The 18 Best Boutique Hotels with Entertainment in Southwest Florida (2025)

Nestled in the heart of Naples, Florida, the Inn at Pelican Bay exudes an air of sophisticated charm, making it a serene oasis for romantic getaways and luxury seekers alike. With elegant design elements that beckon you to unwind, this boutique hotel is only moments away from the golden sands of Vanderbilt Beach, inviting you to indulge in both relaxation and adventure.

Romantic Retreat - With plush accommodations that feature hardwood floors and sumptuous bedding, the Inn sets the perfect stage for romance, where couples can embrace intimacy and escape into their own world of comfort and style.

Total Relaxation - Guests can start each day with a delightful breakfast, serenaded by the gentle strums of live guitar, creating an ambiance that transforms your meal into a memorable experience filled with savory flavors and the warm aroma of freshly brewed coffee.

Outstanding Location - Just steps from the vibrant Mercato Shops and within walking distance of delectable dining options, the Inn serves as a fantastic base for exploring the rich culture and lively spirit of Naples, enriching every stay with local flair.

Guest Experiences - One guest fondly recalls the friendly staff's personal touch, noting how they felt more like family than visitors, especially when Mr. Keane quickly addressed a minor issue with their room, offering not just solutions but genuine hospitality, filling the air with a comforting sense of belonging.

Nestled in the heart of Naples, Bellasera Resort offers an enchanting escape where luxury meets tranquility. With the gentle whispers of palm fronds swaying and the aroma of fresh sea air mingling with the scent of blooming tropical flowers, every moment here feels like a private retreat designed for romance and rejuvenation.

Romantic Hideaway - Experience pure intimacy in lush, beautifully landscaped courtyards, where tranquil water features create a soothing soundtrack for leisurely afternoons spent lounging in poolside cabanas or unwinding on your private balcony under the starlit sky.

Boutique Charm - Each suite at Bellasera is a chic sanctuary, featuring a fully equipped kitchen that invites culinary adventures, while elegant furnishings set the stage for relaxation after a day of exploring the vibrant local art galleries and boutiques just moments away.

Outstanding Location - Situated just blocks from the bustling energy of Fifth Avenue South, guests can easily indulge in retail therapy and gourmet dining, yet return to the resort’s serene atmosphere, punctuated by the calming sounds of nature and the occasional laughter from families enjoying nearby activities.

Guest Experiences - One guest marveled at their spacious suite, complete with a large balcony that became their personal oasis, perfect for sipping morning coffee while basking in the Florida sun. They delighted in the sound of laughter wafting from the pool area, blending seamlessly with warm breezes, creating an inviting, homey vibe.

Nestled along the serene shores of Tarpon Point Marina, The Westin Cape Coral Resort at Marina Village invites you to experience an enchanting blend of luxury and natural beauty. With stunning views of the Caloosahatchee River and the Gulf of Mexico, every moment feels like a sun-kissed escape, perfect for romance and rejuvenation.

Total Relaxation - Unwind in style at our two seasonal outdoor pools, where gentle breezes carry the scent of saltwater and lush palm trees sway peacefully, creating an oasis of calm just steps from your suite.

Spa Breaks - Indulge your senses at our full-service spa and salon, where soothing aromas and expert treatments transport you to a state of bliss, leaving you feeling refreshed and revitalized after a day of pampering.

Romantic Getaway - Stroll hand-in-hand along the marina and savor a candlelit dinner at Marker 92 Waterfront Bar & Bistro, where the sounds of live music meld with the sunset’s golden hues, setting the perfect backdrop for intimate conversations.

Guest Experiences - Guests have raved about the lively atmosphere at The Nauti Mermaid Dockside Bar and Grill, where live bands fill the air with infectious tunes, and the aroma of freshly grilled seafood tantalizes the senses, creating unforgettable nights under the stars.

Nestled along the serene shores of Estero Bay, Hyatt Regency Coconut Point Resort & Spa is a luxurious oasis where elegance meets adventure. The air hums with the gentle sounds of cascading water fountains and laughter from families enjoying sun-soaked days amidst lush tropical landscapes. Each moment here invites you to unwind in an idyllic setting that feels both intimate and expansive, making it the perfect escape for couples, families, and wellness seekers alike.

Total Relaxation - Immerse yourself in pure bliss at the Stillwater Spa, where the scent of aromatic oils wafts through tranquil spaces, inviting you to indulge in rejuvenating massages and revitalizing body treatments. Every touch evokes a sense of serenity, ensuring you leave feeling completely renewed.

