Holiday rentals in Chocolate Hole

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Top-rated holiday rentals in Chocolate Hole

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Top guest favourite
The bedroom features a spacious bed with a light-colored blanket, complemented by wooden furniture, including a nightstand and wardrobe. Natural light enters through multiple windows, illuminating the room with a serene ambiance. A rustic decor adds charm, while a pet dog rests on the floor.
Cottage in Central
4.99 out of 5 average rating, 158 reviews

Caribbean Style Cottage

The 500sq. Tortuga Cottage is located in Fish Bay, St. John in the US Virgin Islands. The property is privately owned and adjacent to the National Park. This charming cottage places you within a 5 minute walk to Reef Bay beach and gives you access to many of St. John's greatest hiking trails. By car, we are 3 miles from town (Cruz Bay), where you will find all of your necessities. This is the ideal cottage for a couple or two friends. We have a full kitchen, a king Casper mattress, and much more

Top guest favourite
A sandy beach offers a serene view featuring clusters of leafy trees providing shade. The calm turquoise waters are visible in the background under a clear blue sky. Beach seating is scattered along the shoreline, inviting relaxation and enjoyment of the landscape.
Apartment in East End
5 out of 5 average rating, 189 reviews

"H2Oh What a Beach!" condo: Walk-out Beach Access!

"H2Oh What a Beach!" condo Building A of Sapphire Beach Resort & Marina: ground floor unit with direct access to one of the most beautiful beaches in the Caribbean. Steps away from Sea Salt fine dining restaurant, Sapphire Beach Bar, Paradise Pie pizza, and Beach Buzz coffee shop. A mile from Red Hook featuring many restaurants & island ferries. Great beach, swimming, snorkeling, parasailing, and relaxing right outside your door. Be among the many visitors who LOVE this totally renovated condo.

Top guest favourite
A spacious wrap-around porch features a round table with four white chairs, inviting outdoor relaxation. Lush greenery and stunning ocean views can be seen in the distance, while bright clouds drift across the sky, enhancing the serene ambiance.
Guest house in Coral Bay
4.99 out of 5 average rating, 115 reviews

A House of Open Arms Cottage with AC

Lovely Cottage with 180 degrees of white water views. You can see and hear the crashing waves below. A/C, Private , Romantic with a gorgeous outdoor shower. Spoon into a nest of intimacy. Immerse yourself in island breezes. Take in the views of the rising sun and moon as they glisten across the crystalline waters of Hurricane Hole. Settle into the rhythm of Island life with solar energy and purified rainwater, resourceful recommendations, advice and insider tips. Welcome to simple elegance.

Top guest favourite
An outdoor patio features tiled stones surrounding a small salt-system plunge pool. Two lounge chairs with cushions are positioned nearby, while lush green banana plants fill the background. A beige umbrella provides shade, and the sky is bright with scattered clouds.
Cottage in Coral Bay
4.99 out of 5 average rating, 128 reviews

Sweet Spice: A Nifty Little Cottage. With A Pool!

This very small 1 BR cottage lives BIG with a screened porch, SOLAR POWER, valley views, ac, dishwasher, outdoor fitness, and plunge pool. With a clean modern vibe, Sweet Spice is more laidback getaway than luxury villa. It’s an ideal HQ for 2 active STJ adventurers - but with a few extra amenities! Located off the beaten path on the quiet side of STJ, it feels secluded but is only a 5 minute drive to the shops of Coral Bay. Note: road is rough and requires a 4WD and there are LOTS of stairs.

Guest favourite
A serene beach scene features soft sand leading to clear turquoise waters. Smooth rocks delineate the shoreline, complemented by lush greenery in the background. A staircase ascends from the sand, providing access to the surrounding vibrant landscape and stunning coastal views.
Villa in Saint Thomas
4.92 out of 5 average rating, 136 reviews

Eau Claire- Magens Bay Affordable Beachfront Villa

Villa Eau Claire is a private gated affordable beachfront home directly on Magens Bay. Walk into the water at roughly half the price of any other waterfront home in the Virgin Islands. The property has 4 private individual villas each with breathtaking views of the bay. The Coral Studio is a 1 Bed/1 Bath villa located on a secluded beach in the world-famous Magens Bay. Guests will find the vibrant nightlife, charming boutiques, and fine dining restaurants just a few minutes away from home.

