Vacation rentals in Cinnamon Bay Beach

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Top-rated vacation rentals in Cinnamon Bay Beach

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Guest favourite

Home in Chocolate Hole

5.0 out of 5 average rating, 37 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.

Apr. 1 – 8

$1,048 CAD per night

Guest favourite

Villa in St. John, U.S. Virgin Islands

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. 3 – 10

$505 CAD 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

Jan. 6 – 13

$459 CAD per night

Guest favourite

Guesthouse in Coral Bay

5.0 out of 5 average rating, 93 reviews

A House of Open Arms Cottage with AC

Lovely Cottage with 180 degrees of white water views. You can see and hear the crashing waves below. A/C, Private , Romantic with a gorgeous outdoor shower, this is a totally separate living space from the art studio where I live and work. My water is UV filtered so buying water is not necessary! I am available for any needs you may have and will help you get the most out of your St. John experience. I provide a romantic welcome dinner on your arrival night. Homemade granola and coffee as well!

Dec. 20 – 27

$625 CAD per night

Guest favourite

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.

Jul. 24 – 31

$202 CAD per night

Guest favourite

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.

Apr. 22 – 29

$283 CAD per night

Guest favourite

Villa in Central

5.0 out of 5 average rating, 24 reviews

Mykonos- freshly built Greek Inspired Luxury Villa

Mykonos Villa- A Greek inspired Luxury Villa. This private property is located in one of the most sought after areas offering un interrupted breath taking views of St. John’s south shore. Conveniently located a short drive from Cruz Bays world class dining, shopping, and the entrance to the North Shore beaches. Our 2 level villa , 3 suite king bedrooms, fully equipped kitchen, living room, balconies, with elegant and modern decor gives a comfy luxury experience plus your own private pool

Mar. 3 – 10

$1,735 CAD per night

Superhost

Cottage in Coral Bay, U.S. Virgin Islands

4.97 out of 5 average rating, 187 reviews

Little Spice: A Modern Tiny Cottage in Coral Bay

Come stay in your very own private tiny cottage in Coral Bay, on the quiet side of St. John! Little Spice is the perfect base camp for an active and adventurous couple interested in exploring the island. While the space is small, it definitely packs a BIG punch including a kitchenette, a/c, wifi, queen bed, full bath, valley views, and a completely private outside lounging space with a grill. And for the beach? Beach chairs, noodle floats and a cooler . What are you waiting for?!

Sep. 9 – 16

$301 CAD per night

Guest favourite

Cottage in Hansen Bay, U.S. Virgin Islands

5.0 out of 5 average rating, 58 reviews

Milk Moon Cottage

Situated on the quiet and serene East End of St. John, Milk Moon Cottage is a private oasis overlooking the British Virgin Islands. The cottage features striking views, convenience to East End beaches, and plenty of amenities to make guests feel right at home. *** KEY FEATURES *** -Two bedroom, two bathroom home with air-conditioning throughout -Full-sized kitchen -Completely private pool -WiFi -Beach chairs, beach cooler with ice packs, & beach towels all provided

Aug. 5 – 12

$857 CAD per night

Guest favourite

Condo in East End

4.97 out of 5 average rating, 108 reviews

Beautiful corner unit condo right on the beach!

Location, location, location! Beautiful 2nd floor studio condo at Sapphire Resort & Marina in building A. This corner unit features a wrap around balcony ideal for enjoying the wonderful view of the sandy beach and turquoise waters. Unit features a king bed as well as a sleeper sofa. Kitchen is appointed with full oven/stove, dishwasher, microwave and refrigerator/freezer with ice maker. Come and enjoy all that St. Thomas has to offer!

Oct. 24 – 31

$414 CAD per night

Guest favourite

Apartment in Cruz Bay, U.S. Virgin Islands

5.0 out of 5 average rating, 101 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.

Dec. 4 – 11

$778 CAD per night

Guest favourite

Guesthouse in Tortola, British Virgin Islands

5.0 out of 5 average rating, 13 reviews

Long Bay Surf Shack

"Location, location, location!" This rustic yet charming guest studio is nestled on a hillside above one of the most sought-after and beautiful resorts in the Virgin Islands. Just a two-minute walk to Long Bay Beach and Resort, which offers an amazing spa, beach bar and restaurant. This guest studio is perfect for a couple or a family of three. Hosts have lived in the BVI for 30 years and love to share local insights.

Nov. 16 – 23

$195 CAD per night