Chocolate Hole Vacation Rentals

Chocolate Hole Vacation Rentals and Vacation Homes!

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These Chocolate Hole vacation homes, condos, villas, cabins, cottages, chalets, and bed & breakfasts are presented by their owners or agents. Please contact them directly with your inquiries. Click on the underlined descriptions below for more details and property photos.

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Bedrooms Sleeps
Weekly Rate  Interests 

  Preferred Listings
Luxurious Large Villa on Chocolate Bay - St John Luxury Vacation Rental
  • Chocolate Hole
  • Villa
  • 6 bedrooms, sleeps 12
  • 6.5 bathrooms
  • Weekly rates
    From $4,255 to $18,235 USD
 

Luxurious Indigo Villa is Perched on the Hillside, Between Chocolate Hole and Great Cruz Bay
  • Chocolate Hole
  • House (single)
  • 4 bedrooms
  • 5 bathrooms
  • Weekly rates
    From $4,195 to $6,695 USD
 

Luxurious Villa With Breathtaking Views
  • Chocolate Hole
  • Villa
  • 4 bedrooms, sleeps 6
  • 4 bathrooms
     

    Beautiful Luxurious 4 BDRM Villa - Chocolate Hole Luxury Vacation Rental
    • Chocolate Hole
    • Villa
    • 4 bedrooms, sleeps 8
    • 4 bathrooms
    • Weekly rates
      From $2,965 to $9,315 USD
     

    Tropical Landscape And Incredible Views From This Beautiful Vacation Home
    • Chocolate Hole
    • House (single)
    • 3 bedrooms, sleeps 6
    • 3.5 bathrooms
       

      Beach Walk is a magical place most noted for quiet privacy right at the water's edge.
      • Chocolate Hole
      • Villa
      • 2+ loft bedrooms, sleeps 6 max
      • 2.5 bathrooms
      • Weekly rates
        From $2,350 to $2,995 USD
       

      Beautiful Vacation Home In Chocolate Hole With Optional Cottage
      • Chocolate Hole
      • House With Or Without Cottage
      • 4 - 6 bedrooms, sleeps 2 - 12
      • 4 - 5 bathrooms
         

        Luxurious Chocolate Hole Beach Garden Villa
        • Chocolate Hole
        • Villa
        • 4 bedrooms
        • Weekly rates
          From $3,654 to $8,050 USD
         

        Elegant Villa Overlooking The Caribbean Sea
        • Chocolate Hole
        • Villa
        • 2 + Den/Bed bedrooms, sleeps 6
        • 2.5 bathrooms
           

          Get away from it all! Villa Serendipity combines a spectacular 270 degree view with a quiet hilltop location.
          • Chocolate Hole
          • Villa
          • 4 bedrooms, sleeps 8
          • 5 bathrooms
          • Weekly rates
            From $4,500 to $6,000 USD
           

           
            Rental Locations   (Listed alphabetically by City or Town)
           

