Anguilla for the Festive Season: Where to Stay in Anguilla — Little Bay vs Long Bay vs the East End
Anguilla is sixteen miles long, three miles wide, and flat enough that no address on it is more than twenty-five minutes from any other. Which is exactly why the question of where to stay in Anguilla matters more here than on islands with mountains and towns: with no geography to force the choice, the choice is entirely about the family. A group of eighteen with three generations wants one thing from the festive fortnight; a couple on a honeymoon wants another; a family with four children under ten wants a third. The island has an answer to each, and the answers are on different coasts.
This piece is the decision. It is built around the three addresses where we actually 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 ferry, because on Anguilla the arrival is a third of the answer to where to stay in Anguilla, and with the festive minimums, because they are what decide whether the answer is still available.
Why the address is the decision on a flat island
On St Barts the villa chooses the view; on the Amalfi Coast it chooses the steps; on Anguilla it chooses the beach, and the beach is the whole day. The island has some of the most beautiful sand in the Caribbean and almost nothing else to do with it but be on it, which is the point of the island and the reason its returning families return. A festive fortnight here — whatever the answer to where to stay in Anguilla — is fourteen days on one beach, with the boat day, the spa, the tennis court and the chef’s table arranged around it.
So where to stay in Anguilla is really three questions. What kind of beach — a private cove reached by a path, a mile of open sand, or a reef-protected bay on the windward side? What kind of house — a compound with its own household of twenty, an estate on the sand with a chef included, or a family villa with housekeeping and a concierge and the rest arranged? And what kind of festive season — the fully inclusive kind where nothing is decided on the island, or the domestic kind where the family runs its own fortnight with the household behind it?
Our guide to the best beaches in Anguilla sorts the sand; this piece sorts the addresses. Meads Bay and Barnes Bay, the famous names on the west, are beaches for the day here rather than places we place festive houses, and they are twenty minutes from every address below.
Little Bay — the private cove, and the all-inclusive answer to where to stay in Anguilla
Little Bay is a small, steep-sided cove on the north shore, reached from the land by a path down the cliff and from the sea by boat, with water so protected that it is the island’s best snorkelling and its calmest swim. It is also the address of the most complete festive house on the island, and the first answer we give to where to stay in Anguilla for a group of twenty.
ÀNI Anguilla sits on two acres above the cove: two contemporary villas, North and South, with ten bedrooms for up to twenty guests across four ocean-view suites, two ocean-view guestrooms and four guestrooms, two heated pools, cliff-edge hot tubs, a tennis court, a spa treatment room, a gym with a Peloton bike, paddleboards, snorkelling gear and mountain bikes, and a four-minute walk down to the secluded beach.
What makes it the answer for a certain kind of family is the household: up to twenty staff around the clock, a private chef, butler service and housekeeping with daily laundry, and an all-inclusive rate that covers breakfast, lunch and dinner in a different setting each day, free-flow beverages, up to six spa treatments daily, tennis lessons, guided tours, cooking classes, a beach barbecue and the airport transfers. The estate also rents in six-, seven-, eight- and nine-bedroom configurations. The festive block runs December 18 to January 10 on a seven-night minimum.
Who Little Bay suits when deciding where to stay in Anguilla: multigenerational groups of twelve to twenty who want nothing decided on the island, hosts who want a private resort with the family’s name on the gate, and families with older parents for whom the flat path to the beach is a consideration. Who it does not: a family that wants a mile of open sand to walk, or a group that wants to run its own kitchen.
Long Bay — the mile of sand, and the estate answer to where to stay in Anguilla
Long Bay is the west-facing beach between Meads Bay and Barnes Bay: nearly half a mile of the softest sand on the island, calm water, sunsets straight down the beach, and a handful of estates set directly on it. For the family that wants the beach to be the house’s front garden rather than a walk from it, this is where to stay in Anguilla, and it is where our returning festive families most often ask to go back.
