Chocolate Hole USVI Vacation Rentals, Condos & Villas

Chocolate Hole is located on the south shore of the St John virgin island, this well-established neighborhood has many attractions such as taking strolls on the beach, chartering boats, or even snorkeling. Chocolate Hole’s location is close to Cruz Bay, making dinners in town an easy affair.

Cruz On Inn a 5 Bedroom Luxury St. John Villa Preview
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
  • No pets
From $2,643 / night
St. John

Season Nightly Rate Minimum Stay High Season $3,250 per night 7 nights Low Season $2,643 per night 5 nights USVI Hotel Tax 12.5% Damage Waiver $250

Cruz On Inn is a brand new luxury beach front, 5 bedroom gated estate in Great Cruz Bay, just minutes from Cruz Bay and the world famous North Shore beaches.

Casa Mare a 5 Bedroom St. John Villa with Private Pool & Hart Bay Views Preview
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
  • No pets
From $1,293 / night
St. John

Season Nightly Rate Minimum Stay High Season $1,465 per night 7 nights Low Season $1,293 per night 7 nights Thanksgiving $1,465 per night 7 nights Holiday Season $1,786 per night 7 nights USVI Hotel Tax 12.5% Processing Fee 3% Casa Mare is a striking modern villa near Hart Bay and Chocolate Hole on St. John, just minutes from Cruz Bay, with ocean views across Hart Bay to St. Thomas through floor-to-ceiling hurricane-rated…

Five king suites, a private pool and rooftop stargazing terrace with views over Hart Bay to St. Thomas. Solar and battery power plus a whole house generator, minutes from Cruz Bay.

Villa Colada, a 4-Bedroom St. John Villa Above Rendezvous Bay Preview
  • 4 Bedrooms
  • 4.5 Bathrooms
  • Sleeps 8
  • No pets
From $650 / night
St. John

Season Nightly Rate Minimum Stay High Season $945 per night 7 nights Shoulder Season $725 per night 7 nights Low Season $650 5 nights Holiday Season $1,285 per night 7 nights USVI Hotel Tax 12.5% Service Fee 3% Damage Waiver $100 Designed for seamless indoor-outdoor living, the villa features winding stone walkways surrounded by lush tropical landscaping, leading to expansive covered patios on both levels. Relax with family and friends on comfortable…

Villa Colada is where Caribbean outdoor living takes center stage. Overlooking Rendezvous Bay, this desirable and affordably priced 4 bedroom villa invites you to embrace the island lifestyle—you may never want to leave.

The Last Resort, a St. John Villa Near Cruz Bay Preview
  • 6 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 19
  • No pets
From $3,500 / night
St. John

Season Nightly Rate Minimum Stay High Season $3,843 per night USVI Hotel Tax 12.5% Damage Waiver $250 7 nights Low Season $3,500 per night 7 nights USVI Hotel Tax 12.5% Damage Waiver $250 What sets The Last Resort apart is its unforgettable, music-themed rooms — each named after a classic song and designed with its own personality. From the master “Here Comes the Sun” suite with sunrise views to the “She’s a…

The Last Resort is nested in the serene neighborhood of Chocolate Hole, this stunning 6 bedroom estate comfortably sleeps up to 19 guests across six thoughtfully designed suites — each with a private balcony, private bathroom, and outdoor shower.

Sea Dream | A Luxury Escape for Adults Preview
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 6
  • No pets
From $1,500 / night
St. John

Season Nightly Rate Minimum Stay Winter Season $1,600 per night 6 nights Summer Season $1,500 per night 6 nights Holiday Season $2,275 per night 7 nights USVI Hotel Tax 12.5% Security Deposit $1000

Sea View Terrace, 5-Bedroom St. John Villa with Infinity Pool & Sunset Views Preview
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
  • No pets
From $1,428 / night
St. John

Season Nightly Rate Minimum Stay High Season $1,570 per night 7 nights Low Season $1,428 per night 5 nights Thanksgiving $1,570 per night 7 nights Holiday Season $1,786 per night 7 nights USVI Hotel Tax 12.5% Processing Fee 3% Perched above the turquoise waters of Devers Bay, Sea View Terrace is a spectacular island retreat designed for guests seeking comfort, privacy, and unforgettable Caribbean views. This beautifully appointed five-bedroom villa combines spacious…

Five bedroom St. John villa above Devers Bay with an infinity edge pool, ocean and sunset views, solar and generator backup power, and a short drive to Cruz Bay. Sleeps 10.

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