The 11 Best Boutique Hotels with Entertainment in The Keys (2025)

Nestled along the pristine shores of Key Largo, Bungalows Key Largo - All Inclusive beckons couples and romantic travelers into a world where luxury meets tranquility. Each luxurious bungalow serves as a private sanctuary, complete with soothing ocean breezes and breathtaking views, ensuring that every moment is tailored for relaxation and intimate connection.

Total Relaxation - Indulge in the serene atmosphere as you bask by the shimmering pools or unwind in your own private hot tub under a starlit sky, where the only sound is the gentle lapping of waves on the shore.

Spa Breaks - Rejuvenate your senses at the full-service spa, where expert therapists blend natural ingredients into treatments designed to melt away stress, leaving you enveloped in tranquility and bliss.

Boutique Beach Life - Discover an exclusive stretch of golden sand where soft towels await, inviting you to sink into plush lounge chairs while sipping on expertly crafted cocktails, all against a backdrop of sapphire waters and swaying palms.

Guest Experiences - As you stroll through the lush grounds, the fragrant aromas of gourmet dishes waft invitingly from the nearby restaurants, mingling with the sounds of laughter from guests savoring sunset sails, capturing the heart of what makes this resort feel like a home away from home.

Nestled along 14.5 serene acres of pristine bayfront in Key Largo, Playa Largo Resort & Spa invites you into a realm where elegance meets tranquility. Picture yourself unwinding under swaying palms, the gentle sound of waves lapping at the shore creating a symphony of relaxation as the warm Florida sun bathes you in golden light—a truly idyllic escape for couples and luxury seekers alike.

Romantic Getaway - With private cabanas dotting the beach and fire pits glowing at twilight, every corner of Playa Largo is designed for romance. Enjoy intimate dinners with fresh seafood while the sunset casts a mesmerizing palette across the sky, perfect for creating lasting memories.

Spa Indulgence - At the full-service Ocean Spa, surrender to soothing treatments that rejuvenate both body and soul. Whether you indulge in a blissful massage right in your room or simply bask in the luxurious ambiance, this is a sanctuary where serenity reigns supreme.

Adventurous Escapades - Water sports enthusiasts will find their paradise here, with opportunities for kayaking, paddleboarding, and diving just steps away from your doorstep. Each day promises exciting adventures amidst the vibrant marine life of the Florida Bay—an exhilarating playground waiting to be explored.

Guest Experiences - Imagine sinking your toes into soft sand while sipping on a freshly crafted cocktail, the air perfumed with hints of grilled seafood from the nearby Sol by the Sea restaurant. Guests often rave about the friendly staff who greet you like family, ensuring every moment feels personalized and genuine, even if it means waiting a tad longer to savor that perfect breakfast made just for you.

Nestled where the turquoise waters of the Atlantic embrace the vibrant spirit of Key West, Oceans Edge Key West offers an oasis of tranquility and romance. With six shimmering pools reflecting the endless sky, this modern resort is a sanctuary designed for couples seeking intimacy and adventure alike, all while indulging in exquisite luxury amid breathtaking vistas.

Romantic Retreat - Each guest accommodation boasts spectacular water views, inviting you to unwind on your private balcony or patio as the sun dips below the horizon, painting the sky with hues of orange and pink.

Waterfront Dining - Savor the enticing flavors of American-Caribbean cuisine at Yellowfin Bar and Grill, where every meal is paired with the gentle sounds of waves lapping against the marina, creating a perfect backdrop for intimate dining experiences.

Active Adventures - For the adventurous soul, the hotel offers complimentary kayak tours and paddleboard rentals, allowing you to glide across the pristine waters while spotting colorful marine life, making unforgettable memories just outside your door.

Guest Experiences - Amid the charming chaos of friendly cockerels and curious lizards wandering the grounds, guests have relished their morning coffee while taking in the serene poolside ambiance, all while enjoying warm smiles from attentive staff members who seem to anticipate your every need.

Nestled at the edge of Stock Island Marina, The Perry Hotel & Marina Key West is a romantic oasis where luxury intertwines with the vibrancy of island life. Here, the gentle lapping of waves harmonizes with the soft rustle of palm fronds, providing an enchanting backdrop for couples and adventurers alike. Embrace the chic decor and artisanal touches that elevate every corner of this boutique haven, beckoning you to unwind in style.

Romantic Getaway - Surprise your loved one with moonlit evenings by the waterfront pools, where shimmering reflections dance on the water's surface, creating an intimate ambiance perfect for stolen kisses and whispered secrets.

Culinary Delights - Indulge in mouthwatering flavors at dockside restaurants like Matt's Stock Island Kitchen & Bar, where the scent of fresh seafood mingles with the salty breeze, inviting you to savor award-winning dishes that celebrate local bounty.

