Chocolate Hole St. John Vacation Rentals, Villas, & US Virgin Islands Resorts


Chocolate Hole Vacation Rentals, Villas, Condos and Short Term Rentals in St. John US Virgin Islands

Book our vacation rentals with selection of 1,2,3 or 4 bedroom homes in Chocolate Hole St. John. Search hundreds of properties, find the best deal when you book directly online.

Treasure Ridge 3
Villa Rentals - Chocolate Hole
3 Bedroom(s) 3.0 Bath  Sleeps: 4-6
Starting at: $1,995.00/Wk
This home is a true treasure waiting to be found! Tucked high into the hillside in Chocolate Hole North, this charming home features 3 equal air conditioned bedrooms. With sweeping views from Rendezvous South to St. Croix and west to the twinkling tw... read more »
Bongo Bongo 0
Vacation Home Rentals - Chocolate Hole
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $3,400.00/Wk
Bongo Bongo is a great vacation home completed in 2006 and designed for traveling couples or small families that are looking for the amenities often found only in larger homes. Bongo Bongo is also close to town, easy to reach and handsomely decorated... read more »
French Cap 0
Vacation Home Rentals - Chocolate Hole
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $2,850.00/Wk
FRENCH CAP: Enjoy the iridescent greens and blues of the Caribbean Sea from every area of this light and airy home. Hear the gentle lap of waves on the rocky beach, just below. This villa features 2 Air-Conditioned Bedrooms, 1 King, 1 King/Twin, 2 ba... read more »
Moonsong 0
Villa Rentals - Chocolate Hole
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $2,170.00/Wk
Moonsong is a quintessential Caribbean style cottage, tucked into the hillside above beautiful Hart Bay. This darling 2 bedroom home is perfect for honeymooners, or anyoe looking for an excellent value in a St. John rental. Providing everythin... read more »
Moonsong 0
Villa Rentals - Chocolate Hole
2 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $1,470.00/Wk
A charming St John villa Caribbean style hideaway overlooking the aqua blue waters of Hart Bay and a distant St. Thomas. A five minute walk on a winding path leads to the pristine waters and coral reefs of Hart Bay Beach, rarely frequented by other i... read more »
Paradise Revisted 0
Vacation Home Rentals - Chocolate Hole
4 Bedroom(s) 4.0 Bath  Sleeps: 8
Starting at: $1,890.00/Wk
Balcony panoramic views of St. Thomas, Pillsbury Sound, and the Blue/Green waters just outside your windows day or night are great, and they come with vivid tropical sunsets. There are great tropical breezes and privacy. Air Conditioned bedrooms is ... read more »
Sundance 0
Villa Rentals - Chocolate Hole
3 Bedroom(s) 3.0 Bath  Sleeps: 8
Starting at: $1,995.00/Wk
A delightful Virgin Island villa nestled on the southwest corner of St. John with a panoramic view of Hart Bay, St. Croix, and St. Thomas. Enjoy the beautiful oval Pool and Spa or a five minute walk to an isolated beach with crystalline waters and ... read more »
Time Out 0
Villa Rentals - Chocolate Hole
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $3,000.00/Wk
Time Out is a fully air conditioned villa. Two equally sized bedroom suites are situated on opposite sides of an open air living/dining room/kitchen area and offer total privacy to two couples or a family with children. Each is furninshed with a k... read more »
Cocotier 0
Villa Rentals - Chocolate Hole
4 Bedroom(s) 4.5 Bath  Sleeps: 8
Starting at: $4,280.00/Wk
Perched high on an emerald hillside above the Caribbean Sea, lies Cocotier. This magical four bedroom luxury home is the perfect base for your St. John vacation. Beautifully finished from the imported tile roof and Mexican tile accents to the designe... read more »
Inn Paradise 0
Duplex Rentals - Chocolate Hole
4 Bedroom(s) 4.0 Bath  Sleeps: 8
Starting at: $4,032.00/Wk
Inn Paradise offers two complete living areas on two separate levels. Each level provides a fully-equipped kitchen, comfortable Caribbean-styled living area, two large elegant bedrooms and two bathrooms providing privacy for everyone in your party. ... read more »
La Papaya! 0
Villa Rentals - Chocolate Hole
5 Bedroom(s) 4.0 Bath  Sleeps: 10
Starting at: $4,595.00/Wk
La Papaya, located high on the hillside in Chocolate Hole North, has commanding views over countless bays an islands to the west and south. Enjoy sunrise over Ditliff Point and the sun setting with a fiery blaze over the tropical sea. The hous... read more »
Meridian 0
Vacation Home Rentals - Chocolate Hole
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $1,680.00/Wk
Meridian is a St. John rental villa, built in the traditional West Indian style with wrap around decks, and painted with charming tropical colors. This inviting home is located in Chocolate Hole, less than a mile and a half from Cruz Bay. The ... read more »
Coyaba 0
Villa Rentals - Chocolate Hole
2 Bedroom(s) 2.0 Bath  Sleeps: 2-4
Starting at: $4,395.00/Wk
As you enter the driveway, you'll be struck by the Caribbean inspired architecture, highlighted by 4 stone and coral sugar mill turrets that add drama and ambiance to this home. As you walk through the front entrance, you'll be amazed by this drama read more »
Ambiance Villa 0
Villa Rentals - Chocolate Hole
5 Bedroom(s) 4.5 Bath  Sleeps: 11
Starting at: $4,995.00/Wk
High on a hillside, on the sunny south shore of St. John, sits the perfect vacation home, designed for privacy, comfort and ease of use. Ambiance is perfectly suited for the holiday of a lifetime - enter the villa through a flower filled arbor and cr... read more »
Haiku 0
Villa Rentals - Chocolate Hole
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $2,520.00/Wk
This private villa is a unique example of living with nature and is situated on an acre of sloping woodland surrounded by gardens of native plants. Enjoy Haiku's open air living room and enjoy St John's fragrant gentle breezes. Capturing the na read more »
Seagate Villa 0
Villa Rentals - Chocolate Hole
5 Bedroom(s) 5.0 Bath  Sleeps: 6
Starting at: $2,995.00/Wk
Seagate Villa is a spacious and breezy indoor/outdoor villa set on a one-acre waterfront lot only 5 minutes from town. There are 5 bedrooms each with its own private bathroom. The villa is designed to be comfortable and provide a true Caribbea... read more »
Tesseract 0
Vacation Home Rentals - Upper Chocolate Hole
3 Bedroom(s) 3.0 Bath  Sleeps: 6
Starting at: $1,750.00/Wk
Tesseract is a comfortable, casual three bedroom, three bath home located in Upper Chocolate Hole. A wonderful home with a large swimming pool where you can spend hours floating on a pool mat and dreaming the time away. Decks located around t... read more »
Ocean Garden 0
Villa Rentals - Chocolate Hole
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: Call for Rates
Island stonewalls & a mature tropical garden make an enchanting home for two couples. Two king master bedroom suites are equipped with air conditioning, but the island breezes make them an unnecessary option year round. Nature is at your doorstep... read more »
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