House holiday rentals in Chocolate Hole

Down Yonder Pool Villa / Full Solar & Battery

Beautiful island memories are made at Down Yonder Pool Villa. Surrounded by lush tropical gardens and conveniently located in Chocolate Hole (less than .5 miles from the Westin resort), this well-appointed, comfortable home features two King suites - one on either side of the huge Great Room. The Great Room and each bedroom enjoys access to the glorious sundeck and 30 foot salt water pool, and every room has the same mesmerizing view of Chocolate Hole Bay and the deep blue Caribbean water beyond. Rates based on four persons occupancy. Additional guest fees apply for more guests up to 6 total. Click "Book Now" for detailed quote.

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

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!

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.

Villa Romance

With uncrowded sugar-white sand beaches, crystal-clear aquamarine waters, and soaring coconut palm trees, Chocolate Hole St. John is a dream getaway beyond your wildest imagination. Beachcombing for seashells and sea glass, snorkeling with fish between coral reefs, and hiking through scenic trails are just some of the many possibilities of the island. Nestled between Rendezvous Bay and Cruz Bay, the island neighborhood of Chocolate Hole is home to an array of magnificent villas.

Caribbean Cottage Near the Sea

Paradise! The cottage is located on Hart Bay, and has an amazing view of the Carribean Sea. You can fall asleep to the sound of waves. You will stay in the upstairs one bedroom apartment with your own private entrance. The owner’s live in the lower level. Private pooI area. It’s an older cottage with an outdoor shower. There are 67 uneven steps down to cottage from parking area. There are steps that lead to a trail and rocky beach. Property has a generator.

Paradisea 2 Bedroom w/ Pool & Backup Solar Power

2 cozy bedrooms, fully equipped kitchen, large decks, pool, solar and backup battery power. Everything you need for a day at the beach: chairs, umbrella, coolers, toys, towels all provided. Close to Coral Bay restaurants and shops. North Shore beaches and hiking trails are only a short drive away. Quiet setting in the hills above Coral Bay. Close to it all with a far away feel. good for couples, solo adventurers, and families with children over the age of 8.

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

Eureka! is a spacious, newly remodeled 2-bedroom 2.5 bath hillside villa with two 40ft decks overlooking Rendezvous Bay & Great Cruz Bay and amazing sunsets. “The location was perfect and the views from the house were breathtaking.” - Janie, 2023 ✔ Stunning views ✔ Modern design ✔ Large deck ✔ High speed internet ✔ Prime location ✔ Yoga mats ✔ Board games ✔ Hammock ✔ Guitar ✔ Echo speaker ✔ Snorkeling gear ✔ Beach chairs & coolers And so much more!

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.

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.

Hoos House

Welcome! Come enjoy a stay in beautiful St. John. Hoos House is a modest 2 bedroom, 1 bath home (Upper level of a Duplex) fully renovated with amazing south facing views. Overlooking Great Cruz Bay and the Westin Resort below and St. Croix in the distance on clear days. Enjoy the covered patio with seating and dining. Amazing breezes and shade all day long. Close to town and parking available. A/C in the bedrooms.

Pool - Ocean View - Large Deck & Pergola - Private

POOL and expanded deck with pergola and exterior dining area. Direct view of the ocean of Hart Bay from the pool and deck. A wonderful open floor plan that is perfect for entertaining, and a downright glorious screened sitting area . The two bedroom suites are private and tastefully appointed with all updated showers and fixtures. Kitchen and all furnishings are new.