
Guesthouse vacation rentals in Anna's Retreat
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Top-rated guesthouse rentals in Anna's Retreat
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Family-friendly guest house rentals

Vieques Tropical Guest House / Room 10 Sun Bay
Very clean and welcoming

Cottage Adore
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!

Our Place in St Thomas, Studio Cottage
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.

A House of Open Arms Cottage with AC
We loved the stay! The stars on a clear night are Just as breathtaking as the view from the deck. THANK YOU!!!

A House of Open Arms Villa with Pool and AC
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!

Vieques Tropical Guest House / Room 6 El Gallito
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.

Beachfront East End of St John
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 Casita @ Mango Fish Guest House
Super lo recomiendo al 100%
Guest house rentals with a patio

Faith
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.

Charlotte Amalie Overlook Ackee
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!

Darling Palms Retreat: Solar Beachside 2BR Oasis
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!

Charlotte Amalie Overlook Soursop Room5-3
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.

Charlotte Amalie Overlook Papaya Room5-2
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!

Private Room with Extraordinary View
Only stayed for one night but it was great! Gorgeous view, good location, very relaxing overall. Recommend for sure!

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

Darling Palm: Solar Beachside Guesthouse
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

La Brisa: Oceanview Escape w/ Included Jeep Rental
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. ❤️

Quiet Studio with Ocean Views
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!

Crown Mountain Manor. Modern Living with a view.
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

Blue Aweigh
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!

Coconut Coast Villas - Petrea Waterfront Studio
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!

Modern 1BR Hideaway | Near Beach | With Workspace
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

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

Casita Magnolia Esperanza
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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- Flamenco Beach
- Honeymoon Beach
- Magens Bay Beach
- Limetree Beach
- Mosquito Bay Beach
- Oppenheimer Beach
- Coki Beach
- Cane Garden Beach
- Chocolate Hole
- Cinnamon Bay Beach
- Cane Bay Beach
- Peter Bay Beach
- Gibney Beach
- Pelican Cove Beach
- Josiah's Bay
- Playa Sun Bay
- Caneel Bay Beach
- Maho Bay Beach
- Playa el Convento
- Salt River Beach
- Virgin Islands National Park
- Oil Nut Bay
- Playa Puerto Real
- Grapetree Beach