Chocolate Hole vacation rentals

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Top-rated vacation rentals in Chocolate Hole

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Guest favorite

Cottage in Central, U.S. Virgin Islands

4.99 out of 5 average rating, 132 reviews

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

Mar 2 – 9

$275 per night

Guest favorite

Villa in St. John

5.0 out of 5 average rating, 125 reviews

Coral Bay Penthouse Gorgeous Tropical Island Views

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.

Oct 17 – 24

$336 per night

Guest favorite

Apartment in Cruz Bay

5.0 out of 5 average rating, 25 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 those seeking tranquility. The space maximizes comfort and functionality. The open layout seamlessly blends the living, dining, and sleeping areas, creating an inviting ambiance filled with natural light. Stylish and modern furnishings complement the apartment's soothing color palette, evoking a sense of relaxation and peacefulness.

Aug 8 – 15

$220 per night

Guest favorite

Condo in East End, U.S. Virgin Islands

4.93 out of 5 average rating, 134 reviews

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.

Oct 1 – 8

$111 per night

Guest favorite

Tiny home in St. John

4.92 out of 5 average rating, 157 reviews

Bogie's Villa, Tektite, Island Tiny Living

Large views directly across Pillsbury Sound over Thatch Cay to St. Thomas from your very own tiny living space. Situated on the pool deck this small space is ideal for a couple or single looking to get away from it all (including heavy packing), and get out exploring. Tektite provides everything you need for meals at home, a shared pool, laundry on site, and solar with battery backup. Beach towels, a small cooler and camp chairs are supplied for your beach days. *Updated with A/C and T/V*

Jul 21 – 28

$162 per night

Guest favorite

Villa in Cruz Bay

5.0 out of 5 average rating, 96 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

Sep 19 – 26

$389 per night

Guest favorite

Guesthouse in Coral Bay, U.S. Virgin Islands

4.96 out of 5 average rating, 140 reviews

Ocean Blue Cottage

Update: New mattress as of Fall 2022! Ocean Blue Cottage located in Upper Carolina, 400' above sea level, overlooking Coral Bay harbor, Bordeaux Mt, Carolina valley and a peek of the Caribbean Sea. 23 steps down from the road, it has a bedroom 9'x12', dining/kitchen area 6'x10', bathroom 3'x10', private outdoor shower 4'x5', deck 8'x4' with grill, furniture, umbrella. Pricing is $150 night. There’s also an $90 cleaning fee per reservation. 5 min drive to restaurants, 10 min to beaches.

Jul 28 – Aug 4

$150 per night

Superhost

Apartment in Cruz Bay

4.89 out of 5 average rating, 114 reviews

Centrally located Cruz Bay Modern Luxury Apt.

Conveniently situated only five minutes away from the heart of Cruz Bay city. This cozy apartment is located on the first floor of the building. Eight minute walk to ferry terminal, shops, restaurants. Laundry facility directly across the street. Two minute walking distance to nearby coffee shops. Three minute walk to grocery stores - Star Fish Market and Dolphin Market. Car Rental agency adjoining the property and others nearby. Five minute walk to tennis court behind of the property.

Oct 14 – 21

$140 per night

Guest favorite

Cottage in Cruz Bay

4.86 out of 5 average rating, 57 reviews

Two Bay View: Perfect for a private getaway

Two Bay View is an octagonal cottage set on three private acres between Great Cruz Bay and Chocolate Hole. The home offers both privacy and convenience to Cruz Bay (approximately 2 mile drive). Facing north-east on St. John's north side, it gets the famous trade-wind breezes nearly all year long. The cottage has an 180 degree view with expansive decks on the two upper levels. The lower bedroom is small and not connected internally to the main level, suitable for a single occupant.

Dec 14 – 21

$297 per night

Guest favorite

Cottage in Cruz Bay

5.0 out of 5 average rating, 56 reviews

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.

Aug 1 – 8

$245 per night

Guest favorite

Apartment in Coral Bay

4.99 out of 5 average rating, 133 reviews

5*****AFFORDABLE LUXURY STUDIOW/ JEEP RENTAL AVAIL

5 ★★★★★ LUXURY AT AN AFFORDABLE PRICE In Coral Bay- the quiet side of St. John. Deluxe private entry studio w/ A/C, king size bed & kitchenette. 5 minute walk to restaurants, grocery stores, shopping. 220 degree view of the Bay from your covered deck -100 ft. above the Bay. Paved road & driveway. 4WD, Auto., Jeep Wrangler & Liberty for rent. Reserved beach space -East End (15-18 m. Dr.) Room Service Menu Avail. Race, religion, & LGBTQ friendly.

Sep 18 – 25

$135 per night

Guest favorite

Apartment in Cruz Bay, U.S. Virgin Islands

5.0 out of 5 average rating, 100 reviews

Sieben Apartment * Pool* next to Hiking trails

Spacious Luxury 2 Bedroom, 2 bathroom apartment with fully equipped kitchen and washer/dryer. Both rooms have memory foam mattresses from Loom & Leaf. The master bedroom has 1 King bed with private bathroom, and the second bedroom can be set up as 2 Twin beds or 1 King bed. 10 min drive from Cruzbay, Restaurants and grocery Stores. Shared brand new Pool (4ft deep) with two other apartments. Shared BBQ by the Pool.

Oct 11 – 18

$299 per night