
Villa holiday rentals in Chocolate Hole
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Top-rated villa rentals in Chocolate Hole
Guests agree: These villas are highly rated for location, cleanliness and more.

Periwinkle Cottage in Coral Bay w/Pool, and Views🏝
Periwinkle Cottage of Coral Bay is a perfect rendition of a traditional West Indian cottage with modern amenities. 🌴 Ceiling fans, large screened in porch and open air porch areas. Located at the end of a private road, Periwinkle has a Million Dollar view of Coral Bay! Located only minutes from grocery stores, shopping & dining in Coral Bay. This cottage offers privacy & sits on over a half acre lot! You are right near the Virgin Islands National Park and some of the best beaches in the world
ValueLocationOutdoor spaces
4.89 out of 5 average rating, 112 reviews
Sailfish Villa Beachfront Magens Bay St. Thomas!
Private beachfront villa on world-famous Magens Bay Beach! 5BR/4.5BA oceanfront property with direct beach access. Features a 1BR/1BA beachfront cottage that sleeps up to 4 guests. Enjoy swimming with sea turtles, snorkeling, and kayaking just steps below the villa. Amenities include an outdoor shower, clear kayak, paddle boards, and stairs to the water. Located in the private neighborhood of Peterborg, just a short shoreline stroll to Magens Bay Beach. Property is equipped with a Generator.
LocationValueCleanliness
4.91 out of 5 average rating, 139 reviews
Sunset View Private Home-Cruz Bay
The Love Palace as named by its original owner for his love of the Island, This 3 bedroom (2 bedroom plus small bunk room) / 2 bath vacation rental in Cruz Bay is perfect for couples, friends or family looking for a comfortable stay on St. John. Wake up to the breathtaking view of the Caribbean Sea and neighboring island of St. Thomas. The Villa is nestled in the lush tropical beauty of St.John with plenty of shade and outdoor patios. You will be surrounded with banana mango and Tamarind trees.
ValueFamilyAccess
4.86 out of 5 average rating, 111 reviews
Couples Retreat w/Panoramic Views
"The view is even better than the pictures". Joy of Life Villa is close to world-class beaches, night-life, wildlife and the good life! Enjoy the trade wind breezes or A/C throughout the villa. Fast WiFi, plus a desk, to work comfortably from home. We are a green villa and fully solar, with plenty of power and no outages, common at other villas. Solid masonry home, Italian tile. Excellent drinking water as rain is UV filtered. Kayaks & paddle boards included at Hansen beach! ALL are welcome.
ValueLocationAmenities
4.97 out of 5 average rating, 116 reviews
Eau Claire- Magens Bay Affordable Beachfront Villa
Villa Eau Claire is a private gated affordable beachfront home directly on Magens Bay. Walk into the water at roughly half the price of any other waterfront home in the Virgin Islands. The property has 4 private individual villas each with breathtaking views of the bay. The Coral Studio is a 1 Bed/1 Bath villa located on a secluded beach in the world-famous Magens Bay. Guests will find the vibrant nightlife, charming boutiques, and fine dining restaurants just a few minutes away from home.
FamilyValueCondition
4.92 out of 5 average rating, 147 reviews
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.
FamilyValueView
4.99 out of 5 average rating, 158 reviews
BLUE VIEW VILLA - Bluest View - Brand New...
Blue View is brand new construction! A classic soft modern Caribbean architecture set on a full acre with sweeping views from sunrise over Ram Head peninsula to sunset over St. Thomas. It is a very special property sited with the utmost care to capture Leeward breezes with an unobstructed view to St. Croix 40mi away. Find the perfect amount of sun or shade you desire at any time during the day. Blue View is a separate villa located adjacent to our main Villa and 6 minutes to Cruz Bay
ValueFamilyCleanliness
5.0 out of 5 average rating, 148 reviews
Bordo Mare: Oceanfront, Heated Salt Pool, 100% A/C
Bordo Mare offers breathtaking oceanfront views, 2 king bedrooms with private baths, a private heated saltwater pool, A/C in every room, backup generator, internal staircase (no "pod" bedrooms), 3-stage UV filtration system for bottled water quality throughout the villa, and accordion doors that blend indoor and outdoor living spaces. Located in the prestigious Maria Bluff neighborhood that is an easy 8 minute drive from downtown Cruz Bay & 15 minutes to St; John's world famous beaches.
LocationFamilyCheckout
5.0 out of 5 average rating, 17 reviews
Villa Catalina, private pool, full generator
At Villa Catalina we offer Incredible ocean views, cool breezes, comfortable furniture, ample wifi and private pool among other amenities. Nestled in an exclusive neighborhood, this beautiful home offers comfort and total privacy. No neighbors upstairs nor downstairs. This 4 bedrooms/3 bathrooms villa provides amazing views of St Croix, Rendezvous Bay, Hart Bay and Chocolate Hole. Located only 7 minutes from town and few minutes to the most amazing beaches and the St John National Park.
ValueLocationView
4.87 out of 5 average rating, 77 reviews
Good Vibes Only Ocean Villa-Views/Pool/Sundeck/Fun
Gorgeous Caribbean paradise w/ a salt water pool. Sleeping for 10 including 3 private bedrooms w/ensuite bathrooms. Sprawling living & fully stocked kitchen. Additional Queen sleepers in living & master + 1/2 bath. Enjoy stunning ocean views w/ direct line of site over to White Bay in the BVI, Tortola, Hans Lollik & Mandahl Beach/Salt Pond. The villa is equipped w/multiple patio areas & stunning pool w/ soothing trade-winds that blow through the property for comfortable outdoor living.
LocationFamilyGetting around
4.98 out of 5 average rating, 100 reviews
Villa w/ stunning views & Solar in Chocolate Hole!
This rental is the entire villa (5 bedrooms/sleeps 10 comfortably) This property has 2 beautifully appointed areas; giving you your own space yet giving you the opportunity to be together! The large sweeping porch with endless beautiful views will take your breath away! Come as adults only groups or bring the family! Lots of parking on a nice flat driveway! Check out the awesome outdoor shower! Make some memories at this unique & family-friendly place. Solar with battery back up!
LocationFamilyComfort
5.0 out of 5 average rating, 25 reviews
Mandavilla| Pool/Cruz Bay Views/Starlink&Generator
Escape to Mandavilla, a charming villa located on a hillside overlooking picturesque Cruz Bay. Designed for the perfect indoor/outdoor living experience, our villa invites you to be captivated by the breathtaking views. Immerse yourself in the island's charm as you enjoy the refreshing breezes throughout the villa. Enjoy stunning sunrises/sunsets right from your private terrace! Mandavilla is designed to provide comfort & connect you to the natural surrounding beauty.
FamilyLocationParking
4.95 out of 5 average rating, 22 reviewsPopular amenities for Chocolate Hole villa rentals
Private villa rentals