Adventure Awaits - With direct marina access, embark on thrilling water activities or enjoy complimentary shuttles whisking you away to the lively pulse of Old Town, where vibrant sights and sounds await just a bridge away.

Guest Experiences - Delight in the personal touch of attentive staff who make every moment feel special, from enjoying a cocktail at the pool as the sun dips below the horizon to lounging in a plush room adorned with artisanal details - the essence of Key West captured perfectly.

Nestled in the vibrant heart of Key West, The Gates Hotel invites you to experience a harmonious blend of modern luxury and tropical charm. As you step through the doors, the salty breeze carries whispers of romance and adventure, making each moment feel like a cherished escape. With thoughtfully designed spaces and an intimate atmosphere, this boutique hotel is your personal haven under the sun.

Romantic Break - With lush palm trees swaying gently beside the sparkling outdoor pool, The Gates Hotel provides a perfect backdrop for couples seeking a romantic retreat. Enjoy candlelit dinners featuring Latin-inspired tapas, where every dish is crafted with locally sourced ingredients that tantalize the senses.

Spa & Relaxation Lovers - Unwind in style with a soothing dip in the pool or rejuvenate at the Rum Row pool bar, where local rum cocktails flow as freely as your worries fade away. Take in the tranquil surroundings, enveloped by the gentle sounds of nature, creating a serene environment for ultimate relaxation.

Local Exploring - Convenient shuttles whisk you away to the historical allure of Old Town, while nearby treasures like the Key West Tropical Forest and Botanical Garden await your adventurous spirit. Embrace the vibrant culture of this island paradise, from bustling markets to hidden gems tucked along charming streets.

Guest Experiences - Guests often find themselves enchanted by the little details—a surprise room upgrade adorned with soft linen sheets and plush pillows, or the delightful aroma of fresh cocktails mingling with the warm evening air. It's always the small gestures that leave a lasting impression, like the attentive staff who seem to anticipate your needs before you even voice them.

Nestled at the vibrant threshold of Key West, Blue Flamingo Resort invites you to indulge in a dreamy escape where island charm meets contemporary luxury. With its lush palm-filled gardens and inviting poolside retreats, every corner whispers relaxation, beckoning couples, honeymooners, and adventure seekers alike to unwind in paradise.

Romantic Retreat - Feel the embrace of romance in our freshly renovated, chic accommodations, designed for comfort and tranquility, where soft linens and the gentle sound of waves create an intimate sanctuary just for two.

Culinary Journeys - Savor the spirit of Key West through a delightful array of dining options—from hearty, loaded burgers at The Backyard to the tranquil, elevated dishes at Toasted Coconut—each meal is an invitation to indulge your senses.

Lively Atmosphere - Immerse yourself in a dynamic social scene at our Backyard Pool & Social Club, where laughter echoes during lawn games, and the smell of sizzling delights fills the air as guests gather for karaoke under the stars.

Guest Experiences - One guest marveled at the soft, tropical breeze that danced through their room, mingling with the fragrant aroma of fresh coffee from Starbucks, while another shared tales of spontaneous poolside chats, where the sounds of laughter and clinking glasses created a backdrop of joyful camaraderie.

Nestled along the shimmering waters of Florida Bay, Parrot Key Hotel & Villas is a tropical oasis that invites you to indulge in luxury and relaxation. With its lush gardens and intimate ambiance, this exquisite retreat offers a perfect escape for couples and solo travelers alike, where every moment feels like a private paradise.

Spa & Relaxation - Immerse yourself in serenity with rejuvenating on-site massages that melt away your stress, surrounded by the gentle rustle of palm fronds and the soft sound of waves lapping at the shore.

Romantic Break - The secluded charm of each villa enhances romance, featuring private terraces where you can sip cocktails while soaking in breathtaking views of vibrant sunsets over the ocean.

Boutique - Every corner of this boutique resort is tastefully designed, from the four distinct pools—each one seemingly hidden by lush greenery—to the chic decor that whispers comfort and sophistication.

Guest Experiences - As you stroll through the winding paths lined with fragrant blooms, the scent of fresh seafood wafts from The Grove Kitchen & Bar, where guests have relished delightful poolside snacks with a side of laughter echoing in the sunlit air.

Nestled in the heart of Key West, The Mermaid & The Alligator beckons you to a sanctuary where romance dances with nature. Surrounded by lush gardens that hum with the soft rustling of leaves and the sweet scent of tropical blooms, this boutique hotel offers an intimate escape from the world, inviting couples and seekers of serenity to indulge in a unique blend of luxury and laid-back charm.

Romantic Retreat - Stroll hand-in-hand through the botanical oasis, where every corner reveals vibrant flora and whispering palms, creating a picture-perfect backdrop for lovebirds seeking blissful moments together.

