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Guesthouse holiday rentals in Anna's Retreat

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Popular amenities for Anna's Retreat guesthouses

Family-Friendly guesthouses

Private room in Vieques
4.76 out of 5 average rating, 136 reviews

Vieques Tropical Guest House / Room 10 Sun Bay

EugenioRating, 5 stars2 weeks ago
Fantastic place with incredible views. It is spacious and with enough space to stay several people although we were only 2. Maybe as a point to improve it is the Wifi since it was constantly falling and having a flashlight on hand since on the island it is often that the light goes away, but I just say it to constructive criticism of improvement since in general we are very happy.
Guesthouse in St. Thomas Virgin Islands
4.84 out of 5 average rating, 43 reviews

Cottage Adore

ErikkaRating, 5 stars13 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 favourite
Guesthouse in Coral Bay
4.99 out of 5 average rating, 107 reviews

A House of Open Arms Cottage with AC

JessicaRating, 5 stars1 month 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 favourite
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 favourite
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!
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
4.86 out of 5 average rating, 98 reviews

Vieques Tropical Guest House / Room 8 Playa Negra

KarlaRating, 5 stars5 days ago
Great place! Parking & A/C was top tier.

Guesthouses with a patio

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!!
Superhost
Private room in Charlotte Amalie
5 out of 5 average rating, 4 reviews

Charlotte Amalie Overlook Ackee

maria joseRating, 5 stars2 weeks ago
The place has an incredible panoramic view, the owner is very friendly, and everything was clean and organized.
Superhost
Private room in Charlotte Amalie
4.57 out of 5 average rating, 7 reviews

Charlotte Amalie Overlook Papaya Room5-2

AaronRating, 5 stars2 weeks ago
Host was always available and responsive. The place has amazing views and was perfect for our stay. I would stay here again when I return.
Top Guest favourite
Private room in St. Thomas
4.98 out of 5 average rating, 61 reviews

Private Room with Stunning View

SethRating, 5 stars11 months ago
Absolutely phenomenal views, unparalleled in all of St Thomas. Everything was perfect. Our favorite stay in the Caribbean!
Superhost
Guesthouse in Cruz Bay
5 out of 5 average rating, 5 reviews

St John, USVI, Hillside Villa, Oceanview, King Bed

ElizabethRating, 5 stars2 months ago
This was an incredible little villa to stay at on the island. Lera is a proactive and responsive host. The home was very clean. We had several questions which Lera answered very quickly. She had her property manager help us out. Slightly hard to find the house for newcomers or describing to taxis (if you’re not renting a car.) About a 6 min drive from downtown Cruz Bay so you’re really close to restaurants or grocery stores if you want to cook at the home. Driveway is very steep (typical) so be prepared to drive up in a high clearance vehicle. Or walk down the driveway to the road to get in a taxi. During “rush hour” around 5 pm or so the street is very loud with cars and large trucks going up and down the street for about 2 hours. Keep that in mind if you’re looking for 100% peace. There were very nice tenants below the floor we were staying. Since the house sits on a hill, the views are beautiful from the balcony! Loved our stay overall!
Guest favourite
Guesthouse in Northside
4.96 out of 5 average rating, 52 reviews

Island vibes and views! 5 min drive to the beach!

JirehRating, 5 stars1 month ago
Taylor was extremely helpful through your stay! She was very responsive and very accommodating! We really enjoyed our stay!

Guest house rentals with a washing machine and dryer

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!
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.
Guest favourite
Guesthouse in Tortola
4.95 out of 5 average rating, 42 reviews

Quiet Studio with Ocean Views

MikaelaRating, 5 stars1 week 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!
Superhost
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!
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!
Guesthouse in Northside
5 out of 5 average rating, 4 reviews

La Brisa: Peaceful Oceanview Retreat

BrettaRating, 5 stars14 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.
Private room in Saint John
5 out of 5 average rating, 9 reviews

Coconut Coast Villas - Alamanda Waterfront Studio

MichaelRating, 5 stars19 months ago
We loved our week at the Coconut Coast Villas. It was a cute little place with a personal touch. We could walk to town for dinner and had a couple close by grocery stores to choose from as well. For the 2 of us we chose to utilize the taxis to get to the beaches and back from dinner each night in Cruz Bay after dark. Free laundry, beach chairs and the cooler were definitely appreciated. Used the pool daily too to wind down and listen to the waves before dinner each night. We’ve already booked for next fall. Great location, great place and great hosts.

Destinations to explore