Pretend You Live Here

For more space and privacy than you'll find at a big resort, consider renting a house. Sites like HomeAway offer many options, but a specialist such as Anne Pawsat-Dressler of Hawaii Hideaways (hawaiihideaways.com) has access to homes you won't find anywhere else- and she can arrange snorkeling trips, surf lessions, and helicopter tours, too. Her Oahu portfolio includes properties for couples (an oceanview condo for $425 a night), families (a waterfront three-bedroom for $1,000 a night), and multi-generational groups (a beachside five-bedroom that sleeps 12 for $3,000 a night).