Villa holiday rentals in Chocolate Hole

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Popular amenities for villa rentals in Chocolate Hole

Private villa rentals

Top guest favourite
Villa in Coral Bay
5 out of 5 average rating, 57 reviews

Memory Daze

BlakeRating, 5 stars3 weeks ago
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.
Guest favourite
Villa in Coral Bay
5 out of 5 average rating, 31 reviews

Breathtaking views, pool, solar: 5 min to beaches

BarbaraRating, 5 stars3 weeks ago
We very much enjoyed our stay at Pressure Drop Villa (PDV). The view is amazing and the location , though private, is close enough to beaches, groceries and restaurants. In addition, the kitchen is well stocked and supplies for the beach are provided. We used the beach chairs, cooler and beach towels almost daily (had a rainy day). It is a short drive to many fantastic beaches. From PDV Salt Pond, Francis Bay, Maho Bay, and Skinny Legs (restaurant) are all a fairly short drive. Trunk Bay and Cinnamon Bay beaches are a bit further. It was easier for us to park at Cinnamon Bay and take a Taxi to Trunk Bay. We also went into Cruz Bay to La Tapa for a fantastic dinner one evening. To end the evening we would unwind on the deck . It’s really nice to sit on the deck and relax and soak up the sights and sounds of Coral Bay. Jean was always available to answer our questions and give us guidance when needed. We would stay here again.
Top guest favourite
Villa in Charlotte Amalie
4.99 out of 5 average rating, 81 reviews

Tropical Modern Loft | SoHo Style | Concierge

LevyRating, 5 stars1 week ago
Zack was an excellent host. Very responsive and proactive communicator with suggestions for restaurants, etc. I can't say enough great things about his place itself. It's an incredibly hip and modern vibe and in a great walkable location to shopping and restaurants. VERY unique. We loved it. Centrally located on the island and he connected us with someone to rent a jeep. He made it so easy. The whole experience was great! We would definitely stay here again and highly recommend his place to anyone staying in St. Thomas!
Guest favourite
Villa in Southside
4.95 out of 5 average rating, 65 reviews

Frenchman's View Villa 2 BD/2.5 BA w/ Pool

StephenRating, 5 stars1 month ago
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.
Guest favourite
Villa in Coral Bay
5 out of 5 average rating, 32 reviews

Gorgeous views from every room, Pool, A/C

StephRating, 5 stars1 month ago
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.
Superhost
Villa in Tortola
5 out of 5 average rating, 9 reviews

Solace Villa - 5 bedroom with pool in Apple Bay

DerekRating, 5 stars2 months ago
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.
Superhost
Villa in Trunk Bay
5 out of 5 average rating, 7 reviews

Ventana - modern villa, walk to Trunk Bay beach

StephenRating, 5 stars3 months ago
The pace was ideal for privacy and only a 5 minute walk to the beach. Which is essentially a private beach. The beach was amazing. There are literally maybe 6 houses that can walk there. We saw four people total in seven days. The property comes with a concierge service that I think is essential for navigating the island and getting things set up. Sam was responsive and everything was first class. Driving in Tortola can be a bit of an adventure, but you get the hang of it after a few drives.
Superhost
Villa in St. John
4.86 out of 5 average rating, 65 reviews

Stunning Views Villa Catalina. Full Generator!

EddieRating, 5 stars3 weeks ago
Claudia was great and very responsive. Also gave helpful info for the ferry and jeep rentals. Curtis, the property manager was also great and helped us with a jeep and fishing & snorkel charter recommendations. Just good people that took good care of us. I'd highly recommend Claudia.

Luxury villa rentals

Top guest favourite
Villa in East End
4.96 out of 5 average rating, 50 reviews

Tropical Palm Villa- Ocean Views From All Rooms!

TravisRating, 5 stars3 months ago
We had an amazing week at the Tropical Palm Villa!! Spencer was extremely helpful and always quick to respond to any questions we had. Mason met us and made us feel right at home while checking us into the villa. The views from villa are incredible! The place was perfect for my family of five to enjoy St. Thomas and all it has to offer. We were especially grateful for the amenities that made cooking and grilling a breeze. We also enjoyed the beach gear that was provided, including chairs, beach umbrella, and snorkel gear. The location of the house is perfect, offering easy access to the beach, or a quick drive into Red Hook for restaurants, groceries, and the ferry to St. John. Overall, we had a tremendous week and hope to make it back soon.
Guest favourite
Villa in VG
4.98 out of 5 average rating, 51 reviews

Stunning Limeberry Villa, a designer's dream.

