There’s no shortage of grand resorts and charming boutique hotels in the Caribbean, but if you’re looking for a little local flair, head to one of these Airbnb rentals.
British Virgin Islands
Fully operational after Hurricane Irma hit the BVIs in 2017, Tortola’s hilltop, one-bedroom Cooten House boasts some pretty prime Caribbean views. Take them in from the outdoor dining area or while soaking in the sunken hot tub on the bedroom balcony.
This sleek, two-bedroom villa (part of a four-villa compound) is across the street from Boca Catalina Beach on Aruba’s posh northwest coast. Mid-century-modern interiors lead out to a shared pool area that feels more Palm Springs than Caribbean, but the snorkeling that beckons a few hundred feet away reminds you of exactly where you are.
Heads up, honeymooners: There’s no roughing it in this tree house in the village of Laborie – you’ve got an air-conditioned bedroom, a plunge pool, a full kitchen, and a private sundeck. The beach is a few yards away, and your on-site hosts are happy to arrange snorkeling excursions, dinner reservations, en-suite massages, and more.
Families vacationing in St. Maarten can settle in at the five-bedroom Summer Hill villa overlooking Cole Bay. There’s a full kitchen, a bunk bed room for the kids, and four bathrooms. Daily gatherings will surely revolve around that extra-large infinity pool.
Plenty of luxurious accommodations await on this 16-mile-long island, including the new Villa Tasha, an uber-modern, one-bedroom space overlooking Limestone Bay. Be ready for spacious living areas, an inviting master bathroom with a spa tub, and million-dollar views from the private pool area out back.
One of the best bang-for-your-buck rentals on Barbados is this oceanfront, two-bedroom house in Saint Joseph on the island’s breezy Atlantic coast. (Pro tip: Reserve a rental car for island exploration.) The roomy, plantation-style estate features vaulted ceilings, a full kitchen, a library, and a gorgeous terrace overlooking the beach.
Everything’s handled at the four-bedroom Villa Maria, located a short ride outside of Montego Bay. The villa comes with a housekeeper, a driver, and a private chef, and other perks include a saltwater pool, private beach access, and a rooftop dining area.
Post-Hurricane Maria, many of Puerto Rico’s resorts and rentals are reopen or plan to return soon. In the heart of Old San Juan, this funky, one-bedroom apartment is right down the street from the Castle of San Cristóbal. It’s a small but well-appointed space, with a kitchenette and a full-sized bedroom.
Turks and Caicos
The one-bedroom Cottonflower Suite is part of the larger Grace Shore Villas complex, which is great for those who don’t want to splurge for the islands’ five-star resorts, but still want amenities. Here you’ll find three pools and many lounge areas, plus reserved access on nearby Grace Bay Beach, a quick walk or bike ride away.
This three-bedroom cottage in Dunmore Town perfectly captures Harbour Island’s chic vibe, with interiors that make it feel like it belongs in a home design magazine. When you’re able to tear yourself away from your adorable digs, hop in the house golf cart and the beach is a four-minute ride away.