Guesthouse holiday rentals in Anna&#x27;s Retreat

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 favourite

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.

Guesthouse in Saint Thomas

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 favourite

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.

5 out of 5 average rating, 96 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.

5 out of 5 average rating, 37 reviews

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

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!

4.95 out of 5 average rating, 39 reviews

The bedroom features a spacious bed draped in colorful bedding, complemented by decorative pillows. Wooden beams rise above, enhancing the airy feel. Nearby, a dresser and a mirror reflect the warm, inviting tones of the room. Natural light streams through shutters, illuminating the cozy seating area.

Guesthouse in Saint John

Faith

Forget your worries in this spacious and serene space. Enjoy outdoor kitchen and dining area in Faith Cottage. Relax in the shared space that makes up Grateful Grotto Gardens. Our one bedroom/ one bathroom cottage is all you need after a day at the beach. Centrally located off of Centerline Road, Minutes from Cruz Bay and less than 20 minutes from Coral Bay. You can feel at peace in the safe and homely residential setting and enjoy a comfortable and restful nights sleep in Grateful Grotto.

Guesthouse in Charlotte Amalie West

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.

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

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!

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.

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.

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.

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!

A well-appointed bedroom features mahogany cathedral ceilings and a spacious bed dressed in coral bedding. A wall-mounted TV is visible, and natural light floods the room from a nearby window. An en-suite bathroom can be seen through an open door.

4.98 out of 5 average rating, 45 reviews

The Guest House of Villa Solare

Upon entering the Villa property, you experience the natural Caribbean artistry of stone & shell archways, brick courtyard and tropical gardens. This accommodation includes access to the upper level of the Guest Cottage with a queen suite (en-suite bath) and attached, separate room with kitchenette, sleeper sofa and second full bath.

4.96 out of 5 average rating, 97 reviews

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

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.

Popular amenities for Anna's Retreat guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

A bright living area features comfortable seating arrangements, including a blue chair and a patterned sofa. A wooden dining table accommodates several chairs. Large windows offer views of the ocean, while a television is situated in an elegant cabinet. Decor includes colorful artwork and a small vase of flowers.

Coconut Coast Villas - Three Bedroom Suite (Bird of Paradise / Bougainvillea)

A bright and airy living area is presented, featuring wicker furniture and large windows that frame views of the ocean. A dining table accommodates several guests, while a wall-mounted television adds to the space's comfort. Ocean hues are reflected in the decor.

Coconut Coast Villas - Three Bedroom Suite (Hibiscus/Alamanda)

A bright living area features comfortable seating arrangements, including woven armchairs and a rattan coffee table. Natural light floods the space through large sliding glass doors, which open to a private oceanfront balcony. A dining table and a television are also visible, enhancing convenience.

Coconut Coast Villas - Hibisuc Two Bedroom Waterfront Suite

A spacious sleeping area features light-colored bedding and is complemented by a casual seating area with a blue couch and decorative pillows. A television is positioned on a wicker stand. Sliding glass doors lead to a private balcony with ocean views and outdoor seating.

Guesthouse in Charlotte Amalie

Coconut Coast Villas - Bougainvillea Waterfront Studio

Guesthouses with a patio

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.

5 out of 5 average rating, 6 reviews

Two Tickets To Paradise Cottage -Tiki Bar & Pool

4.91 out of 5 average rating, 44 reviews

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

Hope

A vibrant display of purple and white flowers is positioned in front of a blue wooden gate, marked with a sign reading 'Pembroke Place.' The gate features a rounded top, complemented by a light blue wall that adds to the welcoming ambiance.

2 Bedroom Cottage, with pool.

Private room in Charlotte Amalie

A spacious living area is showcased, featuring a comfortable sectional sofa accompanied by a side table with greenery. A dining table with several chairs is positioned nearby. In the background, a modern kitchen is visible, with white cabinetry and stainless steel appliances.

4.85 out of 5 average rating, 34 reviews

Charlotte Amalie Overlook Soursop Room5-3

Private room in Charlotte Amalie

A spacious bedroom features two queen-sized beds dressed in blue linens. A flat-screen television is positioned on a dark wood dresser. Natural light filters through sheer curtains covering a window, while a ceiling fan is mounted above for ventilation.

4.67 out of 5 average rating, 9 reviews

Charlotte Amalie Overlook Ackee

5 out of 5 average rating, 15 reviews

A panoramic view of the ocean is captured, showcasing a blend of turquoise water and clouds. Lush greenery is visible in the foreground, featuring swaying palm trees. The horizon is marked by a distant ship, creating a sense of serenity and connection to nature.

Guesthouse in Southside

Darling Palms Retreat: Solar Beachside 2BR Oasis

Private room in Charlotte Amalie

A spacious living area features a comfortable sectional sofa positioned beside a small table with a plant. A dining table with chairs is visible, complemented by a kitchen area in the background. Large windows allow natural light to fill the room.

4.64 out of 5 average rating, 14 reviews

Charlotte Amalie Overlook Papaya Room5-2

Guesthouse in East End

New place to stay

Beautiful & Spacious Guest House w/ Gym

Guest house rentals with a washing machine and dryer

A bright living area showcases a tan leather sofa adorned with decorative pillows. A neutral coffee table sits in front, complemented by a large vase. Light streams in from nearby windows, and an exit to the kitchen is visible in the background.

4.96 out of 5 average rating, 25 reviews

La Brisa: Oceanview Escape w/ Included Jeep Rental

An oceanfront balcony provides a relaxing space with a small table and chairs, complemented by a lounge chair. Beach towels and a shell decoratively rest on the table, with panoramic views of the Caribbean Sea and distant clouds visible in the background.

4.8 out of 5 average rating, 10 reviews

Coconut Coast Villas - Petrea Waterfront Studio

A panoramic view captures the lush coastline meeting the ocean, with a runway leading into the distance. Bright blue skies with scattered clouds stretch overhead, while palm trees frame the scene, enhancing the natural beauty of the surrounding landscape.

Guesthouse in 108-A-15 Estate Contant Northside

5 out of 5 average rating, 11 reviews

Crown Mountain Manor. Modern Living with a view.

An outdoor entertainment area features a unique, curved bar consisting of natural stone, surrounded by tropical plants. The adjacent swimming pool reflects the sky, with lounge chairs positioned around the pool's edge, creating an inviting space for relaxation and socializing.

4.67 out of 5 average rating, 3 reviews

Estate St. Peter Guest House w/ maid

4.74 out of 5 average rating, 42 reviews

Blue Aweigh

A spacious studio room features a large bed with white bedding, complemented by a comfortable seating area with a blue sofa and a wicker coffee table. Natural light floods the space through sliding glass doors leading to a private oceanfront balcony, offering views of the sea.