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Guesthouse vacation rentals in Anna's Retreat

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Anna's Retreat guesthouse rentals

Family-friendly guest house rentals

A well-lit room features a spacious bed adorned with white linens and a decorative pillow. Nightstands with lamps are positioned on either side, creating a balanced look. A piece of artwork is displayed above the bed, and a window allows natural light to fill the space.
Private room in Vieques
4.73 out of 5 average rating, 140 reviews

Vieques Tropical Guest House / Room 10 Sun Bay

AveryRating, 5 stars1 month ago
Very clean and welcoming
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 stars14 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!
A spacious outdoor deck area invites relaxation, featuring wicker seating and a large umbrella for shade. Lush green plants frame the view of the ocean, where soft waves can be seen under a clear blue sky. Coastal islands are visible in the distance.
Guesthouse in East End
4.77 out of 5 average rating, 87 reviews

Our Place in St Thomas, Studio Cottage

AdedoyinRating, 5 stars47 months ago
We had a great time at this airbnb! The view from the balcony was fantastic, and it was relatively close to Red Hook (we would recommend driving or getting a taxi instead of walking though, as the road is curvy and the cars drive quickly). Carmen, the property manager, answered all of our questions and kept us informed about an incoming storm. There isn't a ton of space inside, but that was fine for our group because we spent most of the time outside of the house.
Top 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, 110 reviews

A House of Open Arms Cottage with AC

DanielRating, 5 stars3 weeks ago
We loved the stay! The stars on a clear night are Just as breathtaking as the view from the deck. THANK YOU!!!
Top guest favorite
A serene view of a sparkling pool is complemented by expansive blue waters and lush green hills in the distance. The vibrant sky is adorned with fluffy clouds, enhancing the tranquil ambiance. Palm fronds frame the scene, adding a tropical touch to the picturesque landscape.
Guesthouse in St. John
5 out of 5 average rating, 58 reviews

A House of Open Arms Villa with Pool and AC

HayleaRating, 5 stars5 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!
A spacious bed with white bedding is centered in the room, accompanied by a decorative green pillow. A small black side table with a lamp stands nearby, and light streams through sheer curtains, illuminating the tiled floor.
Private room in Vieques
4.87 out of 5 average rating, 106 reviews

Vieques Tropical Guest House / Room 6 El Gallito

Chef FernandoRating, 5 stars3 months 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 stars4 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!
The entrance to the guesthouse features a vibrant coral exterior with a welcoming open door. A small potted plant sits on a stand beside the door, and lush foliage surrounds the entrance, enhancing the private and serene ambiance of the space.
Guesthouse in Culebra
4.7 out of 5 average rating, 142 reviews

The Casita @ Mango Fish Guest House

Luis ARating, 5 stars2 months ago
Super lo recomiendo al 100%

Guest house rentals with a patio

Guest favorite
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
4.97 out of 5 average rating, 34 reviews

Faith

KurtisRating, 5 stars3 weeks ago
Pink pineapples and bananas, out there but close enough, have a car or a rental, we were nighttime restaurant people but this Place put us right on island time. Loved the outdoor kitchen and environment. We “HAD!” To extend our stay 3 nights. St. John is, just come see. Definitely not a resort & no tourist. After doing it all every which way, pray I do it this way again. Thank you so much. Word of advice talk to Cory Lynn, very intelligent and offers great advice. We hope to be back soon. Thank you very much.
Guest favorite
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
4.86 out of 5 average rating, 7 reviews

Charlotte Amalie Overlook Ackee

ElijahRating, 5 stars1 month ago
This was the best Air BnB experience I have had yet! The property is beautiful and the view from the patio is the best view on the islands. We will definitely be back!
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

JuanitaRating, 5 stars3 months ago
Deena and Charlie were fabulous, I truly felt like I was staying with family! They welcomed us with open arms, so inviting, so informative and very knowledgeable of the island and all there is to do. I loved getting to know them, beautiful people inside and out!!! I was so impressed with Charlies French Quater Bistro and Deenas captains skills!!! Being next door to Lime Tree Resort is just the icing on the cake, because the sunsets are breathtaking. 10/10 will definitely be booking again! Thanks for a fabulous stay!
Superhost
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
4.83 out of 5 average rating, 29 reviews

