Vacation rentals in Chocolate Hole

4.99 out of 5 average rating, 138 reviews

The image captures a stunning ocean view framed by lush greenery and gentle palm trees. The shoreline extends into the distance under a clear blue sky, with hints of distant islands visible on the horizon. The vibrant foliage adds a touch of tropical charm.

Guest suite in Northside

Beautiful! Oceanview Studio- Magens Bay View!

Solar-Powered Luxurious studio w/breathtaking views of Magen’s Bay perfect for a getaway for two. Serenity Northstar is located in the Northside residential area of St. Thomas near Sibs, Mafolie Hotel, and Mountaintop. Full Air conditioning. Private Balcony. Short drive to Magens Bay; 10 min from Charlotte Amalie shopping, dining, bars, etc. 20 min from Red Hook. Includes SmartTV with Netflix etc. King bed. Sleeps up to 2ppl max. Rent a car and live like a local. Private Parking. Killer views!!!

4.99 out of 5 average rating, 158 reviews

A small outdoor seating area features a round marble table with two elegantly designed chairs. Fresh greenery and tropical plants provide a natural backdrop. Light curtains gently drape, adding privacy while allowing glimpses of the surrounding landscape.

Cottage in Central

Caribbean Style Cottage

The 500sq. Tortuga Cottage is located in Fish Bay, St. John in the US Virgin Islands. The property is privately owned and adjacent to the National Park. This charming cottage places you within a 5 minute walk to Reef Bay beach and gives you access to many of St. John's greatest hiking trails. By car, we are 3 miles from town (Cruz Bay), where you will find all of your necessities. This is the ideal cottage for a couple or two friends. We have a full kitchen, a king Casper mattress, and much more

4.97 out of 5 average rating, 223 reviews

A private outdoor lounging area features two cushioned chairs with patterned pillows, positioned on a red wooden deck surrounded by lush greenery. A small wooden table and chairs are placed nearby, offering a serene space to relax and enjoy the valley views.

Cottage in Coral Bay

Little Spice: A Modern Tiny Cottage in Coral Bay

Come stay in your own private tiny cottage in Coral Bay, on the quiet side of St. John! Little Spice is the perfect base camp for up to two active, adventurous adults interested in exploring the island. No kids, please. While the space is small, it definitely packs a BIG punch including SOLAR POWER, kitchenette, a/c, wifi, queen bed, full bath, valley views, and a private outside lounging space with a grill. And for the beach? Beach chairs, noodle floats and a cooler. What are you waiting for?

4.94 out of 5 average rating, 171 reviews

An inviting outdoor seating area is presented, featuring two bar stools and a round table. A scenic waterfront view is visible, with lush greenery framing the space and distant hills under a clear blue sky. Sailboats can be seen gently bobbing on the water.

Condo in East End

St. Thomas USVI, Waterfront Condo, Affordable

Beautiful Waterfront Condo, in gorgeous St. Thomas, U.S. Virgin Islands, overlooking Red Hook and uninhabited islands. All 32 condos were recently renovated as of 2020. Renovations are now complete on all units, and includes new exterior, new windows, doors, glass sliding doors all to building code. Inside the condo recent updates include a new kitchen, new stove, new ceiling fans, new bathroom vanity, new furniture. Air Conditioning a split level 24k unit works great and pumps cold A/C.

4.96 out of 5 average rating, 108 reviews

Lush tropical plants surround a wooden deck, featuring vibrant foliage in shades of green, red, and yellow. In the background, expansive views of the ocean and distant islands are visible, framed by the vibrant vegetation.

Guest suite in St. John

Coral Bay Suite Ocean and Tropical Island Views

With stunning OCEAN VIEWS, this Coral Bay bedroom suite in St John is tucked in the countryside, yet convenient to beaches. Kitchenette for light meals, indoor powder room (outdoor shower), BBQ, AC, TV, Wifi. Great for hikers, nature lovers & other travelers looking for a cozy, tropical little hideaway while seeking outdoor adventure as you visit St John USVI island. 500 ft elevation, fully paved road, convenient drive to all St John beaches, above Coral Bay restaurants/bars, shops, grocery.

