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Guesthouse vacation rentals in Anna's Retreat

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Popular amenities for Anna's Retreat guesthouse rentals

Family-friendly guest house rentals

Private room in Vieques
4.77 out of 5 average rating, 133 reviews

Vieques Tropical Guest House / Room 10 Sun Bay

DanielleRating, 5 stars3 weeks ago
Very responsive hosts. The perfect place to stay for our quick trip to Vieques. Safe and secure, with parking!
A vibrant coastal view is captured, showcasing a turquoise sea bordered by lush greenery and bright red flowers. The scene includes distant islands and a clear sky with a few scattered clouds, highlighting the natural beauty of the surroundings.
Guesthouse in St. Thomas Virgin Islands
4.84 out of 5 average rating, 43 reviews

Cottage Adore

ErikkaRating, 5 stars12 months ago
My fiancé & I had the most amazing time in this beautiful home to celebrate my birthday! Mrs. Lauralie was absolutely great! Gave us very clear instructions on how to get to the home & was even flexible with our check-in time. She was very responsive to any questions once we arrived & even gave recommendations! I am from a Caribbean island, born & raised, & her home reminded me so much of life growing up in Barbados :) The extra mile was definitely taken from the abundance of home amenities, the fully stocked kitchen & the cleanliness of the home! I've stayed at many AirBnB properties before but this is hands down the BEST experience I've had to date! I would DEFINITELY stay here again. Thank you again Mrs. Lauralie!
Guest favorite
A spacious wrap-around porch features a round table with four white chairs, inviting outdoor relaxation. Lush greenery and stunning ocean views can be seen in the distance, while bright clouds drift across the sky, enhancing the serene ambiance.
Guesthouse in Coral Bay
4.99 out of 5 average rating, 106 reviews

A House of Open Arms Cottage with AC

JessicaRating, 5 stars3 weeks ago
Can’t near enough good things about our stay! The views are gorgeous, the space is super comfy and spotlessly clean, and Catherine is an incredibly kind and welcoming host. We loved waking up to the sunrise each morning with views from every angle. The outdoor shower felt so luxurious! We had an incredible breeze for 5 days and never touched the AC. Loved this area of St John - felt quiet and secluded but still just a few mins drive fron some restaurants in Coral Bay, and not more than 25-30 mins drive from everything on the island. Catherine gave us great suggestions in the area! We will absolutely return. Thanks again Catherine!
Top guest favorite
A spacious living area features a wooden coffee table adorned with decorative items, flanked by a plush sofa set against an accent wall. The light-colored walls are complemented by elegant light fixtures, while an archway leads to a dining area and kitchen in the background.
Guesthouse in St. John
5 out of 5 average rating, 58 reviews

A House of Open Arms Villa with Pool and AC

HayleaRating, 5 stars3 months ago
The villa at House of Open Arms was the perfect home base for our honeymoon. The views are breathtaking, the grounds and gardens pristine, and the villa was incredibly warm and inviting. We loved how quiet and peaceful the villa and Coral Bay were. Catherine went above and beyond to ensure our arrival to the island and drive to the villa was seamless. She is also a fantastic cook - our welcome dinner was 10/10! We couldn’t have asked for a better hostess or home for a week. I wish we could give Catherine more than 5 stars! Thank you everything, Catherine! We will be back!
Private room in Vieques
4.87 out of 5 average rating, 106 reviews

Vieques Tropical Guest House / Room 6 El Gallito

Chef FernandoRating, 5 stars1 month ago
My stay was for business purposes, as chefs invited to work at local spot; therefore came in late every night, felt safe in a well lit area and quite neighborhood. Overall very satisfied with this pick, meeting our basic needs. Met Rebecca and Freddy in passing while looking for misplaced keys, and as chefs, we had the pleasure of serving their dinner experience at local restaurant. It was a pleasure hosting them in return on the same weekend. Highly recommended for quiet stay in Vieques.
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, 11 reviews

