
Home rentals with a pool near Chocolate Hole
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Top-rated rentals with a pool near Chocolate Hole
Guests agree: these stays are highly rated for location, cleanliness and more.

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

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.

Sunrise Cottage - Secluded, Romantic, Private
Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Villa Catalina - Summer deals!
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.

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 Almondeen- Peaceful 2bedroom villa with pool
Villa Almondeen sits about 100 feet from the water’s edge in a private and secured area. It is five minutes away from the popular Cane Garden Bay Beach and 15 minutes from other close-by beaches. You can enjoy views of Jost Van Dyke and the boating activities around the “Bay.” To the left is an area called “The Pointe,” a line-fishing and snorkeling area, and to the right is the famous “Smith’s Toe (pronounced “Smittoe”), another fishing area, and home to the blue parrot fish.

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.

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.

Esperance~Pool~New~National Park
Spacious 2BR, 2BA luxury apartment in Fish Bay Skytop with full kitchen and washer/dryer. Both bedrooms feature Loom & Leaf memory foam mattresses. King bedroom with en-suite bath, second bedroom with queen bed and bathroom across the hallway. Smart TV with Netflix and streaming apps (no cable). 10 min drive to Cruz Bay dining, shopping, groceries, 25 min to North Shore beaches. 4 ft shared pool and BBQ with two other apartments.

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.
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Destinations to explore
- Rentals with beach access Chocolate Hole
- Rentals with outdoor seating Chocolate Hole
- Family-friendly rentals Chocolate Hole
- Rentals with a hot tub Chocolate Hole
- Flat rentals Chocolate Hole
- Beachfront rentals Chocolate Hole
- Rentals with a washing machine and dryer Chocolate Hole
- Rentals with a firepit Chocolate Hole
- Rentals with a kayak Chocolate Hole
- Pet-friendly rentals Chocolate Hole
- Rentals with a patio Chocolate Hole
- Villa rentals Chocolate Hole
- Waterfront rentals Chocolate Hole
- Hotel rooms Chocolate Hole
- Resort rentals Chocolate Hole
- House rentals Chocolate Hole
- Fitness-friendly rentals Chocolate Hole
- Apartment rentals Chocolate Hole
- Rentals with pools Cruz Bay
- Rentals with pools St. John
- Rentals with pools U.S. Virgin Islands
- Flamenco Beach
- Limetree Beach
- Honeymoon Beach
- Magens Bay Beach
- Coki Beach
- Secret Harbor Beach
- Cane Garden Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Virgin Islands National Park
- Peter Bay Beach
- Josiah's Bay
- Sugar Beach
- Maho Bay Beach
- Coral World Ocean Park
- Sun Bay Beach
- The Baths
- Cane Bay
- Lindquist Beach
- Brewers Bay Beach
- Paradise Point Tranway
- Point Udall