Charlotte Amalie Overlook Soursop Room5-3

SamRating, 5 stars2 weeks ago
Great shared place to stay(I know lot people miss this part while reading the description or forget this eventually after reserving), amazing views, close to all the great locations not more than 10 minutes(we rented our car). Host was excellent in communicating and responsive. Amenities were good as well. Though locating the home was bit difficult after a long tired day and driving back in night especially the excellent thrilling road(wish we had come during the daytime) and host pulled their family member helping us to find the home. Also sent the right location on the map so can be corrected to all future guests to find this on easy.
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
4.6 out of 5 average rating, 10 reviews

Charlotte Amalie Overlook Papaya Room5-2

KistaRating, 5 stars1 month ago
The kids & i absolutely loved this location and room itself. I was a little thrown off at first not reading deep into it regarding sharing common areas but met some amazing people and the cooking experience was nice. My daughter stated Ja was the absolute best air bnb host she’s ever encountered and made sure we had everything. I would suggest possibly snorkeling gear, 20-40$ a trip to a beach each time was expensive. Chairs were perfect, beach towels, body wash & shampoo. Bring conditioner if you have to use it after a Long Beach day. Beds were comfortable and view was absolutely amazing. Having breakfast and dinner on the balcony was a site to see. Thank you for hosting us and we will definitely love to come back!
Top guest favorite
A private porch is visible, featuring two outdoor chairs and a small table, surrounded by greenery. The setting offers views of the ocean and islands beyond, illuminated by soft evening light. Large windows bring in natural light, enhancing the relaxing atmosphere.
Private room in St. Thomas
5 out of 5 average rating, 50 reviews

Private Room with Extraordinary View

MichaelaRating, 5 stars11 months ago
Only stayed for one night but it was great! Gorgeous view, good location, very relaxing overall. Recommend for sure!
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
4.82 out of 5 average rating, 34 reviews

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

KeylaRating, 5 stars1 month ago
Lera place is wonderful place to spend with friends or family at St John. The house is so comfortable and welcoming and has everything you need and feels like home. Everyone love the beds they were so comfortable we did not want to get up in the morning. It is in a quite area up a hill and close to town and all beaches so perfect location. The driveway up to the house is steep. Lera was very nice and quickly responded to any questions we had and provided all sorts of recommendation of places to go and visit which was very helpful. Would recommend it 💯 for stay in St John
Superhost
A vibrant sunset casts warm hues across the sky, illuminating the silhouette of palm trees in the foreground. The ocean glimmers in the distance, while the landscape showcases a lush blend of greenery and colorful foliage.
Guesthouse in Southside

Darling Palm: Solar Beachside Guesthouse

KellyRating, 5 stars5 months ago
We had a wonderful stay and can't say enough about how many great things these accommodations had to offer. Our family of four stayed in the combined two-bedroom place and studio. We were impressed by all of the beach items: chairs, towels, snorkeling gear, bags, and umbrellas. It made it very easy to go to the beach. And it was nice having the beach within walking distance. Deena and Charlie were super friendly and we enjoyed talking with them. We would also recommend Charlie's restaurant, the French Quarter Bistro, excellent food and service! Deena was very helpful with local recommendations from supermarkets to boat charters. The location of this house made it easy to get to all of our vacation activities. The AC in the bedrooms made it easy to sleep. This house is a slice of paradise and we would love to come back.

Guest house rentals with a washer and dryer

Guest favorite
A private terrace offers a round table surrounded by four chairs, overlooking a scenic view of the Caribbean Sea and lush greenery. The landscape below features a mix of residential areas and distant islands under a blue sky with wispy clouds.
Guesthouse in Northside
4.96 out of 5 average rating, 25 reviews

La Brisa: Oceanview Escape w/ Included Jeep Rental

KarenRating, 5 stars16 months ago
Our stay at La Brisa, St. Thomas was awesome! The place was beautifully decorated and had a fabulous view from the top of the mountain! We enjoyed breakfast and cocktails on the patio overlook! The accompanying Jeep was perfect for the steep hill driving. It was so nice to have our own vehicle and go wherever we wanted, whenever we wanted. Our favorite snorkeling beaches were Coki Point (coral & hundreds of tropical fish)Sapphire Beach (turtle & sting ray)and Magen’s Bay (turtles and diving pelicans!!) Nichole & Gaven did a marvelous job assisting in anything we needed. A beautiful carribbean coastal get away. ❤️
Guest favorite
A sunset view showcases the horizon where the sun descends over the ocean, casting warm orange and yellow hues. Surrounding foliage includes green leaves and vibrant flowers, framing the serene water and distant hills.
Guesthouse in Tortola
4.95 out of 5 average rating, 42 reviews