Family-Friendly Fun - Experience a world of joy with four sparkling pools, five thrilling waterslides, and a lazy river that winds its way through the resort, creating a playground for both young and old. Children delight in the complimentary face painting sessions, while adults can savor poolside cocktails as the sun sets over the horizon.

Culinary Delights - Savor a culinary journey across five exquisite restaurants, where each meal transforms into a memorable experience—from fresh seafood at Tarpon Bay to the lively atmosphere at Cool Beans Marketplace, where the rich aroma of Starbucks coffee fills the air and invites you to indulge as you embark on your day.

Guest Experiences - A warm breeze flows through the open-air dining area as guests recall how their children giggled with delight at the whimsical character balloons floating around the resort. A captivating evening at Mangroves Bar turned into a delightful feast with recommendations that left everyone raving about the unexpected flavors and charming service.

Nestled in the heart of Naples, The Capri Inn invites discerning travelers to indulge in an oasis of tranquility and luxury. The enchanting ambiance, coupled with exquisitely designed interiors, creates a haven perfect for romantic getaways and serene escapes, where every detail whispers elegance and comfort.

Romantic Retreat - Experience love's embrace in our cozy rooms adorned with plush furnishings, where soft linens and ambient lighting set the stage for intimate evenings. Select rooms offer private terraces to savor sunsets over the palm-lined streets.

Wellbeing & Relaxation - Unwind by the heated outdoor pool as gentle breezes carry the scent of blooming flowers, or indulge in our spa-inspired amenities that invite guests to rejuvenate both body and spirit—all while surrounded by a lush garden setting.

Outstanding Location - Just a short stroll from the vibrant culinary scene on 5th Avenue, The Capri Inn positions you perfectly for local explorations, allowing you to drift seamlessly between fine dining and golden beaches, all encapsulated by the charming energy of Naples.

Guest Experiences - As guests step into the inviting lobby, the rich aroma of fresh coffee mingles with soft chatter, instantly making them feel at home. One guest recalled the delightful surprise of finding complimentary beach gear waiting in their room—a thoughtful touch that transformed a simple day by the water into a cherished memory.

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.

Nestled in the charming coastal town of Punta Gorda, the Wyvern Hotel, an Ascend Collection Hotel, invites you into a world of modern elegance and romantic allure. With sweeping views of the city skyline and Charlotte Harbor, every moment spent here feels like a cherished memory waiting to unfold, whether you're lounging by the rooftop bar or indulging in culinary delights at our on-site restaurants.

Rooftop Oasis - Perch 360 beckons with its stunning vistas, where the gentle breeze dances with the sounds of laughter and live music, creating an enchanting backdrop for your dining experience. Sip on nightly crafted cocktails while watching the sun sink below the horizon—a perfect conclusion to your day.

Stylish Comfort - Every room is a sanctuary, featuring plush furnishings and thoughtful amenities. Guests are enveloped in comfort, as large towels hug the body after a refreshing shower, while iPod docking stations subtly remind you to unwind to your favorite tunes.

Conveniently Located - Just steps away from vibrant local markets and the scenic Fisherman's Village, the hotel serves as a gateway to cultural exploration and adventure. From boutique shopping to leisurely strolls along the waterfront, the essence of Punta Gorda is just outside your door.

Guest Experiences - Amidst the alluring ambiance, guests have discovered little moments of joy—like the unexpected thrill of catching a live big band performance at the rooftop bar, or the friendly staff offering warm smiles and helpful recommendations that make you feel right at home.

Nestled in the heart of Naples, the Hilton Naples invites you to bask in an atmosphere where coastal charm seamlessly intertwines with sophisticated elegance. Here, the gentle sound of waves mingles with the laughter of families and friends, creating an oasis that feels like a cherished home away from home while offering the luxuries of a boutique escape.

Beach Life - Indulge in the ease of our signature complimentary beach package—imagine the soft touch of plush towels as you sink into your beach chair, sipping chilled bottled water while the sun warms your skin. A charming shuttle effortlessly transports you to the glistening shores, making your beach day nothing short of bliss.

Total Relaxation - Unwind at our serene waterfall pool, where the soothing sounds of cascading water create a tranquil backdrop for lazy afternoons. The crisp scent of fresh towels fills the air as you lounge in a cabana, leaving worries behind as the sun casts playful shadows across the deck.

