At the crossroads of the Pacific Ocean and the rain forest on Costa Rica's serene Nicoya Peninsula sits Casa Luna, a contemporary white-stone villa. Bifold glass doors and windows facilitate views of mountains and ocean from every room. A private deck and Jacuzzi are a bonus off the master bedroom, but the sleek infinity pool is perfect for experiencing Costa Rica's eco-tourism attractions up close—howler monkeys, scarlet macaws, and agoutis roam the forest canopy, and may even make a cameo on your private patio. Bonus: There are three beaches just down the hill from the villa.
Rates start at $3,500 per week; 877/573-8872 or jetsetter.com.
On 1½ acres of coastal rain forest in Manuel Antonio, dramatic 20-foot glass walls and vaulted teak ceilings are enveloped in 360 degrees of native tropical foliage and wildlife. Inside, a cascading waterfall at the entrance streams along rock-hewn grooves through the house, ultimately spilling outside into the infinity pool. Indoor gardens and white furnishings add to the home's Zen-like feel. At night, 200 inset lights illuminate the villa's four glass-encased bedrooms, decorated with white headboards. The fifth bedroom and bath are located in a separate guesthouse.
Rates start at $5,313 per week; 800/289-0900 or villasofdistinction.com.
Flying high atop Sydney's Fancy—the zenith of the Peterborg Peninsula on the north coast of St. Thomas—this villa gets its name from its famed garden. The Adirondack-strewn lawn is blessed with night views so spectacular that star gazing could trump sunbathing as your favorite pastime. Come daylight, the villa wows with a design that evokes a floating-in-the-sky feeling thanks to infinity edges on multiple sides of the property—the most spectacular is the whitewashed, Santorini-style swimming pool. The view is vast, with the British and U.S. Virgin Islands on the horizon.
Rates start at $6,300 per week; 800/289-0900 or villasofdistinction.com.
Designed by architect Arne Hasselqvist of Mustique fame, the 14 villas at Stonehaven are an interpretation of Tobago's 18th-century good life. In signature theatrical fashion, Hasselqvist re-created spacious, two-story French plantations on panoramic hilltops overlooking the Caribbean Sea (with not-so-18th-century 70-foot verandas and infinity pools). The interior elevates the motif with period-appropriate mahogany wood furnishings. Request the villa that once served as Hasselqvist's home, which is filled with his rare, personal artifacts, including two original Picasso sketches.
Rates start at $1,925 per week; 868/639-0361 or stonehavenvillas.com.
This luxurious hillside villa feels like home—that is, if your primary residence is a 6,800-square-foot estate with antique furnishings, a grand staircase, and a generous pool overlooking the ocean. Relax in the blue-and-white great room with a book from the library, or take in the view from one of the wicker chairs on the spacious sundeck. Upstairs, three suites channel breezy West Indian style with traditional shutters on all windows. Couples may want to claim Kumquat, the one-bedroom guesthouse adjacent to the pool with views of the water.
Rates start at $6,500 per week; 340/227-7899 or mangohillgreathouse.com.
An all-villa resort enclave by the aquamarine waters of the Mayan coastline houses 41 individual Mexican thatched palapa-roof villas. They dot six acres of lush jungle and each have a plunge pool, private terrace, and locally crafted crochet hammock. Verdant foliage surrounds each villa, ensuring privacy for the outdoor shower/garden; wall-to-wall sliding glass doors in the bedroom reveal views of the pool and jungle. Each furnishing and accessory makes a statement: The olive-hued lounger mirrors the pattern of the emerald green mosaic lamps placed on either side of the bed.
Rates start at $6,502 per week; 800/578-0281 or viceroyhotelsandresorts.com/rivieramaya.
This coral- and sunrise-tinted villa sits on a swath of beach on Barbados's west coast. Though new construction, the style of the duplex pays homage to the colonial roots of "Little England," namely in the dining room, where modern re-creations of 19th-century chandeliers and a custom mahogany table steal the show. Bedrooms feature hardwood flooring and white louvered doors that open to views of the sea. The backyard leads to the villa's terraced patio and an idyllic, palm-fringed beach. A housekeeper and cook keep things running smoothly.
