Section I · The Ranked Twelve
From best to twelfth.
Sorted by what each pocket actually does well at its price point, on the peak winter week.
No. I
Peterborg peninsula north-shore villa, six-bedroom.
Bedrooms: 6. Sleeps: 12. Pocket: the Peterborg peninsula, the gated north-shore headland above Magens Bay. View and beach: Magens Bay and Atlantic view, infinity pool, short drive to the beach. Peak weekly rate: $55,000 to $100,000 / wk peak winter, listed through WIMCO and Exceptional Villas. Included: full staff or daily housekeeping, concierge, infinity pool, air-conditioning, welcome provisioning. Not included: private beach frontage, the East End boating life on foot, a marina.
Why it ranks here: the trophy pocket of St. Thomas. The Peterborg peninsula is the gated headland looking down on Magens Bay, regularly named among the best beaches in the world, and the large estate villas here give a group of 12 the island’s finest view and the most privacy. For the postcard outlook and the gated seclusion, nothing else on the island matches it.
What we would change: the villas sit high on the headland, so Magens Bay is a short drive down rather than a walk, and the beach itself is public. The view and the privacy are the draw; the drive to the sand is the trade.
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No. II
Botany Bay gated estate, west end, six-bedroom.
Bedrooms: 6. Sleeps: 12. Pocket: the Botany Bay gated community at the west end. View and beach: Caribbean-sunset view, infinity pool, gated beach access. Peak weekly rate: $48,000 to $90,000 / wk peak winter, listed through WIMCO and Villas of Distinction. Included: full staff or housekeeping, concierge, infinity pool, air-conditioning, gated security. Not included: the East End scene on foot, a marina at the door, a short airport transfer.
Why it ranks here: the gated-seclusion pick with the sunsets. The Botany Bay community occupies the quiet west end, with controlled access, large lots, and the west-facing sunset view the rest of the island cannot offer. Six bedrooms for a group of 12 that wants the gate, the privacy, and the evening light over the boating life of the East End.
What we would change: the west end is the furthest pocket from the airport and the restaurants, a 35 to 40-minute drive, so the seclusion costs convenience. The privacy and the sunsets are the draw; the distance is the trade.
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No. III
Nazareth Bay sea-front villa, East End, six-bedroom.
Bedrooms: 6. Sleeps: 12. Pocket: Nazareth Bay, on the East End near Red Hook. View and beach: sea-front with St. John view, infinity pool, rock-and-cove swim. Peak weekly rate: $42,000 to $82,000 / wk peak winter, listed through Exceptional Villas and WIMCO. Included: full staff or housekeeping, concierge, infinity pool, air-conditioning. Not included: a sandy beach at the door, the gated-estate setting, a marina at the door.
Why it ranks here: the sea-front pick near the boating hub. Nazareth Bay holds some of the island’s few true sea-front villas, with the St. John channel view and a short hop to the Red Hook ferries and marinas. Six bedrooms for a group of 12 that wants the water at the door and the East End boating life within reach.
What we would change: sea-front on St. Thomas usually means rock-and-cove swimming rather than a sandy beach, so confirm the water access suits the group. The frontage and the view are the draw; the rock entry is the trade.
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No. IV
Estate Dorothea hillside villa, northwest, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Estate Dorothea, the northwest hillside near Magens Bay. View and beach: north-shore-and-Magens view, infinity pool, short drive to the beach. Peak weekly rate: $34,000 to $68,000 / wk peak winter, listed through WIMCO and Exceptional Villas. Included: housekeeping, concierge, infinity pool, air-conditioning. Not included: beach frontage, the East End scene on foot, a marina.
Why it ranks here: the Magens-side value pick below the Peterborg rate. Estate Dorothea sits on the northwest hillside with the same north-shore outlook as Peterborg at a lower rate, and Magens Bay a short drive away. Five bedrooms for a group of 10 that wants the north-shore view without the peninsula premium.
What we would change: the hillside roads here are steep and winding, so a capable vehicle and a confident left-side driver are essential. The view and the rate are the draw; the hillside access is the thing to plan for.
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No. V
Sapphire and Smith Bay beachfront villa, East End, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Sapphire and Smith Bay, on the East End. View and beach: beachfront or short walk, pool, snorkeling reef. Peak weekly rate: $32,000 to $62,000 / wk peak winter, listed through Villas of Distinction and WIMCO. Included: housekeeping, concierge, pool, air-conditioning, beach access. Not included: gated seclusion, full staff as standard, a quiet beach in peak hours.
Why it ranks here: the rare walk-to-the-sand pick. Sapphire Beach on the East End is one of the few St. Thomas beaches with villas close enough to walk to, with a snorkeling reef and the St. John view, so a villa here gives a group of 10 actual beach access. Right for a group that puts the beach above the hillside view.
What we would change: Sapphire is a popular beach with a beach bar and day visitors, so it is livelier than the hillside pockets. The beach access is the draw; the daytime busyness is the trade.
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No. VI
Frenchman’s Bay villa, south shore, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Frenchman’s Bay, on the south shore near Charlotte Amalie. View and beach: harbor-and-sea view, pool, short drive to Morningstar beach. Peak weekly rate: $28,000 to $55,000 / wk peak winter, listed through Exceptional Villas and WIMCO. Included: housekeeping, concierge, pool, air-conditioning. Not included: beach frontage, gated seclusion, the East End boating life.
Why it ranks here: the town-convenient pick. Frenchman’s Bay sits on the south shore near Charlotte Amalie, so a villa here keeps the capital’s restaurants, the duty-free shopping, and the cruise harbor within a short drive. Five bedrooms for a group of 10 that wants the town and the south-shore beaches close at hand.
