Play Host | 7 Properties with Incredible Guest Houses

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We live globally—family spread across continents, children on the other side of the country, friends who forgo a home base to travel the world. It takes a consummate host to bring together a far-flung cohort, to create an inviting anchor point worthy of an extended visit. Put up your family and friends in these remarkable guest houses and take a break from coordinating elaborate meetups away from home.

The Sprawling Ranch, Uruguay

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Rosario Lix Klett, Perazzo Inmobiliaria Sotheby’s International Realty

Take your ease at this five-hectare dream home in Maldonado. The main house features soaring ceilings and soothing whites, while the pool house boasts a gym, fireplace, and Turkish bath. The pièce de résistance for visitors is the two-bedroom, two-bathroom guest house that includes a reception hall and laundry facilities. At this South American pied-à-terre, it may be your guests who entertain you.

The Waterfront City Stunner, New Zealand

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Pene MilneNew Zealand Sotheby’s International Realty

Award-winning architect Pete Bossley gave this incredible Auckland-adjacent home a well-deserved redesign, aligning it with the highest standards of comfort and eco-friendly luxury. The 13-meter solar-heated pool and easy harbor access for paddleboarding and boating will have each of the four bedrooms in the separate second home booked solid.

The Aegean Jewel, Greece

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Savvas SavvaidisGreece Sotheby’s International Realty

The bright whites and blues of Greece are enough to lure any traveler, but this stunning home overlooking the Aegean Sea is something else. Guests will love their private villas, the expansive pool for cooling dips, the proximity to two of Mykonos’ most beautiful beaches, and the rugged charm of the surrounding terrain. And with a spa, business center, and professional kitchen at the ready, plus an onsite helipad, you might have more people popping in than you originally planned.

The Historic Equestrian Estate, Poland

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Poland Sotheby’s International Realty

Polo fans will flock to this 279-hectare estate overlooking the Warta River. With its close proximity to Berlin and Warsaw, plus its own airstrip and helipad, the Sowiniec Polo Club and Manor is made to receive. Polo fields and arenas are maintained to perfection, as is the five-suite country-style guest house. Between matches, guests will love the stately decor, beautiful indoor pool, and library-style cigar lounge.

The Waterfront Colonial, New York

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Marian Misad & Mary HardyJulia B. Fee Sotheby’s International Realty

Nestled amongst the Winchester County trees, with expansive views of Long Island Sound, this Larchmont Georgian Colonial adds an air of dignity to even the most idle holidays. House visitors in this property’s spacious two-bedroom guest cottage, and invite them by to laze in the heated pool, recline in the gazebo, and the walk private sandy beach. Twenty-two miles from Manhattan and minutes from Larchmont’s commuter train, this property offers picturesque seclusion within reach of the big city.

The Oceanfront Island Villa, Bahamas

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Nick DamianosDamianos Sotheby’s International Realty

The Bahamian community of Ocean Club Estates is a true gem on Paradise Island, and the elegant Villa Florentine is no exception. The guest villa alone is 10,000 square feet, and includes six bedrooms, three kitchens, and a rooftop deck for more secluded sunbathing. Visitors may choose to revel in the resort-living amenities of the main house, with its European-style décor and resplendent formal rooms. After napping under a coconut palm, you and your guests may fancy a round at the club’s 18-hole championship golf course designed by Tom Weiskopf.

The West Coast Retreat, British Columbia 

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Logan WilsonWinston Chan & Tricia ChenSotheby’s International Realty Canada

Behind a gated, stone drive, overlooking the waters of Satellite Channel, is this nearly two-acre oceanfront estate. Comprising three impeccably-designed, fully-furnished homes, this property makes the most of hardwood flooring, cut-glass accents, and 230 feet of ocean frontage. Guests can curl up in the cozy guest house with its wood-burning fireplace, rear deck, and walkout balcony, or strike out on a whale-watching excursion or winery tour. Enjoy the wilderness, peaks, and coastal charm of British Columbia with as many guests as you please.

However far you are from friends and family, you can rest assured the right property—with a welcoming guest house—is the best spot for a reunion.