City Style - Just a block from the stylish Waterside Shops, embrace the chic energy of Naples as you explore its vibrant boutiques and delightful eateries. Stroll through local markets filled with the aromas of fresh produce and baked goods, weaving moments of discovery into your getaway.

Guest Experiences - Upon entering, guests are greeted with genuine warmth, like visiting old friends—the aroma of freshly brewed coffee wafting through the lobby adds a comforting touch. Kareem and Brad, at the front desk, go above and beyond, offering personalized recommendations that lead to hidden gems, ensuring every moment feels special.

Nestled along the pristine shores of Florida's Paradise Coast, Naples Grande Beach Resort invites you to indulge in a sanctuary where modern luxury meets natural serenity. With its lush surroundings and breathtaking Gulf views, every moment feels like a private escape into romance and relaxation.

Chic Pools & Thrilling Waterslide - Dive into bliss with three sparkling outdoor pools, featuring a thrilling 100-foot waterslide that sends laughter echoing through the air. Whether basking under the sun or enjoying an evening swim, the inviting waters create memories that linger long after the sun sets.

Gourmet Dining with a View - Savor exquisite Mediterranean flavors at Rhode’s End, where each dish is infused with fresh ingredients and served against the stunning backdrop of the Gulf of Mexico. The tantalizing aroma of grilled seafood mingles with the salty breeze, promising an unforgettable culinary journey.

Luxurious Spa Retreat - Rejuvenate your senses at our full-service luxury spa, where soothing treatments incorporate local elements and offer a sanctuary of tranquility. The gentle sound of flowing water and subtle scents of essential oils envelop you, making it the perfect getaway for wellness enthusiasts.

Guest Experiences - As guests step onto their private balconies, they’re greeted by the soft rustle of palms and the distant serenade of waves crashing on the shore. One couple reminisced about how the plush hotel linens cradled them into a deep slumber each night, while the morning brought the delightful scent of freshly brewed coffee wafting in from breakfast.

Nestled amidst the lush landscapes of Naples, The Ritz-Carlton Naples, Tiburon offers a serene escape where luxury meets nature's beauty. With the enticing aroma of the Gulf of Mexico wafting through the air and a tranquil ambiance that invites relaxation, this five-diamond resort is an oasis for couples seeking romance, wellness enthusiasts craving rejuvenation, and luxury seekers yearning for unparalleled service.

Spa Retreats - Indulge in blissful tranquility at the expansive luxury spa, where the soothing sounds of water cascades blend with gentle aromatherapy, creating a sanctuary that nurtures mind and body alike.

Chic Culinary Experiences - Savor gastronomic delights at award-winning restaurants, where each dish is a journey through flavors, complemented by signature cocktails served poolside as laughter dances on the breeze.

Golfing Paradise - Experience world-class golf on the stunning 36-hole Tiburón course, where the crisp morning air invigorates your senses while you perfect your swing, accompanied by complimentary putting lessons to elevate your game.

Guest Experiences - A family raved about the spectacular kids' pool, echoing with joyous splashes and laughter, while the scent of grilled delicacies from the Poolside Grill filled the air, making it impossible not to indulge in delightful bites throughout their stay.

Nestled along the pristine shores of the Gulf of Mexico, The Ritz-Carlton Naples invites you into a world where luxury meets the serene embrace of nature. Here, every sunset paints the sky with hues of orange and pink, while soft waves serenade your senses, creating an oasis perfect for romantic getaways or rejuvenating retreats.

Spa Retreats - Indulge in a sanctuary of tranquility at the on-site spa, where the soothing scents of essential oils blend seamlessly with calming melodies, crafting the ultimate escape from reality. Experience bespoke treatments that leave your skin glowing and spirit lifted, nestled amidst serene decor reflecting the beauty of coastal living.

Culinary Delights - Savor world-class dining at any of the seven exquisite restaurants, where culinary artistry meets fresh local ingredients. From the aroma of gourmet dishes wafting through the air to the elegant presentation that delights both the eye and palate, each meal promises a memorable experience that tantalizes every sense.

Romantic Beachfront - Revel in the breathtaking beach setting, where gentle breezes carry the salty scent of the sea and soft sands cradle your toes. Whether indulging in a candlelit dinner by the shore or strolling hand-in-hand as the sun dips below the horizon, this romantic paradise is designed for intimate moments.

