1. Livin’ easy in Montego Bay

homeaway montego bay p194208 waterfront property
homeaway montego bay p194208 waterfront property
homeaway montego bay p194208 waterfront property
homeaway montego bay p194208 waterfront property

Decisions, decisions. A typical day at Calypso Shores involves making a few choices: Should we spend the morning at the private beach or at the private pool? Do we feel like kayaking or taking the Hobie Cat? This luxurious Calypso Shores feels more like a mini-resort rather than a house, as it’s huge—and fully staffed. This means you and your family or friends won’t be arguing over whose turn it is to do dishes, thanks to the in-house cook and housekeeper. Instead, spend your days lounging by the pool, dining on freshly caught seafood, or playing a lively game of tennis.

2. A whale of a view on the Oregon coast

homeaway oregon p693061vb waterfront property
homeaway oregon p693061vb waterfront property
homeaway oregon p693061vb waterfront property
homeaway oregon p693061vb waterfront property

If you want to spot whales, you could join a whale-watching boat tour—or spend a week at this oceanfront home. It’s located on a clifftop in Depoe Bay, the whale-watching capital of Oregon. Surrounded by pine trees, the deck provides the perfect perch for glimpsing whales, sea lions, and seals. The view might even tempt the kids to put down the iPhone and pick up a pair of binoculars. Just about every room in this cozy, antique-filled home has oversized windows looking out over the rugged coastline. And although it’s secluded and private, the house is just a short drive from town.

3. Royal relaxation in Kailua-Kona

homeaway kona p581519vb waterfront property
homeaway kona p581519vb waterfront property
homeaway kona p581519vb waterfront property
homeaway kona p581519vb waterfront property

Aloha! This Hawaiian retreat is located just 25 feet from the ocean, which means you can fall asleep to the sound of crashing waves. In the morning, open up the sliding glass doors for an ocean breeze. Breezy beach days are the main order of business. Swim in the ocean, walk along the shore, or just kick back and watch the surfers catch a Kona wave. Come sunset, head to the condominium’s private lanai to take in the view. Although this condo will feel palatial, a real palace is nearby for a dose of island culture. Tour Hulihee Palace, the last royal residence in the United States.

4. Lazy days on Lake Michigan

homeaway michigan p159832 waterfront property
homeaway michigan p159832 waterfront property
homeaway michigan p159832 waterfront property
homeaway michigan p159832 waterfront property

Does it get more all-American than a lake vacation with pine trees and sandy shores to set the scene? If your ideal va-cay involves boating, fishing, and swimming in crystal-clear water, this getaway delivers the goods. Access the lake on a short path from the garden—no worries about kids crossing the road. After a day in the water, relax with a glass of wine on the pergola covered deck, and later, huddle around the fire pit for stargazing and s’mores. Got cabin fever? The village of Union Pier has art galleries and ice cream parlors, along with a wide variety of eateries.

5. Find the cure for modern life in Curaçao

homeaway curaçao p241373 waterfront property
homeaway curaçao p241373 waterfront property
homeaway curaçao p241373 waterfront property
homeaway curaçao p241373 waterfront property

Want to vacation like an A-lister? This Caribbean getaway in Curaçao fits the bill. The swoon-worthy décor is straight out of a shelter magazine, and the whole villa has a cool, laid-back vibe. It’s so chill that you can dive into the Caribbean right from the rocks in front of the home. Warm, sun-drenched afternoons can be spent swimming laps in the oceanfront pool or napping in a hammock surrounded by fragrant flora. Inside, take a break from the sun in the airy light-filled gourmet kitchen or spacious family room. At night, sip a glass of wine on the deck while listening to the sounds of birds and breezes.

6. Beauty and the beach in Oceanside, CA

homeaway oceanside p413880vb waterfront property
homeaway oceanside p413880vb waterfront property
homeaway oceanside p413880vb waterfront property
homeaway oceanside p413880vb waterfront property

A quintessential Southern California beach town, Oceanside beckons with near-perfect weather every day. Soak up the coastal cool vibe from this swanky beachfront home—along with 14 of your closest friends. You may need to flip a coin or two to see who gets the bedroom located on the roof, but the others are just as enviable. The home offers all-around views of the sparkling Pacific along with an outdoor bar, hot tub, and plenty of couches for lounging. Oceanside is an outdoor playground where you can spend long days in the sunshine surfing, fishing, or strolling on the beach. If you’d rather learn about surfing than test the waves yourself, check out the local California Surf Museum.