
Holiday houses in Chocolate Hole
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Top-rated holiday rentals in Chocolate Hole
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SKIPPER COTTAGE unit number 1
Skipper is a stand alone cottage: a large 450 sq ft efficiency with 50 sq ft deck. Queen bed, mattress is a Marriott Silver Beauty Rest & full futon along with full kitchen & shower bathroom. The property is all fenced for Skipper, my Portuguese Water Dog. Skipper was the captain of our boat Skedaddle. The yard is very lush & green, seems like a mini rain forest in town. Our place is 'old' Caribbean, wooden cottages, no concrete. Skipper & Skedaddle are two identical cottages next to each other.

76, 5 Star Reviews, "Ultra Modern Cottage for Two"
Sweet St. John -1 , was conceived and built as an ultra-modern, contemporary 1 bedroom, 1 bath, vacation rental home. It features outstanding views from a great location, with polished marble flooring, Italian cabinets, quartz countertops, high-ed stainless steel appliances, central air conditioning, washer/dryer, automatic generator, beach chairs/towels, cooler, sunshade/tent, UV-Filtered water & covered deck . The property is safe/secure, super comfortable with gated private parking on site.

Oceanfront Clifftop Escape Guest Suite
Maridadi Clifftop is perched atop Boatman Point, offering sweeping, south-facing views, and is located just under a 10-minute drive (2 miles) from Cruz Bay. The clifftop boasts a stunning outdoor terrace perched just above the crashing waves, surrounded by lush tropical vegetation. Inside, a modern, air-conditioned unit features a king-size bed, smart TV, ceiling fan, his and hers nightstands, a walk-in closet, a full bathroom, and a living area, creating the perfect romantic Caribbean escape.

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.

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.

Sea Urchin 1-bedroom apt in Cruz Bay (A-3)
Enjoy the colorful sights and sounds of Cruz Bay, St. John, while being a little removed from the action. Our unit in the Caneel Bay Apartments offers the ideal location. Sea Urchin is light and airy, accessed by a short flight of stairs. It consists of a bedroom with a king bed and air-conditioning unit, a bathroom and a well-sized sitting and dining room (with a full-size sleeper sofa) and a fully furnished kitchen. Best of all, there is a furnished terrace with a view overlooking Cruz Bay.

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.

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

Turtle’s Nest : Caribbean Studio Retreat
Turtle's Nest is a thoughtfully designed waterfront studio that offers the perfect escape. Nestled along an ocean fed pond, this enchanting retreat is a haven for tranquility. The open layout seamlessly blends the living, dining, and sleeping areas, creating an inviting ambiance. Stylish and modern furnishings complement the units, evoking a sense of relaxation and peacefulness. Property has solar panels and Tesla powerwalls ensuring there are no interruptions in energy supply.

Rockroom One Bedroom Condo at The Hills Saint John
"The Rockroom" is a one bedroom apartment located within The Hills Saint John. This large space with amazing views of Cruz Bay and St Thomas features a large bedroom with King bed, two full baths, a large living area and a full kitchen. There is also a large private patio with a gas grill and patio furniture. Guests staying at Rockroom will also have access to The Clubhouse Bar (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

Gorgeous Westin Resort St. John 2 Bed/2Ba
Stylish, spacious 2 bed/2 bath timeshare Villa on the SW coast of St. John in the award-winning Westin resort. King master suite with Westin Heavenly® Bed & Bath. Guest suite has 2 double beds & full bath. Well equipped kitchen, sofa bed in living room, 3 HDTV's, internet, washer/dryer & balcony. Resort is packed with amenities incl. private beach, water sports, tennis, pool, restaurants, fitness center & kids club. Very close to Cruz Bay. Unit layout may vary (see below)

Sol~Azul Cozy Studio Cottage w/ Pool & Ocean View
Fully equipped, spacious studio with full kitchen. Beautiful view of the sea and St Thomas in a peaceful neighborhood near Cruz Bay. Easy to navigate roadways with flat driveway and plenty of parking. Enjoy a nice evening on the pool deck to watch the sunset. Conveniently located 10 min from beaches and shopping. Beach Chairs & Towels provided. Laundry on-site. Shared Grill and Pool area w/ the Main Villa on property. Perfect for a couples getaway.
Popular amenities for Chocolate Hole holiday rentals
Other great holiday rentals in Chocolate Hole

Brand new 1BR/1BA Cottage

Sunset Shanti ~ artist’s oasis with sunset view

Cruz Bay Ocean View 2 bed/bath!

Mykonos- freshly built Greek Inspired Luxury Villa

Waterfront Cottage with private beach!

Serene Scene

Beautiful Ocean Views~Key’s in the Conch Shell

Sopra Mare: Oceanfront, Heated Salt Pool, 100% A/C
Destinations to explore
- Punta Cana Holiday rentals
- San Juan Holiday rentals
- La Romana Holiday rentals
- Bayahibe Holiday rentals
- Carolina Holiday rentals
- Sainte-Anne Holiday rentals
- Culebra Holiday rentals
- Saint Thomas Holiday rentals
- Saint Croix Holiday rentals
- Aguadilla Holiday rentals
- Basse-Terre Island Holiday rentals
- Tortola Holiday rentals
- Flamenco Beach
- Honeymoon Beach
- Limetree Beach
- Magens Bay Beach
- Coki Beach
- Cane Garden Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Secret Harbor Beach
- Peter Bay Beach
- Virgin Islands National Park
- Josiah's Bay
- Sugar Beach
- Maho Bay Beach
- Coral World Ocean Park
- Sun Bay Beach
- The Baths
- Lindquist Beach
- Paradise Point Tranway
- Cane Bay
- Brewers Bay Beach
- Point Udall