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 out of 5 average rating, 138 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

Top guest favourite
A tranquil pool area features a glistening pool surrounded by a tiled deck. Two wooden lounge chairs and several sun loungers are positioned nearby, complemented by a textured stone wall adorned with green plants. The setting invites relaxation in a serene environment.
Flat in Cruz Bay
5 out of 5 average rating, 116 reviews

Skytop Studio~Next to Hiking Trail~New Pool

Modern 1 bedroom apartment In Fish Bay Skytop with Hillside View of the National Park, fully equipped kitchen, Saatva Loom & Leaf memory foam mattress. The property is right next to the National Park Great Sieben Trail, which connects to several major hiking trails. Cruz Bay, Grocery Stores and restaurants are 12min drive away. Klein Bay a beautiful Private rocky beach great for snorkeling is 4 min drive away. Shared brand new Pool with two other apartments. Shared BBQ by the Pool.

Top 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.
Flat in Cruz Bay
4.99 out of 5 average rating, 68 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.

Top guest favourite
Apartment in Cruz Bay
4.94 out of 5 average rating, 116 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 Bistro (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

Top guest favourite
A spacious pool area is highlighted by a refreshing private pool, surrounded by a wooden deck. Two black loungers provide comfortable seating, while colorful inflatables add a playful touch to the clear water. The setting is brightened by large glass doors and subtle outdoor lighting.
Home in East End
4.97 out of 5 average rating, 116 reviews

Private Pool in Paradise! Ocean View Steps 2 Beach

Come enjoy the island life at this tranquil villa with private pool...only steps from the beach! Cooler, snorkeling gear, and beach chairs INCLUDED! The entire home has been remodeled. The pool has been fully updated as well as the deck area, which includes brand new furniture and high-end loungers. A new gas grill has also been added for your outdoor grilling pleasure. Stream all your favorites with our strong Wi-Fi. Upscale restaurant, Pangea, is just steps away. Free parking.

Top guest favourite
A panoramic view of the Caribbean Sea is visible, with vibrant blue waters and gentle waves lapping against the shore. Lush greenery and a solitary palm tree frame the scene, enhancing the natural beauty of Hart Bay under a clear sky with scattered clouds.
Home in Cruz Bay
4.98 out of 5 average rating, 56 reviews

Caribbean Cottage Near the Sea

Paradise! The cottage is located on Hart Bay, and has an amazing view of the Carribean Sea. You can fall asleep to the sound of waves. You will stay in the upstairs one bedroom apartment with your own private entrance. The owner’s live in the lower level. Private pooI area. It’s an older cottage with an outdoor shower. There are 67 uneven steps down to cottage from parking area. There are steps that lead to a trail and rocky beach. Property has a generator.

Guest favourite
The outdoor terrace features lounge chairs positioned beside a private plunge pool, with expansive ocean views visible in the background. A comfortable seating area is situated adjacent to the pool, surrounded by lush greenery and a clear blue sky.
Villa in Cruz Bay
5 out of 5 average rating, 10 reviews

Maria Bluff Cottage-Romantic, Ocean Views, Modern,

This newer two-story cottage features ocean views, a private pool, and an exquisite kitchen. Ideal for a couple, small group, or family, it offers easy access from its private driveway. The cottage includes a full kitchen, living room, laundry area, coral stone deck, outdoor dining, plunge pool, and two bedrooms with en-suite bathrooms. Multiple zones of air conditioning ensure comfort for everyone in the group.

Popular amenities for Chocolate Hole holiday rentals