Villa holiday rentals in Chocolate Hole

Our stay at Memory Daze was amazing. It was just as described, and the view was even more stunning in person. Our teenage girls loved having their own villa, relaxing by the pool with the spectacular view. The location is extremely private, and feels very safe - the entry gate is only to keep the goats out! The host/management company was very responsive, before and during our trip. Beach chairs, beach towels, and cooler provided were very helpful. It was hard to leave the villa after an amazing week on St. John. We highly recommend staying here!

The charm of the Hideaway is the quiet, remote location. The views are spectacular! The beach is very private with lounge chairs and a pergola - we were the only ones there! The open-air dining area is spacious and we loved being able to look out at sea while eating. The beds were comfortable and the outdoor shower was a cool experience. The kitchen had all we needed to make simple meals, including a blender for frozen island drinks. :-) Filtered water and an ice-maker in the fridge were key. Libby was a great host - very communicative, helpful and quick to respond to our questions. We did end up renting a Jeep since it is a bit far from from Great Harbour and the roads are very steep, but Foxy's Taboo is a short 1-mile walk down the road and their food is excellent. I do recommend bringing some provisions with you so you don't have to make the trek back to town because once you're there, you won't want to leave!

After being Double booked at another property, we found Jules! We are so happy we did and were thrilled! The property is beautiful! And the views are even better. We stayed in the Master Suite,the views were breathtaking as we looked on towards St John’s. The main town near by was “Red Hook” where there were so many options for restaurants and shops. Local beaches are just a short drive away. We will definitely be back.

Wonderful stay. The house didn’t have hot water and it was fixed immediately when I reached out to the co host. Amazing views and the house was so much better than the pictures! Highly recommend!!!

Our group of 8 stayed in mid March 2025. Heather was an amazing host. Her recommendations from day charters to rental cars and restaurants came in handy. She checked in regularly on how our days went. The home was beyond words. Our driver told us as we arrived “welcome to the castle”. The amazing glass wall of windows in living area bedroom as well as bathrooms gave a beautiful view of the great marina below. It was Such an amazing week we can’t wait to return. Great location. We ate locally at Dove it was delicious. We took our rental car to Cane Garden Bay what a beautiful sunset. We took the ferry to Anegada and splurged with a helicopter ride back through Buzz helicopters. The BVI from the sky was amazing. Heathers recommendations of Quintessence Day Charter and Allure both picked us up in the bay right outside our window were amazing guides to Norman, Peter and Saba rock. Heather and The Lighthouse did not disappoint. Thank You Heather.

Wow, this was the exact peaceful gorgeous retreat we needed. Everything was taken care of and Katie (the property manager) was so wonderful and helpful in every way. We can't wait to visit again. Everything about the place was truly rejuvenating. I could not possibly recommend it more. It's not within walking distance to town or major amenities but that was the whole point of our trip. It's very easy to get everything delivered or to make a quick trip over the hill to grab something.

Exactly as advertised, host was very receptive. One bonus not really mentioned is how close the market is for coffee and anything you’ll need. Kids loved seeing the Iguanas at the tree each morning.

Looking for a luxurious private getaway with unrivaled views and yet still close enough to local restaurants and things to do on Tortola? Look no further than Villa Taino. My girlfriend and I had the pleasure to stay here for a week and it was all we could have wanted and more. You will not find many views better than this on Tortola. It looks out over Long Bay, Smugglers Cove and Jost Van Dyke. There are a handful of great restaurants near by within 10 minutes driving and it’s about 15 minutes from the ferry to Jost Van Dyke. The villa itself is stunning and looks exactly as pictured on Airbnb. The pool was a fantastic addition to the stay and all appliances, furniture, etc. worked as expected and were great in top notch condition. Sam and her team and unbelievably welcoming and responsive and go above and beyond to provide a white glove service to their guests. I would highly recommend Villa Taino or any of Sam’s stays around the island and we’ll be sure to return again.

What a beautiful home! It’s hard to even describe the view. It’s so, so beautiful! Greta location, central to everything we needed access to. The onsite restaurants were great and everyone we met was so kind. The owners were great and very responsive. Highly recommend!

My wife, daughter, and I had a great stay at Elysium for our February vacation. The pool was a nice feature, and the kitchen was well-equipped for our needs. The view of Fish Bay was a highlight—really beautiful. The place was clean and comfortable, and the host was responsive. Five stars from us!

Absolutely Perfect Stay at Just Peachy! Our stay at Just Peachy in St. John was nothing short of incredible! From the moment we arrived, we were blown away by the stunning views of the mountains and ocean—it truly felt like paradise. The villa itself was immaculate, beautifully designed, and had everything we needed for a comfortable and relaxing vacation. Melissa, our host, was phenomenal! She was incredibly responsive, always just a message away, and went above and beyond to make sure our stay was perfect. Whether it was providing great local recommendations, answering any questions we had, or simply ensuring we felt at home, her hospitality was unmatched. Waking up to breathtaking sunrises, lounging on the patio with the cool island breeze, and enjoying the peaceful surroundings made this trip unforgettable. If you're looking for the perfect getaway in St. John, Just Peachy is the place to be. We can’t wait to come back! Thank you, Melissa, for making our trip so special!

