
House holiday rentals in Chocolate Hole
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Top-rated house rentals in Chocolate Hole
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Popular amenities for house rentals in Chocolate Hole
House rentals with a pool

Heated Pool, OceanView, Generator, Local Discounts
Wonderful place to stay! It felt private and safe. It was a little challenging to get to, but as with anywhere on the island, without the adventure you don’t get the views! Stacie had exceptional communication, including a guide for nearby beaches/restaurants/grocery stores. Very clean. What stood out most were the “extra” amenities. We made use of the beach chairs, beach towels, a pair of snorkeling fins, etc., even the first aid kit! Would highly recommend!

Casa Tua - Saint John
We were pleasantly surprised at how quiet and private this home was considering its proximity to restaurants and the main thoroughfare in Coral Bay! It was so convenient for us to get to all the beaches we love to snorkel at AND the very best dinners were at Sharky’s right outside our front gate!! So we did not have to drive to dinner most nights!! We could walk to Crabby’s, practically next door for snorkel rentals. There is also a small market right behind Crabby’s. Any questions we had were answered almost immediately as Jose was living on the premises. We only saw him when we needed help with something. Only concern for Seniors is the winding stairwell to go upstairs to bedrooms and main bathroom. Fortunately, there is a first floor bathroom and shower we also really appreciated being Seniors ourselves!! We LOVED the screened porch surrounding the home and the small pool was refreshing after a snorkel. There is a hose for cleaning sand off everything by the pool.

Tortola, Turpentine House, pool+sunset+aircon
We stayed 4 nights and hope to return another time. The views are absolutely amazing of St. John and Norman Island. The house is huge. The kitchen and indoor living area are in one wing of the house and the 3 bedrooms are in another wing of the house, with the pool in the center connecting the two wings. Each guest room is large with a view. Bathrooms are large with plenty of counter space and high quality towels. The rooms have large closets or armoires for storage. The kitchen was very well equipped with pots, pans, dishes, toaster, coffee makers, microwave, dishwasher, outdoor grill, cutting boards and much more. There are plenty of beach towels, 3 beach chairs, a cooler, plus nice portable speaker for use. A few notes - there is a stray cat that you have feed every night. No shampoo or soap for the shower, which is typical in European AirBnBs. Would not recommend for small children due to pool openness and steep drop offs.

Charming Aerie Cottage
Beautiful, clean, eclectic villa in a great location!! Host representative met us at check in and walked us through everything. House was super clean and the view was great. Definitely want to arrive during daylight as the driveway is a little tricky the guest time up. Also, recommend 4 wheel drive vehicle. Having the beach chairs and cooler was a great addition for our adventures. Location is great for beaches and islands exploring. Was a great place to spend our 25th wedding anniversary:)

Secluded Villa with Caribbean Sea Views
Justins place was everything we wanted and more for our trip to St. Thomas. As soon as you walk in you enter into a gorgeous view of the island. Which you can see from virtually anywhere on the property. The place was very clean, private, and had all the amenities we needed for our stay. Justin provided amazing recommendations which we utilized almost daily especially the food choices. Justin and his team were very communicative and helpful throughout the stay. Overall this place is incredible and I highly recommend it for anyone coming to visit St. Thomas.

The yellow flamingo
We loved the place and the island there was so much to do. The place was clean and peaceful with a lot of amenities. I would highly recommend this place and would definitely visit in the future. The home itself was cozy, well-maintained, and had everything we needed for a relaxing stay. It truly felt like a home away from home. Can’t wait to come back!

