5 Best Resorts in Key West, Florida

Picture this: the sultry, sun-soaked shores of Key West, a gem nestled in the southernmost corner of Florida. The air is thick with the irresistible scent of Cuban cigars, offset by the gentle whispers of palm trees swaying over white sand beaches. You, my friend, have one goal – to unearth the best resorts in Key West, FL. And when it comes to uncovering serendipitous spots where Hemingway would indulge himself in a daiquiri (or two), who better to guide you than a globetrotter with a taste for decadence?

As we embark on this grand adventure together, allow your senses to be seduced by the complex symphony of aromas, textures, and flavors peppering the picturesque island where the Atlantic Ocean and Gulf of Mexico dance in azure harmony.

Let’s dive headfirst into this treasure trove of luxury and partake in the one crucial aspect that defines Key West – a downright refusal to settle for anything less than extraordinary.

TL;DR

Best Resorts in Key West, Florida

1. Ocean Key Resort & Spa

Address: 0 Duval St, Key West, FL 33040, United States

Nestled at the foot of vibrant Duval Street, the Ocean Key Resort & Spa stands proud as a beacon for those seeking a secluded paradise tucked between the turquoise waters of the Gulf of Mexico and the Atlantic Ocean. Stepping into this hidden sanctuary, your senses will be immediately awakened by the refreshing scent of sea salt and the cool caress of Key West’s ocean breeze.

As you traverse its sun-drenched grounds, swaying palm trees and tranquil water features prepare you for the indulgences that lie ahead. A sprawling outdoor pool deck lined with splendid palm-thatched cabanas is the heart of this leisure oasis. Here, you may lose track of the hours spent lounging in the sun with a frozen concoction or delight in a refreshing dip while soaking in the panoramas of the marina and the endless sea beyond.

At the waterfront Liquid Lounge, indulge in a feast for the senses; a dazzling concoction of vibrant island flavors accompanied by the sounds of steel drums and the intoxicating scent of coconut and lime. When night falls, watch the sky blush as it’s brushed by the rays of the setting sun, leaving hints of neon pink and tangerine in its wake – a spectacle made even more unforgettable if experienced from the comfort of your private balcony.

As for rejuvenation, the tranquil Spa Terre beckons you to a soothing refuge where Balinese-inspired treatments cleanse the body and quiet the mind, the perfect prelude to evenings spent exploring the rich and vibrant history of Key West, the new town itself.

This magical hideaway offers a mesmerizing experience that makes you yearn for more – an indelible memory etched in the soul and a story forever worth sharing. 

2. Margaritaville Beach House Key West

Address: 2001 S Roosevelt Blvd, Key West, FL 33040, United States

Margaritaville Beach House Key West beckons weary travelers and Parrotheads, a tropical oasis where island time reigns supreme. Hidden amidst the meticulously sculpted Florida Keys landscape, expect nothing less than a true sense of escapism upon entry. Swaying palm trees and white sands set the stage for an idyllic sojourn.

On a quest to find the ultimate blend of relaxation, artistry, and intoxicating serenity, you’ll feel your cares slip away when your toes sink into those warm, iconic sands. The resort rests in intimate harmony with its surroundings, making it a perfect hideaway for a couple’s retreat or a sun-soaked expedition with your crew.

The resort celebrates the soul of Key West through the decorative touch of local artists, and the open-air spaces harmonize with the island’s natural beauty. The endless horizon frames your view while the Balinese-inspired pool and the sound of crashing waves play their symphony steps away from the luxury hotel.

Savor laid-back indulgence as the resort’s food and drink scene steals the hearts of pirates and poets alike. Fresh, local ingredients unite with Caribbean flavors to orchestrate unpretentious gastronomic experiences at their best.

In the evenings, find your sanctuary in one of the elegantly-appointed guest rooms with all the creature comforts of home, from the plush bedding to the thoughtfully-curated amenities. When not reveling with other kindred spirits at the poolside bars or partaking in water sports, give in to the siren call of the vibrant Key West nightlife.

Margaritaville Beach House Key West is a testament that some of the world’s most cherished moments unfold in the simplest of settings. 

See Related: 10 Best Beach Resorts in Florida

3. Sunset Key Cottages

Address: 245 Front St, Key West, FL 33040, United States

Step onto the idyllic Sunset Key Cottages, and surrender to a serene escape from reality. A mere 500 yards off the vivacious shoreline of Key West, this tropical oasis offers the perfect blend of isolated tranquility and vibrant accessibility. Perched on a 27-acre island, the quaint and luxurious cottages beckon, their elegant white wood shimmering amongst lush palm trees and vibrant bougainvillea.

Each cottage is intricately designed, boasting breathtaking panoramas of the Gulf of Mexico. As warm sunlight pours through the windows, the plush, handcrafted furnishings wrap you in comfort, while the soft scent of sweet orange and coconut evokes a welcome sense of home.

Step onto your private porch and bask in the warm, gentle breeze. Let the radiant hues of the setting sun guide your gaze westward, where the ocean bleeds into the horizon. Indulge in a chilled glass of champagne as your concierge tends to every detail of your stay. Bury your toes in the warm, white sand as you stroll down to the island’s renowned Latitudes restaurant, where your senses will be invigorated by the finest in Floridian seafood and international fare, with unobstructed views of the ocean’s kaleidoscopic palette.

