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Ladera Resort, St. Lucia

The first hotel in St. Lucia to introduce the “missing fourth wall,” Ladera Resort set the bar high for luxurious accommodations on the island. With its trademark open-air, treehouse style villas, stunning Piton views, and exceptional service, Ladera is easily one of St. Lucia’s most exclusive properties — and rates are often half the price of other similarly luxurious hotels (ahem, Jade Mountain). Though it’s not located on the beach, the hotel provides a free shuttle to the pristine white sands of Jalousie Beach, and almost all villas come equipped with private plunge pools. There are no TVs, A/C units, or telephones, but missing these amenities simply adds to Ladera’s rustic appeal.   

Cocobay Resort, Antigua

Perched on a bluff overlooking the Caribbean Sea, Cocobay Resort is a boutique-style, all-inclusive resort with authentic Caribbean charm. Private, colonial style cottages dot the 10-acre property, where rooms have exposed wood beams, private decks with hammocks, and gorgeous Caribbean views. There are two stylish infinity pools, and guests have access to a lovely white-sand beach. Cocobay is an adults-only property, and sees a lot of wedding parties and honeymooners, so guests can expect a rather tranquil stay. 

Natura Cabanas, Dominican Republic

Owned by a hospitable Chilean expat, Natura Cabanas is a secluded retreat on the north coast of the Dominican Republic. The low-key, intimate property features spacious, eco-friendly bungalows with stone walls and brightly colored Caribbean accents, delicious, fresh, food, and a stunning private beach with soft sand and clear waters. Families and couples who’d rather stay away from the cannon ball contests and impromptu dance competitions of large-scale all-inclusives will appreciate Natura’s laid-back atmosphere. There is no air-conditioning, the pool is small, and the grounds are a bit buggy, but the price is more than fair for what you get. 

Tensing Pen, Jamaica

With an intimate collection of 17 cottages, Tensing Pen is where guests come to unplug. Rooms lack any sort of technology, and you’ll find most vacationers lounging poolside with nothing more than a large stack of books and some sunscreen. Tensing Pen’s cliff-top location offers breathtaking views of Negril’s West End, where guests will be treated to some of Jamaica’s best sunsets. The staff here is small, but personable, and the hotel is within walking distance of some of Negril’s best bars and restaurants. Although children are welcome here (unlike at some similar hotels on the island), there is no kids club or child-specific entertainment. The vibe here is mellow and laid-back, but that’s just why guests keep returning year after year. 

Biras Creek Resort, British Virgin Islands

A rustic-luxe retreat with just 31 suites, the sprawling Biras Creek Resort feels like a secluded hideaway, even at maximum occupancy. With a host of on-site amenities — including tons of free water sports, free bicycles, an attractive pool, two distinct beaches, tennis courts, and a (tiny) fitness center — guests will never be bored during their stay. Suites are comfortable, if a bit dated, but premier suites have separate living rooms, large decks, and private plunge pools. Peace and privacy are the mainstays at Biras Creek, and its quiet nature is why guests continually return.   

Pink Sands, Bahamas

One of few hotels on the exclusive Harbour Island, Pink Sands is a luxe property with a vibe of understated sophistication. The unspoiled, three-mile stretch of pink sand beach is without a doubt the hotel’s premier feature (and namesake); but the sleek, modern cottages, excellent on-site restaurants, and rarely crowded freshwater pool are all highlights as well. Rooms are stocked with amenities, and service is top-notch. And activities here run the gamut — from cooking classes with the resort’s executive chef to kayaking and paddle boarding. Though tranquil, the hilly property isn’t ideal for those with limited mobility, and some guests may find the property’s wild, roaming roosters to be a bit of a nuisance. 

Galley Bay Resort & Spa, Antigua

The relaxed environment of Galley Bay Resort & Spa, an adults-only boutique, is a major part of its appeal. This isn’t Antigua’s fanciest property, but it doesn’t need to be: Simple Caribbean style (think: thatched roofs, stone, and rattan), a truly gorgeous beach, and all-inclusive food that’s better than average for the island make for a winning combo. Many of Galley Bay’s cottages and suites sit right on the sand, offering  picture-perfect views of Antigua’s stunning sunsets. Here, “nightlife” consists of nightly live music that shuts down around 10pm; but guests looking for a low-key Caribbean getaway will surely appreciate the resort’s laid-back attitude.