
House holiday rentals in Chocolate Hole
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Top-rated house rentals in Chocolate Hole
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The yellow flamingo
Our Caribbean vacation property in St. John is the perfect destination for your next tropical getaway. There are stunning views of the Caribbean Sea, St. Thomas, Great St. James, and Little St. James make for a truly unforgettable experience. This is 1 of 3 units and sits below another unit. The lower house unit is a 1 bedroom and also has a sleeper sofa. You can unwind and soak up the sun on our pool deck that features a breathtaking saltwater pool and plenty of seating for family and friends.

NEW Villa La Brisa Luxury Hideaway
PLEASE NOTE: The maximum guest capacity at La Brisa is 8 guests. The nightly rate includes up to 6 guests; additional fee of $75 per person, per night applies for guests 7 & 8. Perched atop a scenic hillside, Villa La Brisa offers an exquisite retreat with breathtaking panoramic views of the Atlantic Ocean, Magen’s Bay, and the distant Caribbean isles. This recently appointed, elegantly designed villa features two king en-suites, a private plunge pool, and refined indoor-outdoor living spaces.

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

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!

Your Own Whole House Beach Beach Central 4 Beds AC
Relax with the sound of ocean waves in your private, panoramic-view paradise! This stand-alone home features 2 brand new king beds, 2 New Full Beds, 2 New single couch pull out sleepers,A/C bedrooms, a chef's kitchen w/ gas range & fast WiFi, and standby generator. Breeze-filled living spaces open to stunning views extending to St John! 7-seat SUV for unforgettable island adventures. Kid friendly perfect for families. Easy parking + quiet private location. A super central incredible value!

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!

Panoramic Ocean views and off Grid
Lunazul Villa, 2BR/2.5BA, Solar/Starlink NEW TO AIRBNB!! 180 degree views of Coral Bay, Norman Island, Tortolla, and beyond. Unobstructed views of the sparkling water from every room and heated pool large deck. Both bedrooms with en-suite full baths have comfortable furnishings, each designed to provide a tranquil retreat. You are provided with a clothes washer and dryer, filtered/UV drinking water, and full Solar energy ensuring you will never worry about island power outages.

Tranquil Desires, Villa
Indulge in ultimate tropical bliss at our modern villa. Our sanctuary boasts a sleek interior, a private infinity pool, and breath-taking sunset views stretching across Tortola, and the US Virgin Islands. Perfect for couples or small groups, complete with his-and-her robes and slippers for your comfort. Unwind our cushioned outdoor chairs. Beaches, harbour walks, and adventure are just steps away from your doorstep. Make every moment unforgettable in your luxury island escape!

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.

Seascape Villa with private pool in Cruz bay
Seascape Villa is spacious magnificent four bedroom suites on one floor. It’s located on a private cul-de-sac of Estate Pastory near Caneel Hill Trail with spectacular views of Caribbean water, mountains and surrounding cays. The location is close to the town of Cruz bay but yet peaceful and private. The property is gated for an extra layer of privacy and lush landscaped with a private pool and an outdoor kitchen. AN ENTIRE HOUSE BACK UP GENERATOR FOR POWER OUTAGE.

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.

The Pirates Landing South - St. John USVI
Luxury beach access duplexes on St. John's Chocolate Hole Beach offer your perfect paradise escape. Pirates Landing North & South feature private jacuzzis, en-suite bathrooms, modern kitchens, and open-concept living. Just 5 minutes from Cruz Bay, enjoy tranquility and convenience. Free high-speed Wi-Fi, beach chairs, and coolers make for effortless island living. Book your dream vacation today!
Popular amenities for house rentals in Chocolate Hole
House rentals with a pool

La Sirena Secluded Villa w/Pool+NEW Solar backup!

The Penthouse suite is a Modern Luxury, sleeps 2

St John Brand new 2 bedroom stunner

Long Bay Murry House, ocean views and breezes

2 Bed ⭐️ STAR VILLA HOME ⭐️ 5 Min walk to CRUZ BAY

Stone Cottage with a pool and gorgeous view

VIewtiful: Virgin Islands Views

Texas Embassy
Weekly house rentals

Johnny Horn Trail House St. John

Sunnyside Villa- Downstairs (sleeps 4)

Private Ocean & Stargazing views on the Northside

Sea Cave - Listen to the ocean from your bedroom!

Pond Bay Paradise Villa Ocean Views Beach and Kaya

Folly View by the Sea

Fortuna Hideaway, West End - 1Br. Near Botany Bay

Mission Rest - A True Slice of St. John Paradise
Private house rentals

A secluded "Walk to Beach" villa

Private Saltwater Poolside Cottage w/View and Gate

Island Retreat - Ocean View/Heated Pool/Generator

Seaside Lux: Steps to the sand a true oasis!

Sea Cottage

LUX 2 King BR Villa w/Generator & Pool Cruz Bay

Serenity Breeze: Ocean View Retreat

Villa Isla A: Spacious 1 bedroom 1 bath sleeps 2-4
Destinations to explore
- Punta Cana Holiday rentals
- San Juan Holiday rentals
- Bayahibe Holiday rentals
- La Romana Holiday rentals
- Carolina Holiday rentals
- Culebra Holiday rentals
- Sainte-Anne Holiday rentals
- Saint Thomas Holiday rentals
- Saint Croix Holiday rentals
- Little Saint James Holiday rentals
- Aguadilla Holiday rentals
- Basse-Terre Island Holiday rentals
- Flamenco Beach
- Limetree Beach
- Honeymoon Beach
- Magens Bay Beach
- Coki Beach
- Cane Garden Beach
- Secret Harbor 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
- Paradise Point Tranway
- Brewers Bay Beach
- Point Udall
- Chocolate Hole




