Best Boutique Hotels & Retro Motels

Built in the Jazz Age of the 1920s, The Fenway served both as the area's first radio station and as a hotel that hosted notable musicians, artists and politicians. Now part of the Marriott Autograph Collection, the award-winning boutique hotel still hums with activity, from live music to an abundance of weddings and celebrations. The hotel is beloved for its prime waterfront location across from St. Joseph Sound (many of its rooms flaunt those water views) and its convenience to the shops, restaurants and breweries in downtown Dunedin. The Fenway's newly renovated HEW Parlor & Chophouse is the place to savor perfectly seared steaks and other dishes that showcase locally sourced ingredients. Head to the hotel's Hi-Fi Rooftop Bar for cocktails with water views and to catch the sunset in all its glory.

The quaint, Art Deco-style Palm Pavilion Inn in Clearwater Beach racks up numerous accolades for its laidback style and variety of accommodations located steps from a truly stunning beach (Clearwater Beach was named one of the top white-sand beaches in the world by Travel + Leisure). Guests can choose from newly updated rooms, efficiencies and one-bedroom apartments, and enjoy perks like free parking and Wi-Fi. Check out the scenic beach views and the sunset from the hotel's rooftop observation deck, float in the small pool, or rent chairs and umbrellas for a relaxing beach day. One of the biggest benefits of staying at the inn is the neighboring Palm Pavilion Beachside Grill & Bar, a local institution known for its live entertainment, sunset views, grouper sandwiches and tropical drinks. Many guests find they don’t even need a car, as the inn is within walking distance to the beach, Pier 60, restaurants and attractions, and offers easy access to the vintage-style Jolley Trolley.

Cool and casual vibes and eclectic décor highlight a stay at the historic Hollander Hotel in downtown St. Pete. With colorful furniture and bold walls in guest rooms, and historic pictures sprinkled throughout, this place is dripping in charm and style. The hotel’s biggest draw is its central location, a close stroll to many of the city’s museums, restaurants and attractions. Guests love the pool and cabanas, and the fun escalates at the "Sunday Funday Pool Parties." If you’re in need of some pampering, there’s a small, all-natural day spa. Other notable perks include The Tap Room, an on-site restaurant open for breakfast, lunch and dinner; free parking and no resort fees. Pets up to 35 pounds are allowed for a fee.

With the good looks and peaked gables of a Queen Anne-style home, The Belleview Inn in Belleair is steeped in rich history dating back to 1897 and has played host to prominent public figures like Babe Ruth, Thomas Edison and many U.S. presidents. Guests of the historic boutique inn are greeted with the sounds of a self-playing piano, a grand staircase, and it’s worth walking around the property to search out the hotel’s preserved details and the stunning panels of original Tiffany-stained glass. Guest rooms blend modern amenities with historic appeal, and you’ll wake up to a complimentary breakfast basket delivered to your door. It’ll be hard to tear yourself away from the expansive pool, but you can grab a bike to explore the Pinellas Trail or hit the links at the nearby golf course. Guests have access to the neighboring Belleair Country Club where they can have lunch or dinner. 

Another beloved boutique hotel located near the heart of all the action of downtown St. Pete is The Birchwood, situated on tony Beach Drive, with great views of sparkling Tampa Bay. The historic hotel began as an apartment building in 1924 and remains true to that era in its design choices. With only 18 rooms, each is detailed with 1920s-style character and features a four-poster bed and a bathroom with a rainfall shower and clawfoot tub. The hotel’s upscale restaurant, Birch & Vine, is known for its steaks and pasta dishes. The city's "see-and-be-seen" crowd flocks to Birchwood Canopy, an elegant rooftop lounge known for its incredible bay views, rentable VIP cabanas and signature frosé drinks.