Rates start at $3,850 per week; 800/289-0900 or villasofdistinction.com.
Near the mega-mansions and Greek-style architecture of Anguilla's celeb-studded Shoal Bay West, Covecastles is the brain-child of award-winning architect Myron Goldfinger. The stark white, geometric-shaped villas and beach homes have become a symbol of the island. Inside, a curved staircase connects the ground-floor common areas with the upstairs bedrooms. On both floors, oversize windows frame views of ocean, sand, and sky. Oak plantation shutters, terra-cotta interiors, and rattan furniture play off a theme of classic tropical luxury, while surrounding sea grape trees and well-angled architecture maximize privacy.
Rates start at $5,565 per week; 800/223-1108 or covecastles.com.
On the hills between St. Lucia's iconic Piton mountains, a villa at Sugar Beach is a front-row seat to the island's natural grandeur. Recently renovated plantation-style gingerbread villas alternate in color, representing all spectrums of a pastel rainbow. Inside, the crisp, white-on-white motif pairs with a four-poster bed and hardwood floors. The alfresco lounge area and plunge pool overlook the ocean. This villa has a refrigerator, private bar, and dining area but does not have a full kitchen—for meals, the resort has myriad dining outlets with fresh fare.
Rates start at $5,880 per week; 800/235-4300 or viceroyhotelsandresorts.com/en/stlucia.
The 3,500-square-foot Chateaux Mango embraces storied colonial design with exterior coral renderings, arched ceilings, and exposed beams. Two principal bedrooms center on mahogany four-poster beds and open directly onto the terrace, which overlooks the garden and a private pool landscaped with soaring palm trees and charming orange groves. The kitchen is sleek and spacious, with stainless steel appliances and abundant cabinet space. The bay feels almost entirely yours, with the villa's personal loungers and umbrellas lining the sands and often not a person in sight.
Rates start at $6,509 per week; 866/460-5755 or cottonbayvillage.com.
Beaulieu's open floor plan guarantees views of Baie Rouge beach (a three-minute drive away), the Caribbean Sea, and Anguilla from every room in the house, which is perched cliffside on Falaise de Oiseaux. The stylish living, family, and dining rooms are framed by white walls and vaulted ceilings, with zebra-print ottomans and more understated earth-tone furnishings throughout. Adjacent to the common areas, each of the villa's three bedrooms stands as a separate keyed unit, flanking the perimeter of the 50-foot heated pool. The expansive baths are encased in glass and surrounded by lush landscaping.
Rates start at $6,825 per week; 800/387-2726 or lacurevillas.com.
Eclectic interiors with jeweled lighting, wooden-leaf fans, and bold Indian textiles await you in this 3,500-square-foot hilltop villa on St. Martin's southwest coast. In the master bedroom, an antique Tibetan treasure chest sits opposite a handcrafted armoire from Java, surrounded by Chinese artwork and illuminated by Moroccan lamps. The airy poolside living, dining, and lounge areas offer a rare panorama of Simpson Bay Lagoon, the Caribbean Sea, and the mountains dividing the French and Dutch sides of the island. The view is best appreciated from the sleek, angled swimming pool, with its smooth, Indonesian river rock flooring.
Rates start at $2,800 per week; 646/415-7784 or carimo.com.
Six cottages along the beach and a lagoon on Jamaica's north coast form the core of GoldenEye Hotel & Resort. Each 720-square-foot lodging has an expansive outdoor shower garden and oversize claw-foot bathtub. The over-water veranda and private dock, which extends four feet above the lagoon, feels like the over-water bungalows made famous in Bora Bora. You can dive directly into the lagoon, or use your cottage kayak to navigate the waters of Oracabessa Bay and arrive on the white sands of Low Cay Beach. The clean-edge interiors consist mainly of hardwood furnishings.
Rates start at $4,690 per week; 800/688-7678 or goldeneye.com.
You probably don't need much more than a suitcase full of bathing suits for a stay at this villa. The private, comma-shaped pool overlooks the sea, and is surrounded by comfortable red recliners and smooth marble flooring. Relax here with a drink from the wet bar (your own bartender/butler comes with the villa), or cozy up inside the spacious living room. Five bedrooms have king beds (three in the main house, two rooms in the guest cottage), each decorated in soothing island greens and tans. The hillside villa rental comes with a golf cart, making it easy to zip down to the beach.
