
House holiday rentals in Chocolate Hole
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Top-rated house rentals in Chocolate Hole
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House By The Sea | Idyllic Views, Pool, AC
Huis Aan Zee, “House by the Sea”, offers the perfect Caribbean getaway. Relax in your own private saltwater pool overlooking the turquoise waters of Coral Bay. This modern villa offers breathtaking views of Hurricane Hole and Drake’s Channel, blending seclusion, comfort, and convenience! *Lounge on sun chairs, soak in the pool *Enjoy AC + a fully equipped chef’s kitchen *High-speed Wi-Fi + peaceful work area for remote stays *Located minutes from St. John’s beaches, grocery stores, restaurants

Peaceful Island Getaway w/ Pool & Tropical Charm
Sol-Azul Tropical Island Escape~ This peaceful and stylish retreat is full of Caribbean charm and made for relaxation. *A sparkling pool surrounded by lush tropical landscaping *Spacious covered porch for morning coffee or entertaining *Bright, airy interiors w/ island-inspired decor *Just minutes from town, restaurants, and gorgeous beaches Whether you're here to unwind by the pool, explore island flavors, or soak up the sun on sandy shores, this home is the perfect base for your vacation!

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

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.

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.

Seascape Villa with private pool in Cruz bay
Seascape Villa is spacious magnificent four bedroom suites on one floor. It’s located on a private cul-de-sac of Estate Pastory near Caneel Hill Trail with spectacular views of Caribbean water, mountains and surrounding cays. The location is close to the town of Cruz bay but yet peaceful and private. The property is gated for an extra layer of privacy and lush landscaped with a private pool and an outdoor kitchen. AN ENTIRE HOUSE BACK UP GENERATOR FOR POWER OUTAGE.

Change Your Perspective at Villa Point of View
Change your perspective at Point of View villa, perched high above the historic town of Charlotte Amalie. Point of View is located within a gated community in Estate Mafolie. We are located mid island with an easy drive into town or to world famous Magens Bay. However, you may never want to leave the property once you see the sweeping harbor view. There are three bedrooms in the main house and separate fourth bedroom with a full kitchen on the lower pool level.

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.

The Pirates Landing South - St. John USVI
Luxury beach access duplexes on St. John's Chocolate Hole Beach offer your perfect paradise escape. Pirates Landing North & South feature private jacuzzis, en-suite bathrooms, modern kitchens, and open-concept living. Just 5 minutes from Cruz Bay, enjoy tranquility and convenience. Free high-speed Wi-Fi, beach chairs, and coolers make for effortless island living. Book your dream vacation today!

Amazing Ocean View with a spectacular location!
With our excellent location close to 2 great beaches and the bars/restaurants, shopping, and grocery stores in Redhook will make your vacation go smoothly. We are 5 minute drive from Redhook on the east end of St Thomas. We are on the $1 Safari route as well. Linquist Beach and Sapphire Beach are both about a 3 minute drive away.

Ylang Ylang - Luxury 2 Suite Villa in Cruz Bay...
A perfect spot for two couples to have their privacy but still vacation together. The beautiful view and landscape will make it hard to leave. Your own private pool, large deck to lounge, fully equipped kitchen, very clean and close to town! Luxury bedding and linens for quality comfort.
Popular amenities for house rentals in Chocolate Hole
House rentals with a pool

Villa Rosa

* 3BR/3 BA LUX Pool Villa*Cruz Bay*Amazing Views

The Penthouse suite is a Modern Luxury, sleeps 2

Long Bay Murry House, ocean views and breezes

The Caribbean Farmhouse/Ocean Views, Solar Power

2 Bed ⭐️ STAR VILLA HOME ⭐️ 5 Min walk to CRUZ BAY

Stone Cottage with a pool and gorgeous view

Windchime-Gorgeous View, Pool, Generator-Sleeps 10
Weekly house rentals

Johnny Horn Trail House St. John

Eureka Villa -Stunning Views in Paradise 2BR/2.5BA

Sunnyside Villa- Downstairs (sleeps 4)

HGTV House Hunters | Justin’s 3BR Paradise Retreat

Private Ocean & Stargazing views on the Northside

Sea Cave - Listen to the ocean from your bedroom!

Folly View by the Sea

Mission Rest - A True Slice of St. John Paradise
Private house rentals

A secluded "Walk to Beach" villa

Seaside Lux: Steps to the sand a true oasis!

Sea Cottage

Serenity Breeze: Ocean View Retreat

NEW Villa La Brisa Luxury Hideaway

St John Brand new 2 bedroom stunner

Villa Fratelli Garden

Fortuna Escape, West End - 2 Br. Near Botany Bay
Destinations to explore
- Punta Cana Holiday rentals
- San Juan Holiday rentals
- Bayahibe Holiday rentals
- La Romana Holiday rentals
- Carolina Holiday rentals
- Culebra Holiday rentals
- Sainte-Anne Holiday rentals
- Saint Thomas Holiday rentals
- Saint Croix Holiday rentals
- Aguadilla Holiday rentals
- Little Saint James Holiday rentals
- Basse-Terre Island Holiday rentals
- Flamenco Beach
- Honeymoon Beach
- Limetree Beach
- Magens Bay Beach
- Coki Beach
- Cane Garden Beach
- Secret Harbor Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Peter Bay Beach
- Virgin Islands National Park
- Josiah's Bay
- Sugar Beach
- Maho Bay Beach
- Sun Bay Beach
- Coral World Ocean Park
- The Baths
- Lindquist Beach
- Cane Bay
- Paradise Point Tranway
- Brewers Bay Beach
- Point Udall
- Chocolate Hole