Villa Paradiso was incredible! Hilltop location, overlooking to Jost Van Dyke. The roads are a little harrowing to get up there, but easily navigable, and once there it’s pure solitude. Our kids lived the pool. The kitchen had everything to cook to dinner for our group of 10. The outdoor showers were the cherry on top. Would rate the home 10/10 and Rehanna and Sylvia were so so great to communicate with.

We had a lovely stay at Zack’s unique and special unit/condo. Zack was extremely helpful & responsive from time of booking and time to departure. He was proactive to reach out to see if we’d landed and also was waiting for us when we arrived to welcome us inside. He took the time to give us a tour of his place and he also shared some restaurant recommendations. Zack’s a personable, great all around guy and his place was perfect! Thanks so much Zack from Kelly & Co!! We’d definitely stay at your place again!

We loved our week long stay at Pressure Drop! We were a family of four with an almost 2 year old and 5 year old, plus our au pair. The set up was great, and Jean had a pack and play and blow up twin mattress for the kids. The house was nicely decorated with a well stocked kitchen. We liked having the separate living and sleeping quarters so whoever got up early with kids could let everyone else sleep. The pool was also a great size for our kids with a shallower end where the older one could stand. We also loved how close the house is to Maho and the north shore beaches. We would definitely come back! The only downside is that the driveway is not for the faint of heart, but that’s not uncommon for St John. The only downside

Words can’t express the serenity we felt staying in this incredible home! Alan was an INCREDIBLE host and so very responsive. The VIEWS from every window and angle were breathtaking. The house was immaculate. This is a dream come true! Definitely take his advice and rent a jeep, it’s fun to drive around there. We toured local beaches (and St. John a must) by day and relaxed later afternoons and evenings in this beautiful home. Thank you, thank you!!

You cannot go wrong booking on Magen’s Bay! The views are like none other… how often can you wake up in the morning to watching sea turtles, sting rays and iguanas from your balcony? Our family of five stayed in the main house for two nights to conclude our trip to the VIs. Things we loved: provided beach amenities (chairs, floats, coolers, towels…), pool table (we played with our three teenagers every night), huge rooms and bathrooms, big balcony, and most of all- access to the water with use of paddle boards and kayaks. Things that could use a little improvement: updated linens and a cleaner unit upon arrival (rug was visibly dirty, white couch had a seat stain, appliances in kitchen were visibly dirty). Even with these suggested improvements, this beautiful place deserves a 5 star! On top of that, our host was amazing! She communicated very well and was super helpful!! Very grateful that our family of five got to experience a stay on Magen’s Bay at Sailfish!! Thank you, Calisha!!

The condo was the perfect private getaway - conveniently located walking distance to beautiful Sapphire Beach and close to the ferry and many shops and restaurants nearby. The check-in and check-out processes were quick and easy, and our hosts responded very quickly to questions, which added to ensuring that all we had to focus on was enjoying the condo and its proximity to all the island had to offer. The condo was also stocked with many kitchen, bath, and activity goods and supplies; we particularly enjoyed using the snorkel gear and beach chairs and mats. We look forward to returning as soon as possible, and will be recommending friends to visit as well.

Two couples vacationing in paradise! We loved Kim’s home. It’s perfect for two couples to have their own space yet a communal area to enjoy together. The location was perfect for exploring Choral Bay with a quick way to get to some North Shore Beaches. The road/driveway was challenging but after a few trips up and down we mastered the drive and even walked it a few times just for a workout ;) Kim was very helpful and proactive when the power went out and was always available for any questions or help that was needed. I would definitely rent from her again. We loved the home and location!

Amazing views in a very well equipped home! This place has it all - from the comfortable beds to the peaceful outdoor patio - and was exactly as described. We appreciated the beach towels and chairs and especially the snorkeling gear, which we used every day as we explored different beaches across the island. This home is a decent drive up a steep road so renting a jeep is highly recommended. We will definitely return to this home in paradise!

This unit was very lovely inside and out. Derek was very responsive at all times and gave lots of local recommendations. Overall I would definitely stay here again when visiting Tortola.

What a wonderful stay! Amazing all around, from the villa's accommodations to the view! Just Wow!!!! Thank you Xaverie and Stephanie.

Great location, privacy, and breathtaking views! The home was more space than we needed, but we enjoyed the open layout, and spacious bedrooms and bathrooms, and beautiful views from every room. We appreciated all of the amenities as well - from everything in the kitchen to the A/C units, ceiling fans, extra towels, laundry, etc. We loved the pool area with options for sitting in the sun and shade, and really enjoyed exploring the paths around the home and the “extra” deck and chairs. Great proximity to Magens Bay and our favorite spot, the Northside Grind for coffee, smoothies and sandwiches.

I have to say House Aceso absolutely out weighed all expectations!! It’s even better than the pictures suggest. Kandee has thought of everything as far as amenities (there’s even a crockpot if you do choose). The main is where it’s at, the view, the sound of the wind, and decor is all top notch and just the perfect vacation vibe. The house is super clean and spacious. The bedrooms are exactly what you need. The 2 bathrooms are extremely useful for a larger group. The pool deck is fantastic as well! Book this house and you will not be disappointed!!

We enjoyed our stay. Great location, great service. We were greeted upon arrival and Dina made us feel at home and gave us great tips for the island. Very friendly. The master bedroom was spacious and AC worked great. The living room & kitchen does not have air there was a new AC in loft that my son used at night which kept him cool.