            City BR(s) BA(s) Sleeps Description
          Chocolate Hole BR 1 BA 2 - 4 ARCADIA located in Chocolate Hole, we are only five minutes from Cruzbay and 10 minutes from our famous north shore beaches.
          Chocolate Hole 1 BR 1 BA 2 Meritage Cottage is a charming one bedroom hideaway perfect for romantic interludes, honeymoons. Air conditioned - Jacuzzi
          Chocolate Hole 2 + Den/Bed BR 2.5 BA 6 Elegant Villa Overlooking The Caribbean Sea
          Chocolate Hole 2+ loft BR 2.5 BA 6 max Beach Walk is a magical place most noted for quiet privacy right at the water's edge.
          Chocolate Hole 3 BR 3.5 BA 6 Tropical Landscape And Incredible Views From This Beautiful Vacation Home
          Chocolate Hole 4 BR 5 BA Villa CT SOL - Wonderful ocean views over Chocolate Hole.
          Chocolate Hole 4 BR 4 BA Villa CT SEA - Overlooking the hills of St. John down to the Caribbean sea.
          Chocolate Hole 4 BR 4 BA 8 + Meritage Great House 4 bedroom 4 bath air conditioned, pool, Jacuzzi. Located in Chocolate Hole 3 min to Cruz Bay!
          Chocolate Hole 4 BR 5 BA 8 Get away from it all! Villa Serendipity combines a spectacular 270 degree view with a quiet hilltop location.
          Chocolate Hole 4 BR 5 BA Luxurious Indigo Villa is Perched on the Hillside, Between Chocolate Hole and Great Cruz Bay
          Chocolate Hole 4 BR BA Luxurious Chocolate Hole Beach Garden Villa
          Chocolate Hole 4 - 6 BR 4 - 5 BA 2 - 12 Beautiful Vacation Home In Chocolate Hole With Optional Cottage
          Chocolate Hole 4 BR 4 BA 6 Luxurious Villa With Breathtaking Views
          Chocolate Hole 4 BR 4 BA Villa CT CRY - Panoramic views to south overlooking Chocolate Hole.
          Chocolate Hole 4 BR 4 BA Villa CT SUN - Magnificent sunset views over Dever's Bay.
          Chocolate Hole 4 BR 4 BA 8 Beautiful Luxurious 4 BDRM Villa - Chocolate Hole Luxury Vacation Rental
          Chocolate Hole 5 BR 5 BA 10-11 Maritage Villa and Cottage Complex. Perfect for destination wedding groups or large family gatherings
          Chocolate Hole 5 BR 5 BA Villa CT GAT - Fabulous ocean views.
          Chocolate Hole 5 BR 5 BA Villa CT AVA - View over Chocolate Hole.
          Chocolate Hole 5 BR 5 BA Villa CT VID - Magnificent sunset views over Dever's Bay.
          Chocolate Hole 5 BR 5 BA 2-10 Crystal Seaview Special discounts for Jan/Feb!
          Chocolate Hole 6 BR 6.5 BA 12 Luxurious Large Villa on Chocolate Bay - St John Luxury Vacation Rental



          Luxurious Large Villa on Chocolate Bay - St John Luxury Vacation Rental
          Chocolate Hole Villa, 6 bedrooms, sleeps 12, 6.5 bathrooms Weekly rates from $4,255 to $18,235 USD



          Luxurious Indigo Villa is Perched on the Hillside, Between Chocolate Hole and Great Cruz Bay
          Cruz Bay House (single), 4 bedrooms, 5 bathrooms Weekly rates from $4,195 to $6,695 USD



          Luxurious Villa With Breathtaking Views
          Fish Bay Villa, 4 bedrooms, sleeps 6, 4 bathrooms



          Beautiful Luxurious 4 BDRM Villa - Chocolate Hole Luxury Vacation Rental
          Chocolate Hole Villa, 4 bedrooms, sleeps 8, 4 bathrooms Weekly rates from $2,965 to $9,315 USD



          Tropical Landscape And Incredible Views From This Beautiful Vacation Home
          Cruz Bay House (single), 3 bedrooms, sleeps 6, 3.5 bathrooms



          Beach Walk is a magical place most noted for quiet privacy right at the water's edge.
          Chocolate Hole Villa, 2+ loft bedrooms, sleeps 6 max, 2.5 bathrooms Weekly rates from $2,350 to $2,995 USD



          Beautiful Vacation Home In Chocolate Hole With Optional Cottage
          Chocolate Hole House With Or Without Cottage, 4 - 6 bedrooms, sleeps 2 - 12, 4 - 5 bathrooms



          Luxurious Chocolate Hole Beach Garden Villa
          Chocolate Hole Villa, 4 bedrooms Weekly rates from $3,654 to $8,050 USD



          Elegant Villa Overlooking The Caribbean Sea
          Chocolate Hole Villa, 2 + Den/Bed bedrooms, sleeps 6, 2.5 bathrooms



          Get away from it all! Villa Serendipity combines a spectacular 270 degree view with a quiet hilltop location.
          Chocolate Hole Villa, 4 bedrooms, sleeps 8, 5 bathrooms Weekly rates from $4,500 to $6,000 USD