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.

This boutique hotel not only offers direct access to beautiful Gulf beaches and views of Clearwater Pass, it's also the only hotel in popular Clearwater Beach with a glass wall pool. What's more, it boasts the largest rooftop bar in town, along with many other amenities, such as onsite restaurants and bars. Each stay includes two free tickets to Splash Harbour Water Park. 

On a pretty little spot of sand overlooking the iconic Sunshine Skyway Bridge, SkyBeach Hotel & Marina is one of the few hotels in the area with a marina, which was rebuilt with 29 slips for public access. For guests who love to stay active on vacation, there's a new sports complex called Southside Sports with pickleball courts, a tennis court and beach volleyball courts. During your stay, rent jet skis or paddle boards right on site, or dine at the restaurant.

The Hiatus might just be the perfect spot for a relaxed beach vacation. With its unobstructed Gulf views, rooftop pool, stylish rooftop bar, and fine dining onsite, this new hotel is sure to please. Don't miss the sunset celebration on the pool deck, or walk just a few minutes to Pier 60 and its nightly sunset celebration with vendors and buskers.

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.
 

Directly on the soft, white sands of St. Pete Beach, this family-owned hotel features comfortable suites with kitchen and dining areas, so you'll feel right at home. Eco-conscious travelers will appreciate the fact that this hotel has earned a green certification. Have a tropical drink at the bar, play beach volleyball or games onsite and just relax on one of America's Favorite Beaches.

With views of the Intracoastal Waterway, The Hotel Zamora is a Mediterranean-style boutique hotel in St. Pete Beach that's beloved for its scenic rooftop lounge, kayaks and paddleboards for exploring the waterways, and easy beach access. The hotel recently completed a $7.5 million renovation, resulting in this long-time favorite becoming a four-star luxury property. There's also a new restaurant concept onsite - Azura Coastal Kitchen & Bar, serving Mediterranean-inspired dishes.

Bright, sunny and retro-inspired, The Saint Hotel on St. Pete Beach is a newer hotel with views of tranquil Gulf waters.  Guests can choose from a studio with kitchenette, or book a suite to splurge a little and enjoy separate bedroom, kitchenette, dining and living areas. Be sure to have a sunset cocktail and a delicious meal at the rooftop restaurant, 82 Degrees.

Imagine sipping a tropical drink from your private balcony overlooking the Intracoastal Waterway at the Fusion Resort in the aptly named Treasure Island. Plan your escape soon to stay at one of their spacious waterfront suites, and enjoy easy access to Treasure Island's pretty beaches, just across the bridge. Boaters will appreciate the docking facility, too.

With its New Orleans-style balconies, you'll be tempted to "laissez les bon temps rouler" at Berkeley Beach Club, albeit in a much quieter, beachier way. Its location on 8th Avenue in the heart of tiny, charming Pass-a-Grille Beach couldn't be more perfect for those desiring a laid-back Florida vacation. Walk a few steps to the west and you'll find the turquoise waters of the Gulf. Stroll a few steps to the east and you'll enjoy views of the Intracoastal Waterway. While here, be sure to visit nearby Paradise Grille to eat fresh seafood with your toes in the sand.

This stylish boutique hotel is located in Clearwater's Feather Sound area, and its central location means guests have easy access to Clearwater Beach, St. Petersburg and Tampa. That ease of access would be reason enough to stay here, but you'll find plenty more, including the popular Vantage rooftop bar, a resort-style pool, fitness center and on-site dining at The Katch Bistro.

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.