Section I · The Ranked Eleven
From best to eleventh.
Sorted by what each property does well at its price point, on the peak winter week, pocket by pocket.
No. I
Belmond La Samanna villa, Baie Longue.
Bedrooms: three- and four-bedroom private pool villas. Sleeps: 6 to 8 per villa. Pocket: Terres Basses, on a bluff above Baie Longue and Cupecoy. Beach access: direct on Baie Longue, the island’s longest beach, plus the resort beach club. Peak weekly rate: $70,000 to $120,000 / wk peak winter for a four-bedroom villa (a Belmond resort across 55 acres, the four-bedroom villas over 4,600 square feet, verified on belmond.com May 2026). Included: the resort service register, two pools, the spa, L’Oursin dining, daily housekeeping. Not included: a standalone private compound off the resort, off-site chef, a Dutch-side position.
Why it ranks here: the best service-backed villa booking on the island. The private pool villas sit on the bluff over Baie Longue with a wrap-around terrace and pool, and the full Belmond resort bench behind them on 55 acres. For a group of six to eight that wants a private villa with a resort spa and beach club on call and the best beach on the island at the door, nothing else matches the package.
What we would change: it is a resort villa, not a freestanding compound, so a group that wants total privacy and a single large house should drop to a Terres Basses standalone below. Confirm which villa category sits closest to the resort core if quiet matters.
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No. II
Terres Basses Baie Longue villa, six-bedroom.
Bedrooms: 6. Sleeps: 12. Pocket: Terres Basses, on or above Baie Longue. Beach access: direct or steps to Baie Longue. Peak weekly rate: $60,000 to $110,000 / wk peak winter, listed through Caribbean villa specialists and direct. Included: private pool, full staff (chef, housekeeper, manager), beach access. Not included: resort amenities on site, a Dutch-side position, a marina berth.
Why it ranks here: the trophy private standalone on the best beach. Baie Longue is the island’s longest, quietest beach, and a six-bedroom beachfront villa here is the configuration for a multi-family group of 12 that wants a fully staffed private house with a chef and the sand at the door. The Terres Basses standalones typically include a full staff bench, which is the local norm.
What we would change: Baie Longue has no shade structures or services, so it is beautiful and bare. Confirm the villa provides beach setup, because there is no beach club on this stretch to fall back on.
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No. III
Terres Basses Plum Bay villa, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Terres Basses, on Plum Bay (Baie aux Prunes). Beach access: direct or steps to the Plum Bay surf beach. Peak weekly rate: $45,000 to $85,000 / wk peak winter, listed through Caribbean villa specialists and direct. Included: private pool, full staff, beach access. Not included: resort amenities, calm swimming on a windy day, a Dutch-side position.
Why it ranks here: the sunset-and-surf pick in the enclave. Plum Bay faces west on the Terres Basses peninsula, with the island’s best sunsets and a beach that picks up enough swell for bodysurfing. Five bedrooms for a group of 10 that wants the quiet enclave and the evening light.
What we would change: the west-facing swell that makes Plum Bay fun can also make the swimming choppy on a windy winter day. For glassy calm, Baie Longue next door is the steadier bet.
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No. IV
Terres Basses Baie Rouge villa, six-bedroom.
Bedrooms: 6. Sleeps: 12. Pocket: Terres Basses, above Baie Rouge. Beach access: short walk or drive to the Baie Rouge beach and its two beach bars. Peak weekly rate: $50,000 to $95,000 / wk peak winter, listed through Caribbean villa specialists and direct. Included: private pool, full staff, sea view. Not included: direct beachfront in most cases, resort amenities, a Dutch-side position.
Why it ranks here: the view-and-beach-bar pick in the enclave. Baie Rouge holds a long red-tinged sand beach with the only real beach bars in Terres Basses, and the hillside villas above it carry big sea views and the gated quiet. Six bedrooms for a group of 12 that wants the view and a beach with a little life.
What we would change: most Baie Rouge villas are hillside, not beachfront, so the beach is a short walk or drive. Confirm whether the listing means beachfront or sea-view before you book on the beach.
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No. V
Terres Basses Long Bay villa, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Terres Basses, near Long Bay (Baie Longue’s far end). Beach access: direct or steps to the quiet end of Baie Longue. Peak weekly rate: $42,000 to $80,000 / wk peak winter, listed through Caribbean villa specialists and direct. Included: private pool, full staff, beach access. Not included: resort amenities, services on the beach, a Dutch-side position.
Why it ranks here: the quiet-end pick in the enclave. The Long Bay end of the Terres Basses beachfront is the most secluded stretch, where the original La Samanna villas sat, with the same long beach and even fewer neighbors. Five bedrooms for a group of 10 that wants the most private slice of the best beach.
What we would change: the seclusion means the nearest restaurant and shop are a drive, so a villa here leans hard on the included chef and the provisioning. Confirm the staff bench and the grocery arrangement.
