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House vacation rentals in Chocolate Hole

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Popular amenities for Chocolate Hole house rentals

House rentals with a pool

Guest favorite
Home in Northside
4.94 out of 5 average rating, 52 reviews

Private Saltwater Poolside Cottage w/View and Gate

GaryRating, 5 stars1 week ago
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!
Top guest favorite
Home in NorthSide
5 out of 5 average rating, 42 reviews

Heated Pool, OceanView, Generator, Local Discounts

MatthewRating, 5 stars2 days ago
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.
Guest favorite
Home in Coral Bay
5 out of 5 average rating, 67 reviews

Casa Tua St John

MariaRating, 5 stars1 week ago
Thank you for the amazing week at this fantastic cottage! We relaxed by the pool after the eventful days in the sun. Walked to the nearby cafes for dinners and the Dolphin market. Had breakfasts on the screened in veranda. Would stay there again!
Superhost
Home in Northside
4.91 out of 5 average rating, 43 reviews

PalmPoolVilla - Solar & Battery 4 bed 4 en-suite

QzeenaRating, 5 stars1 month ago
Loved this place! Close to the airport, beautiful view, hosts were helpful and very responsive. The kitchen has everything needed to prepare meals. The pool was pretty cold because it is covered however we didn’t plan on using it much. Would definitely stay here again!
Guest favorite
Home in St. John
5 out of 5 average rating, 30 reviews

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

AshleyRating, 5 stars3 weeks ago
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!
Superhost
Home in Central
5 out of 5 average rating, 3 reviews

Casa Del Palmas ~ SOLAR + pool.

RhondaRating, 5 stars1 month ago
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.
Superhost
Home in Saint Thomas
5 out of 5 average rating, 9 reviews

Villa Paradis II! Private Pool! Amazing Views!

EvelynRating, 5 stars3 months ago
The place was amazing! The view was incredible and place was well furnished. We would detina consider coming back!
Superhost
Home in St Thomas
4.85 out of 5 average rating, 46 reviews

Eden View Book you winter and spring dates!

LaurenRating, 5 stars2 weeks ago
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.

Weekly house rentals

Superhost
Home in Jost Van Dyke, White Bay
5 out of 5 average rating, 25 reviews

Ocean View Villas, on Jost Van Dyke- Sunrise -2BR

KristiRating, 5 stars27 months ago
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!
Superhost
Home in East End
4.86 out of 5 average rating, 49 reviews

Secret Harbor View Villa

EmmaRating, 5 stars4 months ago
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!
Guest favorite
Home in Cruz Bay
5 out of 5 average rating, 55 reviews

* 3BR/3 BA LUX Pool Villa*Cruz Bay*Amazing Views

PriyaRating, 5 stars2 months ago
The view is outstanding. The pool is gorgeous. Linda was so responsive and wonderful. Going down the hill is fine. Going up I’d say you need a cab or car - It is no joke!
Superhost
Home in Southside
4.97 out of 5 average rating, 59 reviews

Salty Sway II - 2bed/2bath Beach House

CallieRating, 5 stars3 months ago
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!
Guest favorite
Home in St. Thomas
4.92 out of 5 average rating, 60 reviews

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

MikeRating, 5 stars1 month ago
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!
Superhost
Home in Southside
4.92 out of 5 average rating, 48 reviews

Ocean View, Sunsets, Near Town, Solar/Backup Power

MicahRating, 5 stars2 months ago
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!!! 🥰🥰
Guest favorite
Home in Charlotte Amalie
4.96 out of 5 average rating, 47 reviews

Berecia's Place

SusanRating, 5 stars1 month ago
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.
Guest favorite
Home in St. Thomas, U.S. Virgin Islands
4.94 out of 5 average rating, 68 reviews

Stunning View, Magens Bay, Pool, Amazing Villa!

ShellyRating, 5 stars2 months ago
We loved our stay at Blue Skies! It accommodated my entire family leaving us with common areas to come together but also separate sleeping spaces for privacy. Shawna and Marina were very responsive and helpful with recommendations and suggestions. The view was amazing….from ability to see Magens Bay and beach to several rainbows during the daily showers.

Private house rentals

Guest favorite
Home in Cruz Bay
4.9 out of 5 average rating, 10 reviews

Eureka Villa -Stunning Views in Paradise 2BR/2.5BA

ShannonRating, 5 stars1 week ago
While St. John is our favorite place in the world, I can’t say enough about our experience at Eureka Villa — it was absolutely perfect for our two-couple group. Great location not far from Cruz Bay (and as a bonus: super close to Windmill Bar!). Was so appreciative of Elise being proactive upon our arrival to the island and personally escorting our Jeep to the location, showing us around the villa, and was more than willing to share her knowledge of the island. The panoramic view was indescribable. Loved having the cross-breeze from large glass/screen doors in the central space, while still having access to bedroom air conditioning for comfortable sleeping at night. Clean, organized, modern updates, STOCKED with home and beach supplies which saved lots of packing space for us — beach chairs, coolers, towels, snorkel gear, even had spare reef-safe sunscreen. Elise & John were immediately responsive to any questions and fantastic to work with. Already counting the days until our return.
Guest favorite
Home in Northside
5 out of 5 average rating, 32 reviews

Private Ocean & Stargazing views on the Northside

JonathanRating, 5 stars2 weeks ago
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!
Home in VI
4.96 out of 5 average rating, 24 reviews

Sierra Villa 3Br/3.5Bths -On Point Pleasant Resort

TriciaRating, 5 stars15 months ago
I would 100% stay here again. I stayed in the 3 bedroom / 3 bath unit. Very clean, great location, beautiful view, pool, grill, fire pit, and responsive host. No need to hesitate… Just book it !
Home in Southside
5 out of 5 average rating, 3 reviews

(Group Villa) Eagles Nest by the Beach

PaulRating, 5 stars29 months ago
This place is awesome. Very clean, great views, and as described on website. To avoid confusion there are two Albert's. Dad who lives on the property and is the taxi driver and Albert the son who is the off site owner. The airport taxi was $18.00 per person. Albert took 8 of us comfortably with luggage. The taxi to a restaurant was $12.00 per person each way.
Superhost
Home in Northside
4.76 out of 5 average rating, 21 reviews

Tropical Shores a Waterfront Villa

TravisRating, 5 stars2 months ago
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!
Guest favorite
Home in Saint John
5 out of 5 average rating, 84 reviews

Stone Cottage with a pool and gorgeous view

ValerieRating, 5 stars1 month ago
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!
Guest favorite
Home in Cruz Bay
4.9 out of 5 average rating, 48 reviews

2 Bed ⭐️ STAR VILLA HOME ⭐️ 5 Min walk to CRUZ BAY

EmilyRating, 5 stars5 months ago
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!
Home in Southside
4.91 out of 5 average rating, 33 reviews

Vista Amalie - 3 BR House / Pool w/ Harbor Views

AmberRating, 5 stars3 months ago
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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