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Holiday houses in Chocolate Hole

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Top-rated holiday rentals in Chocolate Hole

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A spacious master bedroom is featured, with large windows framing a stunning sunset over the Caribbean Sea. A freestanding bathtub is positioned near the window, allowing for scenic views. Light wooden beams enhance the open feel, while a white dresser offers additional storage.
Villa in Cruz Bay
4.86 out of 5 average rating, 111 reviews

Sunset View Private Home-Cruz Bay

The Love Palace as named by its original owner for his love of the Island, This 3 bedroom (2 bedroom plus small bunk room) / 2 bath vacation rental in Cruz Bay is perfect for couples, friends or family looking for a comfortable stay on St. John. Wake up to the breathtaking view of the Caribbean Sea and neighboring island of St. Thomas. The Villa is nestled in the lush tropical beauty of St.John with plenty of shade and outdoor patios. You will be surrounded with banana mango and Tamarind trees.

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Guest favourite
A serene pool setting features a gently cascading waterfall and an octagonal shape. Lounge chairs are arranged around the pool, providing seating for relaxation. Umbrellas offer shade, and lush palm trees line the area, enhancing the tranquil ambiance with views of the bay in the background.
Condo in Cruz Bay
5.0 out of 5 average rating, 6 reviews

Westin St.John 1 BR Villa w/ Resort Pool & Beach

Revel in the days exploring and relaxing at The Westin St. John Resort 1 BR Virgin Grand Villa, a premium vacation resort with pristine beaches just a short walk or drive away. After sightseeing along the coastline, snorkeling, swimming and basking in the sun, return to the resort for a pool, on-site restaurants, activity programs and more. You will appreciate key amenities of signature Westin touches, including a full-sized kitchen, a washer/dryer, balcony and picturesque Virgin Islands views.

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Top Guest favourite
A wooden table and chairs are positioned on a balcony, offering sweeping views of the blue ocean and nearby islands. A glass lantern and a seashell are placed decoratively on the table, surrounded by lush greenery.
Apartment in Cruz Bay
4.98 out of 5 average rating, 103 reviews

Big Ocean View, Minutes From Town

Stunning sunsets and million-dollar views of St. Thomas and surrounding islands! This 600 square foot studio apartment is roomy, comfortable and stylishly decorated. It's in an ideal spot - just a 2-minute drive from town but in a quiet neighborhood. A rental car is recommended but not absolutely necessary for those who are able to walk up long and very steep hills. This apartment is on the lower level of a private home that is currently in the process of being rebuilt after the hurricanes.

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Top Guest favourite
A coastal view captures the vibrant turquoise waters of the Caribbean Sea meeting rugged rocky shores. Lush green hills rise in the background, bordered by scattered homes and palm trees under a clear blue sky with wispy clouds.
Villa in Cruz Bay
5.0 out of 5 average rating, 148 reviews

BLUE VIEW VILLA - Bluest View - Brand New...

Blue View is brand new construction! A classic soft modern Caribbean architecture set on a full acre with sweeping views from sunrise over Ram Head peninsula to sunset over St. Thomas. It is a very special property sited with the utmost care to capture Leeward breezes with an unobstructed view to St. Croix 40mi away. Find the perfect amount of sun or shade you desire at any time during the day. Blue View is a separate villa located adjacent to our main Villa and 6 minutes to Cruz Bay

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Top Guest favourite
An infinity edge pool features built-in seating and overlooks the Caribbean Sea, framed by lush green vegetation. The sky is painted with soft hues of orange and blue as the sun sets over the horizon, creating a serene atmosphere.
Villa in Cruz Bay
5.0 out of 5 average rating, 17 reviews

Bordo Mare: Oceanfront, Heated Salt Pool, 100% A/C

Bordo Mare offers breathtaking oceanfront views, 2 king bedrooms with private baths, a private heated saltwater pool, A/C in every room, backup generator, internal staircase (no "pod" bedrooms), 3-stage UV filtration system for bottled water quality throughout the villa, and accordion doors that blend indoor and outdoor living spaces. Located in the prestigious Maria Bluff neighborhood that is an easy 8 minute drive from downtown Cruz Bay & 15 minutes to St; John's world famous beaches.

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Top Guest favourite
A modern living area features a large flat-screen TV mounted above a stylish wooden media console. A light-colored sofa and accent chairs are arranged around a circular coffee table, with large windows offering views of the ocean and islands beyond. Natural light fills the space.
Condo in East End
5.0 out of 5 average rating, 65 reviews

5 Star NEW Luxury Fully Remodeled 1x2 Pool & Beach

NEW! Spacious 1 Bedroom/2 Bathroom 1200 sq foot -2024 FULLY REMODELED OCEANFRONT Villa in St. Thomas, VI. This spacious villa has an all-new modern interior, spacious separate bedroom, 2 bathrooms, a private balcony and all the amenities! Situated on the sought-after East End, this luxurious retreat offers sweeping ocean/island views. Designed with modern elegance and spacious comfort in mind, the villa provides direct access to three pools, two gourmet restaurants, and a private beach.