Beachfront East End of St John

BarbaraRating, 5 stars2 months ago
What a beautiful place - the views were amazing. The location - astounding! The unit itself had everything we needed. Close to snorkeling and hiking. Be sure to rent a Jeep because the roads are steep and winding. We loved it!
A gated entrance is surrounded by lush tropical vegetation, featuring tall trees and dense green foliage. Two decorative elements hang from the gate, enhancing the entrance's charm. The driveway is visible, leading into the property, providing a sense of privacy and seclusion.
Guesthouse in Charlotte Amalie
4.81 out of 5 average rating, 16 reviews

COTTAGE ON PRIVATE PROPERTY

KarenRating, 5 stars13 months ago
Great location on St Thomas for all points east or west. Quiet and private! We would definitely stay here again.
Private room in Vieques
4.83 out of 5 average rating, 234 reviews

Vieques Tropical Guest House / Room 7 Playuela

Mary KateRating, 5 stars2 weeks ago
Great stay on Viequez, you did hear the roosters crow sometimes but idk about you…sleeping in the jungle or hearing roosters or the ocean makes me sleep like a baby… #vacation!! everything was very clean, the place was an easy walk to the ferry, and the whole place had a cool complex and the hallway smelled like a really good candle that i’ve smelled before…or maybe just in Puerto Rico… <3 free coffee! and respectful neighbors, it’s a bit off the main drag which is nice to sleep because the main drag gets poppin (also nice!)

Guest house rentals with a patio

Guest favorite
A spacious bed is featured in the center, adorned with a light-colored quilt and decorative pillows. A woven wall art piece is displayed above the bed, while a cozy bench with a patterned textile is positioned at the foot of the bed. Soft lighting is provided by a wall-mounted fixture.
Guesthouse in Vieques
4.9 out of 5 average rating, 168 reviews

Casablanca 461, Apt #1 - King Bed

DennisRating, 5 stars2 weeks ago
Had a great 3 night stay with Shalyanne in Vieques! There was lots to do, and the host was super responsive with great local referrals. The house was clean and came with fresh beddings. Would definitely book again!
A cozy covered balcony features a comfortable seating area with a coffee table and a hanging hammock chair. Scenic ocean views extend into the distance, showcasing lush greenery and sparkling blue waters under a bright sky.
Guesthouse in Charlotte Amalie
5 out of 5 average rating, 6 reviews

Two Tickets To Paradise Cottage -Tiki Bar & Pool

JessicaRating, 5 stars2 months ago
Amazing! The views from every room, the pool and tiki bar hangout, naps in the cabana, sounds of the ocean, my list could go on and on. You will not be disappointed in the place, the hosts and the area. My husband and I truly enjoyed every aspect of our trip and couldn’t ask for a better place to stay. Hosts were available for questions, knowledgeable about the area for recommendations. We felt right at home but a home in paradise. We would definitely go back to Two Tickets if we visit the island again. The north side is a quieter side and this place offered Hull Bay with restaurants minutes away which was great if we didn’t want to venture out far. Steve and Amie are great people and you can feel their love for the island in this cottage. We feel blessed to be able to enjoy it as well :) Thank you guys!!
The exterior of a casita is presented, featuring a brick archway leading to a white door. An air conditioning unit is visible on the orange-painted wall. A landscaped area with various plants and a stone seating area can be seen in the yard.
Guesthouse in Vieques
New place to stay

Orchindeas

HaowenRating, 5 stars3 weeks ago
Close to the core area of Vieques, clean and hygienic bedroom, the host will provide some water and physical items, which makes us feel very cozy.It would be better if the toiletries were replenished before check-in.
A spacious balcony offers breathtaking views of the surrounding hills and nearby village. A round table surrounded by wicker chairs invites outdoor dining, while the tiled floor enhances the area’s open and airy ambiance. The landscape is complemented by a partially cloudy sky.
Guesthouse in Tortola
4.75 out of 5 average rating, 4 reviews

Shepherd Hill Villa

AnnieRating, 5 stars3 months ago
Ashley Natasha was responsive and accommodating. This place fit our big group and we had time to collect ourselves before the next phase of our trip.
A modern kitchen area is equipped with stainless steel appliances, including a refrigerator and a stove. The light-colored cabinet doors contrast with the turquoise wall. A round mirror and decorative plants are arranged on a wooden console, adding functional style to the space.
Guesthouse in Flamenco
4.76 out of 5 average rating, 58 reviews

