1. Ultimate Hides

Location: Worldwide

Price range: From $14 per night

ultimatehides.com

UH’s offerings include houses, hotels, and apartments by the likes of Marcel Wanders, Tadao Ando, and Jean Nouvel.

Standout: A forgotten gem by Richard Meier in Darien, Connecticut, known as the Smith House. The four-bedroom white cube is highly influenced by Le Corbusier and has its own dock and private beach (available in December).

2. W Retreat & Spa Vieques Island

Location: Vieques, Puerto Rico

Price: Doubles from $329

wvieques.com

Patricia Urquiola’s paean to island living has ratcheted up the status of this sleepy cay. Picture an outdoor living room with pastel pod chairs, polished concrete, and psychedelic-tropical murals. It’s the opposite of whitewashed minimalism.

Standout: Tropical Oasis suites start at 620 square feet. Splurge on the Fabulous Oceanfront and you get direct access to the shore.

3. Airbnb

Location: Worldwide

Price range: Personal listings from $56 per night

airbnb.com

This three-year-old website (and app) allows owners to list their properties—from private islands to modest modernist apartments—for free, then connects them with like-minded renters.

Standout: Surfer Ron Roozen’s house along the Margaret River in Western Australia. Its 180-degree views overlook epic surf breaks on the Indian Ocean and boasts multiple outdoor spaces.

4. Marina Bay Sands

Location: Singapore

Price: Doubles from $324

marinabaysands.com

Moshe Safdie’s tripod hotel—nicknamed the Ironing Board—has forever changed the skyline of this island nation. It also claims one of the world’s highest public parks, cantilevered above those three stiltlike towers.

Standout: Horizon rooms occupying the towers’ upper floors have floor-to-ceiling windows so large you can practically see the curvature of the earth from them.

5. Parco dei Principi

Location: Sorrento, Italy

Price: From $200 per night

grandhotelparcodeiprincipi.net

Giò Ponti’s white-and-blue jewel dates from 1962, and this Mediterranean jet-setter’s getaway will still make your head spin. Decked out with all the original mid-century furnishings, ceramic egg walls, and 30 custom-patterned majolica floor tiles arranged in myriad com-binations, Ponti sure put the booty in boutique.

Standout: Swim through a sea cave or leap off the angular diving structure that emerges from the depths of the hotel’s oddly faceted cliffside pool. Negronis optional.

6. Living Architecture

Location: England

Price: From $30 per person per night

living-architecture.co.uk

Living Architecture commissions renowned architects—such as NORD, Jarmund/Vigsnæs Architects, and VRDV—in Norfolk, Suffolk, Kent, and London, England, to build their dream homes, then rents the houses out to the masses at reasonable prices.

Standout: Next year, the Peter Zumthor–designed Secular Retreat, made of rammed concrete and acres of glass, set in a wooded riverside in Devon, will open.