British Virgin Islands

Owning a private vacation home sure sounds nice, but people fantasizing about their own beachside property often forget that owning also means cleaning, maintaining, fixing, the list goes on… and it can end up being less of a vacation and more of a job! That’s why we love vacation villas; gorgeous homes nestled within resort communities, hotel villas are the perfect way of getting the best of both worlds — visitors find the privacy and massive size they seek, without having to worry about dealing with any issues that may arise, as hotel staff is willing and waiting to assist! So without further adieu, check out nine drool-worthy (and hassle-free) hotel villas in the Caribbean.

Villa 25 at Round Hill Hotel & Villas, Jamaica

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Round Hill is phenomenal. Sincere, intimate hospitality; private child care; breathtaking grounds; and large, beautifully designed rooms by Ralph Lauren all add up to make it is easily among the best resorts in Jamaica. The property includes numerous standalone villas of varying size; many have private pools and spacious, open verandas.

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For those seeking a truly decadent escape, the Caribbean is certainly not short on options. The islands boast everything from intimate boutiques in hidden, tranquil locales to expansive resorts that wow not only in breadth, but style. These super-luxe properties cater to celebrities and socialites — and you can enjoy them too (for a price, of course — or at least just in pictures). Spoil yourself with these 13 uber-fancy spots!

1. Hotel Le Toiny, St. Barts 

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One of the most prestigious hotels in St. Barts, this exclusive 15-villa resort sits amid 28 lush acres of natural hills and beachfront. The private villas are spacious and airy, and each boasts its own infinity-edge pool. Plus, the views here are jaw-dropping. The French restaurant is one of the island’s most renowned, and you can often spot a celebrity dining during high season. Rates are nothing to sneeze at, but you’ll definitely receive all-star treatment. Read More »

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The perks of the megaresort experience are obvious: free-flowing drinks, lots of chances to socialize with your fellow guests, and a sweeping breadth of amenities. But with these advantages comes an obvious lack of peace and quiet. When all you want to do is escape the crowds, the best bet is to seek out the small, hidden properties dotting the Caribbean shores. From eco-centric boutiques to romantic enclaves, these laid-back properties promise the glorious sound of silence. So sit back, relax, and enjoy these crowdless Caribbean locales.

Anacaona Boutique Hotel, Anguilla 

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Anguilla, a small British territory in the Caribbean, spans fewer than 40 square miles. Less built up than other isles, it manages to exude both an upscale and happy-go-lucky vibe with its gorgeous white-sand beaches and turquoise waters. There are few attractions, so days will mostly be spent sipping on drinks beach-side and dining at one the island’s exclusive hotels. The 27-room Anacaona, for example, offers access to a stunning stretch of sand, rounds of golf at the nearby Greg Norman-designed course, dinner at a great restaurant serving Caribbean fare with a twist, and a massage hut on the beach. The hotel is a great choice for rest and relaxation–and it’s an excellent value to boot. Read More »

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Fun, sun, and…scuba? For many, a trip to the beach just isn’t complete without the possibility of a deep sea dive. Whether you want to explore ship wrecks, meet creatures of the deep, or wonder at gorgeous coral formations, scuba diving can be a fun and athletic opportunity while you’re on vacation. Getting certified is crucial before attempting a dive, and if you choose to give it a go, we’ve compiled some of the best dive sites in North America for you to visit. Some may not realize just how many dive sites await in our own backyard!

1. Dive: Half Moon Caye, Belize

Half Moon Caye in Belize offers divers the chance to go on a wall dive–a dive in which the vertical facades of the earth’s landmasses are explored. The depths at Half Moon Caye (and really at any wall dive) are tremendous, giving you the very correct feeling that you are staring into an abyss. The waters at Half Moon Caye are particularly clear, despite the depth, so you will be able to see all manner of wildlife, including loggerhead turtles, rays, barracuda, and eels.

Stay: Portofino Beach Resort 

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The professional dive shop on-site at the romantic and secluded Portofino Beach Resort is a major draw for adventure seekers. Read More »

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If you’re a water sports junkie or think you could become one, these nine hotels are the perfect place to start your vacation planning. It doesn’t matter if you prefer to surf or snorkel — whatever your pleasure, we’ve chosen an awesome hotel for a variety of different activities. So prepare to leave the winter cold behind (and don’t forget your sunscreen).