What we would change: the south shore is the busy, developed side of the island near the cruise port, so it is less serene than the north shore or the gated pockets. The convenience is the draw; the developed setting is the trade.
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No. VII
Water Island villa, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: Water Island, the small island off the south shore, reached by ferry. View and beach: sea view, pool, near Honeymoon Beach. Peak weekly rate: $26,000 to $50,000 / wk peak winter, listed through WIMCO and Villas of Distinction. Included: housekeeping, concierge, pool, air-conditioning. Not included: a car at the door, a quick mainland connection, a marina.
Why it ranks here: the quiet-island pick a ferry from town. Water Island is the small, car-light island a short ferry from the south shore, with Honeymoon Beach and a near-total absence of traffic, so a villa here gives a group of 10 genuine island calm minutes from St. Thomas. Right for a group that wants the off-island quiet without the distance.
What we would change: Water Island runs on the ferry and on golf carts, so the logistics are slower and a supply run means the boat. The quiet is the draw; the ferry dependence is the trade.
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No. VIII
Red Hook hillside villa, East End, five-bedroom.
Bedrooms: 5. Sleeps: 10. Pocket: the hills above Red Hook, on the East End. View and beach: St. John channel view, infinity pool, short drive to the beaches and ferries. Peak weekly rate: $26,000 to $52,000 / wk peak winter, listed through Exceptional Villas and WIMCO. Included: housekeeping, concierge, infinity pool, air-conditioning. Not included: beach frontage, gated seclusion, a marina at the door.
Why it ranks here: the boating-base pick. The hills above Red Hook overlook the St. John channel and sit minutes from the ferry dock, the marinas, and the charter boats, so a villa here is the easiest base for day trips to St. John and the British Virgin Islands. Five bedrooms for a group of 10 that wants to be on the water every day.
What we would change: Red Hook is the island’s busiest boating-and-bar hub, so the immediate area is lively rather than serene. The boating access is the draw; the busyness below the hill is the trade.
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No. IX
Mahogany Run north hillside villa, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: Mahogany Run, the north hillside by the golf course. View and beach: north-shore view, pool, short drive to Magens Bay. Peak weekly rate: $24,000 to $46,000 / wk peak winter, listed through WIMCO and Villas of Distinction. Included: housekeeping, concierge, pool, air-conditioning. Not included: beach frontage, full staff, gated seclusion.
Why it ranks here: the golf-and-north-shore value pick. Mahogany Run sits by the island’s golf course on the north hillside, with the north-shore view and Magens Bay a short drive away at a rate below the trophy peninsulas. Four bedrooms for a group of eight that wants the golf and the north-shore outlook.
What we would change: the villas here look over the golf course and the hillside rather than straight down at a bay, so the view is good rather than trophy. The golf and the rate are the draw; the lesser outlook is the trade.
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No. X
Cowpet Bay villa, East End, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: Cowpet Bay, on the East End near the yacht club. View and beach: bay view, pool, short walk or drive to the beach. Peak weekly rate: $22,000 to $44,000 / wk peak winter, listed through Exceptional Villas and WIMCO. Included: housekeeping, concierge, pool, air-conditioning. Not included: gated seclusion, full staff, a north-shore view.
Why it ranks here: the East End beach-and-yacht-club pick. Cowpet Bay sits by the St. Thomas Yacht Club with a calm beach and the East End amenities close, so a villa here gives a group of eight a quieter East End base with the beach and the boating nearby. Right for a group that wants the East End without the Red Hook bustle.
What we would change: Cowpet is a developed residential bay, so the immediate setting is suburban rather than secluded. The calm beach and the location are the draw; the developed surroundings are the trade.
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No. XI
Charlotte Amalie harbor-view villa, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: the hills above Charlotte Amalie, the capital. View and beach: harbor-and-town view, pool, a drive to the beaches. Peak weekly rate: $22,000 to $40,000 / wk peak winter, listed through WIMCO and specialist operators. Included: housekeeping, concierge, pool, air-conditioning. Not included: a beach on foot, gated seclusion, the East End boating life.
Why it ranks here: the harbor-view-and-town pick. The hills above Charlotte Amalie give a sweeping view of the historic harbor and the cruise ships, with the town’s restaurants and duty-free shops a short drive down. Four bedrooms for a group of eight that wants the harbor outlook and the town close.
What we would change: Charlotte Amalie is a working capital and cruise port, so the view includes the ships and the town is busy on port days. The harbor outlook and the town access are the draw; the cruise-port traffic is the trade.
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No. XII
East End hillside condo-villa, four-bedroom.
Bedrooms: 4. Sleeps: 8. Pocket: a gated East End hillside condominium development. View and beach: channel view, shared or private pool, short drive to the beach. Peak weekly rate: $20,000 to $38,000 / wk peak winter, the floor of this list, listed through Villas of Distinction. Included: housekeeping, concierge, pool, air-conditioning, gated security. Not included: a private beach, full staff, a standalone house.
Why it ranks here: the entry to a gated St. Thomas base at the floor of the band. A four-bedroom condo-villa on a gated East End hillside puts a group of eight inside the gate with the channel view and the beaches and ferries close at the lowest rate on this list. Right for a group that wants the security and the location without the standalone-villa rate.
What we would change: at this rate the property is a condominium unit rather than a private house, so the pool may be shared and the privacy is development-level. The gated location and the rate are the draw; the shared setting is the trade.
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