Big is not always better, especially when it comes to finding the right accommodations. We scoured the state to find the places that offer all the amenities you need for a great vacation in a setting that’s just the right size. So if you prefer more intimate hotels, where you don’t have to wait in long check-in lines or fight for a poolside lounge, then these Florida gems are perfect for you.

Gale South Beach

The Gale South Beach’s rooftop pool provides views of art-deco architecture and the Atlantic Ocean. Photo: CoreyWeiner/The Gale South Beach

Transforming two 1940s art-deco hotels into one very cool SoBe hot spot is what put the Gale South Beach on the hipster map. The five-story boutique hotel sits on the corner of 17th Street and Collins Avenue, right smack in the middle of the scene with neighbors like the iconic Delano and the oh so trending SLS Hotel. Walk into a lobby where elements of art deco—a chrome backlit front desk—blend with modern white leather chairs and mirrored windows. Black-and-white photos of 1950s Miami Beach are a nostalgic reminder of a former heyday. The hotel’s 87 rooms have raised ceilings for spaciousness, and balconies with faux green-leaf walls provide a glimpse of the Atlantic Ocean. Enter through the former Regent Hotel on James Avenue and you’re in the cozy Regent Cocktail Club where mixologists whip up retro drinks like Negronis and Mai Tais. As for the beach? It’s just across the street. 

Inn on Fifth, Naples

The Inn on Fifth’s prime location offers easy access to downtown Naples restaurants and boutiques. Photo: Inn on Fifth

This elegant three-story hotel sits on Fifth Avenue South, downtown Naples’ palm tree-lined six-block shopping-and-dining stretch. Despite its urban location, the Inn on Fifth is just minutes away from the white-sand beach and fishing pier thanks to a complimentary shuttle. A 2013 redo and expansion gave the hotel a fresh modern décor of red and gray with geometric accents, along with a second building across the street. Book a second-story poolside room and sneak out the door at midnight for a hot-tub soak. If you really want to splurge, the Club Level suites in the new building are huge with balconies overlooking the avenue. Everything old is new again at this meticulous gem in Old Naples. 

The Reach, Key West

Located on Key West’s quieter side, The Reach has private balconies with direct ocean views. Photo: The Reach Resort, Key West

Set off from all the hustle and bustle of Duval Street, Key West’s main drag, The Reach is an intimate and sophisticated hideaway. Painted a cheerful yellow with white trimming, the four-story Waldorf Astoria property sits on the Atlantic Ocean. Cross the front yard—a carpetlike lawn with rows of palm trees, delicate flowers and a life-size chess set—to reach the private beach (the 450-foot-long stretch is a real find on Key West), where a weather-worn pier with its own gazebo extends into the water. It’s the ideal spot for sunset gazers. Crisply decorated rooms, with contemporary furnishings that blend neutrals with bursts of orange and rust, have balconies that look out over the ocean or courtyard. The pool below was designed for sunbathing, and there’s no competition for a lounger since the resort has only 150 rooms. Contrasting with the property’s sunny island vibe is the hotel’s Strip House restaurant. Red walls, mood lighting and provocative photography that picks up on the steak house’s name make for a cozy, and somewhat seductive, dining experience. 

Elizabeth Pointe Lodge, Fernandina Beach, Amelia Island

A Nantucket vibe and direct ocean views make Elizabeth Pointe an attractive year-round escape.  Photo: Elizabeth Pointe Lodge

Deviating with the Sunshine State’s tropical image, this northeast coastal hideaway on Amelia island surprises with its 1890s Nantucket shingle-style main house. Enjoy coffee in a rocking chair on the big wraparound porch facing a shore populated by long slender sea oats and the roaring Atlantic Ocean. Whether you stay in the main house where a turn-of-the-20th-century décor mirrors the Victorian homes in nearby downtown Fernandina Beach, or opt for a room in the newer West Indies-style Ocean House, the relaxed elegance of Elizabeth Pointe Lodge is always present. With 13 miles of beach right in front of you, a sunrise or moonrise stroll is always in order. 

Bentley South Beach

The Bentley is just steps from all of the action, dining and nightlife of Ocean Drive.   Photo: Bentley South Beach

Across the street from the Atlantic’s shore, the Bentley South Beach sits on the corner of Fifth Street and Ocean Drive. It’s a favorite with Europeans and South Americans who appreciate the smaller surroundings. Yet despite its size, all of the rooms, from studios to one- or two-bedroom options, are designed as suites with living space. Plus you score a kitchenette where you can prepare your own mojitos. The Bentley is one of the few SoBe hotels to actually have a rooftop pool, in fact make that a lap pool where you can get some serious swimming in or just cool off with a nice soak. The views of sunrises and sunsets are a bonus. If you’re the beach type, stroll over to the hotel’s private beach club, where beach butlers set up your lounger—as well as serve you cocktails. Located near the edge of the less frenetic South of Fifth (SoFi) neighborhood, the Bentley is walking distance, past art-deco buildings, to landmark restaurants like Joe’s Stone Crab and celeb-fave Prime One Twelve. Or you can head north into the heart of Ocean Drive, where alfresco tables spill onto sidewalks and music blares from crowded bars.