Section I · The Ranked Ten
From best to tenth.
Sorted by overall quality at the property’s price point. The hurricane-season clause and the New Year premium are addressed in the relevant entries.
No. I
The five-bedroom Gouverneur villa, hilltop sea-view.
Bedrooms: 5. Sleeps: 10. Neighborhood: Gouverneur. Peak rate: $42,000 to $72,000 / week (regular peak); $95,000 to $140,000 (Christmas/New Year). Included: housekeeper, gardener, daily breakfast service, two cars, airport transfers. Not included: chef, concierge, boat charter.
Why it ranks here: the Gouverneur position is the strongest on the island. Hilltop with sea views west to Pic Paradis on Saint Martin. Five king bedrooms, a 14-meter infinity pool, and outdoor dining sheltered from the trade winds. The kitchen runs for a chef without anyone losing the master. The owner replaced the AC system in 2023, which matters at this price point.
What we would change: the four-night New Year minimum is actually a seven-night minimum once the staff add-ons are quoted. Negotiate the airport transfer back into the rate at booking.
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No. II
The Pointe Milou four-bedroom, north terrace.
Bedrooms: 4. Sleeps: 8. Neighborhood: Pointe Milou. Peak rate: $32,000 to $52,000 / week; $75,000 to $115,000 (Christmas/New Year). Included: housekeeper, one car, daily breakfast. Not included: chef, second car, gardener visible (handled before guest hours).
Why it ranks here: Pointe Milou is the second-best neighborhood for sea orientation and the best for sunset position. The villa holds a four-king layout with proper en-suites and a kitchen that takes a chef seriously. Walk to Le Toiny restaurant is 12 minutes downhill. The drive back up the hill at 1am is the trip-design consideration.
What we would change: the infinity pool overflow returns to the catchment and recirculates faster than the filter handles. The pool gets cloudy by Wednesday in groups of 8. Ask the manager to schedule a mid-week service.
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No. III
The Lurin six-bedroom, Shell Beach side.
Bedrooms: 6. Sleeps: 12. Neighborhood: Lurin. Peak rate: $55,000 to $85,000 / week; $130,000 to $180,000 (Christmas/New Year). Included: full staff, two cars, daily breakfast, beach club walk-in at Shell Beach. Not included: chef, third car, boat days.
Why it ranks here: the only Lurin villa we keep on the list. Six bedrooms across two terraces, an 18-meter pool, and a position 9 minutes by car from Gustavia. The Shell Beach access matters during the New Year week when the harbor crowd makes Saline a parking problem. Walking to Shellona is 11 minutes downhill.
What we would change: the lower-terrace twin room is the room nobody wants. Designate it for the youngest in the group on arrival.
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No. IV
The Saline four-bedroom, dune-line.
Bedrooms: 4. Sleeps: 8. Neighborhood: Saline. Peak rate: $28,000 to $44,000 / week; $65,000 to $98,000 (Christmas/New Year). Included: housekeeper, gardener, one car. Not included: chef, beach service.
Why it ranks here: the closest villa we recommend to Saline beach. Three minutes walking to the sand on a path that does not require shoes. Four kings across one level, a 10-meter pool, and outdoor dining oriented south. Saline is quieter than Gouverneur or Pointe Milou for the late-night crowd.
What we would change: Wi-Fi at the property runs 30 to 50 Mbps. For a group with anyone working, hire the satellite backup ($90 per day).
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No. V
The Marigot five-bedroom, hillside.
Bedrooms: 5. Sleeps: 10. Neighborhood: Marigot. Peak rate: $30,000 to $48,000 / week; $72,000 to $110,000 (Christmas/New Year). Included: housekeeper, two cars, daily breakfast. Not included: chef, gardener visible.
Why it ranks here: Marigot is the value-pick neighborhood on the island. East-facing, sunrise water, and a 7-minute drive to Lorient beach. Five bedrooms across split terraces, a 12-meter pool, and a kitchen that handles 10. The property holds well at the regular-peak price. The Christmas premium is harder to justify here than at Gouverneur or Lurin.
What we would change: the trade winds run constant on the upper terrace. Add the canvas wind screens. The owner has them in storage.
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No. VI
The Gouverneur three-bedroom, sea-front.
Bedrooms: 3. Sleeps: 6. Neighborhood: Gouverneur. Peak rate: $22,000 to $34,000 / week; $48,000 to $72,000 (Christmas/New Year). Included: housekeeper, one car. Not included: chef, gardener.
Why it ranks here: small-group Gouverneur. Three king bedrooms, an 8-meter pool, and the same hilltop position as our number one at half the bedroom count. Right for two couples and a guest, or a couple with two adult children. Sea views and the same west-orientation sunset.
What we would change: the third bedroom is below the pool deck. Plumbing noise from the equipment room runs from 6am. Designate that room for the heaviest sleeper.
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No. VII
The Pointe Milou three-bedroom, east face.
Bedrooms: 3. Sleeps: 6. Neighborhood: Pointe Milou. Peak rate: $20,000 to $30,000 / week; $44,000 to $66,000 (Christmas/New Year). Included: housekeeper, one car. Not included: chef, beach service.
Why it ranks here: east-facing for sunrise water, three king bedrooms, and a 9-meter pool. The trade-off against the west-facing Pointe Milou villa above is the sunset position. The trade-off in your favor is the calmer late-night noise from Le Toiny.
What we would change: the kitchen handles breakfast and cocktails. Not dinner for six unless you hire the chef. Plan accordingly.
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No. VIII
The Lurin four-bedroom, Gustavia-adjacent.
Bedrooms: 4. Sleeps: 8. Neighborhood: Lurin. Peak rate: $26,000 to $40,000 / week; $58,000 to $88,000 (Christmas/New Year). Included: housekeeper, one car, daily breakfast. Not included: chef, second car.
Why it ranks here: the Gustavia walk-in advantage during the New Year week when the harbor is full and parking is the problem. Four kings, a 10-meter pool, and a 6-minute walk to Bonito or Black Ginger. The property gives up the open-sea view for the harbor proximity.
What we would change: the front terrace overlooks a road. Quieter from the back of the property.
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No. IX
The Colombier two-bedroom, west cliff.
Bedrooms: 2. Sleeps: 4. Neighborhood: Colombier. Peak rate: $15,000 to $24,000 / week; $34,000 to $52,000 (Christmas/New Year). Included: housekeeper, one car. Not included: chef.
Why it ranks here: the honeymoon pick on the list. Two king bedrooms, an 8-meter infinity pool, and the west-cliff position above Colombier beach. The walk to the beach is the 20-minute path that Colombier is known for. Drive time to Gustavia is 18 minutes. Right for two couples or a couple alone.
What we would change: the property is quiet enough that the morning trade winds are the only sound. Some people find that unsettling. Some find it the point.
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No. X
The Saint-Jean three-bedroom, hillside.
Bedrooms: 3. Sleeps: 6. Neighborhood: Saint-Jean. Peak rate: $18,000 to $28,000 / week; $40,000 to $62,000 (Christmas/New Year). Included: housekeeper, one car. Not included: chef, beach service.
Why it ranks here: the airport-adjacent pick. Saint-Jean is the wrong neighborhood for sleep if you are sensitive to small-plane noise (the Saint-Jean approach runs over the bay until roughly 7pm). The villa itself is sound: three kings, a 9-meter pool, and a 4-minute walk to Eden Rock’s beach. For a short stay this is the airport-convenient pick.
What we would change: request the upstairs bedrooms for anyone bothered by the approach. The lower-terrace bedroom hears every landing.
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