
House holiday rentals in Chocolate Hole
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Top-rated house rentals in Chocolate Hole
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Mar de Amores - October special!
At this villa we offer the best cleaning and sanitization practices . Long term rentals are also welcome. This is a three bedrooms villa which offers the most magnificent 180 degree views of four bays: Rendezvous , Hart , Chocolate Hole and Great Cruz Bay, St Croix and Pillsbury Sound to the west, in St John. All bedrooms are under the same roof; the balcony and the pool are facing the sea. 3 bedrooms - 2 bathrooms, amazing garden and ample space for parking. Ample wifi and very private pool.
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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!
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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.
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Entire villa with beautiful views! Amazing
Overlooking Bolongo beach. Perfect for couples traveling together but want plenty of privacy as well. 1200 sf covered patio to enjoy sunning, relaxing, dinners with family and friends while being soothed by waves and wonderful breezes. Two bedrooms, each with full baths in main house AND two private apartments below each having the same wonderful views! Perfectly located between Red Hook for ferry to St. John and Havensight for shopping. Catch the beautiful sunrises and sunsets.
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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.
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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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Stone Cottage with a pool and gorgeous view
Sailors Cottage is located on a knoll overlooking Coral Bay with views to the BVIs. We are a 5 minute drive to restaurants in Coral Bay, 20 minutes to the pristine National Park beaches. The pool is private with a spacious pool deck, lounge chairs, comfortable seating and a picnic table for family BBQs. It’s the perfect place for morning coffee, sunset cocktails and star gazing. Or a relaxing day playing in the pool. The bedrooms have A/C for a great nights sleep.
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Hoos House
Welcome! Come enjoy a stay in beautiful St. John. Hoos House is a modest 2 bedroom, 1 bath home (Upper level of a Duplex) with amazing south facing views. NOW WITH SOLAR AND BATTERY BACKUP! Overlooking Great Cruz Bay and the Westin Resort below and St. Croix in the distance on clear days. Enjoy the covered patio with seating and dining. Amazing breezes and shade all day long. Close to town and parking available. A/C in the bedrooms.
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Brigadoon: RedHook Villa, (sleeps 6) WOW VIEW!
Brigadoon! This recently built villa commands a bird's eye view over “the city” of Red Hook to St. John all the way to the British Virgin Islands. Breezes abound. Enjoy a full kitchen, grill and all the comforts of home. Choose between 6 beaches all within 5 minutes drive. There are 2 king beds, 2 single sofas, and an additional downstairs studio should you need the extra space. Pricing is based on the number of guests.
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Sunset Shanti · Artist's Retreat · Sunset Views
Best enjoyed by those who love fresh air, this stylish indoor-outdoor gem offers a one-of-a-kind Caribbean getaway. Large open-air living space catches Trade Wind breezes and features an open floor plan to the kitchen and back deck with exquisite view. Two air-conditioned bedrooms, each with a King-sized bed, and a tv in each room allow for rest and relaxation. Views across the Caribbean Sea to St. Thomas from every room!
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Pool - Ocean View - Large Deck & Pergola - Private
POOL and expanded deck with pergola and exterior dining area. Direct view of the ocean of Hart Bay from the pool and deck. A wonderful open floor plan that is perfect for entertaining, and a downright glorious screened sitting area . The two bedroom suites are private and tastefully appointed with all updated showers and fixtures. Kitchen and all furnishings are new.
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Nyabinghi
Perched high on Ajax Peak, Nyabinghi Cottage is a peaceful retreat overlooking Coral Bay, St. John and the British Virgin Islands. The standalone cottage features breathtaking views, convenience to Coral Bay, Cruz Bay, and nearby beaches, and all of the amenities to ensure a relaxing getaway. Requested bookings within 48 hours must be approved before finalized
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Popular amenities for Chocolate Hole house rentals
House rentals with a pool

Villa Beso Del Sol - Three Bedroom Cozy Oasis
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Seascape Villa w/ Private Pool & Spectacular Views
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Seascape Villa with private pool in Cruz bay
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Ylang Ylang - Luxury 2 Suite Villa in Cruz Bay...
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Caribbean Cottage Near the Sea
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Seaside Retreat-Pool and Infinity Sunrise Views
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Luxury Villa with Pool, Privacy, Sunsets
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Palladio's View - Private Villa With Pool & AC!
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Weekly house rentals

3BR/3 BA Pool Villa *Discounted rate thru 10/31*
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Eureka Villa -Stunning Views in Paradise 2BR/2.5BA
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Just Right Villa St John
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Mission Rest - A True Slice of St. John Paradise
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Hananeel Palm Villas, LLC
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A secluded "Walk to Beach" villa
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Ocean Kaleidoscope Living
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HGTV House Hunters | 3BR Paradise Retreat + Solar
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Private house rentals

Villa Breizh- Spacious 3 Bdrm- 3 Bath
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Folly View by the Sea
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The TipSea Turtle
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Villa Nesta ~ Epic Views + Solar
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Amazing waterfront condo, walkable to the Ritz!
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IRIE Bliss -Beach front
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The Round House
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Island Breeze: 10% Discount October Solar & AC
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Destinations to explore
- Flamenco Beach
- Magens Bay Beach
- Coki Beach
- Cane Garden Beach
- Secret Harbor Beach
- Cinnamon Bay Beach
- Honeymoon Beach
- Virgin Islands National Park
- Cane Bay Beach
- Limetree Beach
- The Baths
- Peter Bay Beach
- Josiah's Bay
- Coral World Ocean Park
- Maho Bay Beach
- Cane Bay
- Brewers Bay Beach
- Paradise Point Tranway
- Lindquist Beach
- Cruz Bay
- Sandy Point Beach
- Point Udall
- Culebrita Beach
- Coki Point Beach





