São Paulo's first boutique hotel, opened in 2001, remains the city's best, navigating a subtle line between classic luxury and urban cool with reserved aplomb. It's housed in a tall, narrow tower hotel located on the continent's most fashionable street, Rua Oscar Freire, that is full of top-end boutiques, galleries, cafes and restaurants. But particularly winning are the hotel's personalized touches, delicate detail and scattered Asian influence throughout.

The understated lobby is small per the architecture, with limited lounge seating by the Campana Brothers under the nose of a hanging cocoon-like art installment by Siron Franco. An expansive glass-enclosed suspended orchid garden covers one wall in its entirety, announcing straightaway: Brazil. A narrow corridor houses the lobby bar before leading to the small Champagne and caviar bar, part of the very private Italian restaurant space, where another rainforest wall dominates.

The 904-square-foot suites, of which there are 18, are the way to go here, outfitted in masculine tones and rich wooden accents offset by funky contemporary furniture designs like golden cotton rope chairs by the Campana Brothers. Eames chairs and Italian leather sofas are here as well, helping to maintain the balance between timeless and trendy. Modcons like Japanese toilets with temperature-controlled seats share space in the Carrera marble bathrooms with claw-foot bathtubs; elsewhere, 40” LCD screen TVs keep the tech in check while a bottle of red and daily seasonal fruits are standard amenities. There's no pool, but a full-service spa rights your wrongs on the mezzanine.

Rumor has it the owners run a very tight ship so perfection is the norm from a service standpoint, executed by stylish staff decked out in café-colored Ocimar Versolato-designed attire – as smart as the street itself, São Paulo's most discerning.

The Fasano family has been synonymous with top-end hospitality and gastronomy in Brazil since 1902, when Italian immigrant Vittorio Fasano opened his first restaurant, Brasserie Paulista, in São Paulo. The family's flagship hotel is saturated with archetypal Italian elegance in a 1930's style Modernist (yet discreet) building covered in an English red brick façade that hides travertine marble walls and antique furnishings that evoke a bygone era of post-Great Depression glamour.

The unorthodox lobby is peppered with Art Deco-era chandeliers over vintage leather armchairs – handpicked one-by-one by owner Rogério Fasano and famed Brazilian architect Isay Weinfeld in antique shops across England and France. The bar is placed front and center; the reception, flanked by a startling vintage World War II world map used by the US Army, is completely out of view behind the bar's back wall as to shield guests from the more public lobby. Bareto, the intimate jazz bar, is hidden away to the left; Fasano, the award-winning signature restaurant, occupies similar real estate to the right.

Each of the hotel's 20 floors is home to just four rooms, all acoustically-retrofitted for soundproof solitude. The subdued décor provides an air of days gone by, with retro furnishings (Art Deco nightstands, Eames chairs) and Italian embellishment (white marble bathrooms, Venetian-framed paintings, Murano vases). Jardins Europa, the city's greenest and most lavish neighborhood, is exquisitely framed outside each of the hotel's 60 rooms and suites. A rooftop pool, fitness center and small spa claim similar points of view.

Throughout the hotel, no detail is left to chance – even the fire extinguisher signage comes across as fine art rather than obnoxious adherence to fire codes.

The moment Hotel Unique (pronounced Unique-y) comes into view, you quickly understand something different this way comes. Famed Brazilian-Japanese architect Ruy Ohtake wasn't going for subtlety when he built this ultra-trendy, 95-room boutique hotel shaped like a slice of watermelon in order to seize commanding 360° city views from higher floors.

Guests enter through an imposing 25-foot high, 650-pound double entrance door into a glass-framed, open-spaced lobby that certainly feels more MOMA than hotel. Minimalist Italian chairs by Fendi and trendy loungeware by Gaetano Pesce and Hugo Franca lead to a 300-bottle, 36 foot–high Lobby Bar and adjacent library, stocked full of books on architecture, design and fashion. Glance skyward the sky-lit atrium frames a top floor water mirror.

Criminally unlit, curved hallways lead to rooms which are iPod-white from top to bottom, save the slanted hardwood infinity flooring which curves up the side wall in the suites – it is here, a direct result of the curved nature of the building itself, that the TV is mounted. Bathrooms feature a collapsible window separating the bathtub with the bed, allowing for interesting viewing should one chose. As expected, modcons are ubiquitous, including newly introduced Apple TV consoles in every room.

On the roof, the real coup: Skye Bar, a hip lounge and restaurant, which gives way to the 25m-long open-air infinity pool – lipstick red and featuring an underwater soundtrack – that only stops when the astonishing views of downtown São Paulo come into focus across the green-swept Jardims Europa neighborhood.

Close to the business district and the Jardins neighborhood, L’Hotel Porto Bay offers a European boutique hotel experience in bustling São Paulo. The marble-floored lobby is decorated with refined gold accents and features a luxury-brand showroom and a valuable art collection.

Outfitted in luxurious Egyptian cotton sheets, L’Occitane bath products, and designed in a warm, classic style, the accommodations provide a serene base within the city. The rooms are comfortable and stylish, and the suites offer two bathrooms, making them feel very spacious.

There is a beautiful indoor pool area surrounded by large plants and stylish loungers, as well as a full-service spa and a fitness center. Trebbiano Ristorante features Mediterranean cuisine and serves a lavish breakfast buffet, and il Piano Bar opens in the late afternoon for cocktails.

With sweeping black onyx beams in the spacious lobby, Tivoli Mofarrej is a sleek and modern hotel consisting 220 rooms and three restaurants, as well as a spa, gym and pool. Located in the fashionable Jardins district and overlooking the lush Trianon Park and the cityscape, Tivoli is a luxe spot favored by business travelers.

The rooms are comfortable and spacious, designed in the black and neutral tones found throughout the hotel. The top accommodation at Tivoli is the enormous and luxurious Mofarrej presidential suite, which has three bedrooms and bathrooms, a dining area, gym, kitchen and private elevator and offers spectacular views over São Paulo.

The hotel also offers a stylish pool area complete with a circular orange pool and large cabana tents, a glass-enclosed fitness center and a Banyan Tree spa. Three restaurants live within the hotel: dinner is served at the fine-dining choice Arola Vintetres and a more relaxed French-inspired breakfast and lunch is available at Bistro Tivoli. Nara Lounge, a cool spot for drinks and cocktails, offers views of the pool and gardens.