Thanksgiving Vacation Rentals and Early December 2026: The Staffed Caribbean Villas Still Open (as of October 30)
As of this morning, October 30, these are the staffed houses in Punta Cana, Providenciales and Anguilla that still had dates between Thanksgiving and December 13. Thanksgiving vacation rentals in the Caribbean sell in two directions at once. American families want four or five nights around Thursday November 26. A smaller group wants the quiet fortnight after it, before the holiday minimums close the islands to anything under a week. Both are on this page. Owners were asked on Thursday the 29th. The list has changed since a week ago. Two houses have come in. One has gone.
Where a line reads “confirmed”, the owner or the villa manager told us on the 29th. Where it reads “ask”, a hold was on the house that may clear by the next Friday. We update this page every Friday until December 13, and after that it gives way to our Caribbean overview.
What changed since October 23
Casa de Campo has left the list. Our twelve-bedroom house there took its Thanksgiving week and its first December fortnight in the days after the last update. We would rather delete it than leave a stale line. In its place, two additions. On Providenciales, Villa Paradisa on Long Bay Beach has given us its November and December minimums, which it had not the week before. So Turks and Caicos has its own section this week rather than a paragraph. And on Anguilla, Villa Nevaeh on Long Bay has come in beside The Beach House and Cerulean, which gives the island three staffed houses for the fortnight instead of two. Everything else below is Thursday’s answer. As before.
Why Thanksgiving vacation rentals and this fortnight exist, and who takes them
Hurricane season ends on November 30 and the festive minimums begin around December 18. Between those two dates lies the only stretch of the winter when a staffed villa on these islands takes a short stay at terms below the holidays. Thanksgiving week is the busy end of it, with American families on four- and five-night stays.
From the 30th to the 6th comes the quietest week of the whole winter in our records. Then the week of the 7th is when the Miami crowd arrives. Art Basel Miami Beach runs from December 4 to 6, and a share of its guests pair the fair with four nights on an island under two hours’ flight away. Punta Cana and Providenciales are the two we book for that pairing, and both are on this page.
Who takes the fortnight: grandparents who do not travel at Christmas, couples, families whose schools break late, and the Miami pair. Not, usually, families with children in school, which is why the big houses are open.
Punta Cana and Cap Cana: four nights at Thanksgiving, three after it
Villa Yarari Royale in Cap Cana has nine bedrooms for twenty, a butler, a chef cooking breakfast, lunch and dinner, pool and grounds crews and daily housekeeping, fifteen minutes from Punta Cana airport. Its listing sets a four-night minimum for November 20 to 29 and three nights from December 1 to 17, with seven nights from the 18th.
Villa Arrecife Royale has nine bedrooms on a golf-front lot four kilometres from the airport, with a property manager, a chef for three meals a day, a butler, a concierge, a housekeeper and a gardener. Its listing carries four nights from November 23 to December 2 and three from December 3 to 17, with the Thanksgiving week non-refundable once booked. Airport transfers are included. Our Punta Cana villas page lists the rest of the houses there.
Chefs at both houses cook a Caribbean Thanksgiving dinner on request. Turkey is ordered through the house by mid-November. Water in early December is at its warmest of the winter. Pools at both houses can be heated for an extra charge, which almost nobody needs.
Providenciales: five nights at Thanksgiving on Long Bay Beach
Villa Paradisa is the house that brings Turks and Caicos onto this page. Eight bedrooms and eight bathrooms on Long Bay Beach for sixteen guests, with a private chef, a butler, housekeeping and a concierge on call around the clock, round-trip airport transfers included, and two heated pools. Its listing puts the airport at about twenty minutes. Minimums are the useful part. Five nights from November 21 to 28, which covers Thanksgiving exactly. Then the listing jumps to five nights from December 18 to 25 and seven from December 26 to January 3, 2027.\
Long Bay is the kite-surfing coast of Providenciales, shallow and windward, with the water flat enough inside the bar for a family to walk a long way out. A group that wants the quiet south-east of the island and a short drive to Grace Bay for one dinner takes Paradisa. A group that wants to walk to the restaurants does not. Our full list of Turks and Caicos villas covers the other coasts. Their staffed houses confirm on a different day, so their lines are not on this page.
Anguilla: three houses, from four nights to seven
On Meads Bay, The Beach House has eight bedrooms, an assistant chef, food and beverage staff from seven in the morning to eleven at night, a butler and security day and night. By its listing it takes four nights in late November and mid-December, and seven from December 20.
Villa Nevaeh on Long Bay, Anguilla’s other Long Bay, is the addition. Nine bedrooms and eight bathrooms, fully staffed by its listing, with breakfast served daily, a chef, a butler and ground transfers included. Airport sixteen minutes. Ferry eleven. No November or December minimum appears on the listing, which in our experience means the owner sets it by the enquiry, usually four nights before the 18th.
