Guesthouse vacation rentals in Anna's Retreat

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Top-rated guesthouse rentals in Anna's Retreat

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Guest favorite

A serene beach scene is depicted, featuring soft white sand and gentle turquoise waves lapping at the shore. Tall palm trees sway in the breeze, framing a wooden gazebo with bright blue seating options, inviting relaxation against the backdrop of a clear blue sky.

Guesthouse in Southside

5 out of 5 average rating, 15 reviews

Darling Palms Retreat: Beachside 2-Bedroom Oasis

Experience the allure of our charming two-bedroom, one-bath apartment, just a stone’s throw away from a beautiful beach and resort with two restaurants, a pool bar and a market. Nestled amidst a serene oasis of swaying palm trees, this inviting retreat features a full kitchen, perfect for creating delightful meals during your stay and an indoor patio space. This apartment offers convenience and tranquility for your ideal getaway. Please note, it shares a wall with another unit Parking available

Guest favorite

A view from above captures the cottage nestled among lush greenery, showcasing its light-colored exterior and metal roof. The coastline unfolds beneath, revealing turquoise waters and encircling hills, framed by vibrant foliage and flowers providing color and depth to the scenic landscape.

Guesthouse in Coral Bay

4.99 out of 5 average rating, 107 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. Spoon into a nest of intimacy. Immerse yourself in island breezes. Take in the views of the rising sun and moon as they glisten across the crystalline waters of Hurricane Hole. Settle into the rhythm of Island life with solar energy and purified rainwater, resourceful recommendations, advice and insider tips. Welcome to simple elegance.

Top guest favorite

Guesthouse in Saint Thomas

5 out of 5 average rating, 82 reviews

Sunrise Cottage - Secluded, Romantic, Private

Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Guest favorite

An expansive deck overlooks scenic views of the ocean and nearby hills, featuring a refreshing pool and multiple lounge chairs. Lush greenery and decorative planters add a natural element to the inviting outdoor space.

Guesthouse in Charlotte Amalie

4.86 out of 5 average rating, 59 reviews

Bellavista Cottage

The Bellavista Cottage is located on sunny St Thomas in the US Virgin Islands. We are pleased to offer charming and comfortable accommodations with access to the famous Bellavista Pool & Pool Deck. Situated above downtown Charlotte Amalie steeped in island history and architecture, the property is within walking distance of world class dining and shopping. Bellavista Cottage is an ideal off-the-beaten-path escape for savvy and discerning travelers seeking an intimate vacation experience.

Guest favorite

A two-story villa is positioned along the shoreline, featuring a green and white exterior. The spacious patio is adorned with rocks and surrounded by lush greenery and palm trees, enhancing the natural coastal setting.

Guesthouse in Apple Bay

4.94 out of 5 average rating, 33 reviews

SEASIDE 2 BEDROOM VILLA- Cena's Beach Rental

This Newly renovated 2 bedroom Villa at Cena's Beach Rental, sits right at the shores edge with beautiful seaside views and access to crystal blue waters just a few steps from the back door. You are certain to sleep well to the soothing sounds of the calming waves and the cool summer breeze. The sunset view is the perfect backdrop for a romantic evening sitting out on the back patio. This gem will certainly help you understand why the BVI is nicknamed Natures Little Secret.

Top guest favorite

An aerial view of the property reveals a spacious outdoor terrace furnished with lounge chairs and a dining table. Lush tropical vegetation surrounds the area, with a winding path leading from the terrace through well-maintained landscaping and palm trees.

Guesthouse in Cruz Bay

5 out of 5 average rating, 15 reviews

Oceanfront Clifftop Escape Guest Suite

Maridadi Clifftop is perched atop Boatman Point with sweeping, south-facing views located under a 10-minute drive (2 miles) from Cruz Bay. The clifftop boasts a stunning outdoor terrace perched just above the crashing waves and is surrounded by lush tropical vegetation. Inside, a modern designed air-conditioned unit with a king-size bed, smart TV, ceiling fan, his and hers night tables, walk-in closet, full bathroom, and living area create the perfect romantic Caribbean escape.

Guest favorite

Guesthouse in Saint John

4.91 out of 5 average rating, 35 reviews

Hope

Our one bedroom/ one bathroom cottage is all you need after a day at the beach. Centrally located off of Centerline Road, Hope Cottage is minutes from Cruz Bay and less than 20 minutes from Coral Bay. Nestled in a serene garden setting. The surrounding area of Gifft Hill is home to local schools and is a stones throw away from the Emergency clinic. You can feel at peace in the safe and homely residential setting. Enjoy a comfortable and restful nights sleep in Grateful Grotto.

Superhost

A serene beach scene presents soft, white sand gently sloping into calm, clear waters. Lush green hills frame the background, with a few distant structures visible along the shoreline. The overcast sky adds a tranquil ambiance to the coastal setting.

Guesthouse in Charlotte Amalie West

4.9 out of 5 average rating, 269 reviews

OMAJELAN CASTLE (A)

Welcome to the Omajelan Castle. Set amongst the lush mountain canopy of Santa Maria, on the North Western side of St. Thomas, with a view that is befitting of a king and queen. About 5 minutes from the beach and 15 minutes from downtown, Charlotte Amalie, The Omarjelan Castle's regal architecture is further enhanced by a breathtaking yet tranquil view of the Atlantic ocean. These small yet comfortable efficiencies afford you a unique experience you'll not soon forget

Superhost

A sunny coastal view is displayed, framed by lush tropical foliage and cacti. The ocean sparkles in the background, while a light-colored cottage roof is visible. The pathway is made of stone, leading towards an inviting outdoor space.

Guesthouse in Saint John

4.84 out of 5 average rating, 85 reviews

Honeymoon suite across the street from the ocean

Perfect cottage for a couple on vacation. Located in Coral Bay, across the street from the beach, let the sounds of the surf put you to sleep. Full kitchen Enjoy the privacy of your own building. Gated property. Cottage has AC but usually not always necessary because of the cool ocean breeze. Miss Lucy’s restaurant just a short walk away across the street. This listing is for NON CIGARETTE SMOKERS only. Ask me for a car rental recommendation if you like. Thank you

Top guest favorite

Guesthouse in Coral Bay

4.96 out of 5 average rating, 158 reviews

Ocean Blue Cottage

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.

Top guest favorite

A sandy beach stretches along the shoreline, framed by palm trees and lush greenery. A shaded seating area is visible, accompanied by lounge chairs. The tranquil waters reflect the clear blue sky, enhancing the serene coastal atmosphere.

Guesthouse in Tortola

5 out of 5 average rating, 51 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.

Guest favorite

A private balcony is visible, featuring a set of wooden chairs and a small table. Sheer curtains frame the glass door, allowing natural light to pour into the interior space. Lush green hills are seen in the background, contributing to the serene environment.

Guesthouse in East End

4.96 out of 5 average rating, 51 reviews

Large studio

Newly built compact yet spacious one bedroom studio located in a convenient location, minutes from beautiful beaches, grocery stores, gas stations, bars and restaurants. Gated property with multi vehicle parking, wifi, AC, and private balcony seating. The Jungalow is the perfect little gem to nestle into for your next quick island getaway!