
House vacation rentals in Chocolate Hole
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Top-rated house rentals in Chocolate Hole
Guests agree: these houses are highly rated for location, cleanliness, and more.

Just Right Villa St John
Hidden gem! Will definitely book again. Very clean & beautiful. Beyond hospitable and accommodating. -Richard S Wonderful! Beautiful home overlooking the bay. Kitchen was great! Close to the National Park, horse riding, shopping, dining, etc. Peaceful & quiet. Greg & Tracy thought of everything. We'll be back! -Tony & Sue Perfect Vacation! Even more beautiful than the pics! The kitchen was stocked with utensils & spices. The view was gorgeous! We'll definitely stay again. -Stacie Berry 5 Stars

The yellow flamingo
Our Caribbean vacation property in St. John is the perfect destination for your next tropical getaway. There are stunning views of the Caribbean Sea, St. Thomas, Great St. James, and Little St. James make for a truly unforgettable experience. This is 1 of 3 units and sits below another unit. The lower house unit is a 1 bedroom and also has a sleeper sofa. You can unwind and soak up the sun on our pool deck that features a breathtaking saltwater pool and plenty of seating for family and friends.

Disconnect & Reset Here | Pool + Generator
Mango Cove Villa is tucked away in the lush, green, corner of St. Thomas. The northwest side is an area of the island where the rhythm is slower and the crowds feel a world away. If you want to truly disconnect, Mango Cove Villa will deliver. Catch the green streaks of the conures as they depart each sunrise and return each sunset to roost in the surrounding trees. In the summertime, you'll want to be on the pool deck for sunset to watch the light glimmering off the banana leaves below the pool.

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

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

Island Retreat - Generator/Ocean View/Heated Pool
Escape to Sunrise Villas by Stacie, a private tropical mountaintop retreat in St. Thomas. Enjoy panoramic ocean views, a heated pool with Baja sun deck, jets and lights, plus elegant indoor-outdoor living area with 20-ft sliding doors, gourmet kitchen, bar, and fireplaces. With a whole-home generator, comfort is guaranteed. Perfect for couples, families, or friends—book the villa next door for up to 4 more guests. Includes beach chairs, cooler, and Cressi snorkel gear for perfect beach days!

Palladio's View - Private Villa With Pool & AC!
Escape to a tropical oasis at Palladio's View, a stunning villa perched above St. John's East End. This enchanting 3-bedroom, 2.5-bath retreat is the ultimate getaway, offering three luxurious king-sized beds, a private hot tub, and a sparkling pool. With breathtaking views of the turquoise waters below, every corner of this home invites you to unwind and embrace paradise. This home is also equipped with a new HVAC system, which is adds an extra bit of comfort in this tropic environment!

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!

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.

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.

Searenity Villa in Cruz bay
Searenity Villa offers a private pool, outdoor sun deck, covered patio with BBQ grill, lush landscape, amazing view of mountain , surrounding cays and Caribbean blue water. The two bedroom suites come with mini split AC , smart TV for streaming for each bedroom, separate sitting area with queen sleeper sofas for additional guests or office if you have to work remotely. AN ENTIRE HOUSE GENERATOR BACK UP FOR POWER OUTAGES for your comfort without an interruption

Expansive Island Chain Views! Solar Power Backup
Lunazul Cottage has Romantic BVI and Natl. Monument Views – High above Coral Bay. Delightful great room, gourmet kitchen, well appointed living area, picturesque covered deck, 2 air conditioned BR with en-suite full baths. Washer/dryer, Starlink wifi, and fully Solar powered. The best down island view from St John. Pristine waters of Hurricane Hole and the Virgin Islands Coral Reef at your feet along with the rolling Atlantic Ocean and the tranquil Caribbean Sea.
Popular amenities for Chocolate Hole house rentals
House rentals with a pool

IRIE Tides-Sapphire beachfront!

Flannagan's Peak Cozy 1 Bdrm Home-New Pool!

Pool - Ocean View - Large Deck & Pergola - Private

La Sirena Secluded Villa w/Pool+NEW Solar backup!

St John Brand new 2 bedroom stunner

Stone Cottage with a pool and gorgeous view

Luxury Villa with Pool, Privacy, Sunsets

Caribbean Cottage Near the Sea
Weekly house rentals

Private Ocean & Stargazing views on the Northside

The Sea Fan, Long Bay Beach, Tortola

3BR/3 BA LUX Pool Villa*Cruz Bay*Auto Generator

Serene Harbor View - Solberg STT

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

Folly View by the Sea

Pond Bay Paradise Villa Ocean Views Beach and Kaya

VIewtiful: Virgin Islands Views
Private house rentals

Johnny Horn Trail House St. John

A secluded "Walk to Beach" villa

Hoos House

Dolphin Suites - Ocean View

Sunnyside Villa (Upstairs only-sleeps 6)+generator

Welcome to Toti Bella!

Private Pickleball Court - 5 min walk to Beach

Island Daze - Amazing Views
Destinations to explore
- San Juan Vacation rentals
- Higüey Vacation rentals
- Punta Cana Vacation rentals
- Fajardo Vacation rentals
- La Romana Vacation rentals
- Ponce Vacation rentals
- Luquillo Vacation rentals
- Aguadilla Vacation rentals
- Bayahibe Vacation rentals
- Sainte-Anne Vacation rentals
- Dominicus Vacation rentals
- Humacao Vacation rentals
- Flamenco Beach
- Magens Bay Beach
- Honeymoon Beach
- Coki Beach
- Cane Garden Beach
- Secret Harbor Beach
- Cinnamon Bay Beach
- Virgin Islands National Park
- Cane Bay Beach
- Limetree Beach
- The Baths
- Peter Bay Beach
- Sun Bay Beach
- Maho Bay Beach
- Josiah's Bay
- Cane Bay
- Coral World Ocean Park
- Paradise Point Tranway
- Cruz Bay
- Brewers Bay Beach
- Lindquist Beach
- Point Udall
- Sandy Point Beach
- Coki Point Beach