Where to Stay If You Love…

Sailing: Bitter End Yacht Club, British Virgin Islands

View from the Bitter End Yacht Club, British Virgin IslandsThe Bitter end Yacht Club is a top-notch choice for just about any type of water sports enthusiast, but it stands out for its sailing. The resort’s sailing school, established in 1985, offers a number of classes, including Sailing 101 for newbies (included as part of a seven-night stay). The resort also has its own fleet of 100 vessels, including sailboats and catamarans. This relaxed, family-friendly resort has tech-free rooms featuring stunning views from the balconies and the sliding doors allows breezes to sweep through. Read More »

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When many of us dream of the beach, we’re not just dreaming of fine white sand and clear blue waters. (Well, sure, we are dreaming about that part quite a bit.) But we’re also imagining thatched roof bars, decks with hammocks, and rooms with lots of wood or stone. Resorts that blend modern luxuries with a rustic vibe help set just the right tone for relaxation and serenity. Take a look at our faves.

Aqua Wellness Resort, Nicaragua

Aqua Wellness Resort, Nicaragua

Aqua Wellness Resort, Nicaragua

Aqua Wellness Resort is a rustic-luxe retreat set into a hillside overlooking Redondo Bay on Nicaragua’s Pacific coast. The resort has eco-friendly design, lush vegetation (expect to spot wildlife such as howler monkeys and iguanas), and rooms adorned with lots of natural wood; some units include plunge pools and stunning ocean views. The white-sand beach is secluded and beautiful, the restaurant serves simple but tasty local dishes, and group yoga classes on the ocean-view wooden platform are free. For a tranquil, unplugged getaway, this is one of Nicaragua’s premier options — just note that there’s no common pool (yet) and the climb from the beach to reception is extremely long and steep. Read More »

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Hidden among the Caribbean’s many mega-resorts are some of the most unique, intimate boutiques travelers can imagine. With laid-back, eco-friendly attitudes, these petite hotels are some of the best in the region, offering personalized service and truly relaxing atmospheres. So consider passing on that 500-room all-inclusive and indulge in some intimacy at these wonderful boutiques.

1. Fowl Cay Resort, Bahamas

The gorgeous Fowl Cay Resort feels more like a private home than a hotel.

Crowded beaches are unheard of on this private island resort where a maximum of 28 guests at a time have free range of 50 acres and three beaches. Personal boats for daily excursions, on-call service, spacious villas with fully stocked kitchens and wet bars, and a host of all-inclusive activities make Fowl Cay a standout gem in the ExumasRead More »

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Rockhouse Hotel

Rockhouse Hotel

There’s nothing quite like the sense of discovery one feels when arriving at a hidden gem hotel — a truly special spot that is intimate, remote, underrated, or all of the above. Some people like to brag to their friends about their insider find; others prefer to keep it all to themselves. Of course, we at Oyster have never been good at keeping secrets.

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It’s time to get your spring break plans in order, and if you’re looking for some fun in the sun, the Caribbean is a prime destination. But with thousands of islands (although only a few dozen are inhabited) to choose from, that doesn’t narrow things down much. That’s why we at Oyster have created an A to Z (well, actually, an A to V) guide to the Caribbean, so choosing your island and resort will be a piece of cake. First stop: Anguilla.

Anacaona Boutique Hotel, Anguilla

The boutique Anacaona has two pools.

Anguilla is a tiny British territory that covers fewer than 40 square miles and is a popular spot for couples and celebs (Sofia Vergara went on a girls’ trip to the island) due to its small size and upscale vibe. Visitors must either fly to St. Martin and take a short ferry to the island, or fly in directly (by way of a small seaplane) from San Juan, Puerto Rico. Thus, getting to the island can be pricey. So once you’re there, we’d recommend staying at the boutique Anacaona in the island’s West End. Though its not quite as luxe as the CuisinArt or Viceroy, it offers access to the same gorgeous white-sand beach as the neighboring Viceroy – through an off-property path — as well as to the nearby Greg Norman’s golf course and a few restaurants, and its prices are considerably lower. With two small pools, a great restaurant serving Caribbean fare with a twist, and a massage hut on the beach, the hotel is a good pick for value.

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‘Tis the season for annual awards lists, but if you think you know what’s coming, guess again. Oyster’s awards aren’t like the other guys’ — we’re not like the other guys, so why should our awards be? You can find lists of the world’s best luxury hotels in a dozen other places, but only Oyster digs deep to learn every hotel’s secret quirks. Our hotel investigators trot the globe and visit every hotel in person so we can bring you the unvarnished truth, and this year, for the first-ever annual Oyster Hotel Awards, we’d like to show you the wackiest, coolest, weirdest, and most interesting things they came across in their travels. We are thrilled to present the 2012 selection of Oyster’s Most Interesting Hotels in the World. Are you ready for this?

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