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

Private Saltwater Poolside Cottage w/View and Gate
We really enjoyed our stay! The view of the island was amazing. I think it was the the best view we have ever had at an Air BNB. Delano and Beige were very helpful. We enjoyed chatting with Gene while he cleaned the pool everyday. The pool was a nice place to relax after a long day sight seeing. Our room had everything we needed and more, including beach and snorkeling gear. We will definitely stay here again the next time we visit St. Thomas!

Heated Pool, OceanView, Generator, Local Discounts
This house is awesome! Perfect for our family vacation. The house and amenities are exactly as described, the view is even better than the pictures. Huge patio, nice grill, heated pool with jets and lights for nighttime swimming was great. Just a short drive to the best beaches. Stacie and Mark were very friendly and helpful, and responded very quickly every time I reached out to them. I wouldn’t stay anywhere else in Saint Thomas.

Down Yonder Pool Villa / Full Solar & Battery
We had a great week at Down Yonder! Easy access to supermarkets and restaurants. Beautiful view. Private. Great pool for our kids. Extremely clean and nice layout.

Casa Tua St John
We really enjoyed our stay at Casa Tua. The property felt so secluded by all the surrounding plants and trees but we loved how conveniently located it was to restaurants and a grocery store that we could walk to. The inside spaces were very comfortable and we enjoyed the screened in porch area with the Weber grill for cooking. James was very responsive host and helpful during our stay.

PalmPoolVilla - Solar & Battery 4 bed 4 en-suite
CJ and Martina's place is incredible! It's clean and well-stocked with a gorgeous view. Our entire family stayed for our 20th anniversary and for our parents' 50th anniversary. CJ and Martina were so helpful and put so much thought into the house. Staying there made the trip so pleasant and stress-free -- comfortable beds, clean bathrooms, mosquito oil lamps, beach towels and chairs, AC units in the bedrooms, Tesla power generator, the washer and dryer... I could keep going. Not every home on the island has as much thought and care as this one, and certainly not every host is as responsive and exceptional as CJ and Martina. They went above-and-beyond. I have no complaints.

La Sirena Secluded Villa w/Pool+NEW Solar backup!
A stunning location with gorgeous views, this house is an absolute gem! Thank you, Eileen, for all of your local recommendations, responsiveness to all of my questions (we had a lot!), and for sharing your beautiful home with us. Perched on a hill and down a very unassuming road you find this oasis with ocean breezes, sounds of nature, and all of the necessities you could need. Perfect for my family of four, with two young kids. While the location is "on the other side of the island," we didn't mind the drive to Coral Bay or to the main beach area (Trunk, Maho)--- there was so much scenery to take in! We appreciated the beach chairs and towels, along with cooler bags, to make those trips easy. We also loved the beaches near the house, along with hiking the Ram Head Trail. The beds were super comfortable, we slept beautifully. We used the loft and the AC made for an easy sleep. Thank you so much, we will be back!

Casa Del Palmas ~ SOLAR + pool.
I highly recommend Rosanne's home. Tiffany, a member of the Anteres crew, met us in town after picking up our jeep rentals. We followed her to the house. Super welcoming and answered all of our questions. Casa Del Palmas was in pristine condition and beautifully decorated. Rosanne has put great effort and thought into decorating and stocking her entire home from top to bottom with everything you will possibly need for a perfect vacation. The amazingly beautiful views off the back porches will be greatly missed.

Villa Paradis II! Private Pool! Amazing Views!
The place was amazing! The view was incredible and place was well furnished. We would detina consider coming back!
Weekly house rentals

Ocean View Villas, on Jost Van Dyke- Sunrise -2BR
Karen and Nigel are gracious hosts that go above and beyond. They have created a relaxing, welcoming home for your stay. Words that come to mind : Convenient but feels remote, breathtaking views (high enough to look into the bay but still feel connected to the action), extra extra clean and immaculate, perfect house layout, caring and attentive hosts, luxurious, concrete-walled quietness, safe and secure. Safety is so important to us. Their home was built with love and hard work, and it shows! A true tropical heaven!

