Cottage holiday rentals in Anna's Retreat

SKIPPER COTTAGE unit number 1

Skipper is a stand alone cottage: a large 450 sq ft efficiency with 50 sq ft deck. Queen bed, mattress is a Marriott Silver Beauty Rest & full futon along with full kitchen & shower bathroom. The property is all fenced for Skipper, my Portuguese Water Dog. Skipper was the captain of our boat Skedaddle. The yard is very lush & green, seems like a mini rain forest in town. Our place is 'old' Caribbean, wooden cottages, no concrete. Skipper & Skedaddle are two identical cottages next to each other.

Tropical Tree House

Perched high among the trees on Bordeaux Mountain, Tropical Treehouse is a charming Caribbean cottage that offers privacy, cooling trade winds, and sweeping views across St. John, Drake’s Channel, and Tortola. Surrounded by lush greenery, this elevated retreat feels wonderfully secluded while still being close to the best of Coral Bay. Perfect for a romantic island escape or an adventurous home base, this one-of-a-kind treehouse delivers tranquility, comfort, and an authentic island experience.

Island Times in Frenchtown, Centrally Located

We welcome you to the most authentic ISLAND TIMES vacation that we hope you fall in love with. Being on a hill, you will enjoy balmy breezes & beautiful views while appreciating the charm of Frenchtown. Wake up to the sun rising over the bay, spy the seaplane flying by your window, enjoy dinner on the patio with supplied amenities for cooking at home. Walk to bars, restaurants & downtown shopping; take a $1 Safari bus to the beach; pack lightly knowing that we have thought of everything for you!

Verde Cottage (2BR/1BA) Peaceful Rainforest Oasis!

Nestled in the rainforest down a long stairway fringed with tyre palms and tree orchids, a newly remodeled 650 sqft Cottage sits enveloped by virgin St John flora and fauna. The main living areas and bedrooms are all tastefully appointed and fully air-conditioned. The efficiency kitchen is well-equipped. The large wraparound screen porch provides indoor/outdoor living with cozy seating and dining 'al fresco'. Welcome to the Verde Cottage - your peaceful island getaway on Bordeaux Mountain!

Sweet Spice: A Nifty Little Cottage. With A Pool!

This very small 1 BR cottage lives BIG with a screened porch, SOLAR POWER, valley views, ac, dishwasher, outdoor fitness, and plunge pool. With a clean modern vibe, Sweet Spice is more laidback getaway than luxury villa. It’s an ideal HQ for 2 active STJ adventurers - but with a few extra amenities! Located off the beaten path on the quiet side of STJ, it feels secluded but is only a 5 minute drive to the shops of Coral Bay. Note: road is rough and requires a 4WD and there are LOTS of stairs.

Seaside Cottage overlooking incredible White Bay on Jost Van Dyke

Bring your flip flops, friends, and family to White Bay Villas to appreciate our sparkling Caribbean water, soft sand and island vibe of serenity, and relaxation. Our private 18 acre beachfront property features multiple villas overlooking White Bay – a popular British Virgin Island anchorage that includes restaurants, beach bars, incredible snorkeling, and beautiful beaches. Stay in one of our separate, standalone villas with modern amenities and experience the island charm of Jost Van Dyke.

Secluded Beach Front Paradise: Castaway Cottage

A 2BR/2BA secluded cottage perched ~15-20yrds from the shoreline within a hop, skip & a jump to the beach, this fantastic spot offers solitude at the water's edge. The winding road home beckons the person seeking peace and quiet, where the stars shine brighter, the sea breeze seems fresher and is truly a retreat from the day-to-day rat race. Feel free to contact me if you have any questions. Possible 2door Jeep wrangler may be available depending on pick up/drop off times. 4 person maximum

Blue Moon I - 2 BR Villa on Water Island, USVI

Perched above Druif Bay and Honeymoon Beach on picturesque Water Island, Blue Moon I is a charming two-bedroom, one-bath villa. The upper-level, open-air layout offers breathtaking panoramic views of the sea with sailboats and neighboring islands like St. Thomas, Hassel Island, and Culebra. For sunseekers, beach lovers, and snorkeling enthusiasts, Honeymoon Beach is just a stone's throw away. Blue Moon I delivers comfort and affordability, a perfect choice for a memorable island getaway.

Beachfront Cottage #5

Escape into a lush oasis. This cottage is perfect for couples or single travelers looking for a luxurious laidback local vibe. Just steps to the beach, and with direct access to the pool, lawn, and pavilion area. Each cottage blends comfort with character, featuring its own distinct island style, thoughtful amenities, and just the right amount of privacy. Wake up to the sounds of nature, sip coffee on your private porch, and settle into the easy rhythm of life at The Hideaway.

Serenity Breeze: Ocean View Retreat

Welcome to Serenity Breeze, your island paradise nestled in the heart of Peterborg. - 1-bedroom retreat with stunning ocean views - Tranquil atmosphere enhanced by cooling trade winds - Air conditioning for ultimate comfort - Breathtaking sunsets to enjoy every evening - Spacious design that promotes relaxation - Experience the tranquility of island life at Serenity Breeze. - Close to Magen's Bay Beach and vibrant dining in Charlotte Amalie and Red Hook

Private, Perfect for Couples Retreat-Ocean Views

Nestled on St. John’s spectacular South Shore, this tastefully decorated one-bedroom cottage is the ideal home-away-from-home island getaway! Solar panels and back up batteries to fully power the house. The bedroom features a King bed, A/C, & flat-screen TV. The kitchen features granite countertops, stainless steel appliances & island with seating for 4. The cozy living area has A/C, comfortable seating, flat screen tv, dvd player & Bose surround sound speaker.

Seabreeze Cottage with private pool in Cruz bay

The cottage is conveniently located two minutes to the town of Cruz bay and five minutes to National Park. It’s surrounded by lush landscape and gated property. The cottage is fully AC, covered patio, a private pool, outdoor bbq covered patio. AN ENTIRE COTTAGE BACK UP GENERATOR FOR POWER OUTAGES one of a few offer on the island. It will be helpful when the grid goes down of which occurs quite often. You can still have the comfort without any interruption.