Pinellas County’s boutique hotels and retro motels deliver more than just a place to stay—they offer history, charm, and personalized service that set them apart. These one-of-a-kind, family-owned gems make every stay feel like a true getaway. Whether you’re looking for a laid-back beachfront retreat with Gulf views or a stylish downtown escape steps from St. Pete’s best restaurants and nightlife, these stays deliver unforgettable charm and local flavor. Here are some must-visit boutique hotels in Pinellas County for your next vacation or staycation.
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Bon-Aire Resort
4350 Gulf Blvd, St. Pete Beach
Step back in time at the Bon-Aire Resort, an old Florida retreat that has been welcoming visitors to St. Pete Beach for decades. With its pastel-colored façade, vintage neon sign, and laid-back atmosphere, this family-owned beachfront gem captures the essence of a classic Florida vacation. Nestled directly on the powdery white sands of the Gulf, the Bon-Aire offers comfortable, no-fuss accommodations with a mix of cozy efficiencies and spacious apartments, making it a favorite for couples, families, and longtime repeat guests.
The real magic, however, is right outside your door. Spend your day lounging under a tiki hut, swimming in one of the two sparkling pools, or sipping a famous Run-A-Ground Rum Runner frozen drink from the on-site Sandbar Bill’s Bar & Grille. With its prime beachfront location, you can stroll along the shore at sunset, explore local restaurants and shops, or simply relax alongside unbeatable views of the Gulf. Whether you’re seeking a weekend getaway or an extended beachside retreat, Bon-Aire Resort is pure nostalgic Florida charm with all the comforts of today.
The Belleview Inn
25 Belleview Blvd, Belleair
A stay at the Belleview Inn is like stepping into a bygone era of luxury and elegance, where historic charm meets modern comfort. Originally opened in 1897 by railroad tycoon Henry B. Plant, this beautifully restored hotel is a living piece of Florida’s Gilded Age history, offering a refined yet welcoming retreat in Belleair. While the original Belleview Biltmore Hotel once stood as the largest wooden structure in the world, today’s Belleview Inn preserves its timeless beauty, featuring stunning architecture, a grand wraparound porch, and rich historic details.
Beyond its impeccably designed guest rooms and suites, Belleview Inn offers guests daily tea and cookies in the Tiffany Room, a beautiful outdoor pool, and access to nearby golf and waterfront activities. Whether you’re relaxing with a book in the charming library, enjoying a guided historical tour, or taking in the picturesque views of Clearwater Bay, this boutique inn is the perfect escape for history lovers, romantics, and those craving a peaceful getaway.
The Hotel Zamora
3701 Gulf Blvd, St. Pete Beach
Perched along the shimmering shores of St. Pete Beach, The Hotel Zamora blends modern elegance with Mediterranean-inspired charm. Newly renovated, this boutique waterfront retreat offers a refreshing departure from the typical beach hotel. Its brand-new look features sleek, Spanish-style architecture, a rooftop lounge with panoramic Gulf views, and a private marina for effortless coastal adventures.
Inside, spacious, contemporary rooms boast plush bedding, oversized showers, and private balconies, making it easy to unwind after a day in the sun. Guests can indulge in coastal-inspired cuisine at Azura Coastal Kitchen & Bar, where fresh seafood and craft cocktails pair perfectly with stunning sunset views. For the ultimate relaxation, take a dip in the lush, palm-lined pool or sip a cocktail from the rooftop 360° lounge, where the Gulf waters stretch endlessly into the horizon.
The Coconut Inn
113 11th Ave, St. Pete Beach
Tucked away in the historic beach town of Pass-a-Grille, Coconut Inn is a picture-perfect escape that feels like a secret slice of paradise. This cozy, family-owned retreat is just steps from the soft sands of the Gulf and offers a laid-back, intimate atmosphere, perfect for those looking to slow down and soak in the coastal charm.
The bright and airy suites come with fully equipped kitchens, comfortable furnishings, and thoughtful touches that make it feel like home. Outside, guests can relax in the heated saltwater pool, borrow complimentary bikes to cruise around town, or lounge in the shaded courtyard surrounded by swaying palms. The inn’s prime location makes it easy to explore Pass-a-Grille’s quaint shops, waterfront restaurants, and stunning sunsets—all without the crowds of larger beach resorts. Coconut Inn delivers old Florida charm with modern comforts in one of the most idyllic spots on the Gulf, whether you’re looking for a romantic getaway, a quiet retreat, or a home base for endless beach days.
The Fenway
435 Edgewater Dr, Dunedin
The Fenway Hotel, a Jazz Age gem from the 1920s, first made its mark as both a luxury retreat and the region’s first radio station. Over the years, it has welcomed renowned musicians, artists, and politicians, cementing its place in Dunedin’s history. Now part of the Marriott Autograph Collection, this award-winning boutique hotel continues to pulse with energy, hosting live music, elegant weddings, and lively celebrations. Located along St. Joseph Sound, The Fenway offers stunning waterfront views from many of its well-appointed rooms, while its prime location places guests within walking distance of downtown Dunedin’s vibrant shops, restaurants, and craft breweries.
Dining at The Fenway is an experience in itself. The recently renovated HEW Parlor & Chophouse serves expertly seared steaks alongside dishes crafted with locally sourced ingredients, ensuring a meal as memorable as the setting. For a more relaxed yet equally impressive atmosphere, the Hi-Fi Rooftop Bar invites guests to sip handcrafted cocktails while soaking in panoramic water views. As the sun dips below the horizon, the rooftop transforms into the ultimate spot to toast another unforgettable evening in Dunedin.
Hollander Hotel
421 4th Ave N, St. Pete
Nestled in the heart of downtown St. Petersburg, the Hollander Hotel is a boutique gem that blends historic charm with a trendy, social vibe. Housed in a beautifully restored 1930s building, this locally loved spot offers a stylish yet laid-back atmosphere, making it the perfect stay for art lovers, foodies, and those looking to explore the city’s vibrant culture.
Each uniquely designed room features a mix of vintage looks and modern amenities, while the hotel itself boasts a heated pool with poolside cabanas, an on-site spa, and even a craft coffee bar. The lively Tap Room Restaurant & Bar serves up delicious, locally inspired dishes, and on weekends, guests can sip handcrafted cocktails while enjoying live music on the outdoor patio. Plus, with its prime location just minutes from the waterfront, museums, and buzzing Central Avenue, you’re always just a short stroll from St. Pete’s best dining, shopping, and nightlife.
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