Guest Experiences - One couple remarked on how the staff surprised them with an upgrade to a stunning ocean-view room, transforming their special anniversary into an unforgettable celebration. The warmth of the evening breeze mixed with the sweet scent of blooming jasmine made for a magical night they’ll cherish forever.

Nestled along the shimmering shores of Sarasota Bay, The Ritz-Carlton, Sarasota envelops guests in a captivating blend of luxury and tranquility. Here, romance flourishes as gentle sea breezes mingle with the soothing sounds of waves, creating an intimate sanctuary where every moment feels exquisitely curated.

Romantic Getaway - Whisk your beloved away to elegantly appointed rooms featuring private balconies that beckon you to sip wine under the stars, where the soft lapping of water serenades your conversations.

Total Relaxation - Unwind at the newly renovated Ritz-Carlton Spa, where the aroma of lavender wafts through serene treatment rooms, inviting rejuvenation through locally sourced ingredients and expert hands.

Beach Life - Experience the allure of the exclusive Ritz-Carlton Beach Club, just a short shuttle ride away, where golden sands and tranquil waters create the ideal backdrop for sun-drenched afternoons spent lounging in plush chairs or taking refreshing dips in a zero-entry pool.

Guest Experiences - As I strolled through the lush grounds, the scent of blooming tropical flowers mingled with hints of salt from the nearby ocean, while friendly staff members greeted me with warm smiles and personalized recommendations, making every interaction feel like a treasured encounter.

Nestled along the shimmering shores of Sarasota Bay, Hyatt Regency Sarasota exudes a tranquil charm where modern luxury meets tropical elegance. The gentle sound of cascading waterfalls from the outdoor pool invites you to unwind, while lush palm trees sway softly in the warm Floridian breeze, promising an idyllic escape for couples and wellness enthusiasts alike.

Romantic Retreat - With stunning bay views and intimate dining options, every moment feels like a cherished memory waiting to unfold. Sip on handcrafted cocktails as sunlight dances on the water, setting the perfect backdrop for romantic evenings.

Spa & Relaxation Oasis - The hotel offers a serene environment complete with a 24-hour StayFit™ fitness center and an exclusive Yoga Away™ program, ensuring guests can harmonize body and mind amidst the lush surroundings. Let the soothing scents of nature envelop you as you embrace peace and rejuvenation.

Adventure Awaits - For the thrill-seekers and exploration lovers, embark on sailing, kayaking, or leisurely biking expeditions right outside your door. Experience the allure of the local sights, from enchanting museums to vibrant markets, ensuring each day is filled with discovery.

Guest Experiences - Guests have enjoyed lazy afternoons by the lagoon-style pool, where the delightful aroma of tropical drinks wafts through the air, mingling with laughter. Many cherished their private balcony moments, sipping coffee as the gentle rustle of palm leaves created a melodic backdrop, perfect for reading or simply soaking in the peaceful ambiance.

Nestled in the vibrant heart of St. Petersburg, the Ponce De Leon Hotel invites you into a world where modern elegance meets historical charm. This boutique sanctuary is perfect for couples seeking romance or wellness enthusiasts yearning for tranquility, all while being just steps away from the city’s artistic pulse and waterfront allure.

Historic Charm - The hotel’s blend of classic architecture and chic decor creates an enchanting backdrop, ideal for quiet retreats or lively evenings filled with captivating conversations.

Culinary Delights - Savor the essence of local flavors at our on-site Ceviche Tapas Restaurant, where the tantalizing aroma of Spanish dishes wafts through the air, igniting your taste buds in a warm, inviting atmosphere.

Outstanding Location - With the pristine St. Petersburg Marina merely a five-minute stroll away, guests can embark on leisurely walks that reveal stunning sights, from artistic murals to shimmering bay views—each step a reminder of the city’s vibrant spirit.

Guest Experiences - There’s something uniquely comforting about returning to one of our cozy rooms after a day of exploration; the plush beds wrapped in soft linens invite you to sink in, while the sound of laughter and music from nearby tapas bar fills the air, creating an ambiance that feels both lively and intimate.

Nestled along the tranquil shores of St. Pete Beach, The Hotel Zamora invites you to indulge in an enchanting Mediterranean escape where modern luxury meets romantic charm. With the sun casting golden hues across pristine white sands and the gentle sound of waves lapping at the shore, this boutique hotel promises a serene retreat complete with chic accommodations and intimate spaces perfect for couples seeking a memorable getaway.

