Villa vacation rentals in Chocolate Hole

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Top-rated villa rentals in Chocolate Hole

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Top guest favorite
The villa's unique round structure is framed by lush tropical foliage and vibrant flowers. A pathway leads to the entrance, with the sun setting behind distant islands in the background, casting warm hues over the landscape.
Villa in St. John
4.99 out of 5 average rating, 171 reviews

Penthouse Great Views Full AC Coral Bay St John VI

Picturesque TRADEWINDS TERRACE is a penthouse sitting directly above Coral Bay's restaurants, bars, shops, and grocery/convenience stores. This uniquely designed round villa sits in a tropical setting on a hillside overlooking water and islands, providing a panoramic view for miles around. Conveniently located on a fully paved road (Rt. 108) immediately accessible to the main road (Rt. 10/Centerline) leading to St John island’s beaches & Virgin Islands National Park. EASY & free parking on site.

Guest favorite
A panoramic view reveals vibrant turquoise waters and several nearby islands, bordered by lush greenery. The sky is partially filled with fluffy clouds, and the distant shoreline features contrasting structures amidst the natural landscape.
Villa in St. Thomas
4.82 out of 5 average rating, 262 reviews

Amazing Villa in Paradise: Views of 9 Islands

Take advantage of our great rates at one of the 10 BEST places to stay on St Thomas. I personally promise you will love it! Incredible views over 9 islands from everywhere! 50 steps from the pool. This villa has all new furniture, gorgeous new kitchen, remodeled bath, high end sheets and towels, beach towels, beach chairs, snorkel gear, a 42" TV, free WiFi and so much more. I provide a robust info packet with all the best beaches, restaurants, bars, grocery store and more. You will LOVE it!

Guest favorite
A spacious master bedroom is featured, with large windows framing a stunning sunset over the Caribbean Sea. A freestanding bathtub is positioned near the window, allowing for scenic views. Light wooden beams enhance the open feel, while a white dresser offers additional storage.
Villa in Cruz Bay
4.85 out of 5 average rating, 88 reviews

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.

Guest favorite
A serene beach scene features soft sand leading to clear turquoise waters. Smooth rocks delineate the shoreline, complemented by lush greenery in the background. A staircase ascends from the sand, providing access to the surrounding vibrant landscape and stunning coastal views.
Villa in Saint Thomas
4.92 out of 5 average rating, 136 reviews

Eau Claire- Magens Bay Affordable Beachfront Villa

Villa Eau Claire is a private gated affordable beachfront home directly on Magens Bay. Walk into the water at roughly half the price of any other waterfront home in the Virgin Islands. The property has 4 private individual villas each with breathtaking views of the bay. The Coral Studio is a 1 Bed/1 Bath villa located on a secluded beach in the world-famous Magens Bay. Guests will find the vibrant nightlife, charming boutiques, and fine dining restaurants just a few minutes away from home.

Superhost
A covered outdoor patio is captured in warm sunlight, featuring a round dining table surrounded by four cushioned chairs. Lush greenery and distant hills create a serene backdrop, while an archway frames the inviting view of the landscape and water beyond.
Villa in Cruz Bay
5 out of 5 average rating, 22 reviews

Elysium Villa-Natural Surroundings, Ocean Views, P

A beautiful example of Caribbean architecture, Elysium Villa is a private island sanctuary on the south shore in quiet Fish Bay. Elysium features stunning ocean views, swaying palm trees, gentle breezes and stellar night skies. Just a short drive from Cruz Bay and pristine National Park Beaches, Elysium is the quintessential vacation paradise for honeymooners, couples or small families. Enjoy picturesque ocean views from the coral stone sun deck surrounding the exceptionally private pool.

Guest favorite
A modern kitchen boasts sleek black and white cabinetry, with a large island at its center. Stools are arranged around the island, while large windows offer panoramic views of the mountains and water. Natural light fills the space, enhancing its contemporary design.
Villa in St. Thomas
4.87 out of 5 average rating, 141 reviews

NEW WATERFRONt Villa at Magens Bay, hot tub, Jeep

This new waterfront villa is conveniently located steps away from the Platform beach and 5 min. drive to famous Magens Bay Beach. Enjoy morning coffee watching turtles or Eagle rays flying above the turquoise water right from your balcony. This extraordinary furnishing and modern feel will provide cozy and exceptional vacation for your family and friends. The outdoor space offers great relaxing area overlooking the Caribbean sea. Hot tub brings the resort feel with the privacy you deserve.