Secret Harbor View Villa
This home was exactly was we needed for space for our group, great location to our friend’s villa for the wedding was a plus, great location to restaurants and public beaches. Did an excursion per recommendations in the guest book which exceeded our expectations! Very responsive to an issue we had during our stay. Clean and included several beach/pool amenities which helped us out a great deal! Certainly would recommend!

Salty Sway II - 2bed/2bath Beach House
Amazing Airbnb with beautiful sunset views! The villa had all of the amenities my family and I needed for a week stay. Host was very responsive and friendly. Would recommend this place to everyone!

Ocean View, Sunsets, Near Town, Solar/Backup Power
This airbnb is my favorite in ST Thomas! My wife and I stay here everytime we come back home to visit and it is beautiful as always! Thank you so much Christy for everything!!! 🥰🥰

Berecia's Place
Joyce and her daughter Lisa were incredible hosts, responsive and caring, staying with us on whats ap as we navigated the narrow winding streets of the old part of Charlotte Amalie to get to them and proving excellent directions. Couldn't ask for more caring hosts. Be aware Charlotte Amelie is hilly. I was recovering from an injured ankle so I could not take advantage of walking down hill and tgen back up to the waterfront ( a little more than a mile away). I appreciated living in a real neighborhood, not a tourist location.

Stunning View, Magens Bay, Pool, Amazing Villa!
House is beautiful and spacious with several nice suites for multiple couples. Views are stunning, day and night Plenty of iguanas hanging out in trees to watch. Gated entry is added security. Very close proximity to a great beach that has rest rooms and food & drink services On the negative side, we experienced several power outages, one of considerable duration due to an event at the power station. Good news is the home is equipped with a backup generator. Bad news is it has a limited supply of propane on prem so had to ration the run time. Was promised more propane if supply was depleted. Would normally walk the neighborhood, but No shoulders on the roads, so walking is not much of an option. Pool is a nice amenity

Eden View Book you winter and spring dates!
What a great week we had in St Thomas! We were pleasantly welcomed by Camille with communication ahead of time and throughout our trip top notch. Having someone meet us and take us to the villa was very helpful on arrival since we had never been before. Peter communicated and checked in throughout our stay. The villa was gorgeous. Well taken care of and clean. The view was unbelievable, it was exactly what we were looking for. We loved the location, even though it wasn't in the hustle and bustle of it all.

Horizons Cottage w/ Ocean Views!
We had such a lovely vacation! The ocean view from the property is absolutely surreal—waking up to that every morning felt like a dream. The location is perfect, close to world-class beaches that made our days full of sunshine, relaxation, and adventure. The home itself was clean, comfortable, and had everything we needed. We couldn’t have asked for a better stay. Highly recommend!
Private house rentals

LUX 2 King BR Villa w/Generator & Pool Cruz Bay
We had a great stay at Villa Amerigo. It is located on a hillside overlooking the town and bay. The property is well maintained and the views are amazing. We especially enjoyed sitting on the deck and watching the sunset every night. The place has everything you need. Even had coolers and beach chairs we could use when we went to the beach. I particularly liked the location. It was not right in town but yet close enough that you could walk to all the stores, restaurants, and bars in town if you wanted. I have to warn you though that pocket money lane is a steep hill and is a bit of a workout walking back up the hill. Also, there is a very short stretch that you have to walk on the side of Rte10. We didn't mind but wouldn't recommend doing with kids. We walked down town a couple times and one morning even walked to Salomon and Honeymoon beach from the Villa. Great place, great host, would definitely stay there again.

Private Ocean & Stargazing views on the Northside
the place was fantastic as a get away for 2. it was secluded and private with a bit of a steep hill to get down so be warned about that. morning and evenings were great, we always had a nice sea breeze from the bay and could see the sunrise beautifully over the usvi. I would highly recommend this stay to anyone looking!