4 bed/4 bath. Pool/Beautiful Ocean views. Cruz Bay
Beautiful place! The local contact, Abby, was great helping us with anything needed. She referred us to a local taxi driver that was available anytime we needed him. Since the location is rather secluded it was great having someone available to make getting around the island easy and accessible. Great place and we were well taken care of

Oceanfront Private Caribbean Resort!
Sea La Vie was the perfect St. Thomas escape. The space is clean, stylish, and peaceful, with a fully stocked kitchen that made cooking at home a breeze. The pool area was a highlight – quiet, with plenty of lounge chairs and an incredible ocean view that we never got tired of. The hosts were welcoming and responsive, and the location made it easy to explore beaches, restaurants, and local spots. Whether relaxing by the pool or enjoying dinner on the deck, every moment felt like paradise. Highly recommend!
Weekly house rentals

A secluded "Walk to Beach" villa
We had a fantastic vacation thanks to this wonderful place. Short walk to a magnificent beach and the accommodations were just a described and perfect for us, The only downside potentially for some people may be the road to the property but that goes along with many others on Tortola - can be tricky if your not used to hairpin bends, step inclines and in some case rocky terrain. Wasn't an issue for us but maybe for some. There are some fine restaurants not too far away and the bars on the nearby beach (Pirates Cove) serve some great food. Cane Garden Bay is just a few minutes away and also a great beach. Busier but more bars with food as well as a few shops for beach stuff and souvenirs. Overall a highly recommended place to spend your vacation.

3 Bdrm w/ Free Car, Generator & View of Rendezvous
This was a family vacation of 7 and the property was dreamy! Dena and Trevor the property manager were a delight.

Justin's Island Escape-3 Bdrm- Lush Northside
The property is gorgeous; like in the pictures. Spacious, super clean and very well equipped. Getting there was a little frustrating; the Google maps pin originally provided took us to a different home. That homeowner told us that it had been happening lately: strangers showing up at his door. We contacted Emily and she provided another pin that took us to the house. In general, the roads in St. Thomas are very narrow and not in good condition in many places and to get to the house, there are steep hills, hairpin turns and switchbacks. We had 2 families departing at different times on our last day and in spite of contacting many taxi services, only 1 agreed to come to the house and they wanted to charge $150 for a 10-minute ride to the airport! Emily went out of her way to help us but we ended up all going to the airport at the same time.

Private Ocean & Stargazing views on the Northside
Stayed here for 2 days and absolutely loved every second. Location is beautiful, view is priceless and even better than in the photos. Danielle is a great person , drove me and my fiance up the long hill when we were already running a little late after checking out which she didn’t have to do at all. Overall had an amazing experience , only thing I will say is make sure you rent a car or else it will be a lot more difficult for you to get around and see places , area is perfect for a nice romantic getaway but make sure u have a car because transportation/taxis don’t like to come down to pick you up at this location and they’re also much more expensive. Thanks Danielle.

Apple Bay Villa at Seascape
If you're looking for a get away with an amazing view this is the place to be. You feel right at home, at peace and you won't feel like leaving once you arrive. Had an amazing time, and will definitely be back.

Ocean View, Near Town, Backup Power/Strong Wifi
AMAZING studio! views from this deck are unbelievable! Christy did a great job with timely responses. House was full of board games and the Wi-Fi is veryy reliable. The location was also great, it had everything about 15-20 minutes away.

Spectacular Views - 3-5 bedrooms Cruz Bay, St John
Great houses with pool. Super easy to communicate with. Met us at the dock, drove us to the house, showed us around, answered every question and more. House is great value. Parks 2 cars, ac in every room that will get them colder than you could ever want. Great water pressure in showers, soft comfortable beds and linens, tons of towels, beach chairs snorkels floaties. Amazing view. Like perfect view of crux bay, the ocean, st Thomas island, just stunning. Checkout was very easy. Take trash, turn off ac units. Could not recommend more highly. No negatives.

