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Top Caribbean Villas | Villa Booking Tips | Editor’s Picks: Best Caribbean Villas
100 Pond Bay, BVI
At Virgin Gorda’s 100 Pond Bay, it’s all about choices. Is it a snorkeling or lie-by-my-pools kind of day (and which pool?); do I want a cooler of Kaliks and a picnic on the beach (one of few in the BVI with private access) or shrimp skewers on the terrace and a pina colada made with local Pusser’s rum? No doubt this is a dream villa: From each of the six bedrooms is a new jaw-dropping view — and the chance to make yet another impossible decision. From $200 per person per night; sleeps 12. mclaughlinanderson.com — Audrey St. Clair
Caribbean Club, Grand Cayman
My parents introduced me to the Caribbean when I was a towheaded tot. In fact, it was at their urging that I applied for a job at this very magazine. So it was about time I thanked them with an invite to the Caribbean Club, on Grand Cayman’s jewel, Seven Mile Beach. Three bedrooms overlooking the ocean meant we had plenty of privacy but could still share quality time making dinner together in the full-size stone-and-steel-wrapped kitchen stocked to our specifications before we arrived. Some days we spent recalling memories like my first snorkeling trip to Coki Beach, on St. Thomas, USVI. Other days we relived them. Mom would watch from our private balcony as Dad and I zipped across the water in a Sunfish, the wind in my face and him proudly at the tiller — just as I remembered. From $750 per week. caribclub.com — Zach Stovall
Eco Serendib, St. John, USVI
Beach bars have their place, but sometimes mind-body therapy is the real cure-all. Notched into the hillside in Point Rendezvous, this eight-bedroom villa doubles as a destination spa. Relaxing in a mosaic-tiled soaking tub worked out all of my kinks. So did a walk over a recycled glass path to the meditation garden. From $275 to $1,000 per person per night. ecoserendib.com — Debbie Snow
Fleming Villa, Jamaica
GoldenEye — an estate once owned by James Bond creator Ian Fleming, since transformed into a 20-suite hotel — melds the privacy and comforts of a staffed five-bedroom home with the conveniences of a chic boutique resort that has welcomed the Clintons, Naomi Campbell and Martha Stewart. The villa’s real star, however, is Fleming’s original desk, where “Bond … James Bond” sprang to life. A centerpiece of the Caribbean-casual-meets-midcentury-modern interior, the desk overlooks the garden and beach that inspired the author. But I’m partial to the outdoor bathroom surrounded by lilies and palms — an inspiring spot for an adventure of my own. One-bedroom villas from $1,500 per week. goldeneye.com — Sarah Greaves-Gabbadon
Amitabah, Bequia
Our very own butler and chef are on call. The gardener picks fresh flowers each morning and puts them in the bathroom. The housekeeper does our laundry every day. We’re just 300 feet from the beach. In this six-bedroom mansion overlooking sunsets on Bequia’s Lower Bay, it’s just me and my girlfriend. If we had invited five couples (next time, I promise), we’d each pay less than $200 per couple to live like rock stars here at Amitabah. For that, my friends would all think I’m a genius, and I’d feel like a hero. From $95 per person per night; sleeps 12. grenadine-escape.com — Zach Stovall
La Belle Helene, Saint Lucia
The majesty of the Pitons can’t be appreciated from a photo. You’ve got to be on the ground, straining up to see these rocks thrust through the Earth’s crust like a nail through a two-by-four. That same grandeur could steal some thunder from 11-bedroom, 10,000-square-foot Villa La Belle Helene, but it only enhances the property. The Pitons feel like huge garden gnomes bookending Helene’s lush estate. And it will be several days (and cocktails) before I can decide whether the best view is from one of the verandas overlooking the flower-dotted lawn, with Petit Piton stretching below, or if it’s from the pool staring back at the French colonial estate set against the larger Piton. Luckily that’s the toughest decision I have to make. From $155 per person per night; sleeps 22. villasofdistinction.com — Zach Stovall
Nandana, Grand Bahama
