Harbour Island, Bahamas
Interior design icon David Hicks' daughter—who is undeniably a tastemaker in her own right—India Hicks calls Harbour Island home. No wonder, the homes are as magical as the pink sand beaches. See what makes Harbour Island such a destination and stay at this historically reconstructed 3 bed/3 bath home (pictured above) in the heart of Dunmore town. .
East Hampton, New York
If you're infatuated with Grey Gardens in it's prime or Diane Keaton's house in "Something's Got To Give," then, maybe it's time to take a weekend (or a week off!) and visit The Hamptons. This East Hampton cottage (pictured above; that rents for a ridiculously-cheap-by-Hamptons-standards $250 a night!), steps away from town, is an idyllic place to bunk-up. .
Nantucket is the quintessential American summer town. Get the full New England experience and rent this circa-1850s home (pictured above; complete with shingles, shutters and an American flag!) a block away from Main Street. .
Sea Island, Georgia
Sea Island, off the coast of Georgia, is a traditional Southern hot spot. The homes are unbelievable and decorated to the nines. If it's just you and another, why not rent a guesthouse on the property of a historical estate? Stay at this cozy, colorful find (pictured above) for far less than a night at any comparable island resort. .
Punta Cana, Dominican Republic
Find out what it is about Punta Cana that is inspiring interior design aesthetes like Celerie Kemble, Oscar de la Renta, Bunny Williams, and John Rosselli (who all have homes here). This villa (pictured above), that happens to be located in the same exclusive enclave of Tortuga Bay as de la Renta's picturesque place, features four bedrooms and 5.5 baths, formal living and dining rooms, a library, a pool and an expansive outdoor living space. Oh wait, there's also a full time staff and chef included in the rate! .