Total Relaxation - Unwind in the sun-soaked garden or soak in the tranquil hot tub, where the soothing sounds of nature serenade you as you embrace the island's leisurely rhythm, enhancing your journey towards rejuvenation.

Culinary Delights - Awaken your senses each morning with a delightful breakfast served under the gentle shade of sprawling trees, featuring handcrafted dishes prepared with local ingredients, echoing the flavors of Key West’s culinary heritage.

Guest Experiences - One guest marveled at the gentle warmth of the ocean breeze while enjoying breakfast on the patio, enveloped by the fragrant aroma of fresh herbs from the garden, all while being attended to by staff whose genuine kindness made every morning feel like a special occasion.

Nestled just a block away from the shimmering Atlantic Ocean and the vibrant pulse of Duval Street, Santa Maria Suites Resort is an intimate oasis that blends modern luxury with the charming quirks of Key West. Here, spacious all-suite accommodations invite you to unwind in style, surrounded by lush gardens and the gentle sound of water lapping at nearby shores, creating an atmosphere ripe for romance and relaxation.

Romantic Retreat - Indulge in the ultimate romantic escape, where each suite offers stunning decor and a full kitchen, perfect for intimate dinners or lazy breakfasts in bed, complemented by the scent of fresh muffins wafting through your door each morning.

Total Relaxation - Two heated outdoor pools beckon for leisurely dips amidst tropical gardens, while complimentary poolside smoothies refresh your spirit under the warm Florida sun—a dreamy backdrop for unwinding after exploration.

Outstanding Location - Just moments from historic sites and local markets, you can easily stroll to iconic attractions like the Ernest Hemingway House, returning to the sanctuary of your suite equipped with everything you need—truly a hub for cultural explorers and adventure seekers alike.

Guest Experiences - Guests have delighted in the unexpected treats awaiting them daily: imagine opening your suite to the allure of freshly baked muffins alongside Dove ice cream mini bars, while the friendly staff members, particularly Matilda, go above and beyond, offering personalized tips on dining and sights with genuine warmth.

Tucked away in the vibrant heart of Key West, H2O Suites invites discerning travelers to immerse themselves in an oasis of romance and tranquility. This adults-only sanctuary blends modern luxury with a tropical charm, offering a serene escape that captures the essence of island living while remaining just steps from the bustling energy of Duval Street.

Romantic Hideaway - Every suite at H2O is designed as a personal retreat, featuring lush tropical views and private pools, perfect for stolen moments beneath the sun. The ambiance whispers intimacy, where soft ocean breezes mingle with the scent of exotic flowers, creating a seductive atmosphere that's ideal for couples.

Chic Rooftop Oasis - The year-round outdoor rooftop pool beckons with its sparkling waters and inviting sun terrace, providing the perfect perch for basking in the glorious Florida sunshine or sipping cocktails under a starlit sky. You'll relish the sound of gentle waves lapping against the shore as you unwind in this elevated haven.

Total Relaxation - Luxuriate in your well-appointed suite, complete with plush furnishings, a soothing palette, and indulgent amenities like complimentary bathrobes and slippers. Each detail has been thoughtfully curated to ensure a serene experience—perfect for those seeking peace and rejuvenation amid the lively island backdrop.

Guest Experiences - One guest described their arrival as stepping into a world of calm, noting the delightful welcome drink that tasted like a burst of tropical fruit, instantly lifting their spirits. They savored lazy afternoons by the rooftop pool, where the occasional sounds of laughter drifted up, perfectly complementing the serenading song of island birds.

Nestled in the heart of Key West, the Truman Hotel invites you to embrace an intimate coastal retreat where chic modernity meets laid-back island charm. Feel the gentle ocean breeze as you sip your morning coffee by the shimmering outdoor pool, basking in the sun-drenched ambiance that only this paradise can offer.

Boutique Charm - Each room at the Truman is a stylish haven, adorned with warm wood floors and marble vanities, creating a sanctuary of comfort that whispers elegance while providing all the modern conveniences you desire.

Romantic Retreat - With private patios for quiet moments and a tranquil sun deck beckoning you to unwind, the Truman serves as a serene backdrop for couples seeking romance amidst the vibrant energy of Key West.

Outstanding Location - Just a leisurely stroll away from iconic attractions like the Ernest Hemingway Home and the lively Duval Street, guests find themselves perfectly situated to explore local markets and indulge in the colorful nightlife.

Guest Experiences - The air was filled with the aroma of fresh pastries during breakfast, where the attentive staff greeted each guest like old friends. A couple shared laughter over their cozy balcony, the soft chirping of birds harmonizing with the sounds of distant waves, creating a soundtrack to their idyllic getaway.