
Villa holiday rentals in Chocolate Hole
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Top-rated villa rentals in Chocolate Hole
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Popular amenities for Chocolate Hole villa rentals
Private villa rentals

Memory Daze
This is the greatest place we’ve ever stayed. It had a breathtaking view, was well appointed, quiet, peaceful, and tranquil. Memory Daze is a dream and we will be coming back. The hosts were supper communicative and helpful and the house had everything we needed to have a great vacation. I literally teared up when we were about to leave because it was such a happy place for my wife and I. If you are reading this and contemplating a vacation here in St. John, do it! Book this place now. You won’t regret it.

Elysium Villa-Natural Surroundings, Ocean Views, P
We returned to Elysium this spring, having rented the same home 18 years ago for our honeymoon. The living area is upstairs, with 2 bedrooms downstairs on the second level, each with a separate entrance and bathrooms. It is ~15min from Cruz Bay, but worth the drive - private with unbelievable views. There is lots of outdoor space on both levels, and of course the private pool. There are lots of beautiful native plants on the property, and there are birds everywhere to serenade you. BookVI was very proactive and flexible. They guided us to the property and were in communication every day to make sure that all was good. You will want a jeep as the road from town is a little hilly, there is a very short strip of unpaved road just before the driveway, and the driveway is paved but steep. (as is the case with many of the hillside homes!) This was a peaceful place to wake up every morning, and to spend the evening after exploring beaches and hiking. Highly recommend!

Just Peachy - Pool Villa + Bronco + WE’RE SOLAR!
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!

Gorgeous ocean view penthouse! Walk to Cruz Bay!
We really enjoyed this condo on St. John!! It was so comfortable and had everything we needed. We loved sitting out on the covered balcony, enjoying the view, both in the morning while having our coffee and in the evening watching the sunset! The location was fantastic! We walked to town for restaurants & groceries, and we walked to the taxi area to get a ride to the beautiful beaches! There was a steep hill walking back to the condo, but it was worth it for the condo and its location! It was just right for us and our two teenagers:)

Tropical Modern Loft | SoHo Style | Concierge
We just stayed at Zack’s a couple of days ago and can’t recommend enough! We stayed for 2 days after coming back from a boat charter in the BVIs and we really wanted to explore St. Thomas. Zack met us at the apartment/studio. The place was super cool like a New York loft and had lots of room for 2 adults and 3 teenage boys! We walked to restaurants and the Diamond District and Zack arranged for a car to the airport! Loved the vibe!

Frenchman's View Villa 2 BD/2.5 BA w/ Pool
I would absolutely recommend this place for anyone! Everything was as advertised the views were stunning the home was absolutely beautiful and sabrina was an excellent host. My favorite part was that it wasn't dead in the center of town nor was it too far away from Charlotte Amalie or anything else, really 10/10 on all fronts.

Gorgeous views from every room, Pool, A/C
If I could give Kandee's place 10 stars, I would. The photos don't do this place justice. When you open the front door the view is breath taking. Kandee has thought of everything to make your stay so easy. So many beach and pool toys and all the kitchen appliances and cooking spices etc you need. She was incredibly helpful when we had an issue with the lock on the bedroom building and fixed the issue right away. This place is split in to 3 levels, upstairs is living, a separate buidling down a level has bedrooms, then the pool is on the level below. All with amazing views. We watched the sunrise over the bay every morning from the bed, incredible. The photos don't do this place justice. Go ahead and book right away. And don't forget your 4 wheel drive for the drive up to the property and around the island in general.

Solace Villa - 5 bedroom with pool in Apple Bay
Solace Villa was an absolutely amazing place for our family to spend our vacation. The views from every part of the property are stunning. There was more than enough room for our family of six to spread out and have space to relax in the evenings after a full day exploring the British Virgin Islands. Thomas was a wonderful host, reaching out prior to our stay, offering to fully stock our kitchen for us prior to our arrival. When we declined, not knowing what we would want to have, he gave excellent recommendations for the best locations for us to stock up ourselves. Thomas put together a great binder loaded with recommendations for anything we could need to know to stay entertained while visiting. I would highly recommend staying at Solace Villa.
Luxury villa rentals

Stunning Limeberry Villa, a designer's dream.
Great host and property. Unique,great view,comfortable,well equipped. Great pool. 5 star across board except star on location as represented due to advertising of "short walk to beach ". Was short drive to multiple beautiful beaches,Smugglers Cove most beautiful secluded beach ever

Water View, 2 King Primary Suites, pool, private
This place was amazing. The property was very well maintained and clean. Everything worked and it had everything we needed. The location is close to hiking, beaches, grocery and food. Kim was a great host we will be back for sure.

Paradise with Exquisite Ocean View
I cannot say enough about how beautiful this house and location is. A beautiful view of the water in almost every location in the home. Very clean and the ere was plenty of room for 5 of us. We loved the spacious dining room with a huge dining table to seat a large group. When on the deck, you are almost directly above the water-feels like you are on a cruise ship! Andrew responded immediately whenever we had a question. I would definitely recommend this home!

Modern, Serene, and a view you must see. Modere’
View is amazing. You are close to a few marinas, restaurants & and grocery store. You MUST have 4-Wheel drive or use their driver. The driveway/road is 1/2 mile to main street with gravel & it’s very steep. The house could use a little TLC. It is an island, I understand but the house is damp smelling upstairs. The master downstairs ceiling came down during the freak tropical rain storm while we were there. It can also use some more kitchen supplies. It is not conducive to really cooking/eating for a group. There was no laundry supplies even tho there was Washer/Dryer so bring if u want to wash clothes. Outside needs fans & citronella desperately. It’s very buggy day or night. The place is amazing and a great deal. Especially for large groups or multiple families. We would stay there again. Claudia the concierge was amazing. Lionel the driver equally great and gave us history every time we drove somewhere. I would recommend this house.