Succumb to the soothing notes of the steel drums as they harmonize with your sense of adventure. Explore beneath the crystalline waves, where vibrant coral reefs teem with technicolor marine life, such as playful parrotfish, slithering barracuda, and the secret smiles of angelfish.

Discover a world where every path offers the prospect of uncovering hidden secrets within the island’s tangled foliage. In the captivating realm of Sunset Key Cottages, embrace the freedom to wander and the wisdom to know when to pause. 

See Related: Best Vacation Spots in Florida

4. Hyatt Centric Key West Resort & Spa

Address: 601 Front St, Key West, FL 33040, United States

Nestled like a best-kept secret on the edge of the azure waters of the Gulf of Mexico, the Hyatt Centric Key West Resort & Spa emerges like an oasis, delivering on the dream of an idyllic Key West getaway. Unpretentious yet luxurious, quiet yet vibrant, this 4.5-star resort is a balmy sanctuary for romance and adventure, with world-class amenities that delight even the most discerning travelers.

As you stroll through the lush, palm-studded grounds, the air laden with the salty-sweet scent of the ocean mingles with the intoxicating perfume of tropical flowers, ushering you into a haven of pure relaxation. The turquoise infinity swimming pool, a shimmering oasis seemingly suspended between sky and sea, tempts you to take a refreshing dip or lounge lazily on the poolside sun beds, cold cocktail in hand.

The essence of Key West runs deep within the resort’s DNA, reflected in its thoughtful design and unpretentious elegance, all while providing the intimacy and ambiance of an upscale beachfront hideaway. Rooms and suites, adorned with laid-back Florida Keys décor, welcome you with expansive views of either the charming city streets, the resort’s secluded gardens, or the mesmeric Gulf of Mexico.

In true Key West fashion, the resort’s dining establishments celebrate the region’s multicultural heritage, with on-site restaurants serving phenomenal seafood caught fresh from the bountiful waters that surround the island. As the sun dips below the horizon, painting the sky in shades of tangerine and crimson, the waterfront Jala Spa calls out to your senses, inviting you to indulge in decadent treatments infused with pure island botanicals and potent marine elements, rejuvenating your body and soul.

The Hyatt Centric Key West Resort & Spa is a transcendent retreat of artful indulgence, nurturing your spirit of wanderlust and discovery in this exotic corner of the world. 

5. Southernmost Beach Resort: A Slice of Tropical Paradise

Address: 1319 Duval St, Key West, FL 33040, United States

Picture yourself strolling along the sandy shores of a tranquil, palm-fringed beach on a quest to escape the mundane. The palm trees swaying to a gentle rhythm, the briny air invigorating your senses, decadent conch fritters, and ice-cold mojitos patiently waiting to tantalize your taste buds—this is the Southernmost Beach Resort experience. An establishment that speaks to the heart and soul of weary travelers seeking reprieve in the welcoming embrace of Key West’s vibrant and rejuvenating spirit.

Situated on the beachfront, this storied haven is a melange of classic Floridian charm and contemporary luxury. Rest your bones in one of the 261 impeccably appointed rooms, or stake your claim to a more private beach or oceanside cabana and let the words “stress” and “reality” drift away like wayward seagulls. With three on-site pools, the Southernmost Beach Resort has crafted pockets of aquatic oases, designed to cater to the full spectrum of aqueous indulgence.

A stay at this resort would be incomplete without reveling in the melodic folk tunes and salty tales regaled by local troubadours at the nearby Sunset Pier or plunging into the azure depths with ample aquatic activities on offer. Snorkeling among a cavalcade of shimmering fish, paddleboarding against the backdrop of a fiery sun dipping beneath the horizon—this is the stuff of sun-kissed dreams.

The Southernmost Beach Resort captures the essence of Key West—a mesmerizing symphony of vibrant culture, luscious flavors, and immaculate scenery—a recipe for an unforgettable experience. Here lies the embodiment of a glorious seaside retreat, placed at the threshold of an enchanting island odyssey punctuated by sun, surf, and adventure.

FAQs

What is the cheapest time of year to go to Key West?

The cheapest time of year to go to Key West is during the fall, specifically from September to November. During this period, room rates can drop by 50 percent or more. The hot, storm-prone summer months also see lower prices and decent discounts can be found in April and May after the winter crowds thin out. However, it’s important to note that tropical storms are common from June to the end of October.

What is the most popular part of Key West?

The most popular part of Key West is the historic and vibrant area known as Old Town or Downtown Key West. This is where you’ll find many of the island’s key attractions, including the Ernest Hemingway Home and Museum, the Southernmost Point, and the famous Duval Street, known for its lively nightlife, shops, and restaurants. The waterfront area, with its beautiful views and Mallory Square’s famous sunset celebration, is also highly popular.

Which of the Florida Keys is best for couples?

The best Florida Key for couples can depend on personal preferences. Key West, with its lively atmosphere and rich history, offers a variety of activities and attractions. For those seeking a more tranquil getaway, Islamorada is known as the “Village of Islands” and offers beautiful beaches, excellent fishing, and a relaxed pace. Marathon, located in the middle of the Keys, offers gorgeous beaches and a variety of water sports and is home to the Turtle Hospital, a must-visit for animal lovers.

How many days is good to stay in Key West?

The ideal length of a stay in Key West can vary depending on your interests. A common recommendation is three to four days. This allows time to explore the main attractions, enjoy leisure time on the beaches, and soak up the island’s unique atmosphere. If you’re interested in water sports or want to explore the other islands in the Florida Keys, you might consider a longer stay.

Related Resources

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