Villa 11 Flamenco Beachfront Villa

SandraRating, 5 stars3 weeks ago
Cozy beach villa. You are there for the location which is amazing!! Plan ahead for food and beverage as there are not many options open all the time. Steps to one of the most beautiful beaches I have seen in the Caribbean!!
A spacious balcony offers a scenic view overlooking the coastline and ocean. Two sturdy chairs are positioned for relaxation. The railings are painted white, and the wall is accented in vibrant yellow, enhancing the bright and open atmosphere.
Guesthouse in Threllfall
5 out of 5 average rating, 9 reviews

Hidden Gem Tucked Away

TheresaRating, 5 stars3 months ago
Was a great place for our 9 day stay. Very close to our dive operator in Nanny Cay. Would have been good to know we needed to pick up drinking water ahead of time but there were plenty of easy access stations once we figured it out. Xyla was kind enough to provide a few starters to get us going. The picture she sent of the exact turn was also super helpful. You are on the top of the hill at the end of the road.
Superhost
A vibrant mural is showcased on a red wall, featuring palm trees and birds against a colorful sunset backdrop. Two individuals are seen painting, highlighting the creative atmosphere. The ocean and palm trees can be glimpsed in the distance, contributing to the tropical setting.
Guesthouse in Vieques
4.65 out of 5 average rating, 128 reviews

2 Blocks 2 Ferry - apartment on lighthouse point

RaphaëlRating, 5 stars4 days ago
We definitely recommend Darla’s accommodation if you want to stay in Vieques. We were there for Easter holidays and we could stay in two different apartments due to the high demand at this season. Both places were perfect.

Guest house rentals with a washer and dryer

Guest favorite
A scenic view of the ocean and surrounding mountains is captured from a patio. Lush greenery frames the scene, with potted plants positioned on the stone floor. The tranquil waters reflect the blue sky, offering a serene atmosphere.
Guesthouse in Tortola
4.95 out of 5 average rating, 41 reviews

Quiet Studio with Ocean Views

ChelseyRating, 5 stars1 month ago
Perfect base camp with everything needed for exploring Tortola and surrounding islands! It is close to some of the best beaches on the island, easy to catch the ferry to Jost Van Dyke, and close to Omar’s and Pussars on the West side for dinner. Sophie and her husband were so friendly and helpful with local recommendations. As others mentioned, renting a 4WD is needed for the driveway, but also will be needed for exploring some of the beaches/steeper roads on island. Would highly recommended!
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

TiffanyRating, 5 stars7 months ago
We loved staying at Cassis and will do it again! My husband and teen son stayed for one week in Sept. We found her place to be relaxing, close enough to town and loved our view from the living and bedroom. The pool was a nice way to cool off and special treat after remarkable beach days. Having Cassi being on property gave us a sense of comfort that anything we needed would be address. Etc we never felt it was an intrusion to our privacy. We felt right at home, pretending to be locals for a week! We love STJ and definitely will return to Cassis place! Tip; the address will not be found on maps so follow Cassi's through directions when heading to her place. They truly have a little gem of a spot!
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
New place to stay

Charlotte Amalie Overlook Ackee

LaurieRating, 5 stars2 months ago
Beautiful view, very clean. If you want to meet folks you can in the kitchen area or on the balcony. If you want your privacy you can have that as well. I walk everywhere and the only downside for me is you have to rent a car or take a taxi. The roads don't have room on the side to walk safely. Ja was great with my inquiries. Have fun.
Superhost
A panoramic view of Charlotte Amalie showcases a vibrant seascape dotted with boats. The coastline features a mix of residential buildings and greenery. The sky appears bright and clear, enhancing the natural beauty of the landscape and inviting exploration of the surroundings.
Private room in Charlotte Amalie
4.5 out of 5 average rating, 6 reviews