Rates start at $6,050 per week; 800/238-5290 or tryallclub.com.
Along Flamands Beach, Villa VW ART was recently reinvented as a modernist retreat. After a 2011 face-lift, the three bedrooms of this two-story home are dressed in white on white, contrasted by original works of monochromatic modern art. The rest of the villa is also stylish and contemporary, with clean-edge oak cabinetry in the kitchen and baths. Foodies will love the gourmet kitchen and state-of-the-art grill. The expansive wooden deck and beautiful pool have great views of the beach, a five-minute walk away, which puts you near the grounds of the celeb-studded Hotel Saint-Barth Isle de France and shabby-chic beach bars.
Rates start at $4,900 per week; 800/449-1553 or wimco.com.
Sit back and enjoy the view of Coral Bay and the Caribbean Sea at this hillside sanctuary. Inside, common spaces are decorated with bright Caribbean art, tropical patterns, and antiques. The air-conditioned bedrooms are situated in two, two-story pavilions with the beautiful outdoor pool in the middle. The rooms are spacious but cozy; the gracious living and dining area opens to a covered veranda perfect for alfresco meals on the gas grill. The ideal mid-island location is close to North Shore beaches (about a 10-minute drive) and the village of Coral Bay for boating and nightlife.
Rates start at $3,288 per week; 800/537-6246 or mclaughlinanderson.com.
In a residential community on Maui's Napili Bay, this villa recently had a floor-to-ceiling renovation. The fresh, new, open-air layout has bold furnishings and luxurious touches such as Oriental rugs in every room. The master bedroom and bath assume a Hawaiian eco-chic persona with green canvassed artwork, avocado throw blankets, and mint wall trim complementing the hardwood floors. Large windows open to the Pacific, and the living room doors fold back completely, facilitating ocean views and allowing the covered lanai and common spaces to merge. The town of Kapalua is just a few minutes drive north.
Rates start at $5,950 per week; 866/962-5642 or hawaiihideaways.com.
Seaside Escape is a modernist fantasy brought to life on the rock-hewn Sonoma coastline. From the exterior, the villa's daring asymmetries and eye-catching juxtaposition of wood and glass have been known to turn heads along Bodega Bay's country roads. Partitioned within a single expanse, the living room, dining room, and kitchen are walled by a jigsaw puzzle of oversize glass windows offering unobstructed vistas of the Pacific Ocean. In the common areas, the gray walls and stained concrete floors convey industrial chic; the bedrooms are decorated in blues and greens. When the sundeck gets too chilly, curl up in front of the living room fireplace or jump into the hot tub. Don't forget to stock up on wine—Sonoma's most prized vineyards are just a short drive away.
Rates start at $2,245 per week; 877/809-7819 or bodegabayescapes.com.
In greater Charleston's Isle of Palms community, this 3,500-square-foot oceanfront villa, part of Wild Dunes Resort, grants direct access to some of South Carolina's most pristine beaches. The stature of this three-story rose-colored home recalls San Francisco's archetypal slim-and-stacked style. Each level has its own ocean-view deck with comfortable loungers. The common spaces, including the two-room gourmet kitchen, are all located on the first floor. The family-friendly villa showcases multiple examples of sea-cottage-chic style, with furnishings cast in light blue, white, and earth tones. The second floor is great for kids, and holds a bunk bed, a sleeper sofa, and twin beds.
Rates start at $3,675 per week; 888/778-1876 or wilddunes.com.
Tranquility Bay Beach Houses have a quiet Keys state of mind. Tranquility's three-bedroom white beach homes are built in classic Key West style, crafted of wood and inspired by the town's quaint gingerbread houses. All of the beach homes have views of the Gulf and offer access to the resort's private beach. There is a separate dining area off of the oak kitchen, which opens to the comfortable living room. Natural light illuminates the house through French doors and white plantation shutters; three small bedrooms upstairs are decorated with brightly colored painted furniture.
Rates start at $2,100 per week; 888/755-7486 or tranquilitybay.com.