The 9 Best Boutique Family Hotels in Key West (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 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 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 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 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 along the shimmering shores of Key West, Opal Key Resort & Marina is a tranquil oasis where the gentle lapping of waves and the warm ocean breeze create an enchanting atmosphere. This chic retreat promises an indulgent escape, offering not just luxury but also a heartfelt connection to the vibrant culture of the island, making it the perfect backdrop for romance, adventure, or relaxation.

Romantic Getaway - Surrounded by lush tropical gardens and breathtaking water views, each room invites you to unwind in style with plush furnishings, soft linens, and thoughtful amenities. The intimate ambiance makes every moment special, from sunrise breakfasts overlooking the marina to moonlit strolls along nearby Duval Street.

Spa Breaks - Rejuvenate your senses at the resort's spa, where soothing aromas fill the air and skilled therapists offer personalized treatments that transport you to a state of blissful relaxation. Every detail, from the calming music to the use of locally sourced ingredients, enhances your wellness journey.

Outstanding Location - With its prime position adjacent to the historic Duval Street and the vibrant local markets, guests can easily immerse themselves in Key West's eclectic charm. A short walk leads to unforgettable sights, including the renowned Mel Fisher Maritime Heritage Museum, while the tantalizing scent of saltwater beckons just outside your door.

Guest Experiences - Upon arrival, the warmth of the staff enveloped me like a gentle hug, their cheerful greetings setting the tone for my stay. I was particularly touched when Shawna from housekeeping went above and beyond to track down a beautiful sweater I had left behind, ensuring it was sent to me promptly—a small gesture that carried the essence of this welcoming haven.

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 on the sun-kissed shores of Marco Island, the JW Marriott Beach Resort stands as a bastion of luxury and serenity. With each wave lapping at the pristine shoreline, this elegant oasis invites you to indulge in a world where your every desire is met with impeccable service and breathtaking views of the Gulf of Mexico.

Total relaxation - Immerse yourself in tranquility at the Spa by JW®, where the air is infused with soothing aromas and the gentle sound of water evokes a sense of calm as skilled therapists work their magic to rejuvenate your body and spirit.

Romantic Break - Bask in the golden glow of sunset from your private balcony, where the vibrant hues of the sky create a picturesque backdrop for intimate evenings spent savoring fine wines and delectable dishes, handpicked from the resort's diverse culinary offerings.

Beach Life - Step onto the soft sands just steps from your door, where the rhythmic lull of the ocean mingles with laughter and the playful splash of families enjoying the outdoor pools—each moment a reminder that paradise is within reach.

Guest Experiences - As you lounge by the pool, the gentle breeze carries the tantalizing scent of grilled seafood, and friendly staff members glide past, ensuring your glass is never empty while the sun dips lower, inviting you to lose track of time amidst the serenity.