Romantic Getaway - Settle into stylish rooms adorned with Frette® linens, where soft whispers of the sea breeze mingle with the scent of fresh coffee brewing from your personal machine, creating the perfect atmosphere for romance to blossom.

Spa & Relaxation - Unwind in the rejuvenating hot tub or take part in the evening wine hour, where glass clinks and laughter fill the air—an invitation to relax as the sunset paints the sky in vibrant shades of pink and orange.

Beach Life - With the sandy beach just a short stroll away, mornings here awaken to the warmth of the sun, accompanied by the salty kiss of ocean air that beckons you to explore the gentle surf or bask in the sun with a good book.

Guest Experiences - Returning from an afternoon by the pool, guests have been captivated by the warm, welcoming embrace of staff members who greet them with genuine smiles, their laughter echoing through the lobby, while the alluring aroma of freshly grilled seafood wafts from the hotel's restaurant, enticing even the most discerning palates.

Nestled in the heart of St. Petersburg, The Birchwood is a charming escape where vintage elegance dances with modern comfort. As you step into this enchanting hotel, the soft glow of antique chandeliers and the sweet aroma of freshly brewed coffee invite you into a world where every detail whispers romance and allure.

Romantic Break - Indulge in intimate moments surrounded by the hotel's exquisite 1920s decor, where claw-foot bathtubs and luxurious linens create a sanctuary for couples seeking a getaway steeped in love and history.

Outstanding Location - Just moments away from the Museum of Fine Arts and other cultural treasures, The Birchwood places you at the doorstep of vibrant downtown St. Pete, perfect for leisurely strolls through bustling markets or quiet evenings under the stars.

Total Relaxation - Surrender to bliss at The Birch and Vine, where globally-inspired dishes are served in a serene setting. Enjoy a glass of fine wine as you unwind on the Canopy Rooftop Bar, with breathtaking views of Tampa Bay and the mesmerizing skyline cradling you in tranquility.

Guest Experiences - Guests often find themselves enchanted by the friendly staff, who greet them with warm smiles, making even the smallest interactions feel personal. One visitor remarked on the delightful surprise of stepping into their room to find not just cleanliness but a refreshing scent of citrus that lingered in the air, inviting them to relax and indulge.

Nestled along the shimmering Tampa Bay coastline, The Vinoy Resort & Golf Club stands as a timeless oasis of elegance and romance. With its historic charm blending seamlessly with modern luxury, every corner of this exquisite resort invites you to unwind and indulge in life’s finer pleasures, whether it’s a tranquil afternoon by the pool or a candlelit dinner overlooking the bay.

Romantic Retreat - Every moment at The Vinoy beckons couples into a world of intimacy, with private terraces offering spectacular sunset views and lush gardens perfect for quiet strolls hand-in-hand.

Total Relaxation - The on-site spa envelops you in soothing aromas and tranquil sounds, where expert therapists tailor treatments to melt away your stress, leaving you revitalized and serene.

Historic Charm - Step back in time as you wander through the hotel's elegant halls adorned with rich history, where each photograph tells a story, and the whispers of past guests linger in the air.

Guest Experiences - One guest marveled at how the gentle rustle of palm leaves mingled with laughter by the pool, while another cherished the fragrant aroma of fresh pastries wafting from the café, inviting them to start their day with sweetness and serenity.

Nestled in the vibrant heart of downtown St. Petersburg, the Avalon Hotel Downtown exudes a timeless charm with its classic art deco architecture and chic interiors. This boutique gem promises an intimate escape where romance flourishes amidst the bustling city, inviting you to unwind on the spacious porch as the sun sets over the lively streets.

Romantic Break - With cozy nooks and whimsical decor, every corner of the Avalon whispers romance, making it an ideal retreat for couples looking to celebrate love or rekindle their connection.

Outstanding Location - Just a leisurely stroll from Beach Drive's eclectic shops and renowned restaurants, guests find themselves perfectly positioned to explore the cultural tapestry of St. Petersburg, from the vibrant nightlife to serene waterfront views.

Spa & Relaxation Lovers - Guests can indulge in calming moments at the sister property next door, where a gorgeous outdoor pool beckons beneath swaying palms, providing a tranquil oasis just steps away.

Guest Experiences - Upon arrival, the sweet aroma of freshly brewed coffee mingles with the cheerful clink of glasses as guests are greeted with complimentary champagne, setting a warm, welcoming tone for their stay.