Minutes to Magens Bay - POOL - Views - Dining
The view is amazing, plenty of room and very spacious. AWD is a must for the driveway, pool are is very nice. No complaints at all. We loved our week here !!!!

Luxury LongView Villa with Stunning Sea views
There's not much to add as a review of Nick's wonderful home that hasn't been said already. We just spent 10 days there for the third year in a row, and this is our third review. Because of the 4 king bed rooms (two on each side of the center living area), his place can certainly accommodate four couples with plenty of privacy (our trips have been just my wife and myself), each bedroom and a number of outdoor dining and relaxing spots all having world class views of the Carribean from about 200 feet above the sea. Being right above a nice beach provides a constant sound of waves hitting the beach that adds to the ambience of the villa. The villa is well equipped (we cooked every meal there), clean and comfortable. Has WiFi and TV's for those who need or want Internet access and entetainment. Nick (the owner) and Jon and Jude (the on island management team) are terrific people and very accommodating. We hope to be back again to our personal favorite vacation spot on the planet.

Amazing Pineapple Village Villa in Margaritaville
Absolutely perfect for a few couples trying to get away. Everyone has their own rooms and private patio. The living room was beautiful and spacious. very close to the beach and Margaritaville. We did have some issues with the hot water while on site but the hosts were insanely responsive and got the issue fixed immediately. I was not a huge fan of the beach as we came during the seaweed season, but Coki beach which is a short walk away was amazing.

Cliff House One - stunning modern home above surf
Thoroughly enjoyed our stay at Cliff House One in Apple Bay. Pinky met us while picking up our rental car and led us to the villa, which is a few minutes' drive from the West End ferry dock. The villa is perched on a cliff above the coast and every room except the first floor bedroom has amazing views of the water and islands. The main floor opens to the outside and is cooled by the breeze and the bedrooms have great A/C. Sam and her team were very responsive and informative. Would definitely stay again.
Villa rentals with a pool

Villa - Private Pool!
This place was even better than described. Anything you could think of or might need was available to use. Peaceful, private and clean. One of the best places I’ve ever stayed! We would definitely book with this host in the future. Thank you 😊

Villa Royale
Kristen's place was top-tier!! Not to mention the beautiful views and over accommodations. She offered more amenities than we expected. Overall, we had an amazing time and would definitely consider staying there again.

Coconut Breeze, Mesmerizing Views, Generator
Coconut Breeze was as good as advertised. The home was comfortable, well stocked and had spectacular views, absolutely perfect for our group of 6. Definitely get a 4 wheel drive vehicle as the roads leading up are steep and a bumpy, but hey it’s St John and that’s what you signed up for. While the home is tucked into the private, lush jungle hillside it’s also conveniently located a short drive away from multiple restaurants, grocery stores etc. We had an issue with an AC unit in the cottage, but it was promptly resolved by our host. The cottage porch was not screened in, but maybe this is something that will be done in the future. If you are staying in Coral Bay Coconut Breeze is the way.

Escape Ordinary: Villa Calvo
The place was amazing! Best vacation we have ever been on. Beautiful views of the water. Snorkel gear and chairs come in handy! My advice would be to rent a car, so you can explore multiple beaches. We felt very at home at Ryan’s place. We were sad to leave.

Seagrape Villa on Water Island
From start to finish, April made our stay one of our most memorable vacations. Having visited the island multiple times, we knew exactly what we wanted—and this property checked all the boxes. Anything we needed or requested was promptly addressed by either April or her property managers. This property is truly one of a kind, offering both stunning sunrise and sunset views. The ocean breeze is strong but refreshing, keeping you cool throughout the day. We also opted to have April provision our groceries, and she went above and beyond—everything was neatly put away upon our arrival. Water Island has always held a special place in our family’s heart, and staying here made it even more unforgettable. We can’t recommend it enough!

Villa View Caribe
I appreciate Randall meeting near the property to provide directions and information. The house was very clean and the views are stunning from the back patio.

Villa Almondeen- Peaceful 2bedroom villa with pool
Janice and her family are absolutely amazing! From the moment we arrived, she went above and beyond to make our stay seamless and welcoming. She provided clear instructions on where to meet and was incredibly flexible with our check-in time. Janice even personally drove us to the villa, gave us a full tour, and made sure we knew where everything was. As a thoughtful touch, she welcomed us with a fresh bowl of mangoes picked right from the tree on her property—such a lovely gesture! The villa itself is private, peaceful, and perfectly located. We were no more than 20 minutes away from everywhere we wanted to go on the island, including all the ferry ports. Each evening, we relaxed by the pool and watched the sunset—truly a breathtaking experience. We felt completely at home and safe throughout our stay. Without a doubt, we’ll be returning to Tortola—and when we do, we can’t imagine staying anywhere else!

Heated Pool/Views/SpaTub/Outdoor Shower/Generator
I’ve had staying in many airbnbs before, and Stacie’s place has been one of the best I’ve stayed at. It had everything we needed and wanted plus more. Don’t even think twice to book this place! It’s beautiful. Also bathrooms were recently remodeled and they’re both beautiful. I will say that this home is not for children under or the elderly.
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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
- Salt River Beach
- Virgin Islands National Park
- Oil Nut Bay
- Grapetree Beach
- Secret Harbor Beach
- Hull Bay Beach