
House vacation rentals in Chocolate Hole
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Top-rated house rentals in Chocolate Hole
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IRIE Tides-Sapphire beachfront!
Location is everything, and this place has it! Located in Sapphire Beach Resort & Marina, you have all you need at your fingertips. Restaurants, bars, snorkeling, a pool, beach volleyball, and you're only 1 mile from Redhook and the ferry. If that isn't enough, this unit is located in building C. You are right in the middle of everything and sitting directly on the sand. And did I mention that amazing view? unwind on the balcony each night and watch the sunset. You will love your stay here!
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Mar de Amores great Views, private pool generator
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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Seascape Villa w/ Private Pool & Spectacular Views
Discover the ultimate tropical retreat at this exclusive 3-bedroom, 3-bathroom villa, perched high above the pristine waters of St. John’s East End. Indulge in luxury accommodations complete with a fully equipped kitchen, spacious indoor & outdoor living areas, and both SOLAR power & backup generator Step out to a private saltwater pool, where you can bask in the Caribbean sun while enjoying the tranquility of this serene hideaway all just minutes from local restaurants, shops and 3 markets
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Your Own Whole House Beach Beach Central 4 Beds AC
Relax with the sound of ocean waves in your private, panoramic-view paradise! This stand-alone home features 2 brand new king beds, 2 New Full Beds, 2 New single couch pull out sleepers,A/C bedrooms, a chef's kitchen w/ gas range & fast WiFi, and standby generator. Breeze-filled living spaces open to stunning views extending to St John! 7-seat SUV for unforgettable island adventures. Kid friendly perfect for families. Easy parking + quiet private location. A super central incredible value!
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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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Villa Beso Del Sol-Three Bedroom Cozy Oasis
Villa Beso Del Sol is a three bedroom, three bath beach oasis nestled into the hills above the historic town of Charlotte Amalie. We are located in estate Solberg, once you arrive you may not want to leave, the pool is partially covered so you have the option of soaking in the shade or soaking in ALL the sun. Morning coffee or afternoon cocktails, the outdoor pool area is where you'll want to be your entire vacation.
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Oceanfront Villa W/ Pool & Stunning Bay Views!
Life’s a breeze when you’re on holiday at the beautiful Beach Garden. Set close to the water near Great Cruz Bay, this unique St. John vacation home offers stunning waterfront living spaces, a luxurious pool-side patio and even an unforgettable ocean-view outdoor shower. Despite its secluded location and private atmosphere, Beach Garden is also just minutes from shopping, dining and the beach.
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Popular amenities for Chocolate Hole house rentals
House rentals with a pool

Ylang Ylang - Luxury 2 Suite Villa in Cruz Bay...
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Pool - Ocean View - Large Deck & Pergola - Private
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Flannagan's Peak Cozy 1 Bdrm Home-New Pool!
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Seaside Retreat-Pool and Infinity Sunrise Views
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Searenity Villa in Cruz bay
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Palladio's View - Private Villa With Pool & AC!
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The yellow flamingo
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Welcome to Tòti Bella!
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Weekly house rentals

Pond Bay Paradise Villa Ocean Views Beach and Kaya
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Folly View by the Sea
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Johnny Horn Trail House St. John
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Just Right Villa St John
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Hoos House
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Caribbean Cottage Near the Sea
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HGTV House Hunters | 3BR Paradise Retreat + Solar
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3BR/3 BA LUX Pool Villa*Cruz Bay*Auto Generator
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Private house rentals

The Round House
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Island Breeze: 10% Discount August Solar & AC
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VIewtiful: Virgin Islands Views
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Waterfront 2Bedroom with Private Pool
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Amazing waterfront condo, walkable to the Ritz!
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N-Joy Cottage located in Cruz Bay, St. John
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Tucked Away in Coral Bay
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Someday Soon has arrived! 2 bedroom large pool!
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Destinations to explore
- Flamenco Beach
- Magens Bay Beach
- Coki Beach
- Cane Garden Beach
- Honeymoon Beach
- Secret Harbor Beach
- Cinnamon Bay Beach
- Virgin Islands National Park
- Cane Bay Beach
- Limetree Beach
- The Baths
- Peter Bay Beach
- Maho Bay Beach
- Josiah's Bay
- Coral World Ocean Park
- Cane Bay
- Paradise Point Tranway
- Lindquist Beach
- Brewers Bay Beach
- Cruz Bay
- Sandy Point Beach
- Point Udall
- Culebrita Beach
- Coki Point Beach