5 out of 5 average rating, 124 reviews

A spacious bedroom features vaulted ceilings with exposed beams. A king-size bed is positioned to offer views through large sliding glass doors, which open to a balcony overlooking the ocean. A television stands beside the bed, and sheer white curtains frame the doors.

Villa in Cruz Bay

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

A rocky beach area is depicted, featuring clear blue waters gently lapping against the shore. Green hills frame the background, with a few trees visible along the coastline. The sky is bright and sunny, enhancing the inviting atmosphere of the natural landscape.

5 out of 5 average rating, 106 reviews

Skytop Studio~Next to Hiking Trail~New Pool

Modern 1 bedroom apartment In Fish Bay Skytop with Hillside View of the National Park, fully equipped kitchen, Saatva Loom & Leaf memory foam mattress. The property is right next to the National Park Great Sieben Trail, which connects to several major hiking trails. Cruz Bay, Grocery Stores and restaurants are 12min drive away. Klein Bay a beautiful Private rocky beach great for snorkeling is 4 min drive away. Shared brand new Pool with two other apartments. Shared BBQ by the Pool.

An outdoor dining area is set with a wooden table surrounded by four black chairs. Soft turquoise bowls are positioned alongside plates, with napkins neatly placed. A scenic view of the ocean-fed pond and lush greenery can be seen in the background.

4.98 out of 5 average rating, 60 reviews

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.

4.8 out of 5 average rating, 132 reviews

An outdoor terrace features multiple seating arrangements, including cozy sofas and wooden chairs, under large shaded umbrellas. A central coffee table enhances the inviting space, offering sweeping views of the landscape and water in the background, framed by lush greenery.

Condo in Cruz Bay

Sunset Villa Studio Condo at The Hills Saint John

You have to see Sunset Villa for yourself! Sunset Villa is a stunning one bedroom studio with kitchenette, in a gated community, offering resort like amenities with amazing views! You will have access to The Clubhouse bar and restaurant (open seasonally), the game room including a pool and ping pong table and big screen television, sunset terrace, and community pool. Sunset villa has a private entrance and large windows so you can take in the view. You will not be disappointed!

5 out of 5 average rating, 31 reviews

A panoramic view captures the shimmering turquoise waters of Coral Bay, bordered by lush green hills. The rocky shoreline is complemented by patches of sand, creating a tranquil atmosphere. The clear sky is filled with scattered clouds, enhancing the natural beauty of the landscape.

Cottage in Saint John

One bedroom cottage on the water

Take it easy at this unique and tranquil getaway. The property is on the water, and is located in Coral Bay. Brand new, and boasts a king size memory foam bed, custom kitchen with quartz countertops and a two burner Miele stove, full bathroom, air conditioning and deck overlooking a salt pond and coral bay. Vaulted Cyprus ceiling, Kohler faucets, 600 thread count cotton sheets and a 60″ tv, and gas grill. Solar power with batteries and generator for consistent power!

4.98 out of 5 average rating, 50 reviews

Large windows frame a breathtaking view of the Caribbean Sea, allowing natural light to fill the space. A potted plant adds a touch of greenery, while a round wooden table occupies the center. The floor features natural wood grain, enhancing the cottage's rustic feel.

Home in Cruz Bay

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.

4.88 out of 5 average rating, 267 reviews

A private balcony presents a round dining table accompanied by four chairs, overlooking lush greenery and sparkling coastal waters. Sailboats can be seen in the distance against a backdrop of blue skies and fluffy white clouds, inviting relaxation and outdoor enjoyment.

Condo in East End

Ocean View Sapphire Condo-Balcony & King Bed

Located at Sapphire Village-Amazing balcony and views of Sapphire Beach and its glimmering turquoise waters. Short walk to the beach and beach bar! 1 King bed, and one queen sleeper sofa. Property has hotel amenities including 2 pools, great snorkeling, 3 restaurants, beach bar, coffee shop & deli! Secure, safe location. Taxis are readily available nearby for rides to grocery stores, Red Hook for dinner, St. John Ferry, local beaches. 25 min from airport!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Hotels

Stylish accommodations and amenities

Popular amenities for Chocolate Hole vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chocolate Hole

A person is seated on a large rock, overlooking a vast expanse of water dotted with small islands. Sunlight is breaking through the clouds, casting a luminous streak across the water's surface. Lush green hills frame the scene, showcasing the natural beauty of the surrounding landscape.

