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Guesthouse vacation rentals in Anna's Retreat

Find and book unique guesthouse rentals on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Anna's Retreat guesthouse rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly guest house rentals

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.
Private room in St. John

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.
Private room in St. John

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.
Private room in St. John

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.
Private room in St. John

Coconut Coast Villas - Bougainvillea Waterfront Studio

Guest house rentals with a patio

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

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.
Guesthouse in Northside

2 Bedroom Cottage, with pool.

Guest favorite
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.
Private room in Charlotte Amalie
4.85 out of 5 average rating, 33 reviews

Charlotte Amalie Overlook Soursop Room5-3

Superhost
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.
Private room in Charlotte Amalie
4.67 out of 5 average rating, 9 reviews

Charlotte Amalie Overlook Ackee

Guest favorite
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
5 out of 5 average rating, 15 reviews

Darling Palms Retreat: Solar Beachside 2BR Oasis

Superhost
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.
Private room in Charlotte Amalie
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

Superhost
A hillside villa is set against a backdrop of ocean views, showcasing neighboring islands in the distance. Lush greenery surrounds the property, while a spacious balcony offers a welcoming space to enjoy the scenery. The blue sky above complements the serene atmosphere.
Guesthouse in Cruz Bay
4.84 out of 5 average rating, 37 reviews

St. John Oceanview Stone Villa, 4BR w/King Suite

Guest house rentals with a washer and dryer

Guest favorite
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.
Guesthouse in Northside
4.96 out of 5 average rating, 25 reviews

La Brisa: Oceanview Escape w/ Included Jeep Rental

Guest favorite
The view features lush greenery in the foreground, including colorful flowering plants and dense foliage. Beyond, the serene ocean is visible with boats gently floating on the water, framed by distant mountains under a clear sky.
Guesthouse in Tortola
4.96 out of 5 average rating, 46 reviews

Quiet Studio with Ocean Views

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.

A shared pool is framed by a wooden deck and surrounded by lush greenery. Two lounge chairs are positioned near the water, while a basketball hoop stands on one side. The sky is filled with clouds, reflecting softly in the calm pool surface.
Guesthouse in Cruz Bay
4.74 out of 5 average rating, 42 reviews

Blue Aweigh

Guesthouse in Tortola
5 out of 5 average rating, 30 reviews

Panoramic Ocean Views and Secluded Beach

Guest favorite
The villa is positioned on a hillside surrounded by lush greenery and vibrant tropical flowers. A wooden deck extends from the structure, offering views of the turquoise waters and rugged coastline. Soft clouds drift overhead, enhancing the serene seaside atmosphere.
Guesthouse in Saint John
5 out of 5 average rating, 12 reviews

Beachfront East End of St John

Guest favorite
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.
Private room in St. John
4.8 out of 5 average rating, 10 reviews

Coconut Coast Villas - Petrea Waterfront Studio

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.
Guesthouse in Northside
4.67 out of 5 average rating, 3 reviews

Estate St. Peter Guest House w/ maid

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