy hour every day, free poolside smoothies, and even a nightly delivery of muffins. Did we mention that they also have beach chairs and umbrellas set up at South Beach? Yes!

The rooms here are in six two-story buildings completely surrounded by towering date palms and verdure. Moreover, they’re spacious and modern with a touch of tropical verve and many mod-cons like sleek bathrooms and a high-end chef’s kitchen.

The Marker Key West

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The Marker Key West is a maverick when it comes to opulence in Key West. Not only is it the first new-build hotel in Old Key West in two decades, but its thoughtful construction and design mean that the tight island community welcomed it with open arms. On the inside, the resort pays homage to the island culture in many ways, starting with the seven-foot sculptures, the “Five Watchovers,” sitting right out front. Key West artist Adam Russell designed them to represent various aspects of Key West’s island culture. There was also more artwork from local artisans and avant-garde and eclectic light fixtures.

We had the choice of three sparkling pools, ensuring we could have fun in the sun without stepping out of the property. The plush white chaise lounges and poolside service that extended well into the evening make the place all the better. Besides free Wi-Fi and the beach out front, the restaurants here made us feel like we never wanted to step out for food. While the main restaurant near the pool offered a delicious Cal-Mex menu, our favorite was the massive poolside bar doling out the most amazing cocktails.

The rooms and suites impressed us the most, though. They all featured private balconies and views of the courtyard or Key West Harbor. What’s more, they’re all decked out in white with pops of turquoise, sleek bathrooms, and mod-cons. The best of the lot are the ones that boast stunning ocean views.

Parrot Key Hotel & Villas

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Welcome to Parrot Key Hotel & Villas, where views are the mainstay. Imagine staying in a historic renovated property where none of the 148 rooms are the “B” team; they all have views of the Gulf of Mexico! Now, that’s what we call a luxurious stay. That is why it’s one of the best beachfront hotels in Key West.

This gorgeous resort had everything we needed for the perfect Key West holiday, starting with not one but four pools. Thanks to that, we never had to fight for a lounge chair and could spend the entire day simply lounging at and swimming in one or the other pool. What’s more, they charged a USD 42 resort fee, which included four guests’ access to the amazing Smathers Beach Club. Not only that, but they even offered a complimentary shuttle service, so we didn’t have to worry about getting there either. Finally, the Grove Kitchen & Bar on the property serves casual but filling fare and a complete bar menu.

All rooms, suites, and cottages here boasted huge 55-inch TVs, small fridges, plush beds, and patios with alfresco furniture. The waterfront suites and cottages are the best of the lot, separated from the water by just a strip of sand and lush vegetation. The best bit? They had sun loungers on the sand for us to unwind on our “personal beach” just outside the comfort of our digs.

Sunset Key Cottages

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Best private island hotel. Sitting at the top of this list is the private island splurge, Sunset Key Cottages. The 27-acre-huge property is easily the most exclusive destination in the Key and is a mere seven-minute boat journey from Old Town. The fact that it was accessible only by boat or ferry excited us, and we decided to enjoy a second honeymoon here. It turned into an experience we’ll never forget. The best bit? The ferry, which operated between the island’s dock and the Margaritaville marina, ran 24/7 for continuous access to the mainland. Now, that’s what we call real luxury.

The activity roster here runs the gamut from spa treatments and pool time to sports courts and parasailing. Water sports and activities take centerstage, whether it’s sunset trips, kayaking, jet skiing, guided tours, diving, fishing, or snorkeling, all arranged by the concierge. We loved lazing the day away on the pristine white-sand private beach, followed by a cooling dip in the lagoon-style zero-entry swimming pool. We also took advantage of all the property freebies, including daily room-delivered breakfasts, poolside popsicles, fishing off the pier, and daily spirits tastings. Finally, the restaurant here served delicious seafood, among other things, and offered stunning views of the waters.

With just 40 cottages, staying here felt truly intimate and extraordinary. Ranging from one- to four-bedroom ones, they all boasted sleek kitchens, wraparound balconies, and luxe bathrooms. The best bit? Some, like ours, even came with private pools. Sigh.

Our Verdict!

While we loved every last one of Key West’s luxurious stays, here’s a specialized list so you can make an easy decision about where to stay.

• Best private island hotel: Sunset Key Cottages
• Best location: Santa Maria Suites Resort
• Best sea-facing hotel: Hyatt Centric Key West Resort & Spa
• Best adults-only: H2O Suites, Adults Only

Where to Stay in Key West?

Despite its smaller size than most of the cities we’d visited in the continental United States, Key West is huge and has many amazing neighborhoods. So, the best neighborhood to stay in really boils down to one’s travel style and what one wants to do. For instance, we’d highly recommend that those visiting Key West for the first time stay in and around the Duval Street area. This island’s most famous street is home to its drinking, dining, shopping, and entertainment hub.

Obviously, many travelers come to Key West primarily to indulge in water sports and adventures. They should look to staying in and around the Historic Seaport. It not only has many waterports and water-based activities on offer but also has plenty of scenic ocean views from almost everywhere. Are you a culture vulture like we are? The southern Bahama Village is a great sport to stay for immersing yourself in the local culture and having authentic experiences.

Finally, we have the utterly gorgeous and enchanting Old Town, which has vibrant wooden structures dating back to the 1800s. Couples will find a romantic or adults-only B&B or hotel on practically every corner of this walkable neighborhood. What’s more, it’s also home to many bespoke galleries and museums, like the former winter residence of former President Harry Truman. It’s also the only presidential museum in Florida even today.

What is the most expensive area in Key West?

That would be Sunset Key, which lies just off the Duval Street area. It’s home to the Sunset Key Cottages, the most expensive hotel on the island.

What month is good to go to Key West?

The shoulder season of spring between March and May is the best time to visit Key West. At this time, the winter crowds are tapering off, the weather is turning warmer but not hotter, and the hotel rates become reasonable.

Why is Duval Street famous?

It’s a popular street lined with nighttime hotspots, restaurants, and famous retail shops. For instance, the Sloppy Joe’s Bar opened in 1933 and is now a designated National Historic Landmark.