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Top Guest favourite
A wooden bench with a sign reading 'SAIL AWAY' is positioned on a patio, overlooking the vibrant blue waters of a beach. Lush green foliage and palm trees frame the view, with rolling hills visible in the distance under a partly cloudy sky.
Condo in East End
4.95 out of 5 average rating, 145 reviews

Sail Away II-WOW Beachfront to Paradise Remodeled

Full property generator. Sail Away II at Sapphire Beach Resort and Marina is located on the beachfront just steps away from the sparkling Sapphire Beach. The patio leads you to a dazzling infinity pool and the option of 2 immaculate beaches. Caribbean water and amenities galore await you. No need to leave the tranquility of your room thanks to the many home furnishings within your vacation paradise. Beach level, beachfront & lush surroundings is yours to escape the hub of city life.

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Guest favourite
A sheltered patio space features woven lounge chairs and potted plants, providing a tranquil view of the surrounding greenery and water. A ceiling fan enhances airflow, while the gravel flooring adds textural interest. Sunlight filters through, creating gentle patterns on the ground.
Apartment in Cruz Bay
4.99 out of 5 average rating, 94 reviews

Turtle’s Nest : Caribbean Studio Retreat

Turtle's Nest is a thoughtfully designed waterfront studio that offers the perfect escape. Nestled along an ocean fed pond, this enchanting retreat is a haven for tranquility. The open layout seamlessly blends the living, dining, and sleeping areas, creating an inviting ambiance. Stylish and modern furnishings complement the units, evoking a sense of relaxation and peacefulness. Property has solar panels and Tesla powerwalls ensuring there are no interruptions in energy supply.

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Top Guest favourite
Condo in Cruz Bay
4.93 out of 5 average rating, 150 reviews

Rockroom One Bedroom Condo at The Hills Saint John

"The Rockroom" is a one bedroom apartment located within The Hills Saint John. This large space with amazing views of Cruz Bay and St Thomas features a large bedroom with King bed, two full baths, a large living area and a full kitchen. There is also a large private patio with a gas grill and patio furniture. Guests staying at Rockroom will also have access to The Clubhouse Bar (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

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Top Guest favourite
A vibrant red ginger flower stands tall amidst lush green foliage, showcasing intricate layers of petal-like bracts. The natural lighting enhances its striking color, creating a vivid focal point within the tranquil garden setting.
Home in Cruz Bay
4.99 out of 5 average rating, 100 reviews

Wild Ginger at Casa Tre Fiori

Wild Ginger at Casa Tre Fiori is located in beautiful, peaceful Fish Bay on St John. Sit and relax over the garden on the large covered deck while listening to the birds and watching the deer. The property enjoys an acre filled with fruit trees and gardens. Enjoy the shared pool and hot tub after a fantastic day of snorkeling and exploring St John’s world famous beaches. Wild Ginger is on the the main level of Casa Tre Fiori. Located approximately 4 miles from Cruz Bay.

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Top Guest favourite
A spacious screened-in porch features comfortable seating with vibrant cushions. The area is surrounded by large windows, offering views of the nearby hills and water. Natural light filters through, enhancing the inviting atmosphere for relaxation.
Condo in Cruz Bay
4.94 out of 5 average rating, 72 reviews

Ocean Views · Walk to Cruz Bay · Beach Ready

Wake up to ocean views and unwind on the spacious screened porch with relaxing porch swings overlooking the Caribbean. Perfect for couples seeking an easy island escape, Stay Salty is thoughtfully equipped with everything you need for a carefree vacation and effortless beach days. Enjoy an easy walk to Cruz Bay's restaurants, shops, ferries, and nightlife, then return to your own peaceful retreat to relax and soak in the island breeze.

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Top Guest favourite
A bright living area features large windows that frame scenic mountain views. A light-colored sofa and two armchairs surround a wooden coffee table, complemented by a natural stone accent wall. Decorative plants add a touch of greenery, while a television is mounted on the wall.
Apartment in Cruz Bay
5.0 out of 5 average rating, 126 reviews

Esperance~Pool~New~National Park

Spacious 2BR, 2BA luxury apartment in Fish Bay Skytop with full kitchen and washer/dryer. Both bedrooms feature Loom & Leaf memory foam mattresses. King bedroom with en-suite bath, second bedroom with queen bed and bathroom across the hallway. Smart TV with Netflix and streaming apps (no cable). 10 min drive to Cruz Bay dining, shopping, groceries, 25 min to North Shore beaches. 4 ft shared pool and BBQ with two other apartments.

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Popular amenities for Chocolate Hole holiday rentals