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House holiday rentals in Chocolate Hole

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Popular amenities for house rentals in Chocolate Hole

House rentals with a pool

Guest favourite
Home in Northside
4.95 out of 5 average rating, 57 reviews

Private Saltwater Poolside Cottage w/View and Gate

JerryRating, 5 stars1 week ago
The view and pool are amazing! The inside was nicely done and well equipped. If you’re looking for something with a view and pool and not far from town, this is a great option.
Top guest favourite
Home in NorthSide
5 out of 5 average rating, 46 reviews

Heated Pool, OceanView, Generator, Local Discounts

MeganRating, 5 stars1 week ago
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!
Guest favourite
Home in Cruz Bay
4.85 out of 5 average rating, 26 reviews

LUX 2 King BR Villa w/Generator & Pool Cruz Bay

SusanRating, 5 stars1 month ago
This was BY FAR the BEST Airbnb experience of our travel history. The space was fabulous! Very comfortable beds. Fantastic kitchen amenities - Did not need anything we couldn't find there. The AC worked great- Power went out once and the generator kicked right in and we never even noticed. Huge bathrooms with TWO showers (one inside one outside) - the veranda had a dining table and chairs as well and a relaxation spot with even more chairs. Washer and dryer means we shouldn't have brought so many clothes - we will scale down the packing next time (and there WILL BE a next time. The Sunset views were fabulous. Parking was good and the beach equipment was more than we could have hoped for. Chairs, cooler and even an umbrella! (two would have been fabulous but that is NOT a complaint!) If we could give more than 5 stars we would! Local contact Linda was so so helpful and full of great suggestions. I sit here trying to think of something to improve - Nope, I got nothing!..
Superhost
Home in Coral Bay
4.92 out of 5 average rating, 65 reviews

Charming Aerie Cottage

IlsaRating, 5 stars5 months ago
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:)
Superhost
Home in St. Thomas
5 out of 5 average rating, 32 reviews

Secluded Villa with Caribbean Sea Views

BryantRating, 5 stars1 week ago
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.
Guest favourite
Home in St. John
5 out of 5 average rating, 32 reviews

La Sirena Secluded Villa w/Pool+NEW Solar backup!

MadelynRating, 5 stars1 month ago
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!
Guest favourite
Home in Cruz Bay
4.98 out of 5 average rating, 48 reviews

New 3-bdrm villa, pool, ocean views, & concierge!

WhitneyRating, 5 stars6 days ago
This was probably the best airbnb we’ve stayed in. It was perfect for our family of five. Drew was great and also helped us with a jeep rental. He was extremely communicative with us and made sure we were all set and ready to go when we hopped off the ferry. Bailey sweetly greeted us with a charcuterie platter and showed us around the house. The house is completely true to the listing photos and is absolutely stunning! The deck is large and we enjoyed sitting with coffee each morning looking out at the gorgeous ocean and hillside views. We slept wonderfully in the comfortable beds. The bedroom air conditioners worked perfectly and the cross breezes in the main living area kept the house cool and comfortable. Drew continued to stay in touch throughout the week. He even met us at the house one morning to help us find parking for our boat excursion. I’m already dreaming of our next visit to Back In The Day. Many thanks to Drew, Bailey and the homeowners for a wonderful stay on St. John!
Guest favourite
Home in Cruz Bay
4.88 out of 5 average rating, 43 reviews

4 bed/4 bath. Pool/Beautiful Ocean views. Cruz Bay

HarvieRating, 5 stars3 weeks ago
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

Weekly house rentals

Top guest favourite
Home in Cruz Bay
4.92 out of 5 average rating, 100 reviews

3 Bdrm w/ Free Car, Generator & View of Rendezvous

DeidreRating, 5 stars1 week ago
This was a family vacation of 7 and the property was dreamy! Dena and Trevor the property manager were a delight.
Superhost
Home in Havers
4.8 out of 5 average rating, 30 reviews

Tortola, Turpentine House, pool+sunset+aircon

TomRating, 5 stars2 months ago
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.
Guest favourite
Home in Northside
5 out of 5 average rating, 40 reviews