Villa Isla A: Spacious 1 bedroom 1 bath sleeps 2-4
This was our second year in a row at this incredible home, and we adore it. The views are unbeatable, and morning coffee on the patio is pure heaven. The house has everything we need, and Erin, the manager, is responsive, proactive, and a joy to work with. We cooked most meals, stopping at the grocery store when we landed in STT. The kitchen was well-equipped, but we did enjoy a Friday night dinner and amazing fish tacos at Heidi’s Hilltop Grill. TIP: Our first year, we rented a golf cart from Rachel’s, which was great. The second year, we walked everywhere—and wow, did we get our steps in! Easily 10K+ a day between morning walks and beach time. Honeymoon Beach is less then 10 minutes downhill, but uphill on the way back. If you’re looking to tone your calves, this is the place—our neighbors thought we were nuts! The Beach is absolutely pristine, with soft sand and crystal-clear water. Drinks and food at Dinghy’s make it even better. This is THE place to stay on Water Island!

Tropical Shores a Waterfront Villa
This house added to our vacation experience on St. Thomas. The pool and deck were overlooking AMAZING views, the house was roomy, comfortable, and well apportioned. It had character and charm and all of the comforts of home. The kitchen was easy to cook in. Great for families- in a quiet area behind a gate and located close enough to groceries and restaurants. We would book this again!

Dream House
We wish we were there right now! This home was exceptionally well supplied for our group of nine; plenty of dishes, utensils, kitchen tools, pots, and pans and towels (bath & beach), and beach equipment. We cooked all our dinners there, and the appliances all worked well. There was an abundance of comfortable outdoor furniture by the pool where we loved sitting in the shade, looking out at the amazing view. The beds and sheets were also very comfortable. We did not use the air conditioning because there was a nice ocean breeze the whole time we were there. Emma was extremely responsive and helpful in all her communication. I would highly recommend a four-wheel-drive car to come down the steep and bumpy driveway.

Stone Cottage with a pool and gorgeous view
Kim’s place if fabulous! Waking up and going to bed each night with the view over Coral Bay was definitely a highlight and worth the adventurous drive up! Definitely needed a jeep! We loved staying on east end and found it to be quieter than the west. Easy drive to all the beautiful beaches and loved having the pool to cool off in after a long day at the beach! Kim was the best host and really went above and beyond! Highly recommend! We would stay here again!

2 Bed ⭐️ STAR VILLA HOME ⭐️ 5 Min walk to CRUZ BAY
Star villa was a great find in an amazing location (5-10 min walk into town) on St. John. Bob and Marlene were out of town during our stay but Mike took amazing care of us the whole week. The AC in the bedrooms was amazing after long days at the beach. The pool is large, clean and perfect for cooling off after hot days. The view from the villa porch was amazing. I definitely recommend renting a jeep or some other 4 wheel drive car to terrain the steep hills and rough roads on the island. I highly recommend this place to anyone needing a well rounded place to stay in beautiful St. John and the amazing hosts (and Mike) were the icing on the cake!

Vista Amalie - 3 BR House / Pool w/ Harbor Views
This place is GREAT. Owners are responsive, view is AMAZING, everything we did was about 20 min away. Locals are friendly, private pool at the house is a plus. Plenty of room with all the amenities necessary for a wonderful vacation. Christmas in the islands was the BEST! We rented a car so it was very convenient to stroll around town. Easy to use Google maps with their pinpoint location. Friendly rooster that hangs out there too we enjoyed watching him eat. We named him Clark Waters. !! We are already looking forward to coming back to the island. Highly recommend having your own vehicle, and trying out the local cuisine. Stay away from Lanai restaurant (service was slow and food awful). Sea salt on Sapphire beach is a terrific high end restaurant (our favorite). Linguistics Beach was our favorite. Clear water, soft sand and swam with a stingray and sea turtle! Recommend parasailing and swimming with a dolphin at Coral World. Definitely would stay here again. Thank you!! ENJOY
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- Virgin Islands National Park
- Limetree Beach
- Morningstar Beach
- Salt River Beach
- Sugar Beach
- Turquoise Beach
- Mandahl Bay Beach
- Hull Bay Beach
- Hansen Bay Beach
- Playa Media Luna
- Sandy Point Beach
- Cormorant Beach Club
- Cathys Fancy Beach
- Grassy Point Beach
- Luis Pena Beach
- Johns Folly Beach
- Coral World Ocean Park
- Sun Bay Beach
- Vessel
- Sprat Hall Beach
- Isaacs Bay Beach
- Reef Beach
- Buccaneer Beach
- Frederiksted Beach