Am I really standing just 65 miles from South Florida? I enter Nandana through 18-foot-high, 12-foot-wide 250-year-old hand-carved teak doors that were salvaged from a Javanese temple. Inside, the teak floors are from Myanmar. I’m told a lion statue in the main garden hails from India, while six Thai-inspired beach pavilions stand among Asian temple reliefs that dot the landscape of 300 varieties of imported palms. Transcending my notions of a Caribbean escape, I’m thankful to have this faraway experience, minus the jet lag. From $708 per person per night; sleeps 12. nanadanavilla.com — Debbie Snow
Scrub Island, BVI
Being marooned on a private island in a private villa is the ultimate in freedom, with endless possibilities: some romantic, others contemplative. Morning walks lead to nature trails and eventually to North Beach, where sand paths lead to more seclusion and more pretty views. Privacy is everything on Scrub Island, but when it’s time to mingle, Matina Village offers music, dancing and dining. All of it enhanced by the knowledge that my terrace refuge is never far away. From $10,325 per week. scrubisland.com — Debbie Snow
Villa DOL, St. Barts
As luck would have it, I’m visiting St. Barts in a tropical storm. But I’m doing it in style at Villa DOL, a stone-columned three-bedroom villa on the tip of scenic Pointe Milou. Somewhere below, there should be a sprawling view of Baie de St. Jean Bay, where colorful sailboats usually play offshore. Today curtains of rain sweep across the island stage. I can’t enjoy Villa DOL’s two-tier patio areas nor will I stroll through its private gardens, but I’m entranced. The villa’s view is making this storm captivating and has turned my bad-weather experience into a memorable one. From $470 per person per night; sleeps 10. sibarth.com — Jon Whittle
Villa Tara, Barbados
Four bedrooms, a private pool, a media room, a private chef and a housekeeper for less than $60 per person per night — Villa Tara offers the royal treatment but doesn’t break the bank. The on-site staff caters to every need, and the views, furnishings and amenities rival higher-priced villas, but what I really like is what Villa Tara’s savings enable. Thanks to the laundress, for example, we packed fewer bags, saved money at the airport and were able to tote along our golf clubs. Villa Tara’s savings let us enjoy more of Barbados. Does it get any better? From $2,500 per week. villasofdistinction.com — Debbie Snow
Villa GEM, Palm Springs; St. Barts
The day begins with fresh coffee and beignets on the Caribbean’s most exclusive island. Then it’s an alfresco massage next to my infinity pool, where I’ll linger later with a mojito and that book I never have time to read at home. My four-bedroom haven on the hilltop of acclaimed Gouverneur Beach is the good life at its best, which I’m reminded of each time I take in the panoramic view of neighboring St. Maarten and Saba from my outdoor shower. Two-bedrooms from $715 per person per night; sleeps 4. sibarth.com — Cami Webb
Seven Stars, Turks and Caicos
So it turns out you don’t need an actual villa to have a villa-style vacay. On a jaunt to Providenciales, or Provo, I discovered that a “deluxe apartment in the sky” can be equally indulgent. Seven Stars’ 100 condos were originally designed for residential use, so the layouts (ranging from studios to 5,000-square-foot four-bedrooms) are thoughtfully planned, with broad balconies, marble bathrooms and chef-standard kitchens. There’s a spa, gym, beachfront pool and three restaurants too, so you’ll want for nothing. From $4,595 per week. sevenstarsgracebay.com — Sarah Greaves-Gabbadon
Bird of Paradise, Anguilla
Sleep eight at this Asian-tropical escape on Sandy Hill Bay in Anguilla. Four suites connected by serpentine pools were designed by Wilson Associates, award-winning architects of luxury villas and resorts like the Four Seasons in Hong Kong and the Armani in Dubai. From $300 per person per night, including a rental car. anguillabird.com — Sarah Greaves-Gabbadon
Flower Hill, Jamaica
