Time Out

2 Bedroom, 2 Bath | Chocolate Hole


Beds Baths Location Max Guests
2 2 Chocolate Hole 4


Year In Season Off Season Holiday Additional Info
2024 $4,595/2

2024 In Season: January 7, 2024 - May 3, 2024
2024 Off Season: May 4, 2024 - December 17, 2024
2024 Holiday Weeks: December 18, 2024 – January 5, 2025 (10 night minimum stay over holidays)*
2025 In Season: January 6, 2025 - May 2, 2025
2025 Off Season: May 3, 2025 - December 17, 2025
2025 Holiday Weeks: December 18, 2025 – January 5, 2026 (10 night minimum stay over holidays)*

* Holiday rates MAY include Christmas/New Years, Thanksgiving, Easter, Presidents' Week and Carnival week

2025 $4,595/2

2024 In Season: January 7, 2024 - May 3, 2024
2024 Off Season: May 4, 2024 - December 17, 2024
2024 Holiday Weeks: December 18, 2024 – January 5, 2025 (10 night minimum stay over holidays)*
2025 In Season: January 6, 2025 - May 2, 2025
2025 Off Season: May 3, 2025 - December 17, 2025
2025 Holiday Weeks: December 18, 2025 – January 5, 2026 (10 night minimum stay over holidays)*

* Holiday rates MAY include Christmas/New Years, Thanksgiving, Easter, Presidents' Week and Carnival week

Additional Guests up to Max Guests, $250/week each.
Hottub Pool Net A/C Kids
View Availability Call Now
Be sure to call to check the very latest availability since bookings can change at any time.

About Time Out

No children 6 months to 13 years
No rental to guests less than 27 years old

NEWLY FURNISHED and recently renovated Villa with amazing views that will immediately take your breathe away!

A beautiful NEW Caribbean look for one of our favorite vacation homes! The view from the house overlooking the pool out onto Chocolate Hole and the Caribbean Sea is what makes this Villa a hidden gem. Perfect spot to relax after a day at the beach sipping on some wine or cocktails!

Time Out is a wonderful home, perched on a hillside providing exceptional accommodations to unwind after a long day at one of our world-famous beaches.

This fully air-conditioned villa is perfect for two couples or a romantic getaway. It is tastefully furnished, and the owners wanted to create a true Caribbean Island feel the minute you walk in the door.

Two equally sized master king suites are situated on opposite sides of an open-air living/dining room/kitchen area and offer total privacy for two couples or family and friends.

These rooms each have direct access to the pool deck, yet still provide desired tranquility. Each is uniquely furnished in a beach theme with accents of seahorses, starfish and coral. Newly furnished king-sized beds with new comfortable mattresses and bedding, each with its own private bath with exotic stone accents.

The central "great room" and both bedrooms open through sliders onto a spacious deck which spans the entire front of the villa. Its focal point is the spectacular pool (5 feet at its deepest) with a built-in Jacuzzi for those refreshing dips between other island adventures.

Enjoy the sunset and the ever-changing views over Chocolate Hole and the glorious Caribbean Sea. Many memories will be made with Happy Hours by the pool waiting for the sun to set.

This entire villa is freshly renovated and newly painted with comfortable furnishings and "beachy" décor, all with traditional Caribbean style vaulted ceilings. Some of the artwork was photographed by the owners when they fell in love with coming to St. John. The villa is accented by island pieces that have been collected from Islands across the Caribbean. The new deck furniture layout is perfect for relaxing après beach! A newly upgraded kitchen with custom cabinetry with fun silver accents, along with granite surfaces, has just been added. Perfect for having dinner on the spacious counter peninsula all with new Bali wicker seating.

Nothing has been overlooked in an effort to provide for your ultimate comfort and every need. All this with new appliances, cookware and kitchen items that will make preparing dinner a breeze! Beach Towels, beach chairs and coolers are all there for ease of hitting the North Shore Beaches around the island.

Time Out offers an elegant combination of Caribbean style and comfort with a stunning view that goes on for days. This, along with its beautiful hillside location, proximity to the beaches, restaurants, shopping, and Cruz Bay... make this the perfect, much needed "TIME OUT" from your busy lifestyle.

