The opera house, the dramatic harbor, the golden sand beaches with their perfect surfers (and perfect waves) – what could be chicer than a winter sun vacation in Sydney?

As you’d expect from such a vibrant, cultural city, the boutique hotels here are ultra-desirable and ultra-cool. From sassy views over the water to bold visual designs, the boutique hotels of Sydney have everything a visitor to the city could want, and more.

1. Blue, The Harbor

Built in a former warehouse overlooking the eccentric-sounding Woolloomooloo Bay, Blue is as sleek, sexy and sharp as its name suggests. The interior is a masterpiece of industrial art, subtle lighting and futuristic furniture – all of which combines to make you feel like you’re sitting (or sleeping) at the bottom of the ocean.

On the edge of the Botanical Gardens, Blue is also perfectly situated for exploring the city – the Opera House is just a stroll away. When evening comes, sip a cocktail in the trendy Water Bar before you hit the town and enjoy a complimentary a la carte breakfast to recover the next morning.

2. Medusa, Darlinghurst

This stylish boutique bed and breakfast is a delightful mixture of clashing bright colours and Victorian architecture. Red carpet, pink walls and a Caravaggio above the fireplace are what first meet the eyes of confused visitors, but the whole effect is both cheerful and creative and compliments the trendy vibe of the Darlinghurst area.

The 17 rooms all have a different colour scheme and original touches, from feature walls and rustic timber shutters to a cleverly designed bathroom inside what seems to be a fitted wardrobe. Downstairs, a gym, fitness centre and modern business facilities offer everything the cool advertising types that frequent the hotel could need.

3. The Observatory Hotel, The Rocks

It might not be big and flash, but The Observatory Hotel has an excellent location within easy walk of many of those must-see attractions – plus an old-fashioned Colonial design that is pure Old World luxury. Spacious and classically stylish, the décor has a country house theme, with plenty of chunky oak furniture and fine linen.

Aside from the beautiful luxury of the hotel, it’s the little quirks that really make this place special. The indoor pool has a domed ceiling with a fiber-optic representation of the night sky, whilst guests missing their pets can enjoy a ‘goldfish on loan’, or perhaps an under-the-weather package of broths and teas delivered to their door.