4.93 out of 5 average rating, 43 reviews

Hibiscus Suite at Sunset Serenade

MadisonRating, 5 stars3 weeks ago

Our group of 3 found this Airbnb to be perfect for our few nights in town. The space was clean, stocked with towels soap detergent and beach essentials, and the porch area was our favorite part. Checkin was easy and simple. Beware!!!! The hike into town is not for the weak - but we did it multiple times. Decent spot if you aren’t renting a car, taxis are around and 2/3rds of the walk has a sidewalk.

4.82 out of 5 average rating, 28 reviews

Flamingo House • ISLA • Sunset view • Walk to town

MikaelaRating, 5 stars1 month ago

Amanda and her husband were amazing! We requested to book our stay very last-minute due to an issue with our original Airbnb reservation somewhere else and they were beyond accommodating. Amanda responded extremely fast and we showed up to a very cute and clean place to stay. Plus the view was amazing, too! Thanks again!

5 out of 5 average rating, 5 reviews

Home in Central

Villa Nesta

LeslieRating, 5 stars3 months ago

This was our second visit to St. John, and Villa Nesta was the perfect spot for us! If you’re looking for a perfectly appointed house, with breathtaking views, peace and quiet, a friendly and helpful host, and easily navigable roads to and from local beaches and restaurants, look no further. We especially loved the gorgeous back deck and the tranquility of the outdoor shower. We had one full day of rain this trip, which we took as an opportunity to stay in, relax, and simply appreciate the seascapes all around us. We will absolutely be back!

4.88 out of 5 average rating, 77 reviews

Floor-to-ceiling windows frame a stunning view of the Caribbean Sea, revealing vibrant blue waters and lush greenery. A dining table is adorned with a decorative yellow pineapple and a pot of white orchids, enhancing the coastal ambiance of the space.

Condo in Southside

Coral cove studio - ocean view

JenniferRating, 5 stars1 month ago

My husband and I recently stayed at Coral Cove and between the beautiful view directly from our living room window, great location to all of the things we wanted to experience on the Island, and the amenities available in the community it couldn’t have been more perfect! We loved starting or ending our day looking out from the cliff side pool, the community is quiet and relaxed and the location of the unit adds an element of privacy. We were very happy with our choice of the place we called home for the week. Thanks for all of your help Lizzie, super responsive and was helpful in any way she could!

4.96 out of 5 average rating, 25 reviews

A sleek white catamaran is anchored in the clear turquoise waters, with a sandy beach and resort buildings visible in the background. Lush greenery surrounds the resort, and a dock extends into the water, offering access to various water activities.

Villa in Cruz Bay

Ring in Spring at the Westin St. John!

SamRating, 5 stars3 months ago

The Westin is the premier resort on St. John and Dehdan's unit was comfortable and well-furnished. We enjoyed the lovely balcony, the nice kitchen and the convenience of the washer and dryer. Dehdan was responsive to our requests for local information.

5 out of 5 average rating, 17 reviews

Villa in Cruz Bay

EdgeWater Villas/sleeps 2-4; 10min walk to town

ShariRating, 5 stars2 months ago

Nora & Bruce were absolutely exceptional host and hostess. Even before we got there she was always so responsive . Bruce checked us in and made us feel right at home from the start. His hospitality went above and beyond any AirBNB I’ve stayed in. He even dropped us off at the beaches while we were there and showed us around the island. Place was very clean, with beautiful views and excellent walkable location to Cruz Bay with all the restaurants, shopping and bars close by. I would recommend this place to anyone staying on the island. You will not be disappointed and truly have a wonderful experience and time!!

5 out of 5 average rating, 37 reviews

A two-story building is framed by tropical landscaping, featuring a staircase leading to the entrance. Below, the shoreline showcases calm waters and a palm tree, with distant islands visible under a partly cloudy sky.

Home in East End

Waterfront Condo near The Ritz

PaulaRating, 5 stars1 week ago

Place was clean and comfortable. Quiet and relaxing location. The host was very friendly and responsive; quickly assisted us when the door lock battery needed to be changed. Would stay again.