Superhost
A serene outdoor scene captures the luxurious poolside area of the villa, framed by vibrant tropical landscaping. The pool reflects the surrounding lush hills and turquoise waters. The villa's Mediterranean architecture and terracotta-tiled roof complement the expansive views of Hurricane Hole and distant islands.
Villa in Coral Bay
4.93 out of 5 average rating, 128 reviews

Heaven's Gate - Off Grid Ocean View Villa

This Mediterranean style, four bedroom luxury villa sits at the top of a mountainside overlooking St. John’s pristine Hurricane Hole, designated a Virgin Islands Coral Reef Monument in 2001. Heaven’s Gate is a serene and very private hilltop vacation villa. Each of the four handsomely furnished bedroom suites includes its own private bath, three with outside showers, and each suite has access to outside terraces. Please review the House Rules prior to booking. Compliance is mandatory.

Top guest favorite
A coastal view captures the vibrant turquoise waters of the Caribbean Sea meeting rugged rocky shores. Lush green hills rise in the background, bordered by scattered homes and palm trees under a clear blue sky with wispy clouds.
Villa in Cruz Bay
5 out of 5 average rating, 135 reviews

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

Guest favorite
A private infinity pool is surrounded by several lounge chairs, each featuring soft blue towels. Lush tropical vegetation frames the area, while unobstructed ocean views stretch into the distance, capturing serene coastal hues under a clear blue sky.
Villa in Northside
5 out of 5 average rating, 20 reviews

Private Villa*MagensBay *Ocean front* Private Pool

Del Mar Dos is a luxurious villa for up to four guests, featuring two elegant king suites with en-suite baths, walk-in closets, private terraces, and individual A/C units. The villa includes a spacious great room, three dining areas, and four ocean-facing terraces. Enjoy breathtaking views from every space, including the private pool. Suite One boasts a stunning outdoor double shower framed by palm trees. Experience total privacy and Caribbean luxury—this entire estate is yours to enjoy.

Guest favorite
Lush tropical landscaping surrounds the cottage, featuring vibrant green leaves and colorful plants. Chaise lounges are positioned on a stone patio, inviting relaxation. The backdrop reveals expansive views of the Caribbean Sea and distant islands under a partly cloudy sky.
Villa in Cruz Bay
4.96 out of 5 average rating, 48 reviews

Alexandra Cottage in Cruz Bay

Alexandra Cottage - Studio with amazing views! Alexandra Cottage offers a romantic getaway with spectacular, unobstructed and breathtaking views of the Caribbean and surrounding islands. This cottage is located on Pocket Money Lane, a private cul-de-sac. The town of Cruz Bay and the ferry dock are .4 miles from the cottage. The cottage has a King size bed, is fully air conditioned, has Starlink Wi-Fi , which is extremely high-speed and always available, and an automatic generator.

Top guest favorite
A refreshing pool is visible with azure water shaded by surrounding greenery. The pool, framed by a vibrant blue tile border, offers views of the calm waters and lush hills in the background, enhancing a connection with the natural landscape.
Villa in Cruz Bay
5 out of 5 average rating, 21 reviews

EdgeWater Villas/king bed; 10min easy walk to town

New Waterfront Studio Villa, great location to walk into town. Free Parking, Pool, 1 King, 1 Bath, Kitchen, Dining/Living, Open Floor Plan. Brand new listing offers- High Speed Internet, 55" Smart TV, AC, Ceiling fan, Tile Floors, remote led dimmer switches, Dual Shower Heads, Defog Bath Mirror; Spacious Bath Vanity. Centralized to all Cruz Bay has to offer, this location is easy walking to businesses, National park, & beaches. For your beach outing beach towels, chair & cooler.

Guest favorite
An open and airy kitchen features white cabinetry complemented by colorful accents. A large island with bar stools invites gathering. Natural light floods the space through a window, illuminating shelves filled with tableware. A coastal chandelier hangs gracefully from the vaulted ceiling.
Villa in Coral Bay
4.9 out of 5 average rating, 87 reviews

Periwinkle Cottage in Coral Bay w/Pool, and Views🏝

Periwinkle Cottage of Coral Bay is a perfect rendition of a traditional West Indian cottage with modern amenities. Ceiling fans, large screened in porch and open air porch areas. Located at the end of a private road, Periwinkle has a Million Dollar view of Coral Bay! Located only minutes from grocery stores, shopping & dining in Coral Bay. This cottage offers privacy & sits on over a half acre lot! If you need a Jeep while you are on St John, we rent out our 4 door Jeep Wrangler

Popular amenities for Chocolate Hole villa rentals