Villa Nevaeh is the estate for the large festive group: nine bedrooms across a main house with five king suites, a guest house with three and a freestanding suite, for up to eighteen guests, directly on the beach with a heated infinity pool, a private heated plunge pool off one suite, a home theatre, a golf simulator, tennis and basketball courts, a gym, a hot tub, and the kayaks, paddleboards and snorkelling gear on the sand. The household is complete and included — a private chef, butler service and maid service, with full breakfast service and the ground transfers in the rate — which for a party of eighteen at Christmas is the difference between a holiday and a logistics exercise.
Villa Sand is the same beach for a single family deciding where to stay in Anguilla: four king master bedrooms and a children’s room with bunk beds for up to ten, an infinity-edge pool with a jacuzzi, an alfresco dining pavilion, a gourmet kitchen, private beachfront with a path straight from the terrace to the sand, shared tennis courts and a fitness centre, and daily maid service and a concierge included, with the chef arranged for the stay. The festive minimum is seven nights over December 21 to January 3.
Who Long Bay suits: families with children who want to be on the sand from breakfast, groups who want the sunset from the pool, and anyone deciding where to stay in Anguilla for whom the beach itself is the reason to come. Who it does not: guests who want the reef-protected water of the north shore, or couples who want to be far from other estates.
The East End — Island Harbour, The Valley and the domestic answer to where to stay in Anguilla
The east end is the windward side, the working side, and the quiet side: the fishing village at Island Harbour, the capital at The Valley a few minutes inland, the reef-protected water off Shoal Bay East to the west of it, and the trade wind that keeps the afternoons cool. It is the answer to where to stay in Anguilla for families who want the island rather than the resort — the version of the festive fortnight where the family runs its own house and the household runs it with them.
Sandcastle Villa and Beach House is the east end’s estate: a five-bedroom villa and a four-bedroom beach house on the sand at The Valley, rentable together for twenty, with two pools — one lit for the evening — a jacuzzi, kayaks, paddleboards, snorkelling gear, a beach volleyball court, a fire pit and a private “zen den” on the beach itself. The household is included and complete: daily maid service, butler service, a private chef for three meals a day, twenty-four-hour concierge and a house man on the beach for the day’s essentials. It is the house for a family that wants the estate scale of Long Bay with the east end’s quiet.
Villa Amarilla, at Island Harbour, is the domestic answer at family scale: five suites — Pearl, Emerald, Sapphire, Turquoise and Coral — for up to ten, with a sofa bed in the media room, a heated infinity pool with a spa that runs to the edge of the terrace above the Atlantic, a separate gym cottage, a media room, alfresco dining and shower, and nine thousand square feet of house. Daily housekeeping seven days a week and a concierge are included; the private chef, butler, transfers and babysitting are arranged for the stay. The beach coves are a walk, and Shoal Bay is a two-minute drive.
Who the east end suits: families who want to shop the fishing boats and cook, guests who prefer the trade wind to the leeward calm, and anyone deciding where to stay in Anguilla who wants the island’s own rhythm. Who it does not: groups for whom the west’s sunsets and calm water are the point.
Pelican Bay — where to stay in Anguilla for the smaller party
For couples and two-couple groups, and for the anguilla honeymoon that a surprising share of our festive enquiries turn out to be, the west end above Pelican Bay is the fourth address. Villa Beaches Edge is a two-storey oceanfront house with five en-suite bedrooms for ten, a private pool and hot tub, a small secluded cove a few steps away and the west’s beaches a short drive, with a concierge and daily maid service included and the chef arranged. Its neighbour can be rented alongside it for a combined ten bedrooms, which is how one family’s honeymoon house becomes the following year’s festive house for twenty.
An anguilla honeymoon in the festive fortnight is a particular thing: the island at its most festive and its most private at once, the boat day to the cays, dinner from the chef on the terrace, and no scene to attend. For couples deciding where to stay in Anguilla in late December, the west end’s smaller houses and the east end’s Villa Amarilla are the two we propose first.
