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Not Born a Hilton? Who cares, when you can buy a piece of the Ritz? The 411 on the boomlet in to own (part of) the fantasy

Of course, even fractional membership and long-term rentals are only an option for a wealthy few. And hotels compete hard for this coveted market slice. Hard enough to lure Orlando Bloom for cocktails? Maybe. It’s a convincing sales pitch: Orlando reaches out his hand. “Hi, I’m Orlando” is all he has to say to sell me. But the truth is, Orlando — “Orly” to his friends — is on-island for the opening of his indie flick Haven, set on Grand Cayman. In his signature white t-shirt and jeans, Orly easily joins the cocktail conversation and gamely poses for dozens of photos before heading off to the movie premiere. But he and the movie’s cast will be back: The Ritz is the poshest spot on this posh island, its suave lobby bar the gathering place for the island’s beautiful people, from entrepreneurs and expats to international movie stars.

And really, what else was our resident celebrity going to do all evening, given that the other main attractions on the isle seem to be duty-free shops and beachfront rum bars? Just as no one is really from Grand Cayman, as many a Caymanian will tell you, almost nothing is made here. (Even the rum is imported.) Not that we’re complaining. The weather is warm, the sky blue, the water clear but for the shadow of the tame stingrays, and the Ritz-Carlton, all 144 acres stretching the entire width of the island, isn’t really selling the island experience, anyway. None of these residence programs are. Ultimately, they’re selling the comfort and blessed predictability found at the top tiers of luxe living, where predictable might just mean cocktails with a movie star.


Sometimes, even the stress-free ownership of a hotel-managed residence is too much work for a proper vacation. Enter the destination club, an updated, upscaled approach to the often-maligned time-share. The time-share meant dividing the cost and use of a single vacation as many as 52 ways. A destination club works more like a country club: For a buy-in of anywhere from $105,000 to $425,000 and annual dues from $7,700 to $29,900, members of these clubs have access to million-dollar vacation homes around the world and amenities that can trump those of a luxury hotel. There are potential drawbacks — this is a big investment without a deed in return; be sure you’re working with a stable, reputable company — but undeniable perks. Like: jet service and a personal sommelier.


One of the first — and largest — among the luxury destination clubs, Exclusive Resorts, run by AOL co-founder Steve Case, considers itself a country club without boundaries, offering stays in expensive homes around the world. The spacious multimillion-dollar homes often attract groups or extended families.

What you pay: A partially refundable initiation fee of up to $425,000 to join, plus annual dues from $12,900 to $29,900 for 15 to 45 days of vacation.

Where you go: To one of more than 300 residences in 33 destinations across North America, the Caribbean, Western Europe — even on the open ocean, aboard cruise ship The World.

What you get: Concierge service and — depending on the residence’s location — special access to area golf (the golf program is overseen by Jack Nicklaus), tennis (overseen by Andre Agassi), and spa and dining facilities.