Holiday houses in Chocolate Hole

Villa De Vida

This stunning Chocolate Hole property combines luxury, privacy, nature, ocean views and outdoor living seamlessly. Floating in the pool listening to the ocean below it's easy to see why a budding young country star loved coming to Villa De Vida, his first home, to get some inspiration for some of his many number one hits. Each of the three bedroom suites is situated in its own private building, connected to the great room via covered walkways and picturesque arched entrance ways. Set up to to maximize privacy, each bedroom suite has their own deck and full bathroom, including an outdoor shower. A spacious kitchen and living room area opens to an expansive wood deck with a large mahogany table that is perfect for group dinners. In the mornings you can take a nature walk through the property while enjoying a cup of coffee and take in all of the natural beauty that you're surrounded in. You can spend all day enjoying the pool and relaxing on the daybeds, watching sunset and then taking in the twinkling lights of St. Thomas across the ocean. Video Tour Here

Maria Bluff Cottage Villa- Ocean Views, Generator,

This newer two-story cottage features ocean views, a private pool, and an exquisite kitchen. Ideal for a couple, small group, or family, it offers easy access from its private driveway. The cottage includes a full kitchen, living room, laundry area, coral stone deck, outdoor dining, plunge pool, and two bedrooms with en-suite bathrooms. Multiple zones of air conditioning ensure comfort for everyone in the group. This Villa has a generator that will automatically kick on if the power goes out so

BEST REVIEWS on the East End - HANDS DOWN!

ALWAYS BOOK with an ON-SITE LOCAL to get the INSIDE SCOOP. Book this condo to gain access to custom-made handouts to help you plan a memorable vacation! You'll love the KILLER VIEW of the Caribbean Sea about 200 feet away. This condo includes toys and games, and plenty of beach toys, noodles, and extra chairs for beach hopping! I'm frequently booked, so check out my other condos in Cowpet Bay West. airbnb.com/h/stthomasparadise10 airbnb.com/h/stthomasparadise26 airbnb.com/h/stthomasparadise42

Sail Away II-WOW Beachfront to Paradise Remodeled

Sail Away II at Sapphire Beach Resort and Marina is located on the beachfront just steps away from the sparkling Sapphire Beach. The patio leads you to a dazzling infinity pool and the option of 2 immaculate beaches. Golden sand, pristine Caribbean water and amenities galore await you. No need to leave the tranquility of your room thanks to the many home furnishings within your vacation paradise. Beach level, beachfront & lush surroundings is yours to escape the hub of city life. KING SIZE BED!

Orchid at Casa Tre Fiori (Three Flowers House)

Casa Tre Fiori's Orchid is a large, private and peaceful one bedroom apartment with a large deck overlooking the labyrinth garden. There is a fully equipped kitchen and air-conditioned bedroom. Enjoy the sounds of nature from the deck. Walk to some of the National Park hiking trails. Easy 4 miles to town and short drive to North Shore beaches. Fish Bay is adjacent to the National Park on the south shore of the St John. The shared pool and hot tub are located nearby along the Zen Garden path.

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.

Big Ocean View, Minutes From Town

Stunning sunsets and million-dollar views of St. Thomas and surrounding islands! This 600 square foot studio apartment is roomy, comfortable and stylishly decorated. It's in an ideal spot - just a 2-minute drive from town but in a quiet neighborhood. A rental car is recommended but not absolutely necessary for those who are able to walk up long and very steep hills. This apartment is on the lower level of a private home that is currently in the process of being rebuilt after the hurricanes.

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!

Sweet Spice: A Nifty Little Cottage. With A Pool!

This very small 1 BR cottage lives BIG with a screened porch, SOLAR POWER, valley views, ac, dishwasher, outdoor fitness, and plunge pool. With a clean modern vibe, Sweet Spice is more laidback getaway than luxury villa. It’s an ideal HQ for 2 active STJ adventurers - but with a few extra amenities! Located off the beaten path on the quiet side of STJ, it feels secluded but is only a 5 minute drive to the shops of Coral Bay. Note: road is rough and requires a 4WD and there are LOTS of stairs.

Esperance~Pool~New~National Park

Spacious freshly built 2 Bedroom, 2 bathroom luxury apartment with fully equipped Kitchen and washer/dryer. Both Rooms have a memory foam mattress from Loom and Leaf. One king bedroom with en-suite bathroom, the second bedroom has a queen bed with a bathroom right across the room. Conveniently located 10min drive from Cruzbay's world class dining, shopping, grocery markets, and entrance to the North Shore Beaches. 4ft deep, shared new Pool with 2 other Apartments. shared BBQ by the Pool.

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.

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.