Just Peachy - Pool Villa + Bronco + WE’RE SOLAR!
LocationFamilyBeach
4.99 out of 5 average rating, 74 reviews
Gorgeous 4 bed villa with pool and amazing views
LocationFamilyComfort
5.0 out of 5 average rating, 45 reviews
Luxury LongView Villa with Stunning Sea views
FamilyLocationTV
4.98 out of 5 average rating, 96 reviews
Artemis
LocationBathroomIndoor spaces
5.0 out of 5 average rating, 29 reviews
Gorgeous ocean view penthouse! Walk to Cruz Bay!
FamilyLocationLaundry
4.94 out of 5 average rating, 33 reviews
Magical Limeberry House, walk to stunning beaches
LocationFamilyGetting around
5.0 out of 5 average rating, 76 reviews
Water View, 2 King Primary Suites, pool, private
FamilyLocationKitchen
5.0 out of 5 average rating, 44 reviews
IRIE Paradise Sapphire Beach
FamilyLocationPool
4.95 out of 5 average rating, 40 reviewsLuxury villa rentals

The Tile House
FamilyLocationDecor
4.88 out of 5 average rating, 51 reviews
4 bed/4 bath. Pool/Beautiful Ocean views. Cruz Bay
FamilyLocationNearby
4.88 out of 5 average rating, 51 reviews
Blue Pearl Villa in St. John USVI | Ocean Views
LocationFamilyOutdoor spaces
4.93 out of 5 average rating, 15 reviews
Water Cliff Villa
FamilyLocationAccess
4.91 out of 5 average rating, 11 reviews
Caribbean Jewels ~ Pool & Backup Power!
LocationFamilyCleanliness
5.0 out of 5 average rating, 34 reviews
Amazing Views, Private Pool, Close To Beaches!!!
FamilyLocationAir conditioning
4.95 out of 5 average rating, 22 reviews
Frenchman's View Villa 2 BD/2.5 BA w/ Pool
ValueLocationOutdoor spaces
4.96 out of 5 average rating, 77 reviews
Solace Villa - 5 bedroom with pool in Apple Bay
LocationValueNearby
4.93 out of 5 average rating, 30 reviewsVilla rentals with a pool

Honeymoon-Worthy w/ Pvt Pool Walk 2 Sapphire Beach
ValueLocationIndoor spaces
4.8 out of 5 average rating, 276 reviews
Romantic Villa with Private Pool - Rave Reviews!
ValueLocationCondition
4.88 out of 5 average rating, 346 reviews
Amazing Villa with Views of 9 Islands + Generator
FamilyLocationQuiet
4.82 out of 5 average rating, 296 reviews
Fort Recovery Oceanfront 2BR Signature Villa
LocationViewBeach
5.0 out of 5 average rating, 4 reviews
Escape Ordinary: Villa Calvo
LocationValueCleanliness
4.86 out of 5 average rating, 95 reviews
Park View Villa
ValueLocationView
4.88 out of 5 average rating, 33 reviews
Healing Sea Glass Oasis
FamilyLocationCheck-in
4.95 out of 5 average rating, 19 reviews
Breezy Deck VIEW Chill Studio, 24hrPower, Pool/Gym
LocationComfortLong stay
5.0 out of 5 average rating, 71 reviewsDestinations to explore
- Flamenco Beach
- Magens Bay Beach
- Coki Beach
- Cane Garden Beach
- Secret Harbor Beach
- Honeymoon Beach
- Cinnamon Bay 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
- Cruz Bay
- Lindquist Beach
- Sandy Point Beach
- Point Udall
- Culebrita Beach
- Coki Point Beach





