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

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 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 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 Peninsula Bed & Cocktails invites you into a world where chic decor meets warm hospitality. Just a leisurely stroll from the sun-kissed shores of Gulfport Beach, this boutique hotel whispers romance and relaxation, offering an intimate escape for couples and adventurers alike.

Romantic Retreat - With its thoughtfully designed spaces and cozy nooks, each corner exudes an allure perfect for lovers seeking solace or honeymooners embarking on their first journey together. Enjoy the gentle rustle of palm leaves as you sip signature cocktails under the soft glow of twinkling lights.

Culinary Delights - Start your day with a continental breakfast that tempts the taste buds—fresh pastries paired with aromatic coffee will awaken every sense, while complimentary snacks throughout the day keep the energy flowing as you explore nearby attractions.

Artful Exploration - Immerse yourself in a vibrant local art scene just moments away. From the stunning Chihuly Collection to eclectic street murals, culture enthusiasts will find inspiration around every corner, making each day a new canvas waiting to be painted with memories.

Guest Experiences - As you wander back to your room after a delightful evening, the comforting scent of freshly baked cookies wafts through the air, courtesy of thoughtful staff who ensure no detail is overlooked. Guests cherish the quirky beach tote filled with towels, a charming touch that adds to the joy of spontaneous seaside sunsets.

Nestled on the sun-kissed shores of St. Pete Beach, Island Grand at TradeWinds invites you to escape to a paradise where the rhythmic lullaby of the Gulf of Mexico meets unparalleled luxury. Here, the vibrant energy of seaside adventures blends seamlessly with tranquil moments of relaxation, making it the perfect retreat for couples and families alike.

Beach Life - Immerse yourself in the golden sands just steps away from your room, where the gentle waves beckon you to unwind under the sun or embark on thrilling water sports adventures.

Romantic Break - Stroll hand-in-hand along the beach at sunset, where the sky transforms into a canvas of oranges and pinks, setting the stage for intimate dinners at the Palm Court Italian, surrounded by the aroma of exquisite cuisine.

Spa breaks - Indulge in rejuvenating treatments that harmonize body and mind, with soothing sounds of nature creating an ambiance that melts away stress as you transition from spa bliss to poolside lounging.

Guest Experiences - Guests delight in spotting playful dolphins dancing in the surf while sipping cocktails blended with local citrus at the poolside bar, their laughter mingling with the soft sound of beach volleyball matches echoing nearby.

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 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.