Holiday houses in Chocolate Hole

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Top-rated holiday rentals in Chocolate Hole

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Top Guest favourite
Condo in East End
4.99 out of 5 average rating, 102 reviews

Killer View; Book w/a Local for the Inside Scoop!

Check out my reviews - Top Tier Service from the Local St. Thomian! Sherri has lived in St. Thomas for 20+ years! JUST 200 FEET to the BEACH, Kid Friendly, Gated Community w/ Parking. On the BEACH: 2 Restaurants, lounge chairs, pool, & hot tub, 2 bars, & beach toys to rent. Within MILES: Ferry to nearby islands, Restaurants, Charter Boats, Grocery stores, Banks, Boutiques, Jewelry, Postal service, Pharmacy, Medical care, & more. ASK for Sherri's Custom Handouts including her BEACH GUIDE

Superhost
The exterior of Dove Cottage is showcased, featuring a spacious pool surrounded by a sun terrace. Loungers are positioned for relaxation, while a dining area is visible on the patio. Lush greenery and landscaping complement the stonework of the home, highlighting its serene environment.
Cottage in Hansen Bay
4.78 out of 5 average rating, 18 reviews

Amazing Views- Stunning Pool - Eco-Luxury Getaway

Dove Cottage is perched magically on a ridge with jaw dropping views. A luxury Eco Villa with views out and down and up and beyond to the white sand kissed emerald islands floating on the azure sea. A simple elegant home with impeccable design, an amazing pool and patio. Unmatched privacy from this East End location near the famous Lime Out floating taco bar and the great snorkeling beaches of St John's unspoiled remote peninsula. Perfect for couples or small families, NOT ideal for 4 adults.

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, 94 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.

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, 144 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.

Top Guest favourite
A spacious living area features high vaulted ceilings with wooden beams. A large dining table accommodates guests, surrounded by cozy seating options. Along one wall, an extensive book library is displayed, complemented by vibrant artworks. Soft rugs enhance the inviting atmosphere of the room.
Villa in Charlotte Amalie
4.99 out of 5 average rating, 137 reviews

Tropical Modern Loft | SoHo Style | Concierge

Single night bookings welcome! A luxe art loft experience in the heart of St. Thomas, this exclusive space in a convenient central location provides a chic home base, with sleek design, concierge options, + creative vibes. Perfect for both adventure and serenity. Ample space to lounge, with a balanced historic/contemporary aesthetic, and near beaches, restaurants, historic landmarks, boutiques, + ferry/airport/transportation. Private gated parking and a cafe and art gallery right downstairs.

Top Guest favourite
A private infinity pool is situated on a terrace, overlooking lush greenery and a panoramic ocean view. A vibrant rainbow arcs across the horizon, while gentle waves suggest a tranquil atmosphere. The pool's edge blends seamlessly with the surrounding landscape.
Guesthouse in Saint Thomas
5 out of 5 average rating, 113 reviews

Sunrise Cottage - Secluded, Romantic, Private

Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Top Guest favourite
A modern living area features a comfortable seating arrangement with a dark sectional sofa and light accent chairs. Natural light filters through large windows, highlighting the room's stylish decor, including a unique chandelier and a tasteful area rug, all with views of the harbor.
Apartment in Charlotte Amalie
4.96 out of 5 average rating, 136 reviews

Stylish & Luminous 2BR-spectacular water views!

Welcome to a newly renovated 1,800 sq foot 2 bedroom located in the heart of historic Charlotte Amalie! Our space is perfect for travelers who wish to experience the beauty of the US Virgin Island. Each room is oversized, with tall ceilings, and boasts stunning panoramic views of the Caribbean that are sure to take your breath away. The space is as stylish as it is comfortable, with modern furnishings and luxurious touches throughout, yet contextually appropriate for the historic setting.

Top Guest favourite
A balcony railing frames a sweeping view of the turquoise waters and lush greenery of the surrounding landscape. Palm trees are visible, and distant islands can be seen in the horizon under a clear blue sky.
Home in St Thomas
4.96 out of 5 average rating, 193 reviews

2BR/2BA AMAZING MagensBay View! SerenityNorthstar⭐️

Solar-Powered Luxurious 2BR w/breathtaking views of Magen’s Bay. Serenity Northstar is located in the Northside area of St. Thomas near Sibs, Mafolie Hotel, and Mountaintop. Full Air conditioning. Rent a car and live like a local. Short drive to famous Magens Bay Beach; Less than 10 min from shopping, dining, bars, etc. Includes SmartTVs with Netflix etc. 2 rms w/ King beds. Queen sofa-bed also included. 1 Rollaway cot. Sleeps up to 6ppl. Laundry. Private Parking. Patio. Killer views!

Top Guest favourite
Home in Coral Bay
5 out of 5 average rating, 7 reviews

Panoramic Ocean views and off Grid

Lunazul Villa, 2BR/2.5BA, Solar/Starlink NEW TO AIRBNB!! 180 degree views of Coral Bay, Norman Island, Tortolla, and beyond. Unobstructed views of the sparkling water from every room and heated pool large deck. Both bedrooms with en-suite full baths have comfortable furnishings, each designed to provide a tranquil retreat. You are provided with a clothes washer and dryer, filtered/UV drinking water, and full Solar energy ensuring you will never worry about island power outages.

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.
Apartment in Cruz Bay
4.99 out of 5 average rating, 87 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
Condo in Cruz Bay
4.93 out of 5 average rating, 135 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.

Guest favourite
The cottage is set within a vibrant garden, with lush tropical plants and colorful shrubs surrounding the property. Tall palms provide shade, while a covered patio is visible through the greenery. A gated entrance adds a sense of privacy to the peaceful setting.
Cottage in Cruz Bay
4.92 out of 5 average rating, 39 reviews

Seabreeze Cottage with private pool in Cruz bay

The cottage is conveniently located two minutes to the town of Cruz bay and five minutes to National Park. It’s surrounded by lush landscape and gated property. The cottage is fully AC, covered patio, a private pool, outdoor bbq covered patio. AN ENTIRE COTTAGE BACK UP GENERATOR FOR POWER OUTAGES one of a few offer on the island. It will be helpful when the grid goes down of which occurs quite often. You can still have the comfort without any interruption.

Popular amenities for Chocolate Hole holiday rentals