Villa Photos

Location Map

Carrie B
Posted: Jul 18, 2023
The house was wonderful and had amazing views. The pool was great and very refreshing after being at the beach all day. The house was well equipped with kitchen items and the perfect size for our family of four. We were also thankful for having a washer and dryer. We were grateful for the escort to the villa and for the delicious food basket left in the fridge. Thank you!
Posted: May 30, 2023
Beautiful villa with excellent view. Loved the king size beds...very comfortable. The pool is the perfect.
Posted: May 11, 2023
WHAT A VIEW!! From the moment we walked in the door our breath was taken away with the beauty of the Caribbean Sea as well as the Chocolate Hole Bay. The Caribbean feel of the villa was very warm and inviting; the furnishings and decorations really made it feel like a tropical paradise. The new beds were very comfortable and the showers were unique and beautiful. The kitchen had everything you needed and more. The pool area was perfect for apres beach days and Happy Hour! The pool was very warm at night to take a dip which is a plus compared to other villas we stayed at. My husband and I are already planning to be back!
Posted: Feb 6, 2023
Everything was perfect for the two of us. The view was amazing. The outdoor space we loved and some afternoons we shared it with an iguana friend. We loved everything about it and hopefully will be back next year.
Lisa B
Posted: Dec 27, 2022

Nicely appointed two bedroom, two bath villa with beautiful sunset views of the water. Has A/C units in both bedrooms and in main room - helpful during afternoon sun. Nice pool with attached small heated jacuzzi area. Perfect for 1-2 couples.
Posted: Dec 21, 2022
Time Out is set in a wonderful location, with beautiful sunsets. The new decor is just perfect. King bedrooms on opposite sides afford privacy and the great room and deck are expansive and welcoming. Having plenty of beach chairs and coolers was very helpful. Three A/C units and strong wifi gave it a home like feel. We really enjoyed our 10 night stay.
Posted: Nov 15, 2022
Time Out is the perfect getaway!! Beautiful view any time of the day and a perfect spot to watch the sunset. It is a great location and just a short drive to any beach of your choosing. The villa is gorgeous and definitely has a Caribbean vibe! We can't wait to go back and have some "Time Out" of our busy lives!!
Posted: Nov 5, 2022
My husband and I stayed at Time Out with another couple from November 5th-9th 2022. This Villa has 2 ensuites each with incredible views and sliding glass doors leading out to the expansive deck and pool area. The bedrooms are separated by a spacious, open concept living , dining room and kitchen area. The home is fully equipped and newly furnished. The bed and linens were extremely comfortable. The tasteful decor and colors truly remind you that you are in the Islands. This Villa is perfectly situated near beaches, shopping and dining. We did experience that we were out of propane for the BBQ grill just as we were getting ready to cook. With one quick phone call the very responsive Property Manager was there with a full tank in minutes!
25th Anniversary Paradise
Jaime S
Posted: Jun 24, 2022
This was the perfect villa for our 25th anniversary. Great, quiet location. Beautiful views. Enjoyed relaxing in the private pool after a day at the beach with perfect sunsets.
Posted: Apr 29, 2022
This villa has a beautiful view. Pool great! It's in a good location for travel into Cruz Bay, North Shore beaches, Windmill Bar area & Coral Bay. Perfect for 2 couples. Destination St. John excellent! Quick prompt response to issues. Thank you!
Patricia S
Posted: Aug 23, 2021
This is a great place for 2-4 people max. Very clean and bug-free inside the house. Great location overlooking Choc. Hole (with a very steep driveway!), great a/c, comfy beds, wifi, pool, deck furniture, grill. Nicely updated kitchen (with apt. size dishwasher) and 2 bathrooms; provided amenities of soaps, shampoo, detergents, paper products were a nice surprise. The furniture is big and heavy for the space - not a beachy feel but good quality. The view is wonderful, and it's fun every day to search for the iguana family in the trees near the deck!
Irina C
Posted: Feb 23, 2021
Great location and a million dollar view! The house is very nice. All the necessary amenities. It is quiet and private. Good sun all day for tanning and a sunset! 10 minutes drive from Cruz Bay and the grocery stores, 25 minutes drive from the north shore beaches. Go to Maho Bay! The driveway to the house is long and steep. All wheel drive car is a must!
Posted: Dec 21, 2020
Great villa to celebrate the holidays. Beautiful view & saw two rainbows after brief morning showers-both rainbows ended in the bay. Updated kitchen, well equipped and easy to navigate.
Tanner A
Posted: Jul 20, 2020
Honeymoon Trip!
My wife and I just returned from our stay at Time Out in Chocolate Hole. This was our honeymoon and it was everything we ever dreamed of. The view is absolutely incredible! When we arrived, the house was very clean. We could not wait to take a dip in the pool! The location is extremely convenient to Cruz Bay and just a short drive to the north shore beaches. We would definitely stay here again.