Welcome to Tòti Bella!
Our family of 5 had a great week at Toti Bella! The owners were very informative and responsive. It was fully stocked with everything you may need from kitchen essentials to beach gear. We loved enjoying our morning coffee on the deck and its beautiful views. The pool was a refreshing way to end the day after hiking, & the beach. With May temperatures in the 90s we were concerned about only having AC in the main floor bedroom but the island breeze made the entire unit very comfortable. We would definitely stay at Toti Bella again!!
Private house rentals

Haagensen House- An Old World Estate
I’ve stayed at a variety of Airbnb properties in St Thomas and Haagensen House is my favorite for its uniqueness and privacy. The property manager, Harold, met me near the airport to ensure I found my way - I encourage future renters to do the same as nav systems can be spotty on the island. The decor was refreshing and nailed the old town vibe of Charlotte Amalie - I loved the colors and wood details throughout. The entry garden is breathtaking and the expansive patio overlooking the water was such a pleasant surprise - I couldn’t believe it was all mine. The AC in the bedrooms worked well and at night, there was a nice breeze if you kept the doors open in the main space. The hosts are the NICEST people!! I travel with my small dog and finding dog friendly accommodations in STT is very difficult. We were welcomed with open arms. They were so thoughtful, following up to make sure we were settled okay and didn’t need anything. I cannot thank them enough for their hospitality

PalmPoolVilla - Solar & Battery 4 bed 4 en-suite
Matina's place was outstanding! Convenient to downtown Charlotte Amalie and not terribly far to popular beaches. Kitchen had everything we needed to cook full family meals. Beach toys, chairs and cooler also provided. The pool is always shaded, so can be cool, even on the hottest days and at nights. We found it refreshing.

Hibiscus Haven USVI
Our stay was amazing. The host provided us with a driver for the duration of our stay and we felt so safe in the home. Very responsive when anything was needed and very friendly. We would definitely stay here when we visit St Thomas again!

La Sirena Secluded Villa w/Pool+NEW Solar backup!
La Sirena is absolutely BEAUTIFUL! The location is private which was perfect for us. Eileen was helpful and answered all of my questions! Few tips she had was to rent a car from St. Thomas, get groceries in St. Thomas (very important if you want variety and to save some money), local beach recommendations, etc! Definitely recommend future guests to follow those tips! The kitchen was stocked with most things a person needs to cook with. La Sirena had storage containers for left overs, a toaster, a blender, a toaster oven, a coffee maker, microwave, grill & grill utensils, coolers for the beach, ice packs, etc! WiFi was great! AT&T did get service at the house, but I did loose reception on the way to the house. The Salt Pond Beach was our favorite place to go! It was absolutely beautiful and the crowd was few (especially compared to the North side). I’m confident anyone would find La Sirena as an awesome place to relax and enjoy the island!

Villa Fratelli Garden
Our stay at this property was excellent. The views were remarkable, the house was well-equipped (including a generator), and the location was convenient to Red Hook and the East End. Groceries, pharmacies, restaurants, and shopping were easily accessible. The photographs accurately depicted the premises. Host Randall and his staff were very responsive and helpful. We enjoyed our week here and hope to stay at this home again.

‘Lots Of Knots’ cute Upper Carolina cottage
The view is literally breathtaking! It’s even better in person. We were visiting for our honeymoon and it was the perfect little villa! So beautiful that it’s hard to leave. I would definitely stay again!

Villa Carolina. Views for miles! Peaceful. Private
The house and property were absolutely incredible. The view was amazing, especially at sunrise where we could see for miles and miles offshore. The location about 10 minutes outside of Coral Bay was perfect with easy access to restaurants and beaches. We would absolutely love to stay here again!

Waterfront Condo near The Ritz
Great place. Good price. Convenient location for exploring. We had a great trip and enjoyed our stay. The place was stocked with anything we may possibly have needed.
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- Flamenco Beach
- Honeymoon Beach
- Magens Bay Beach
- Limetree Beach
- Mosquito Bay Beach
- Oppenheimer Beach
- Coki Beach
- Chocolate Hole
- Cane Garden Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Peter Bay Beach
- Pelican Cove Beach
- Gibney Beach
- Josiah's Bay
- Playa Sun Bay
- Caneel Bay Beach
- Maho Bay Beach
- Virgin Islands National Park
- Oil Nut Bay
- Secret Harbor Beach
- Grapetree Beach
- Hull Bay Beach
- Mandahl Bay Beach