Hotel Santa Isabela
This grandiose former 18th-century palace of the Count of Santovenia enjoys a superb location on Plaza de Armas, Havana's oldest square. Furnished with period pieces, the 27-room Santa Isabel embodies colonial grandeur, transporting guests back in time to the era of the Spanish viceroys. When you check-in, you'll understand why the wow-worthy list of recent guests includes President Jimmy Carter, Jack Nicholson, Robert Redford, and Sting.
Hotel Raquel
Before the Cuban Revolution in the 1950s, the neighborhood west of Plaza Vieja thrived as the Jewish quarter. Honoring that heritage, the Hotel Raquel induces a double-take at every turn, beginning with its extravagant bas-relief façade—a dramatic example of Art Nouveau styling. The building began life in 1905 as a bank and looks the part: its palatial lobby is a forest of marble columns beneath a massive stained-glass skylight featuring chandeliers patterned after the Star of David. Rooms are named for Biblical matriarchs and patriarchs, and the restaurant serves kosher food, such as borscht and latkes.
Hotel Los Frailes
At the Hotel Los Frailes, you'll find bellmen dressed as monks with brown habits. The monastic theme of this 22-room hotel—a former townhouse mansion of the fourth Marquis Duquesne—reflects its proximity to the Convent of Saint Francis of Assisi. Timber-beam ceilings, stained-glass windows, and wrought-iron chandeliers evoke an ecclesiastical mood, and a house quartet plays chamber music in the lobby bar. There's nothing ascetic, however, about this intimate charmer a stone's throw from Plaza Vieja.
Hotel Terral
Its sublime location on the Malecón, with vast views over El Morro castle and the Atlantic Ocean, is reason enough to lay your head at the Hotel Terral. Throw in modern conveniences such as flat-screen TVs, minibars, and spa tubs, plus ultra-contemporary furnishings that make bold use of travertine tile and stainless steel, and you'll be lodging in style. It does lack a restaurant, but treat that as a bonus, as several superb paladares (private restaurants) are nearby.
Hotel Saratoga
There's a reason Beyoncé and Jay-Z chose to indulge at the Hotel Saratoga, Havana's premier boutique hotel. In the early 2000s, architects and designers refurbished Saratoga's derelict edifice into a visual stunner, imbuing a Moorish-inspired colonial theme with contemporary touches. Lavish works of modern art adorn the mezzanine bar—a perfect setting to savor a mojito and fine cigar. A rooftop sun deck with a pool offers sensational views over the Capitolio and Gran Teatro.
Casa Vitrales
If you're seeking historic charm, look no farther than Casa Vitrales, located in the hip Cinco Esquinas quarter of Habana Vieja. Owner Osmani Hernández has adorned this restored nine-room, four-story, 18th-century townhouse with a quirky mix of antiques (a barber's chair in the hallway), IKEA-style furniture, and vibrant contemporary art. Breakfast on the rooftop terrace is icing on the cake, and climbing up and down the narrow staircase will help you work off the calories.
Apartamentos Chacón 162
You get the best of both worlds at the boldly contemporary Chacón 162 in the heart of trendy Cinco Esquinas. The stylishly modern loft-suite combo occupies two floors above an excellent private restaurant. Its Canadian-Cuban owners have curated a design scheme featuring industrial flair melded with colonial-era elements like tile floors and louvered doors that open to balconies with views of the street life below.
Casa Concordia
An English-Cuban couple invested plenty of money and love into rehabbing Casa Concordia, a self-contained apartment in delightfully funky Centro Habana. Its elevated position guarantees rooms with fab views. Perfect for a family, the three airy bedrooms feature antiques, and maid service is offered. The Malecón is five blocks away, as are La Guarida and Casa Miglis—two of Havana's premier paladares (private restaurants).
Casa Jorge Coalla Potts
Book early to reserve a room at Casa Jorge Coalla Potts, a popular two-bedroom casa particular (homestay) run by a delightful family (Jorge, Mari, and daughter Jessi). Although furnishings are relatively modest, its location in the heart of Vedado (three blocks from the Coppelia ice cream parlor and the Hotel Habana Libre) is a winner. The cozy lounge with rockers invites lazing the day away. The care and attention here are top-notch.
VIP Le Blanc
For those who don't mind spending a little extra, the VIP Le Blanc, a private six-bedroom boutique guesthouse, defines elegance. An architectural stunner, the remarkable 1940s villa—a fusion of Art Deco and Spanish Renaissance styling—resembles a museum stuffed with precious antiques. All rooms are air-conditioned, and bathrooms are 21st-century chic, as are furnishings in some bedrooms. Concierge service, uniformed staff, gourmet meals, and a huge swimming pool with a bar summon images of Italy or France. Welcome to the new Havana!