Where to stay in Anguilla — the addresses, side by side
| Address | Beach | House type | Household | Best for |
|---|---|---|---|---|
| Little Bay (north) | Private cove, calmest water, snorkelling | Compound of two villas, 6–10 BR | All-inclusive, up to 20 staff | Groups of 12–20, hosts, older parents |
| Long Bay (west) | Half a mile of soft sand, sunsets | Beachfront estates, 5–9 BR | Chef and butler included (Nevaeh); arranged (Sand) | Families with children, beach-first groups |
| East End (Island Harbour, The Valley) | Reef water, trade wind, fishing village | Estate for 20 or family villa for 10 | Chef included (Sandcastle); arranged (Amarilla) | Domestic festive season, island over resort |
| Pelican Bay (west) | Small cove, west beaches nearby | Oceanfront house for 10 | Concierge and housekeeping; chef arranged | Couples, honeymoons, two-couple groups |
Getting there — the ferry from St. Martin decides the arrival
There is no long-haul flight into Anguilla, and in the festive fortnight the arrival is a third of the decision about where to stay in Anguilla. Private aviation lands on the island directly; the scheduled routes come through St. Martin, followed by a private boat transfer of around twenty minutes or the public ferry from the French side, or by a short hop from St. Martin’s airport. Our guide to how to get to Anguilla covers the routings from New York, Boston and Miami, and the transfer is booked with the house — because in the last week of December the private boat slots and the hop’s seats fill the way the villas do.
Where to stay in Anguilla changes the arrival slightly. Little Bay and the west-end houses are closest to the ferry terminal at Blowing Point; the east end is a twenty-minute drive across the island, which for a family arriving with small children after a full day of travel is a detail worth knowing. On every house above, the household meets the boat.
What where to stay in Anguilla costs in festive minimums
The festive season on Anguilla runs on minimums, and they are the practical constraint on where to stay in Anguilla in December. ÀNI Anguilla holds a seven-night minimum across December 18 to January 10 at its festive rate. Villa Sand asks seven nights over December 21 to January 3.
The larger estates on Long Bay and the east end are typically committed as a block by returning families months ahead, and what remains in late September is real but thin — which is why this decision belongs in September rather than November. Our guide to the best time to visit Anguilla covers the calendar for the rest of the year, and our Anguilla experiences guide is the reference for what the concierge builds around the beach.
Frequently asked questions
Where to stay in Anguilla with young children? Long Bay. The sand is soft, the water is calm, the estates sit directly on the beach, and Villa Sand has a bunk room built for exactly this. Little Bay’s path down the cliff is manageable but not a stroller.
Where to stay in Anguilla for a large multigenerational group? Little Bay for the all-inclusive compound with up to twenty staff, or Long Bay’s Villa Nevaeh and the east end’s Sandcastle estate, both with a chef included and room for eighteen to twenty.
Where to stay in Anguilla for a honeymoon? The west end above Pelican Bay, or Villa Amarilla at Island Harbour: five-bedroom houses that work beautifully for two, with the chef and the boat day arranged and no scene to attend.
How do we get to Anguilla for the festive season? Private aviation direct, or scheduled flights to St. Martin followed by a private boat transfer of around twenty minutes or a short hop. We book the transfer with the house; in late December the slots are the constraint.
What are the festive minimums? Seven nights on the houses above over the Christmas–New Year block, with the largest estates typically committed as a fortnight by returning families. September is the last month with real choice.
Is Meads Bay not an option for where to stay in Anguilla? It is the island’s most famous beach and twenty minutes from every address in this piece; we send families there for the day. The festive houses we place are on Little Bay, Long Bay, the east end and Pelican Bay, and our Anguilla collection is the complete inventory.
Choosing the address
Little Bay for the family that wants nothing decided on the island; Long Bay for the family that wants the beach at the door; the east end for the family that wants the island itself; Pelican Bay for two. Where to stay in Anguilla is the only decision the festive fortnight really asks of you, because once the address is chosen the island does the rest — and the addresses are committing now.
Request a Tailored Selection — tell us your group, your dates, whether the beach or the household matters more and how you plan to arrive, and a concierge will return a festive shortlist from our Anguilla collection and the wider Caribbean collection, with the minimums and the transfer already confirmed, usually within one business day.