Its my happy place
Stephanie Yagerman
Posted: Jul 25, 2018
Wonderful views,A/C, affordable
Posted: Feb 29, 2016
We enjoyed our stay and Destination St. John was accommodating and responsive.
Posted: Jan 17, 2016
We stay with two couples at Time Out in January of 2015 and returned January, 2016. Just that fact that we returned speaks to our satisfaction with this villa. We have stayed at six different villas on St. John and really like the location and layout of Time Out. The house is perfect for two couples with matching master suites and wonderful sunshine all day long. While we do enjoy trying different villas we would have no problem staying once again.
Posted: May 5, 2015
Well appointed with modern kitchen. Pool is a nice feature. Nice views of Chocolate Hole and sunsets. Only minutes from town.
Posted: Nov 1, 2014
Lovely villa. Outstanding view as you relax in the pool. Nice amenities and short drive to Cruz Bay where there is an abundance of restaurants & local crafts for sale. Fairly easy to get around once you get comfortable driving.
Posted: Oct 25, 2014
This villa has the perfect size, location and amenities for up to two couples or a family with a few children. The two master suites at opposite ends of the house all have direct access to the pool deck, yet provide desired privacy. The view from the pool overlooking Chocolate Hole couldn't have been better. The proximity to the North Shore beaches, restaurants, the ferry dock and grocery and liquor stores was very convenient - far better than when we stayed previously in Coral Bay area. The well provisioned home was clean and well cared for. The management group we booked through (Destination St. John) was very responsive to our questions. Having the entire house air conditioned was a definite plus. Thanks for our wonderful stay in paradise!
Posted: Jul 28, 2014
Time Out was the ideal vacation rental! Everything we needed was there & useable - from beach chairs to dryer sheets. They have attended to every detail. The views from Chocolate Hole & Time Out are beautiful. I don't think I could have picked a better rental for the two of us for our wedding on the island & honeymoon. The staff at Destination St. John was wonderful & made everything super easy to arrange. Time Out is a winner, by far one of the easiest and best rentals we've done anywhere. If all DSJ vacation rentals are this well equipped, we wouldn't hesitate renting any of them. Thanks again to the staff!
Posted: Jul 28, 2014
The staff at Destination St. John was wonderful & made everything super easy to arrange. Time Out is a winner, by far one of the easiest and best rentals we've done anywhere. If all DSJ vacation rentals are this well equipped, we wouldn't hesitate renting any of them. Thanks again to the staff!
Posted: Jun 28, 2014
Things we loved: spectacular views & sunset, tasteful renovation, great pool, excellent kitchen, air conditioning & fans kept house sufficiently cool, love the location, great arrival good basket from Sam & Jack's Deli.
Posted: May 29, 2014
My husband and we couldn't have been more satisfied with the Time Out villa. It was so quiet and has the most breathtaking view. I would highly recommend it to any couple wanting to escape! We got engaged in St. John, had our honeymoon in St. John, and will continue to visit. I would rent this villa again! My Dad is the one who booked the villa as a wedding present. He with my mother visit St. John often and got us hooked! The Destination St. John website was very informative and well put together, we knew exactly what to expect and couldn't wait to get there. It was also great that it's located so close to town. We had the time of our lives!
Posted: Apr 23, 2014
As always, our time in St. John was perfect & makes other Caribbean destinations pale in comparison. After snorkeling a different, pristine beach everyday, we would look forward to grilling on the deck and star gazing while floating in the pool. The house was beautiful, comfortable and had amazing views.
Posted: Jul 28, 2013
We stayed at Time Out in Chocolate Hole.July 21-30, 2013. What a beautiful villa with even more beautiful views! This was our third trip to St. John and our 2nd time renting through Destination St. John. Eric met us at the ferry dock and took us to St John car rental to pick up our jeep. He even had a basket of goodies for us in the fridge! We enjoyed the beaches every day and would come back to the villa to just relax and refresh. The pool was such great place to relax and watch the gorgeous sunsets. We stayed out on the patio or in the pool almost everynight watching the cruise ships , the twinkling lights of St. Thomas , and the shooting stars over Chocolate Hole...amazing!.The villa had everything we needed, the bed was very comfortable, the kitchen was stocked with anything we could possibly need, and the bathrooms were just the right size. We are already talking about coming back and would definitely stay in Time Out again. Thanks Destination St John!
Posted: Jul 11, 2013
