Originally built in 1921, The Pier Hotel (253 2nd Ave. N., 800/735-6607, www.thepierhotel.com , from $148 d) achieves the unique grace note of being historical, comfortable, and extremely convenient. Located within easy walking distance of all of downtown St. Petersburg ’s sights, the hotel underwent an extensive renovation in 2000 that maintained its original charm—the era-specific decor in the lobby extends to the guest rooms—while subtly incorporating modern conveniences. The staff are exceedingly friendly, and the complimentary evening happy hour is the perfect excuse to relax on the spacious front porch and chat with other guests.
The Ponce De Leon (95 Central Ave., 727/550-9300, www.poncedeleonhotel.com , from $129 d) has a similar historic vibe (it was built only a year later than the Pier) but evokes a considerably hipper and more contemporary attitude. Guest rooms are spacious and airy; you’d do well to splurge on the Queen suite as the bay views from its balcony are stunning. Be advised that the downstairs piano bar hosts live music every night and is open until 2 a.m.
The enormous Rennaissance Vinoy Resort & Golf Club (501 5th Ave. NE, 727/822-2785, www.marriott.com , from $369 d) is a Marriott property but has been a St. Pete institution since the ’20s. From the Mediterranean revival–style architecture that looms high over the nearby marina to the ornate and high-ceilinged lobby, the four-diamond facility is steeped in history and luxury. The guest rooms, however, are somewhat less charming as they’re done up in business-friendly contemporary styles, which is nice but not exactly in keeping with the hotel’s legacy. Multiple on-site restaurants and a private golf course cater to the hotel’s steady stream of business meetings.
Located directly on Clearwater Beach, Shepard’s Beach Resort (601 S. Gulfview Blvd., 800/237-8477, www.shepards.com , from $120 d) has a seemingly endless variety of configurations for its 97 rooms and suites. The resort facility is clean and well-kept; tower rooms feature Spanish tile floors, plantation shutters, flat-screen TVs, and contemporary furnishings. The on-site bars and nightclubs are reflective of its popularity with a younger party crowd.
The East Shore Resort (473 East Shore Dr., 888/449-3636, www.eastshoreresort.com , weekly rates from $825) is a charming old-school motel converted into one- and two-bedroom apartment suites. Catering more to anglers than beachgoers (it’s just a few minutes’ walk from the Clearwater Marina, but four blocks from Clearwater Beach), it’s frequently booked solid. Suites are outfitted with TVs and full kitchens, and some even have screened porches; on-site amenities include a private 60-foot fishing pier and a swimming pool. What the East Shore lacks in modern decor (which is a lot), it more than makes up for in personality.
With an unbeatable location, Palm Pavillion Inn (18 Bay Esplanade, 800/433-7256, www.palmpavillioninn.com , from $130 d) doesn’t have to be too fancy, and it’s not. Rooms are basic and on the small side, but they’re clean and have all the basics (mini-fridges, TVs, in-room safes). For beach lovers, though, the luxury of the room will surely be secondary to the fact that the Palm Pavillion is located just steps from the white sands of Clearwater Beach—in fact, it’s located in the parking lot for the public beach. As most of the beachfront real estate in the area is taken up with high-rise resorts and condos, the Palm Pavillion is a rarity indeed.
For a considerably more upscale lodging experience, Sandpearl (500 Mandalay Ave., 727/441-2425, www.sandpearl.com , from $359 d) is a more recent addition to the beach. Plush mattresses, iPod docks, flat-screen TVs, and furnishings that reflect a classic Florida  elegance make the 200 guest rooms exceptional. Fifty one- and two-bedroom suites occupy the top floor, providing particularly well-heeled guests with water views, private balconies, deluxe full kitchens, and in-room laundry facilities. The resort has two restaurants and a café, as well as a spa and fitness facilities.
The tiny Inn On The Beach (1401 Gulf Way, 727/360-8844, www.innonbeach.com , from $125 d) looks more like a cozy apartment building than a hotel, and the individually appointed rooms only add to the homey feel. Five of the accommodations actually are apartments with full kitchens and living rooms. The rest of the rooms are decked out in colorful hues with stylish quirky furnishings. You’ll feel more like you’re staying in a friend’s large spare room than at a hotel. That would be a friend who’s lucky enough to live right across the street from Pass-A-Grille Beach; the location means the beach’s legendary sunsets can be viewed just by wandering out onto the Inn’s wraparound porch.
For resort accommodations with a little less legacy (and a little easier on the pocketbook), the Alden Beach Resort (5900 Gulf Blvd., 727/360-7081, www.aldenbeachresort.com , from $199 d) is an all-suite facility with 143 units, many of which are right on the beach. In either one- or two-bedroom configurations, all of the suites have full kitchens and living rooms along with standard amenities. The resort is arranged shotgun-style, so staying in the quieter less-populated area near the front lobby means you’ll end up with a hike past two pools, a Jacuzzi, and the tennis courts before you hit the beach. Despite all the facilities on-site, the Alden doesn’t tack on a resort fee; many other properties in the area do.
The shell-pink exterior of the Don CeSar Beach Resort (3400 Gulf Blvd., 866/728-2206, www.doncesar.com , from $339 d) has become something of a St. Pete Beach  icon. In the Jazz Age, notables like F. Scott Fitzgerald and Al Capone visited the “Pink Lady,” but by the 1960s it was a vacant eyesore scheduled for demolition. Rescued and reopened in 1973, extensive renovations throughout the 1980s brought the hotel back to its original glory. Unsurprisingly, the classic architecture and sense of history mean that the Don CeSar is high on the list for weddings and romantic vacations, but for such luxe accommodations, the resort’s kid-friendliness is noteworthy; not only are there extensive daily children’s programs at “Camp CeSar,” there’s an ice cream shop downstairs. All 277 guest rooms have water views, some of the gulf and some of Boca Ciega Bay; two penthouse suites are also available.