As vaccines roll out and travel restrictions lift, many Canadians are looking to make up for lost time by the way of new passport stamps to palm tree and beach-filled destinations. For many of us, it’s simply been too long since we’ve breathed in salty ocean air, been kissed by the Caribbean sun, or sipped a tropical cocktail straight from the source.
If nothing else, an endless series of lockdowns will inspire a desire to live – and travel – like we never did before. While “cheap and cheerful,” or a cookie-cutter all-inclusive vacation may have done the job in the past, the next vacation for many of us involves something a little more meaningful and splurge-worthy.
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After all, after being trapped inside for so long, a tiny hotel room isn’t exactly the most enticing option right now. On that note, for those looking to take their next vacation to new heights, check out these 10 completely dreamy and luxurious Caribbean Airbnbs.
The Residence at The Loren at Pink Beach; Tucker’s Town, Bermuda
For those with deep wallets and their sights set on Bermuda, there’s The Residence at The Loren at Pink Beach. The sweeping sleek and modern villa sits on 5.5 acres of unspoiled landscape swept by rocky cliffs and offers all the amenities of a luxury resort. At this eight-bedroom, 10.5-bathroom escape, guests can enjoy things like a sophisticated swimming pool, a private sandy beach, incredible interiors, ocean views throughout, and indoor/outdoor lounge space.
Villa Sublime; Providenciales, Turks & Caicos Islands
In the unforgettable Turks & Caicos Islands, the stunning three-bedroom (with an optional fourth), four-bathroom Villa Sublime mixes traditional Caribbean pieces with European touches for a refined one-of-a-kind style. At this modern and impeccably designed spot, you can expect unbeatable views of the crystal-clear ocean (including memorable sunsets), a private swimming pool, easy ocean access, a covered outdoor dining area, and a waterfront gazebo.
The Palms at Oracabessa; St. Mary Parish, Jamaica
If you’re looking to go all out with a group of a dozen or so of your nearest and dearest, book the sprawling The Palms at Oracabesssa. The breezy and luxurious 14-bedroom, 13-bathroom all-inclusive villa offers all the trappings of a memorable vacation with friends or the extended family: a large pool, Jacuzzi, two dining areas, a spacious and open kitchen, a games room with a pool table, and big bedrooms. Taking any work out of the equation, the rental includes both chef services and housekeeping services.
Villa Seaclusion; Koolbai, Sint Maarten
If you have a soft spot for pristine, photo-worthy infinity pools that flow into the endless sea and luxurious vacations that cut no corners, book a stay at the postcard-esque Villa Seaclusion in Sint Maarten. The nine-bedroom, 8.5-bathroom escape houses six luxurious villas with communal outdoor areas, like the said infinity pool (a decided star of the show) and an outdoor bar, and an outdoor entertainment/games area. The property boasts stunning ocean views throughout, complete with unforgettable sunsets.
Villa Eli; La Vega, Dominican Republic
For a sleek, yet soul soothing and view-filled Dominican Republic escape that’s a far cry from the country’s sprawling all-inclusive counterparts, call Villa Eli home for a week (or two). In this sun-soaked paradise nestled in the Jarabacoa mountains, you’ll find room for more than 20 fellow vacationers. The lush and luxurious seven-bedroom, eight-bathroom villa is complete with a pool, Jacuzzi, games area, cinema area, and no shortage of postcard-perfect views throughout the home and property.
Luxury Miramar; La Habana, Cuba
If you’re in the market for a refined trip to Cuba’s capital city of Havana, book a stay at the editorial-worthy Luxury Miramar villa. Classic luxury meets modern chic décor in this six-bedroom, six-bathroom mid-century home, which features unobstructed water and city views from almost anywhere in the house. Perks of this pristine property include a large waterfront swimming pool, Jacuzzi, entertainment area with a bar and pool table, maid service, security, and daytime chef service. The interior features talking points like a stunning spiral staircase, spa-worthy bathrooms, and large and open spaces throughout.
SayaSara Villa; Mayreau, Grenadines, St. Vincent & Grenadines
For a five-star experience in one of the most breathtaking parts of the Caribbean, book a stay at the dreamy SayaSara Villa in St. Vincent and the Grenadines. At the exclusive beachfront paradise, guests can expect double tap-worthy moments, thanks to reliable sunsets and 20,000 feet of secluded white sand. The stylish villa features four separate and private pavilions, with common areas that feature a pool, and a large outdoor dining room with BBQ area, fully equipped kitchen, a bar, laundry area, private gazebo, outdoor shower, and luxurious bathroom.
Simba House; Las Terrenas, Samaná, Dominican Republic
The sprawling and impeccably designed Simba House in Dominican Republic offers a stylish five-star stay for elevated group travel. Set in lush surroundings with no shortage of green space, the airy eight-bedroom, 22.5-bathroom(!) villa features stylish and spacious rooms throughout, an elegant swimming pool, a private hot tub, and inviting indoor/outdoor lounge areas to use rain or shine. A large dining area is ideal for groups of fellow sun-seekers.
Villa Caramba; St. Barts, St Barthélemy
Though a little more intimate (i.e., slightly smaller) than some of its sprawling St. Bart’s counterparts, the refined Villa Caramba offers all the sought-after luxury Caribbean villa must-haves: a private swimming pool, alfresco dining, a sun terrace, incredible ocean views, and a nearby beach. The bright and open modern villa features no shortage of windows throughout (including a floor-to-ceiling in the main building, which offer peaceful views of the Caribbean Sea and lush landscape.
Tarasand; Rum Point, Cayman Island
Located within Rum Point, on the North coast of Grand Cayman Island, Tarasand is an extremely private villa built right on the pristine beachfront. At this luxurious four-bedroom, five-bedroom villa, guests can expect white sand, crystal clear water, endless ocean views, and an inviting open-concept design throughout. Floor-to-ceiling windows in common areas offer picture-perfect, palm tree-filled vacation views.