Where to Stay in Anguilla for the Festive Season: Little Bay, Long Bay or the East End

For the festive season in Anguilla, stay at Little Bay if the group wants a private resort with everything included, on Long Bay if it wants the beach at the door, at the east end if it wants the island rather than the resort, and above Pelican Bay if it is two. The island is about sixteen miles long and three wide, and flat enough that no address is more than twenty-five minutes from another, so the choice is about the family, not the map. See all our Anguilla villa rentals.

The holidays are Anguilla’s season. In August 2026 the Virtuoso travel network ranked Anguilla third in the world and first in the Caribbean for festive travel, from December 15 to January 7, behind only the United States and Mexico; West End, Anguilla, was No. 8 among individual destinations. Anguilla is one of our six signature Caribbean destinations for winter 2026–27, with Turks and Caicos, St Barts, Barbados, the Dominican Republic and St Martin. The island welcomed 81,907 stayover visitors in the first half of 2026, 19.9% more than a year earlier, and 73.8% of them came from the United States, according to the Anguilla Statistics Department.

This guide is built around the three addresses where we place festive groups, the private cove at Little Bay, the long beach at Long Bay and the quieter east end around Island Harbour and The Valley, with a fourth, Pelican Bay on the west, for the smaller party. It ends with the arrival and the festive minimums, because they decide whether the house you want is still available.

Why the beach is the whole decision on a flat island

On St Barts the villa chooses the view, and here it chooses the beach, which is the whole day. A festive fortnight is fourteen days on one beach, with the boat day, the spa, the tennis court and the chef’s table arranged around it. So the choice comes down to three questions: a private cove reached by a path, a long open beach, or a reef-protected bay on the windward side; a compound with its own household, an estate on the sand with a chef included, or a family villa with housekeeping and the rest arranged; and whether nothing should be decided on the island, or the family runs its own fortnight with the household behind it.

Our guide to the best beaches in Anguilla sorts the sand; this one sorts the addresses. Meads Bay and Barnes Bay, the famous names on the west, are beaches for the day as much as places to stay, and they are a short drive from every address below.

Little Bay is the private cove with everything included

Little Bay is a small cove on the north shore, under cliffs, reached by a path from the land and by boat from the sea, with water protected enough for the island’s best snorkeling and its calmest swim. It is also the address of the most complete festive house on the island, and the first one we propose to a group of twenty.

ÀNI Anguilla

Above Little Bay · 10 bedrooms · sleeps 20

Two acres above the cove: two contemporary villas, North and South, with two heated pools, cliff-edge hot tubs, a tennis court, a spa treatment room, a gym with a Peloton bike, paddleboards, snorkeling gear and mountain bikes, and a four-minute walk down to the beach. It also rents with fewer bedrooms.

It suits multigenerational groups of twelve to twenty who want nothing decided on the island, and families with older parents. It does not suit a group that wants a long open beach, or one that wants to run its own kitchen.

Staff and service: all-inclusive, with up to twenty staff around the clock, a private chef, butler service and daily housekeeping; meals in a different setting each day, drinks, up to six spa treatments a day, tennis lessons and the airport transfers are part of the stay. The festive block runs from December 18 to January 10 on a seven-night minimum.

Long Bay is the long beach with the estates on it

Long Bay is the west-facing beach between Meads Bay and Barnes Bay: soft sand, calm water, sunsets straight down the beach and a handful of estates set directly on it. For the family that wants the beach as the front garden, this is the address, and the one our returning festive families most often ask for again.

Villa Nevaeh

Long Bay · 9 bedrooms · sleeps 18

A gated estate on nearly half a mile of Long Bay beachfront: a main house with five king suites, a guest house with three bedrooms and a freestanding suite, a heated infinity pool, a heated plunge pool off one suite, a home theater, a golf simulator, a tennis and basketball court, a gym and a hot tub. It can also be taken with five to eight bedrooms.

Staff and service: fully staffed, with a private chef, butler service and maid service, full breakfast and the ground transfers included.