Private Ocean & Stargazing views on the Northside

AryaRating, 5 stars2 weeks ago
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.
Guest favourite
Home in St. Thomas
4.89 out of 5 average rating, 63 reviews

Villa Isla A: Spacious 1 bedroom 1 bath sleeps 2-4

KaileahRating, 5 stars2 months ago
Water Island was absolutely beautiful! Our stay was amazing—even when we ran into island-related issues like a power outage, both Isla and Erin were quick to jump in and get everything up and running again, even over Easter weekend! This was our first time visiting the islands for my birthday trip, and it couldn’t have been more perfect. The location was stunning, with the best views! Haze was an angel—such a sweet boy who kept us company while we missed our own cats. We’ve already decided to make this a yearly tradition and plan to stay at Isla’s for many years to come. We absolutely loved this place—it was the perfect getaway!
Guest favourite
Home in Coral Bay
4.94 out of 5 average rating, 16 reviews

Sea Cave - Listen to the ocean from your bedroom!

JenniferRating, 5 stars5 days ago
Kevin’s place was beautiful! I didn’t think the view from the porch could actually match the photo but it surpassed it. That view is breathtakingly beautiful! And the sunrise in the morning from the porch is so peaceful. This is a wonderful home to stay in the Coral Bay Area. Our favorite out of all the homes in Coral Bay where we have stayed over the years. This home has everything you need and the grandeur of St John’s natural beauty as well!
Guest favourite
Home in Central
4.94 out of 5 average rating, 68 reviews

‘Lots Of Knots’ cute Upper Carolina cottage

HannahRating, 5 stars1 week ago
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!
Superhost
Home in Cruz Bay
4.92 out of 5 average rating, 62 reviews

Spectacular Views - 3-5 bedrooms Cruz Bay, St John

AndrewRating, 5 stars2 months ago
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.
Guest favourite
Home in Cruz Bay
4.94 out of 5 average rating, 33 reviews

Welcome to Tòti Bella!

AaronRating, 5 stars3 weeks ago
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

Guest favourite
Home in Coral Bay
4.99 out of 5 average rating, 70 reviews

Casa Tua - Saint John

EllenRating, 5 stars1 month ago
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.
Home in Cruz Bay
4.97 out of 5 average rating, 36 reviews

Pool - Ocean View - Large Deck & Pergola - Private

ReynetteRating, 5 stars1 month ago
Pura Vida was lovely! The entire home was spotless. The views and the outdoor pool was our favorite. The kitchen had everything we needed to cook our meals. The grounds were beautiful and interesting. The ruins had its own little history lesson and we loved the shell book and its history to previous owners of the home. We couldn’t have had a better experience. Thank you so much!
Guest favourite
Home in Anna's Retreat
4.91 out of 5 average rating, 35 reviews

Hibiscus Haven USVI

KandaceRating, 5 stars3 weeks ago
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!
Superhost
Home in East End
5 out of 5 average rating, 3 reviews

3 bedroom Villa Great End Location

JudyRating, 5 stars15 months ago
Check in was easy and the Mgr Jerscilla provided recommendations with airport transfers, jeep rental, and excursions. She greeted us and walked us through the layout and use of modern electronics of the villa. It was stocked with snacks, coffee, water, paper towels, seasoning, and basic condiments that were very appreciated. Those items add up when you need to buy a few things from local grocery stores. The villa set up has the courtyard in the center with pool, games, outdoor dining, outdoor bar, TV lounge area, and Sonos speakers. I have these at my home. Kitchen, dining and living on one side with bedrooms and bathrooms on the other. We really liked the bidets and quality TP! A perfect set up for privacy that was gated. We will go back and will stay here again if it’s available.
Superhost
Home in East End
4.82 out of 5 average rating, 17 reviews

Villa Fratelli Garden

AmielRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Northside
5 out of 5 average rating, 33 reviews

Oceanfront Private Caribbean Resort!

MargaretRating, 5 stars1 week ago
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!
Guest favourite
Home in Southside
5 out of 5 average rating, 17 reviews

Ocean View, Near Town, Backup Power/Strong Wifi

SamanthaRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Central
5 out of 5 average rating, 22 reviews

Villa Carolina. Views for miles! Peaceful. Private

ChrisRating, 5 stars2 months ago
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!

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