
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.

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

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.

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.

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.

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.

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.

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.

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!

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.

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.

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.

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
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- Flamenco Beach
- Limetree Beach
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- Magens Bay Beach
- Coki Beach
- Secret Harbor Beach
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- Cinnamon Bay Beach
- Cane Bay Beach
- Virgin Islands National Park
- Peter Bay Beach
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- Maho Bay Beach
- Coral World Ocean Park
- Sun Bay Beach
- The Baths
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- Point Udall
- Chocolate Hole
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