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No. VI
Oyster Pond villa, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Oyster Pond, straddling the French and Dutch border on the east coast. Beach access: short walk to Dawn Beach or the Oyster Pond marina coves. Peak weekly rate: $35,000 to $68,000 / wk peak winter, listed through Caribbean villa specialists and direct. Included: private pool, staff, sea view. Not included: the Terres Basses beaches on foot, a calm-water beach at the door, resort amenities.
Why it ranks here: the marina-and-sailing pick on the east coast. Oyster Pond is a protected harbor on the Atlantic side, the departure point for the day sail to St. Barts, with hillside villas over the marina and Dawn Beach close by. Five bedrooms for a group of 10 that builds the week around the boat and the St. Barts day trip.
What we would change: the east coast faces the Atlantic, so the water is livelier and the beaches smaller than the west. The sailing access is the asset; the calm-beach swimming is on the other side of the island.
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No. VII
Orient Bay villa, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Orient Bay (Baie Orientale), the French northeast coast. Beach access: short walk or drive to the Orient Bay beach and its beach clubs. Peak weekly rate: $30,000 to $58,000 / wk peak winter, listed through Caribbean villa specialists and direct. Included: private pool, staff, sea view. Not included: the Terres Basses calm, a private beach, resort amenities.
Why it ranks here: the beach-scene pick on the lively side. Orient Bay is the island’s most animated beach, a two-kilometer arc of sand lined with beach clubs and watersports, the St-Tropez of the Caribbean in feel. Five bedrooms for a group of 10 that wants the day-club energy and the action over the gated quiet.
What we would change: Orient Bay is busy and public, so the villas back from a scene rather than front a private beach. For privacy and calm, Terres Basses beats it; for the party, this is the pick.
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No. VIII
Anse Marcel villa, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Anse Marcel, the protected cove on the French north tip. Beach access: short walk to the Anse Marcel beach and marina. Peak weekly rate: $30,000 to $56,000 / wk peak winter, listed through Caribbean villa specialists and direct. Included: private pool, staff, cove access. Not included: the Terres Basses scene, a long beach, resort amenities on site.
Why it ranks here: the protected-cove pick on the quiet north. Anse Marcel is a sheltered bay with a marina and a small beach, the most secluded developed pocket on the island, with the hiking to Grandes Cayes and the offshore islets close by. Five bedrooms for a group of 10 that wants seclusion and calm water.
What we would change: Anse Marcel is at the far north end, so it is a drive from the Terres Basses beaches and the Dutch-side services. The seclusion is the asset; the distance is the cost.
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No. IX
Dawn Beach villa, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Dawn Beach, the Dutch-side east coast. Beach access: direct or steps to Dawn Beach. Peak weekly rate: $28,000 to $54,000 / wk peak winter, listed through Caribbean villa specialists and direct. Included: private pool, staff, beach access. Not included: the French restaurant scene on foot, calm Atlantic swimming, the Terres Basses enclave.
Why it ranks here: the Dutch-side beachfront pick with the St. Barts sunrise. Dawn Beach faces east toward St. Barts, with good morning light, a reef close in for snorkeling, and beachfront villas at rates below the French-side enclave. Five bedrooms for a group of 10 that wants beachfront on the Dutch side and easy airport access.
What we would change: the Atlantic-facing reef break means the swimming can be rough on a windy day, and the Dutch side trades the French restaurant culture for the casino-and-marina scene. Confirm the reef and surf conditions for your dates.
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No. X
Cupecoy and Lowlands villa, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: Cupecoy, the Dutch-side cliffs near the Terres Basses border. Beach access: short walk to the Cupecoy cliff beaches. Peak weekly rate: $22,000 to $44,000 / wk peak winter, listed through Caribbean villa specialists and direct. Included: private or shared pool, concierge, sea view. Not included: a full staff bench in many cases, a quiet enclave, calm family swimming.
Why it ranks here: the value-and-airport pick near the border. Cupecoy sits on the Dutch-side cliffs minutes from both the airport and the Terres Basses gate, with cliff-backed beaches and condominium-style villas at lower rates. Four bedrooms for a group of eight that wants proximity to everything at a sensible price.
What we would change: Cupecoy is built up with resort condominiums, so many villas here are units in a complex rather than standalone houses, and the beaches sit below eroding cliffs. Confirm the villa is genuinely private and the beach access is safe.
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No. XI
Pelican Key villa, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: Pelican Key, the Dutch-side peninsula above Simpson Bay. Beach access: short drive to Simpson Bay and Mullet Bay beaches. Peak weekly rate: $18,000 to $38,000 / wk peak winter, the floor of this list, listed through Caribbean villa specialists and direct. Included: private pool, sea view, concierge. Not included: beach frontage, full staff, the French-side calm.
Why it ranks here: the entry to a private villa at the floor of the St. Martin band, close to the marina life. Pelican Key is a residential peninsula above Simpson Bay with big lagoon-and-sea views, minutes from the airport, the marinas, and the restaurant strip. Four bedrooms for a group of eight that wants a private pool and the Dutch-side action without the trophy rate.
What we would change: Pelican Key sits under the Princess Juliana flight path, so there is aircraft noise through the day, and the staff bench at this rate is concierge rather than full-time. Confirm both before booking.
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