Guesthouse vacation rentals in Anna's Retreat

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Top-rated guesthouse rentals in Anna's Retreat

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Superhost

The exterior of a charming guest suite is shown, featuring a light-colored building with decorative shutters. Surrounding planters with vibrant greenery are visible, along with a path of stepping stones leading to the entrance. A seating area is partially seen to the left.

Guesthouse in East End

Garden Suite at Sapphire Beach Retreat

Very comfortable guest suite with direct access to Sapphire Beach. The garden suite boasts a queen bed in the main room and 3 twin beds in the bunk room... 2 bunks and a trundle. The Suite has a refrigerator, microwave and coffee maker. In addition, there is a private patio for your enjoyment. The location is premium. The home is just 5 minutes from Red Hook. You'll enjoy the ability to walk unto Sapphire Beach and enjoy all of Sapphire's offerings... coffee shop, restaurants and bars.

Top guest favorite

An outdoor terrace is highlighted by two loungers draped with towels. A stone pathway leads towards the ocean, where a sunset casts warm hues over the water. Lush tropical plants frame the area, enhancing the serene coastal ambiance.

Guesthouse in Cruz Bay

5 out of 5 average rating, 18 reviews

Oceanfront Clifftop Escape Guest Suite

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

Superhost

Two comfortable lounge chairs are positioned on a private deck, facing breathtaking views of the Caribbean Sea and surrounding islands. Bright blue skies and fluffy clouds create a serene backdrop, while lush greenery is visible in the distance.

Guesthouse in St. Thomas

Take your Breath Away Views Upper Cottage

OUTSTANDING views of BVI's, ST John & Caribbean Blues! Spacious, tranquil & breezy Cottage perched on the top of Harmony Hill! Newly remodeled with YOU in mind & all the comforts of home. Privacy, million dollar views from all rooms, designated office/work area and 2 private decks and abundant closet spaces for all your needs. Indoor & outdoor dining. Centrally located on island & less than 10 min Magen's, Coki, Lindquist, Sapphire Beach. Take it easy at this unique and tranquil getaway.

Top guest favorite

A private infinity pool is situated on a terrace, overlooking lush greenery and a panoramic ocean view. A vibrant rainbow arcs across the horizon, while gentle waves suggest a tranquil atmosphere. The pool's edge blends seamlessly with the surrounding landscape.

Guesthouse in Saint Thomas

5 out of 5 average rating, 93 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.

Top guest favorite

A stunning view reveals a vibrant blue ocean, dotted with fluffy clouds under a bright sky. Lush palm trees sway gently in the foreground, framing the picture and adding to the tropical ambiance. A glimpse of greenery and a hint of land are visible in the distance.

Guesthouse in Southside

5 out of 5 average rating, 37 reviews

Darling Palms: Solar Tree House Studio

Solar powered, battery back up! Our spacious studio apartment is nestled among a paradise of palm trees, with a ‘tree house' atmosphere. Just a short stroll away, discover the allure of a nearby beach and resort, offering two restaurants, a market, and a pool bar for ultimate relaxation. Embrace the outdoor ambiance on our patio, complete with comfortable seating and a grill, perfect for alfresco dining. Please note that the studio shares a wall with another rental unit. Parking available!

An outdoor area features a vibrant tiki bar with lights illuminating the space, accompanied by a refreshing saltwater pool. Surrounded by lush tropical foliage, the deck offers various seating options, creating an inviting atmosphere for relaxation and entertainment.

Guesthouse in Charlotte Amalie

5 out of 5 average rating, 6 reviews

Two Tickets To Paradise Cottage -Tiki Bar & Pool

Welcome to Two Tickets To Paradise Cottage. The coolest place to stay on St Thomas. Enjoy a quiet piece of paradise and live like a local. Our beautifully renovated cottage, pool & bar has everything you need to relax or party. Solar & Tesla batteries keep the power on. The saltwater pool is refreshing at your own private tiki bar. Honor bar, 55" tv and bluetooth surround sound. Red's Rum Roost is island famous and has it's own t-shirt. The owner is a retired Hilton Hotels sales manager.

Guest favorite

A spacious bedroom is highlighted by a vaulted ceiling with exposed wooden beams. A colorful patterned bedspread covers the bed, complemented by two bedside lamps. A seating area with chairs is arranged next to a small table, adding to the cozy ambiance.

Guesthouse in Saint John

4.9 out of 5 average rating, 41 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

The exterior of Omajelan Castle is depicted, showcasing its regal architecture with pointed turrets and large white shutters. A staircase leads to the entrance, framed by lush greenery. The structure features a distinct blue facade, harmonizing with the surrounding natural landscape.

Guesthouse in Charlotte Amalie West

4.9 out of 5 average rating, 279 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

Guest favorite

A bright living area features a spacious blue sofa and light-toned furnishings, with large windows that invite natural light and offer views. A modern kitchen is visible in the background, complete with stainless steel appliances. A ceiling fan enhances airflow in the open space.

Guesthouse in Northside

4.96 out of 5 average rating, 57 reviews

Incredible Views!- Solar Power- 5 min to beach!

- You’ll have a private newly renovated apartment (middle level) that sits within the jungle high up on the mountain side. - Views of Charlotte-Amalie Harbor, St Croix, and a glimpse of St John. - 5 minute drive to Hull Bay and the best fish tacos on the island. Magens Bay is just 10 minutes away. - Starlink internet so you’ll never lose internet! - House complex is powered by solar panels and back up batteries!

Superhost

Two vibrant blue chairs are positioned around a glass table, offering a cozy seating area. In the background, a well-lit kitchen features modern appliances and bar stools at the counter. Natural light fills the space through a nearby window, complemented by sheer curtains.

Guesthouse in Cruz Bay

4.9 out of 5 average rating, 10 reviews

St John villa 7min to Cruz bay, Oceanview, King Bd

This charming villa is conveniently located just 7 minutes from Cruz Bay, offering easy access to restaurants, a grocery store, and beautiful beaches. Situated on a steep hill and on the second floor, the home provides spacious accommodations perfect for a family of four, with both queen and king-size beds and a full bathroom. Guests will also appreciate the added perks of free parking and WiFi during their stay.

Superhost

A cozy living area features a leather sofa adorned with neutral-toned accessories. A coffee table, complemented by decorative items, sits in the center. Natural light brightens the space through a nearby window, while doorways lead to the kitchen and entrance.

Guesthouse in Northside

5 out of 5 average rating, 4 reviews

La Brisa: Peaceful Oceanview Retreat

Escape to La Brisa, a serene oceanview retreat perched 1,100 feet above sea level on Skyline Drive. This luxurious one-bedroom suite offers breathtaking Caribbean views, modern coastal decor, and thoughtful amenities for a tranquil island getaway. Perfectly located near Magens Bay and vibrant Red Hook, La Brisa is ideal for relaxation, exploration, or a romantic escape. Your paradise awaits!

Top guest favorite

A close-up view of a cactus plant showcases vibrant red flowers blooming atop green, textured stems. The stems are dotted with small white protrusions, emphasizing the unique features of this desert plant.

Guesthouse in Fish Bay

4.96 out of 5 average rating, 96 reviews

Cactus Flower Cottage

Beautiful Cactus Flower Cottage overlooking Fish Bay and the Caribbean. Hike directly out of Fish Bay to the most well known National Park Reef Bay Trail, L'Esperance Trail, Fish Bay Gut, etc! Hikers delight. Close to Cruz Bay. Beautiful, peaceful and friendly area of St John. Quick drive to Cruz Bay and the North Shore Beaches.