Villa Sand

Long Bay · 5 bedrooms

The same beach for a single family: four king bedrooms and a children’s room with bunk beds, an infinity-edge pool with a hot tub, an alfresco dining pavilion and a path from the terrace straight to the sand, with shared tennis courts and a fitness center.

Staff and service: daily maid service and a concierge included, and a chef arranged for the stay. The festive minimum is seven nights from December 21 to January 3.

The east end is for the family that wants the island

The east end is the windward, working and quiet side: the fishing village of Island Harbour, The Valley a few minutes inland, the reef-protected water off Shoal Bay East and the trade wind that keeps the afternoons cool. It is the version of the festive fortnight where the family runs its own house, with the household behind it.

Sandcastle Villa and Beach House

The Valley · 9 bedrooms · sleeps 20

A five-bedroom villa and a four-bedroom beach house on the sand, taken together for twenty, with two pools, a hot tub, kayaks, paddleboards, a beach volleyball court and a fire pit.

Staff and service: daily maid service, butler service, a private chef for three meals a day and a 24-hour concierge.

Villa Amarilla

Island Harbour · 5 bedrooms · sleeps 10

Five suites above the Atlantic at Island Harbour, with a heated infinity pool and spa at the edge of the terrace, a separate gym cottage and a media room. The coves are a walk away and Shoal Bay a two-minute drive.

Staff and service: daily housekeeping and a concierge included; a private chef, a butler, transfers and babysitting arranged for the stay.

Pelican Bay is the fourth address, for two

For couples and two-couple groups, and for the honeymoons that a good share of our festive requests turn out to be, the west end above Pelican Bay is the fourth address. Edge Anguilla is a two-story oceanfront house with five bedrooms for ten, a private pool and hot tub, and a small cove a few steps away, with a concierge and daily maid service included and the chef arranged. For couples arriving in late December, the west end’s smaller houses and Villa Amarilla are the two we propose first.

The four addresses side by side

The arrival decides the first day

This winter there are two ways in. American Airlines flies nonstop to Anguilla from Miami, in about three hours, and from mid-December 2026 BermudAir’s AnguillAir flies nonstop to Anguilla’s Clayton J. Lloyd International Airport from Boston and from Newark twice a week, on Mondays and Fridays, and from Baltimore-Washington on Mondays, with one-stop flights via Providenciales from Newark, Baltimore-Washington, St Pete–Clearwater in Florida and, from December 19, Toronto. From anywhere else, most guests fly to St Martin and cross by private boat in about 25 minutes to Blowing Point, which is a short drive from the west-end houses; the east end is about twenty minutes across the island. In the last week of December the boats and the seats fill the way the villas do, so we book the crossing with the house, and the household meets the boat. Our guide to how to get to Anguilla has the routes.

What the festive minimums mean for where to stay

Over Christmas and New Year most of the houses we checked in October 2026 ask for seven nights: ÀNI Anguilla from December 18 to January 10, Villa Sand from December 21 to January 3, and Villa Le Bleu and The Beach House over the two holiday weeks. Some of the largest estates are taken as a fortnight. Both figures for ÀNI and Villa Sand come from the rate calendars on the listings. The larger estates on Long Bay and the east end are often committed months ahead by returning families, and what remains in October is real but thin. We suggest booking Christmas, New Year and Easter nine to twelve months ahead, and January to March six to nine months ahead; shoulder and summer dates can often be confirmed within 60 days.

More Anguilla guides

• Anguilla villa rentals
  Our collection, beach by beach, with a shortlist in 24 hours.
• Christmas and New Year villas
  Our festive collection across the Caribbean and beyond.
• How to get to Anguilla
  The new nonstop flights and the boat from St Martin.
• The best time to visit Anguilla
  The seasons month by month, and when to book.

Anguilla for the festive season: your questions answered

Updated October 2026. Villa details and festive minimums are taken from each villa’s listing, checked in October 2026; festive ranking from Virtuoso, reported by Caribbean Journal; visitor figures from the Anguilla Statistics Department, reported by TravelDailyNews; AnguillAir routes reported by TravelDailyNews.