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  4. Chocolate Hole Luxury Villas

Chocolate Hole is a quiet harbor frequented by locals and fishermen, ideally located between the attractions of Cruz Bay and Rendezvous Bay in St. John. With a small sand beach and clear turquoise water, Chocolate Hole is perfect for swimming and snorkeling, and the island’s pristine National Park beaches are just a short drive away. St. John is known for its untouched landscapes and diversity of flora and fauna, and when you stay in a Chocolate Hole villa, the island’s best hiking, scuba diving, and wildlife excursions are all within easy reach.

Our luxury vacation rentals in Chocolate Hole are situated just steps from the harbor with expansive views of the sea beyond. Featuring private swimming pools, spacious outdoor terraces, and special extras like Jacuzzis or poolside bars, our vacation home rentals allow you to take full advantage of the year-round sunshine in the US Virgin Islands. As with all of our luxury rentals, you can also arrange for additional concierge services to customize your St. John vacation, including grocery pre-stocking, private chef service, boat charters, and more.

For more waterfront and beachfront villas, explore more St. John villas or all Caribbean vacation rentals

7 Villas
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Solaris

Solaris

St. John / Chocolate Hole

4
Bedrooms
Sleeps
8
from $386+
per night

'Solaris' combines classic, Mediterranean-inspired architecture and modern island luxury to deliver a one of a kind vacation experience.

Crystal Seaview

Crystal Seaview

St. John / Chocolate Hole

5
Bedrooms
Sleeps
10
from $571+
per night

With incredible Caribbean vistas outside and charming tropical décor inside, your stay at Crystal Seaview will be an unforgettable island experience.

Great Expectations

Great Expectations

St. John / Chocolate Hole

8
Bedrooms
Sleeps
20
from $700+
per night

Great Expectations offers 4 pools, 2 hot tubs, a private basketball and tennis court, sunrise & sunset views, plus all the amenities you would expect of a first-class private villa.

Reefside Villa

Reefside Villa

St. John / Chocolate Hole

5
Bedrooms
Sleeps
10
from $786+
per night

Set on a private sand beach in Chocolate Hole on St. John's south shore, Reefside Villa boasts a wonderfully spacious floor plan and a downright glorious pool area.

Estate Rose

Estate Rose

St. John / Chocolate Hole

4
Bedrooms
Sleeps
10
from $857+
per night

Estate Rose is a four+ bedroom luxury villa located on 1.1 acres spanning a ridge top between Great Cruz Bay and Chocolate Hole.

Beach Garden

Beach Garden

St. John / Chocolate Hole

4
Bedrooms
Sleeps
8
from $914+
per night

This expansive, stylish, waterfront villa has a large infinity-edge, glass-tile pool, Jacuzzi, multiple dining areas, a media room, a meditation garden and koi pond.

Villa St. John

Villa St. John

St. John / Chocolate Hole

6
Bedrooms
Sleeps
12
from $1,800+
per night

Come and enjoy this one of a kind, palatial, Mediterranean-style, six-bedroom retreat, perched on a beautifully landscaped bluff overlooking a secluded bay on the island paradise of St. John, U.S. Virgin Islands.