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    ARRIVAL > DEPARTURE
    September 2026
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    October 2026
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    Everywhere > Caribbean > U.S. Virgin Islands > St John > Chocolate Hole

    Chocolate Hole Villas & Luxury Vacation Rentals

    Luxury Villa Rentals for 2+ people

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    September 2026
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    October 2026
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    2 GUESTS
    DISPLAYING PROPERTIES 1 to 24 of 3876
    DISPLAYING PROPERTIES 1 to 24 of 3876
    • Sugar Apple Villa - 1
      Sugar Apple Villa - 2
      Sugar Apple Villa - 3
      Sugar Apple Villa
      Kira Island, Turks & Caicos
      8
      4
      4 + ½
      from $1,000 / night
    • Farniente - 1
      Farniente - 2
      Farniente - 3
      Farniente
      Cupecoy, St Martin
      8
      4
      4 + ½
      from $1,022 / night
    • Ebbtide - 1
      Ebbtide - 2
      Ebbtide - 3
      Ebbtide
      Fitts Village, Barbados
      8
      4
      4
      from $1,070 / night
    • Villa Nuit Jade - 1
      Villa Nuit Jade - 2
      Villa Nuit Jade - 3
      Villa Nuit Jade
      Les Terres Basses, St Martin
      10
      5
      5
      from $1,200 / night
    • Fresh Wind - 1
      Fresh Wind - 2
      Fresh Wind - 3
      Fresh Wind
      Apes Hill Club, Barbados
      8
      4
      4
      from $1,200 / night
    • Casa Marazul - 1
      Casa Marazul - 2
      Casa Marazul - 3
      Casa Marazul
      Cancun, Riviera Maya
      8
      5
      5 + ½
      from $1,250 / night
    • Casa Uno Mas - 1
      Casa Uno Mas - 2
      Casa Uno Mas - 3
      Casa Uno Mas
      La Serenata, Punta de Mita (Punta Mita)
      10
      4
      4 + ½
      from $1,250 / night
    • Libellule - 1
      Libellule - 2
      Libellule - 3
      Libellule
      Les Terres Basses, St Martin
      10
      5
      5 + ½
      from $1,272 / night
    • One - 1
      One - 2
      One - 3
      One
      Westland Heights, St. James
      10
      5
      5 + ½
      from $1,350 / night
    • Esprit de la Mer - 1
      Esprit de la Mer - 2
      Esprit de la Mer - 3
      Esprit de la Mer
      Les Terres Basses, St Martin
      10
      5
      5 + ½
      from $1,400 / night
    • 10% DISCOUNT!
      Beau Rivage - 1
      Beau Rivage - 2
      Beau Rivage - 3
      Beau Rivage
      Les Terres Basses, St Martin
      6
      3
      3 + ½
      from $1,500 / night
    • Vittoria - 1
      Vittoria - 2
      Vittoria - 3
      Vittoria
      Simpson Bay, St Martin
      12
      6
      5
      from $1,515 / night
    • Villa Langosta - 1
      Villa Langosta - 2
      Villa Langosta - 3
      Villa Langosta
      Cancun, Riviera Maya
      16
      6
      6 + ½
      from $1,600 / night
    • Avanti - 1
      Avanti - 2
      Avanti - 3
      Avanti
      Les Terres Basses, St Martin
      10
      5
      5 + ½
      from $1,655 / night
    • Banyan House - 1
      Banyan House - 2
      Banyan House - 3
      Banyan House
      Porters, Barbados
      10
      5
      5 + ½
      from $1,800 / night
    • Turtle Nest - 1
      Turtle Nest - 2
      Turtle Nest - 3
      Turtle Nest
      Les Terres Basses, St Martin
      8
      4
      4 + ½
      from $1,838 / night
    • Casa Buena Suerte - 1
      Casa Buena Suerte - 2
      Casa Buena Suerte - 3
      Casa Buena Suerte
      Soliman Bay, Riviera Maya
      12
      6
      6 + ½
      from $1,850 / night
    • Aqua Dream - 1
      Aqua Dream - 2
      Aqua Dream - 3
      Aqua Dream
      Indigo Bay, St Martin
      12
      6
      6
      from $1,929 / night
    • Infinity Blue - 1
      Infinity Blue - 2
      Infinity Blue - 3
      Infinity Blue
      Les Terres Basses, St Martin
      16
      8
      8
      from $1,980 / night
    • Villa Reve Bleu - 1
      Villa Reve Bleu - 2
      Villa Reve Bleu - 3
      Villa Reve Bleu
      Black Garden, Anguilla
      8
      4
      5 + ½
      from $2,000 / night
    • La Bulle - 1
      La Bulle - 2
      La Bulle - 3
      La Bulle
      Corossol, St. Barts
      8
      4
      4
      from $2,143 / night
    • Karma Bay - 1
      Karma Bay - 2
      Karma Bay - 3
      Karma Bay
      Tryall Club, Jamaica
      12
      6
      6
      from $2,164 / night
    • The Dove House - 1
      The Dove House - 2
      The Dove House - 3
      The Dove House
      Agios Stefanos, Greece
      12
      6
      6 + ½
      from €1,929 / night
    • Villa Ohana - 1
      Villa Ohana - 2
      Villa Ohana - 3
      Villa Ohana
      Puerto Aventuras, Riviera Maya
      14
      7
      7 + ½
      from $2,250 / night
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