JimRating, 5 stars3 months ago
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
Guest favourite
Villa in Coral Bay
5 out of 5 average rating, 34 reviews

Water View, 2 King Primary Suites, pool, private

JasonRating, 5 stars3 weeks ago
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.
Superhost
Villa in Saint Thomas
5 out of 5 average rating, 18 reviews

Paradise with Exquisite Ocean View

CathyRating, 5 stars1 month ago
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!
Guest favourite
Villa in Northside
4.83 out of 5 average rating, 48 reviews

Minutes to Magens Bay - POOL - Views - Dining

JasonRating, 5 stars1 week ago
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 !!!!
Top guest favourite
Villa in Tortola
5 out of 5 average rating, 32 reviews

Gorgeous 4 bed villa with pool and amazing views

ScottRating, 5 stars4 weeks ago
Excellent communication with the host. Quickest responses from any other host I have ever dealt with. Gave some info on possible additions to the stay for future guests and was well received. Most spectacular view looking at St John and Jost Van Dyke. Great sunsets and very convenient to West end of Tortola for dining and beaches. Thank you so much!!
Guest favourite
Villa in Long Bay
4.99 out of 5 average rating, 82 reviews

Luxury LongView Villa with Stunning Sea views

BruceRating, 5 stars4 months ago
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.
Top guest favourite
Villa in St Thomas
5 out of 5 average rating, 15 reviews

NEW - Renovated - Belleview Horizon Villa

AnnaRating, 5 stars2 months ago
Highly recommend this place! 100000/10 Everything was perfect- location, VIEW, accessibility to bars, restaurants, shops. House and porch with pool itself is stunning. Very spacious and clean. Great place to relax but also have a nice dinner in if you want to. And huge shut out to our host Gaven!! Super nice and friendly. Helped us with whatever we needed and it was so fun to be around! His kindness and sense of humor made us feel very welcomed and definitely put us in a fantastic mood throughout our stay. Thank you Gaven! Definitely we would stay at this villa again and again and again!!

Villa rentals with a pool

Guest favourite
Villa in Southside
5 out of 5 average rating, 12 reviews

Villa Royale

JameenRating, 5 stars3 months ago
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.
Superhost
Villa in St John
4.86 out of 5 average rating, 66 reviews

Coconut Breeze, Mesmerizing Views, Generator

IanRating, 5 stars1 month ago
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.
Superhost
Villa in St. Thomas
4.79 out of 5 average rating, 58 reviews

Escape Ordinary: Villa Calvo

BonitaRating, 5 stars1 month ago
Enjoyed our stay. Wished it was a little warmer in the pools and definitely wanted a hot tub! But yes we enjoyed our stay!
Guest favourite
Villa in Coral Bay
5 out of 5 average rating, 18 reviews

Close enough to hear the ocean! Pool!

SarahRating, 5 stars3 months ago
This was an absolutely WONDERFUL AirBNB! It is very well appropriated and has everything you could possibly need, including supplies for the beach, linens, towels, and good recommendations for local activities. The views are breathtaking, the pool is delightful, and the beds are comfortable. Something that would have been helpful for us to know is that the main house contains two bedrooms and a common space. The other three bedrooms are stand alone and they open up onto the pool with doors that do not lock (to my knowledge). This influenced where we felt comfortable sleeping small children in our group and may be worthwhile for families to know ahead of time. We would stay here again in a heartbeat. Thank you for this little slice of paradise!
Superhost
Villa in Water Island
5 out of 5 average rating, 5 reviews

Seagrape Villa on Water Island

CodyRating, 5 stars3 months ago
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!
Superhost
Villa in Cruz Bay
4.82 out of 5 average rating, 33 reviews

Aqua Bay Villa #3~A' La Plage~1 BR~Ocean View~Pool

AlexRating, 5 stars2 weeks ago
Great and safe location! Right by all the action in Cruz Bay
Guest favourite
Villa in Southside
4.93 out of 5 average rating, 14 reviews

Villa View Caribe

MaryRating, 5 stars4 months ago
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.
Guest favourite
Villa in Ballast Bay
4.91 out of 5 average rating, 65 reviews

Villa Almondeen- Peaceful 2bedroom villa with pool

NatalieRating, 5 stars2 weeks ago
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!

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