Charlotte Amalie Overlook Papaya Room5-2

MoisesRating, 5 stars4 weeks ago
We had a great experience in this place. we loved the view it was breathtaking. We had everything we needed. As a family, we definitely recommend this place. Ja was very attentive and ready to answer all our questions.
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 Saint John
4.78 out of 5 average rating, 9 reviews

Coconut Coast Villas - Petrea Waterfront Studio

MackenzieRating, 5 stars36 months ago
Location, location, location! William and I loved this AirBnb for our honeymoon. It’s walkable to the “downtown” area. Restaurants and transportation are easily accessible. Sun Dog was one of our favorites! We also enjoyed Sam and Jack’s for sammies. The view from The Petrea Suite was unmatched. We swam in the bay just outside of our room frequently. Julie makes a fabulous hostess. She met us earlier than check in time (and gave very specific instruction, making it a breeze). The condo has an honor bar filled with libations and snacks. There are guest laundry hours and supplies. Julie provides beach towels, chairs, noodles, and snorkel gear. The bed was comfortable and room was spacious. The bathroom was updated and cleanly. The kitchen was stocked with basic supplies, a coffee maker, and dish soap. There is plenty of parking for those guests who rent vehicles. Pro tips for Saint John: *ASK before you go- some information online may not be up to date. Simply ask waiters and clerks, they are super friendly and informative. *using taxis are easy and affordable but be prepared to wait (syncs up with ferry schedules)….you’re on island time! 😉 *double down on sunscreen!
The airy bedroom includes a queen-sized bed with high-quality linens. A wall-mounted TV with streaming services is visible, along with a work station. Natural light fills the space through large windows, offering a view of the serene outdoors. A door leads to the bathroom area.
Guesthouse in Brandywine Bay
New place to stay

Modern 1BR Hideaway | Near Beach| With Workspace

KadeemRating, 5 stars1 month ago
Comfortable cannot begin to describe this place. Comfortable furniture, tastefully decorated, modern kitchen, sinfully comfortable bed. Really what wasn’t there to like about Chantal and Lincoln’s place. The amenities are great, fast internet, large tv’s in both the living and bedroom. Honestly we couldn’t ask for more. Chantal is very responsive and quick to answer any questions you may have. 10/10 We highly recommend. Perfect for a couple or even a family with 1/2 small children. The couch is so comfortable it might as well be a second bed. To get to the bnb a decently raised vehicle in low gear can make it up and down. If you are not a confident driver please get a 4x4.
Superhost
A modest concrete building is framed by lush tropical foliage. Potted plants adorn the exterior, and textured gravel leads to a small step area. Light and shadow play across the surface, with window shutters providing ventilation and aesthetic detail.
Guesthouse in Vieques
4.8 out of 5 average rating, 60 reviews

Magnolia Esperanza Cottage

AnnRating, 5 stars1 month ago
We loved our stay at Casita Magnolia! It was perfect for us as a couple. The location was walkable to beaches, groceries and restaurants (it is up a hill.) The amenities made our stay easy - beach chairs, towels, coolers, great kitchen with dishes, pots, pans, outdoor eating area was lovely, even access to a washer and drier. The surrounding area was beautiful as the Caribbean beaches can’t be beat. We loved being off the road in back of the main house. As stated in the description there are roosters around and they do make noise, but it’s all part of the charm of the area. If you want simple, private, clean, reasonable cost, with good access to the area, this can’t be beat. We were there for a week and would have loved to stay longer - we felt like we were just getting into the island vibe. Highly recommend!
A private terrace features a round dining table surrounded by four light-colored chairs. Lush greenery frames the space, while the expansive view of the Caribbean Sea and nearby islands fills the background under a bright blue sky.
Guesthouse in Northside
5 out of 5 average rating, 4 reviews

La Brisa: Peaceful Oceanview Retreat

BrettaRating, 5 stars13 months ago
If I could give this place 100 star rating I would. The hosts were so helpful and accommodating. They even allowed us to rent a car on the property. The view was spectacular and they gave us great suggestions on things to do close by. I will always book with them when I visit USVI.

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