The 9 Best Boutique Hotels with Entertainment in Havana (2025)

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.

Nestled in the vibrant heart of Key West, Southernmost Inn Adult Exclusive offers an enchanting escape tailored for romantic souls and discerning travelers alike. With lush tropical themes adorning each room, you'll find yourself serenaded by the gentle sound of palm fronds swaying in the breeze, just moments away from the bustling energy of Duval Street and the tranquil Atlantic shores.

Total Relaxation - Indulge in a serene day by one of the two heated outdoor pools, where the warm sun kisses your skin and the soothing sounds of splashing water create a symphony of relaxation. The inviting hot tub provides a perfect retreat for couples seeking intimacy and warmth after a day of adventure.

Outstanding Location - With a mere minute’s stroll to the lively Duval Street, guests can easily explore local markets, savor delectable bites from food vendors, or embrace the vibrant nightlife. The iconic Southernmost Point is just a brief walk away, making it easy to capture those unforgettable moments against the backdrop of stunning ocean views.

Spa Breaks - Relaxation meets rejuvenation with complimentary wellness touches throughout your stay, including a refreshing wine and cheese happy hour that fills the air with rich aromas, enticing both body and spirit. The fitness center beckons those seeking invigorating workouts amid the allure of the tropical landscape.

Guest Experiences - One evening, the subtle scent of blooming hibiscus filled the air as guests gathered on the spacious patio, sharing laughter and stories during the happy hour. A couple remarked on how the tranquil ambiance enveloped them like a warm embrace, making every sip of wine feel like a moment captured in paradise.

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 on the vibrant Duval Street, Orchid Key Inn - Adults Only invites couples and romantic wanderers into a sanctuary of lush gardens and refined elegance. This boutique hotel harmoniously blends modern luxury with the historic charm of Key West, offering an intimate escape where every detail whispers relaxation and indulgence.

Romantic Hideaway - With its serene atmosphere and beautifully landscaped grounds, this adult-only inn provides a tranquil oasis ideal for lovebirds seeking solace amidst the lively backdrop of Key West.

Boutique Charm - Each meticulously designed room offers a perfect blend of comfort and sophistication, featuring upscale furnishings and thoughtful amenities like Keurig® coffee machines and spa baths, creating a uniquely personal touch for every guest.

Total Relaxation - Unwind in the heated pool or soak in the hot tub surrounded by vibrant tropical foliage, while sipping on specialty cocktails crafted with fresh herbs from the Orchid Bar—an idyllic setting for leisurely afternoons.

Guest Experiences - Stepping onto the property feels like discovering a hidden paradise, where the sweet scent of blooming orchids mingles with the sound of gentle water splashes from the pool. Guests have delighted in the attentive staff, who greet them with warm smiles and a complimentary drink, instantly making them feel at home.

Nestled in the vibrant heart of Key West, just a whisper away from the lively pulse of Duval Street, Andrews Inn & Garden Cottages invites you to immerse yourself in an oasis of tranquility and charm. Picture yourself strolling through lush gardens, where the scent of tropical blooms dances on the warm breeze, and each sunrise brings the promise of adventure, relaxation, or romance—tailored perfectly to your heart's desire.

Romantic Retreat - With cozy nooks and beautifully decorated rooms capturing the essence of island life, every corner of Andrews Inn whispers romance. Enjoy quiet moments by the pool, framed by swaying palms, or bask in the soft glow of candlelight during evening happy hours under the stars.

Culinary Delights - Start your day with an exquisite breakfast featuring fluffy quiche, succulent sausage, and fresh seasonal fruits that invigorate your senses, setting the stage for a day filled with exploration. The complimentary happy hour by the pool offers a delightful array of refreshments, echoing laughter and the clinking of glasses as guests share stories of their adventures.

Local Exploration - Positioned less than five minutes from the historic Ernest Hemingway Home and Museum, your stay at Andrews Inn seamlessly blends relaxation with cultural immersion. Complimentary bikes await your eager spirit, encouraging leisurely rides through the charming streets lined with colorful architecture and hidden gems waiting to be discovered.

Guest Experiences - As I settled into my room, the inviting aroma of fresh coffee wafted through the air, mingling with the enticing beats of laughter from the poolside happy hour. It was a delight to find Isabella always nearby, her warmth and genuine care making me feel like part of a close-knit family, whether she was sharing tales about local sights or ensuring I had everything I needed for a perfect escape.

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.

Nestled within the lush embrace of Key West, the Paradise Inn - Adult Exclusive offers an idyllic escape where tranquility reigns supreme. With its winding brick paths leading through vibrant gardens and a serene koi pond, this boutique haven invites couples and romantic travelers to indulge in luxury and intimacy under the balmy Florida sun.

Romantic Retreat - Each suite exudes warmth and comfort, adorned with plush furnishings and thoughtful amenities, creating a private oasis for lovebirds to unwind and connect amidst the tropical allure.

Total Relaxation - Bask in the soothing ambiance of the outdoor pool, where the gentle sound of cascading water complements lazy afternoons spent soaking up the sun, or take a dip in the hot tub, enveloped in lush greenery that enhances your serene experience.

Outstanding Location - Just a stone's throw from Higgs Beach and the Key West Aquarium, the hotel's prime location allows guests to explore local treasures at their leisure, while charming cafes and lively markets are a short stroll away, ensuring each day is filled with adventure and discovery.

Guest Experiences - As the sun dipped below the horizon, a delightful cheese and wine hour unfolded, where guests mingled over the vibrant flavors and aromas of fresh cheeses, laughter echoing softly through the beautifully landscaped grounds, creating a tapestry of shared moments that linger long after the visit.

Nestled among lush tropical foliage, The Gardens Hotel is a serene adult-only retreat in the heart of Key West, where each moment feels like an intimate escape. With fragrant blooms filling the air and the gentle sound of rustling leaves, this upscale haven invites couples and romantic travelers to unwind in its elegant ambiance, just steps away from the vibrant pulse of Duval Street.

Romantic Retreat - With private balconies overlooking verdant gardens, every room at The Gardens Hotel offers a tranquil space to bask in the romance of island life. The soft whisper of palm fronds swaying creates a soothing backdrop for candlelit evenings and leisurely mornings.

Charming Oasis - Two inviting outdoor pools beckon you to lounge under the sun or find solace in shaded nooks, while the property’s hidden hammocks offer perfect spots for afternoon daydreams. Guests often delight in discovering quiet corners, making it feel like a personal sanctuary amidst the lively surroundings.

Live Entertainment - Every Sunday evening, immerse yourself in the soulful sounds of live jazz as it serenades the garden, creating a magical atmosphere that enhances the romantic setting. The enchanting melodies blend seamlessly with the evening breeze, painting memories that linger long after your stay.

Guest Experiences - As you sip coffee by the poolside, the aroma of freshly prepared breakfast wafts through the air, teasing your senses with promises of delightful flavors. A chance encounter with the gracious owner adds a personal touch, leaving guests feeling not just welcomed but truly at home in this beautiful, immaculately kept oasis.

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.