Best Caribbean Island to Visit in February 2027: St Barts, Turks and Caicos and the Presidents’ Day Houses Still Open

Every February the same three islands take most of the families we place. St Barts for the couples and the small groups who want the restaurants, Turks and Caicos for the families with children, Anguilla for the groups who want neither crowd. The best Caribbean island to visit in February is therefore a question with three answers, and the honest way to give them is by who is travelling, not by a ranking. Below each answer we have put the houses that still had the week of February 13 to 21, 2027 open when we asked the owners on Thursday, October 15. At the end are the Alps, for the family that cannot decide between sun and snow.

We update this page every Friday until the holiday. Where a line says “ask”, an owner had a competing request on the 15th and the 24-hour hold described further down is the way to settle it.

Why February, in one paragraph

Across the islands we work in, February is the driest month and the coolest. In the Caribbean that means days in the low eighties, sea at seventy-eight or seventy-nine, and a trade wind that keeps the evenings at a sweater rather than a fan. Hurricane season ended in November. Rain comes in ten-minute showers, two or three a week most years.

Sargassum, which troubles the eastern beaches from spring to autumn, has not started. It is also the month of Presidents’ Day, Monday February 15, 2027, in the same week as the British half term, so the villas with chefs fill from both sides of the Atlantic at once. Caribbean weather in February is the easy part. The week is the hard one. Book the week.

For couples and small groups who want the restaurants: St Barts

St Barts in February is the island at its most expensive and most alive, and for a couple or two couples it is the answer we give first. In Gustavia and St-Jean the restaurants are open and booked, the harbour is full. Up on the hills the villas are the quietest place on an island that is otherwise not quiet at all. Four of ours still have the week.

Villa Blanc Bleu in Gouverneur has six bedrooms that can be taken as three to six, a twenty-metre heated infinity pool with a built-in jacuzzi, and sits 2.6 kilometres from Gustavia and 3.8 from the airport. A concierge before and during the stay, daily cleaning except Sundays and holidays. Villa Eclipse in Camaruche, six bedrooms for twelve above Marigot Bay, has an infinity pool off the covered terrace, housekeeping daily except Sundays and French public holidays, and a private chef and butler on request.

Villa Antares in Mont Jean, five suites for ten, keeps its pool heated between 27 and 30 degrees from November to April, ten minutes from the airport and fifteen from Gustavia, with a concierge seven days. Villa Lao above Corossol, three bedrooms with a heated infinity pool and a seven-night minimum on its listing, is five to seven minutes from Gustavia.

Two things to know about St Barts in February. Most villas there include a concierge and housekeeping and offer the chef as an extra. Turks and Caicos houses work the other way round, so a family that wants a chef cooking every night should ask us for the chef at the contract. And the flight from the United States connects through St Maarten or San Juan onto a twenty-minute hop.

Our guide to how to get to St Barts from the US has the connections, and the best time to visit St Barts sets February against the rest of the year. Our full list of St Barts villas runs past a hundred houses, and the where to stay in St Barts guide covers the areas we have not named here.

For families with children, the best Caribbean island to visit in February is Turks and Caicos

For a family of ten to eighteen with children, Providenciales is the best Caribbean island to visit in February, and the reason is the staff. On Grace Bay and Long Bay the large beachfront houses, and at Leeward the canal houses, come with a chef, a butler or villa host and housekeeping as standard. The St Barts villas mostly do not. And the direct flights from the north-east make the Saturday arrival a morning rather than a day.

Footprints on Grace Bay, eight bedrooms with two butlers, a chef and a complimentary airport transfer, carries a five-night minimum from February 8 to March 5 on its listing and prices the holiday week on its own. Dune House on Long Bay, eight bedrooms with a villa host, a chef and two heated pools, five nights minimum in February. Cabuya at Leeward, six bedrooms on the channel with a dock, a villa manager, a chef, a butler and night security, five nights minimum. We have written the full comparison of the three coasts for this month separately, and the Turks and Caicos villas page holds the rest of the inventory.