Quiet Studio with Ocean Views

MikaelaRating, 5 stars1 month ago
Overall, we loved our stay at Sophie’s place. Her and her husband are both super nice and very helpful. The studio is as listed - very cute, clean, and perfect for what we needed. The view is even better in person! If you are staying here, having a 4WD car is a MUST! Make sure the rental car agency actually gives you a 4WD or you will not be able to make it up the driveway. It was one of the steepest roads we have ever tried to drive up and our car struggled because it was only 2WD. But, Sophie came running to our rescue and she even offered to drive us down to our car the morning of our departure since we had all of our luggage. We had a great time here and loved the view!
Guesthouse in 108-A-15 Estate Contant Northside
5 out of 5 average rating, 11 reviews

Crown Mountain Manor. Modern Living with a view.

CortinaRating, 5 stars47 months ago
Kirk and his wife Tracy was very helpful and available anytime we needed them for anything. The house is just like the pictures. The house was very clean and spacious. I would highly recommend this Air BNB!! The best host and hostess ever! I give them and their home 5 plus stars!!! St Thomas Summer 2021
A vibrant sunset is captured over the ocean, with hues of orange and yellow blending into the sky. Lush greenery frames the coastline, where gentle waves meet the shore. The silhouette of a hillside is visible in the distance, complementing the tranquil scene.
Guesthouse in Cruz Bay
4.74 out of 5 average rating, 42 reviews

Blue Aweigh

TiffanyRating, 5 stars9 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!
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 stars38 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!
A modern bathroom features a sleek black vessel sink on a light countertop, accompanied by neatly arranged towels. A walk-in shower with glass doors showcases a stylish tile design. Natural light flows in through a small window, adding to the fresh atmosphere.
Guesthouse in Brandywine Bay
5 out of 5 average rating, 4 reviews

Modern 1BR Hideaway | Near Beach | With Workspace

SudarshanieRating, 5 stars1 month ago
Our stay in Tortola was absolutely incredible, and Chantal and Lincoln’s apartment made it even more memorable. From the very beginning, communication was excellent. Even before we finalized the booking, Chantal and Lincoln were quick to respond, super helpful, and made everything feel easy and straightforward. The apartment itself is absolutely spectacular. Spotlessly clean, beautifully designed, and incredibly comfortable—it had everything we needed for a relaxing, stress-free stay. The space was quiet and peaceful, and every detail felt thoughtfully prepared. It truly felt like a home away from home. Throughout our visit, Chantal and Lincoln continued to be amazing hosts. We had zero issues the entire time, and the whole experience—from booking to check-out—was seamless. We can’t thank Chantal and Lincoln enough for their hospitality. We would absolutely stay here again and highly recommend this apartment to anyone visiting Tortola. It was truly a five-star experience in every way
Guest favorite
A panoramic view is offered through sliding glass doors, showcasing lush greenery and the serene blue waters of Pillsbury Sound. Blue barstools are positioned at a countertop, inviting relaxation while enjoying the scenic landscape.
Guesthouse in Cruz Bay
4.9 out of 5 average rating, 10 reviews

BRAND NEW In-Town w/View, King Bed Carriage House

JulieRating, 5 stars1 week ago
We loved it here. The carriage house was exactly as described. Great location, great view, and about a 10 minute walk from downtown. The only noise we heard was from the roosters in the morning. I definitely recommend following the host's provided directions since the address on Google maps is slightly off.
Superhost
A stack of beach chairs is neatly arranged against a wall. The chairs feature a blue and white striped design, with one displaying a red lobster motif. The metallic frames are visible, adding to the practical appeal of the seating options.
Guesthouse in Vieques
4.76 out of 5 average rating, 62 reviews

Casita Magnolia Esperanza

KaciRating, 5 stars1 month ago
Dave and Michelle’s place was a wonderful choice for our stay in Vieques. We were pleasantly surprised by the beach chairs and towels on premises and the in unit laundry was very useful towards the end of our trip! There are also two very friendly community cats that stay outside the property who greeted us whenever we came in and out. We were also very appreciative of Aurelio, who was accommodating of our check in and check out times and quick to help solve any issues that came up.

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