Holiday rentals in Chocolate Hole

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Top-rated holiday rentals in Chocolate Hole

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Guest favourite

Home in Chocolate Hole

5.0 out of 5 average rating, 36 reviews

Down Yonder Private Pool Villa

Beautiful island memories are made at Down Yonder Pool Villa. Surrounded by lush tropical gardens and conveniently located in Chocolate Hole (less than .5 miles from the Westin resort), this well-appointed, comfortable home features two King suites - one on either side of the huge Great Room. The Great Room and each bedroom enjoys access to the glorious sundeck and 30 foot salt water pool, and every room has the same mesmerizing view of Chocolate Hole Bay and the deep blue Caribbean water beyond. Rates based on four persons occupancy. Additional guest fees apply for more guests up to 6 total. Click "Book Now" for detailed quote.

24–31 Mar

$939 SGD per night

Guest favourite

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

2–9 Mar

$430 SGD per night

Guest favourite

Flat 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.

8–15 Aug

$345 SGD per night

Guest favourite

Villa in Cruz Bay

5.0 out of 5 average rating, 7 reviews

Nautilus Villa - Brand new - Beach front!

Beautiful, BRAND NEW spacious beach-front villa in Chocolate Hole - only steps away from putting your feet in the sand. Enjoy a fantastic view of the crystal clear Caribbean water right from your window and back porch! Only 5 minutes from the bustling shopping/restaurant town of Cruz Bay. Great amenities - beach chairs and towels, snorkel gear and noodles to enjoy in our private bay which is known to have the most sea life to enjoy on the island! Great restaurants right around the corner.

11–18 Dec

$980 SGD per night

Guest favourite

Apartment in East End

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.

23–30 Aug

$137 SGD per night

Guest favourite

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

30 Nov – 7 Dec

$607 SGD per night

Guest favourite

Guest house 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.

27 Dec – 3 Jan

$236 SGD per night

Superhost

Flat 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.

27 Oct – 3 Nov

$223 SGD per night

Guest favourite

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.

12–19 Oct

$447 SGD per night

Superhost

Apartment in Cruz Bay

4.84 out of 5 average rating, 80 reviews

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, 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!

6–13 Nov

$275 SGD per night

Guest favourite

Cottage in Cruz Bay, U.S. Virgin Islands

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.

1–8 Aug

$385 SGD per night

Guest favourite

Flat 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.

12–19 Mar

$690 SGD per night