For the group that wants neither crowd: Anguilla

Anguilla in February is the quiet answer. We give it to groups of adults who want the food of St Barts without the harbour and the beaches of Providenciales without the families. Reached through St Maarten by boat or short flight, the island has its beaches at Meads Bay, Shoal Bay and Long Bay at their calmest, and villas that are mostly staffed.

We hold fewer houses there than on the other two islands, and the February week at the large ones went in September this year. As of October 15 we have two four- and five-bedroom houses with the week open. We will name them on request rather than here, because the owners asked us to. Our guide to the best time to visit Anguilla and our Anguilla villas page carry the rest.

Barbados, which guests from Toronto and London ask about in the same breath, is warmer by a degree and further by two hours, and its west coast houses are the right answer for a group that wants a long stay rather than a week. We have left it out of the February list for that reason, not for lack of houses.

The 24-hour hold, and why it exists this year

Owners on all three islands stopped holding houses without a name in the autumn of 2025. After a December in which three families held the same villa for the same week and none of them signed, the rule changed. So this is how it now works with us. You send the dates, the headcount and the island. Within the hour we confirm against the owners’ calendars, not against this page, because the page is Friday’s and the calendar is today’s.

Then the owner grants a hold of 24 hours in your name, during which the contract goes out and nobody else can take the house. At the end of the 24 hours it is signed or it is released. We do not ask for a second hold on the same house. And we tell you if another family is in the queue, because in the week of Presidents’ Day they usually are.

What the week asks of the booking on each island

Five nights is the minimum on the Turks and Caicos houses named here for the holiday week, seven at Villa Lao in St Barts and the owners’ preference everywhere. Transfers are included at Footprints and at the St Barts villas as a meet-and-greet at the airport or the port; at the others we book the villa’s driver. Chefs in St Barts are an extra booked at the contract.

In Turks and Caicos they are on the staff and the food is billed at cost plus a shopping fee, fifteen per cent at Cabuya by its listing. Housekeeping in St Barts stops on Sundays and French holidays at every villa in this piece. In Turks and Caicos it does not stop, and the difference surprises American guests every year. We say it on the first call.

The alternative that is not an island: the Alps in the same week

A third of the families who call us in October about the Caribbean in February end up in the mountains. In Courchevel the same week is the half-term and Presidents’ Day week, and a staffed chalet with a chef, a chalet manager and a chauffeur is the same product with snow. Our Courchevel 1850 chalets page lists the twenty-two we represent, most at a seven-night minimum for February 13 to 20. From Geneva the transfer is two and a half hours by road or under one by helicopter. Families who choose the snow usually have children over ten who already ski. Families who choose the sun have a four-year-old, or a grandmother.

For the months on either side, our guides to the best Caribbean islands to visit in March and the best Caribbean islands to visit in June follow the same logic. By who is travelling, not by a list. After the holiday this page will be kept as the February guide, with the availability lines removed.

On October 9 a couple from Chicago asked us for “the best Caribbean island to visit in February, somewhere with real restaurants, no children”. We sent St Barts, Villa Eclipse and Villa Blanc Bleu, and on the 10th the owner of Eclipse granted a 24-hour hold. They signed on the 11th. A family of twelve from Boston asked the same question the same day with three children under eight. They were on Grace Bay at Footprints by the 13th, with the chef’s questionnaire already answered. Same question. Two islands. Both right.

Three questions we are answering this week

Which is the best Caribbean island to visit in February for weather alone? They are within two degrees of one another. St Barts, Turks and Caicos and Anguilla all sit in the low eighties by day with the sea at seventy-eight to seventy-nine, dry, with the trade wind steady. Barbados runs a degree warmer. Nobody chooses by the weather in February. They choose by the group. The best Caribbean island to visit in February is the one your group fits.

Is there anything still open for Presidents’ Day week 2027? As of October 15, yes, on all three islands, at the houses listed above with their holds noted. Large Grace Bay houses and the St Barts villas near Gustavia go first. By the end of October the choice on both narrows to what is left in this list.

Does this page update? Every Friday until February 12, with the date in the title, and then it stays as the February guide, like our March and June pages.

Tell us who is travelling, the dates and whether the group wants restaurants or a chef. Within the hour we will tell you which of these houses is open today and ask the owner for the hold. Request a Tailored Selection