Cerulean on Barnes Bay, the West End estate with a staff of eighteen, holds seven nights from November 1 to December 14. Seven nights fit the week of the 30th or the week of the 7th exactly. Anguilla is reached through St Maarten, by boat or a short flight, and the transfers at Cerulean and Nevaeh are included. The rest of the island’s houses are on our Anguilla villas page.
The Thanksgiving dinner, island by island
Of all the meals in the fortnight, Thanksgiving dinner is the one that needs planning before the flight. In Punta Cana the turkey is a special order through the house by the middle of November. Chefs cook it on the Thursday at five, and the Dominican dishes beside it are the part the family remembers. On Providenciales the chef at Paradisa shops on the island, where a large bird is a request rather than a shelf item. Dinner goes on the beach if the wind on Long Bay allows, which at five in the afternoon it often does not. Then the terrace.
On Anguilla the kitchen at The Beach House runs with an assistant chef and the food and beverage staff, so the dinner is ordered through the manager rather than cooked on a whim. At Nevaeh breakfast is already part of the service. Friday morning takes care of itself. We confirm the dinner with the deposit, not the week before, because a twenty-pound bird in the Caribbean in December is not on the shelf. By eleven the football is on the terrace television at both Punta Cana houses. Nobody has yet asked us to turn it off.
Getting there in the fortnight, which is easier than at Christmas
Punta Cana is the easy one: direct flights from the north-east and from Miami, the airport fifteen minutes from Yarari Royale and four kilometres from Arrecife Royale, transfers included at Arrecife. Providenciales has nonstop flights from the same cities, and Paradisa’s included transfer covers the twenty minutes from the airport in both directions.
Anguilla goes through St Maarten and the boat to Blowing Point, about twenty minutes on the water, then ten minutes to Meads Bay or eleven, by Nevaeh’s listing, to Long Bay. In the first fortnight of December the immigration halls on all three islands are a fraction of what they are on the Saturday before Christmas. One more reason to take it. Thanksgiving Wednesday is the exception. We book the transfers for the scheduled arrival plus an hour that day, and the chef holds dinner.
A hedge, because the fortnight has caught us before. Late systems do cross the Dominican Republic in the first week of December some years, two days of rain at Punta Cana and none on Anguilla or Providenciales. Chefs still cook, pools are still warm, and the families play dominoes with the butler. Rain in the Caribbean in December is rare after the first week. Not impossible. So we put the pool heating on the contract as an option, for exactly that reason.
How the three windows read, in one call
Thanksgiving week, November 26: Punta Cana and Cap Cana at four nights, Paradisa at five, The Beach House at four, Nevaeh on request. Quiet week, November 30 to December 6: every house on this page, at the shortest minimums of the winter, and the chefs at their least hurried. Art Basel week, December 7 to 13: Punta Cana or Providenciales for the Miami pair, under two hours’ flight, with the Thursday departure from the fair and the Monday return. Cerulean for the group that wants the estate and the seven nights. After the 13th the festive terms begin to apply, house by house, and this page stops.
Two rules of ours for the fortnight. We do not hold a house without a name and dates, because owners stopped allowing it after last December. And every availability line on this page is Thursday’s. By the time you read it on a Tuesday we check again before quoting. One hour.
Our full list of luxury Caribbean villas is the hub this page will point to once December has passed. Thanksgiving rentals elsewhere in our portfolio, Mexico above all, are on their own pages. Thanksgiving vacation rentals on this page are the Caribbean only, and only the fortnight.
On October 27 a family of fourteen from Connecticut asked us for Thanksgiving “on a beach the children can walk into, with a chef who will do the turkey”. We sent Villa Paradisa and The Beach House for November 25 to 30. They chose Long Bay on Providenciales for the shallow water and asked the owner for the Wednesday arrival; the five-night minimum fit it exactly. Same week we lost Casa de Campo to a group of twenty-two who had asked in September. That is the fortnight. Houses move in days.
What to know before you ask, in three lines
Weather before the holidays means the warmest sea of the winter, low eighties by day on all three islands and dry, with hurricane season over on November 30. Anguilla’s north coast has the steadier trade wind, Punta Cana the stiller air, and Long Bay on Providenciales the wind that the kite-surfers come for.
Minimums for Thanksgiving vacation rentals in 2026, by the listings, run four nights at Yarari Royale, Arrecife Royale and The Beach House, five at Paradisa, seven at Cerulean, and on request at Nevaeh. Festive minimums of seven to fourteen nights begin between December 18 and 26 depending on the house. And this page updates every Friday until December 13, with the date in the title. After the 13th it redirects to our Caribbean overview, so that a search in January lands on the right page.
Send the dates, the headcount and whether the week includes Miami, and within the hour we will tell you which of these houses is still open today, not last Thursday. Request a Tailored Selection
Angelica Crudo · Haute Retreats
Angelica runs editorial and search for Haute Retreats, the villa agency founded by Sabrina Piccinin, and keeps this page current with the team that confirms December dates with owners in Punta Cana, Providenciales and Anguilla every Thursday. Listings checked October 27, 2026; availability lines to be confirmed October 29.