I crave peace and privacy on vacation, while my husband prefers the hotel action. A stay at five-bedroom Flower Hill, which includes access to the property at Half Moon Resort, just five minutes away, will satisfy us both. While he’s playing volleyball on Half Moon’s beach, I’ll be flat out in the villa’s spa, enjoying a stint in the cedar-lined steam room. Free Wi-Fi and U.S. calls will be handy when, inevitably, he needs to check in with the office. And the private gym will be waiting for me when, inevitably, I need to work out. Although my hubby and I have disparate vacation styles, Flower Hill will allow us to enjoy the best of both — and each other. From $229 per person per night; sleeps 10. jamaicavillas.com — Sarah Greaves-Gabbadon
Villa Mer Soleil, St. Barts
Of course, the inside of Villa Mer Soleil wasn’t short on space, but it was this outside spot that I never wanted to leave. Every night I watched the sun fall over St. Kitts, Saba and St. Maarten in the distance, mojito in hand, never once missing that we weren’t right on the beach (the sunset tradeoff was way worth it, and the beach was just a 10-minute walk). A week goes too fast. From $215 per person per night; sleeps 8. stbarth.com — Cami Webb
Fortlands Point, Jamaica
You may not be a millionaire, but you can live like one for a week (or three) in this iconic waterfront spread, arguably one of Jamaica’s best. Even though it’s on what locals call Millionaire’s Row, a beachfront lane bordered with grand holiday homes, don’t think you can’t afford it. Set on three acres, the seven-bedroom, 14,000-square-footer sleeps 14 (at an easy price of $183 each per night), offering plenty of space for a family reunion, as well as numerous nooks for that much-needed getting away. Spend the day on the beach, kayaking or playing squash in the private court, and come evening, gather the clan for an alfresco dinner served with sublime views. From $18,000 weekly. jamaicavillas.com — Sarah Greaves-Gabbadon
Los Arcos, Vieques, Puerto Rico
Old-world Mexican, Moroccan, Indian and Chinese furnishings embellish dramatic arches and thick walls in the style of Spanish castles at Los Arcos, whose commanding view of Vieques’ southern coast is unmatched. And it won’t break the bank: three couples in three bedrooms for just $222 per couple per night. flipkey.com — Zach Stovall
Sol Y Sombra, BVI
Two Indonesian gates welcome you to this four-bedroom estate on prime BVI real estate. Invite four other couples, and it can be yours for less than $400 per couple per night. Thai teak furnishings and handcrafted mahogany fill the interior, where no staff are on-site except on the second night, when you’ll enjoy a complimentary dinner by one of Virgin Gorda’s best chefs. From $12,500 weekly. mclaughlinanderson.com — Audrey St. Clair
St. Bernard’s Hill House, BVI
Atop this 8-acre hilltop sit four pavilions (a total of five bedrooms) cloaked in bougainvillea, sea-almond trees and royal palms for the ultimate in privacy. Split the property 10 ways for the family reunion in paradise, and everybody’s contributing $390 a night. Book the Main Pavilion for its unique location overlooking Sopers Hole, with a stream of luxury yachts that come and go. And from the pool you can spot Smugglers Cove and the occasional pink flamingo. A gourmet chef comes with the all-inclusive price here at one of the BVI’s best spots for views. From $27,500 weekly. mclaughlinanderson.com — Audrey St. Clair
The Cove, Eleuthera, Bahamas
Ask me to share, and I say “of course” — unless it’s my beach towel. When it comes to loafing on white sand and studying the flight patterns of clouds, I do my best work alone, or at least with those who share my low-volume agenda. So thank goodness for villas Donecio and Savoie, the Cove’s three-bedroom chateaus that offer private pools, butler service and, yes, a just-for-you beach. You can rock out or, like me, maintain a library-esque level of fervor. If I fail to pack reading material or an iPad charger, butler Kezang Dorji makes them appear. Same with paddle boards, bathrobes or, well, anything. Says Kezang, “The answer is ‘yes.’ Now ask the question.” He’ll arrange a lobster dinner on the terrace if that’s my desire. So if you ask nicely, I might share the rum cake with you because, darling, Kezang can bring us more. From $290 per person per night; sleeps 12. thecoveeleuthera.com — Brooke Morton