We stayed at Time Out from June 11 to June 19, 2013. We have been coming to St John for 28 years. We stay anywhere from 3 to 6 weeks. This is our home away from home. Time Out is a perfect two bedroom, fully AC villa that fit our needs this time perfect. Two master suits are mirror image of each other. pool is just out side your door....Perfect A great view of St Thomas. Driveway is a little tough....but once you figure out how to make a u turn at the top...It's all fine. Destinations St John took care of any problem we had immediately. A perfect little place..we will rent it again.
Posted: Apr 2, 2021
My wife and I have made many trips to St John over the last 20 years. We have used several different agencies and also booked directly from villa owners. One thing we have come to expect is the island moves at a different pace than the mainland. However, the team at Destination St John turned that expectation upside down on our most recent visit. We decided to use our grill one night but discovered it was out of gas. They delivered a full tank the next morning! This is just one example. All interaction with them was prompt and courteous from initial booking to checkout. We will definitely be using them for future visits.
Posted: Dec 5, 2020
Destination St. John was top notch at helping us out with needs, questions and concerns. Easy and fast communication and transactions. What a surprise to find a welcome basket with delicious snacks - great after a long travel day!
Posted: May 30, 2016
...Destination St. John was extremely helpful and quick to respond with all questions, excellent management company! We can't wait to book again for another vacation in paradise!!!!
Posted: May 26, 2016
...The management company (Destination St. John) is always a pleasure to work with.
Posted: May 8, 2016
...The property managers were great. Destination St. John rep met us at dock, and showed us around, and the office promptly answered a few questions we had. They even left a wonderful basket of goodies for us to enjoy on our arrival. We will be back! Thank you Destination St John!
Posted: May 1, 2016
...The folks at Destination St. John were helpful as always. Can't wait to go back!
Posted: Feb 29, 2016
...We also appreciated the Destination St. John staff welcoming us and being helpful. We hope to be back again next year!
Posted: Nov 2, 2015
...We've used Destination St. John many times to rent on St. John and cannot wait to do it again! -truly!
Posted: Aug 6, 2015
...My expectations were far exceeded by the incredibly generous hospitality of Leslie and the team at Destination St. John. There was a special hositality basket with delicious treats.
Posted: Jul 16, 2015
...Destination St. John was easy to work with and our greeter did a great job of getting us settled. We also enjoyed the basket of snacks left in the fridge. I wouldn't hesitate to recommend this property at all!
Posted: Jul 11, 2015
...We highly recommend using the management company Destination St. John to rent this Villa, we have used them for the past 8 years and they are simply the best!!!
Posted: May 28, 2015
...We rented through Destination St John both times and they are professional, friendly, curtious and a pleasure to work with. Thank you Kelly for making both of our stays amazing.
Posted: Mar 24, 2015
...The staff at Destination St. John were very nice, accommodating, and quick to respond to our (literally) last minute request. They had the villa cleaned & ready the next day, with a staff member ready to meet us & show us to the villa...they even put a very nice welcome basket of food/snacks in the refrigerator. Another villa rental company sent me a rude email saying they were too busy to schedule a cleaning service...I'm so glad we stayed with DSJ...Great service!...I plan to use them exclusively in the future.
Posted: Aug 4, 2014
...Destination St John was excellent to work with. We enjoyed the welcome basket after a very long day of travel.
Posted: May 29, 2014
...The Destination St. John website was very informative and well put together, we knew exactly what to expect and couldn't wait to get there.
Posted: May 16, 2014
...Hope to return someday and visit the beautiful island again. And we would contact Destination St. John for accomodations again.
Posted: Jul 13, 2013
...We've been using Destination St. John for the last 6 years for villas and couldn't be more pleased....This Company is the BEST and so are all their employees, they take care of any need/question you may have 24/7.
Posted: Jul 11, 2013
...Destinations St John took care of any problem we had immediately.
Posted: Jul 9, 2013
...Thanks to Destination St John for taking care of us.
Posted: Apr 20, 2013
...Destination St. John left a wonderful gift basket in the fridge which made us feel very welcome. We plan to return to St. John and would certainly book our trip through Destination St. John again!

Security/Cancellation Policy

A $1000 security deposit may be required. Cancellations 60 or more days prior to arrival are non-refundable unless property can be re-committed for reserved dates. If property is recommitted for your dates, a 15% service fee will apply. No refunds will be issued within 60 days of arrival, under any circumstances. We STRONGLY urge you to purchase travel insurance.

Reservation Payment


We accept:

Visa, Mastercard, Discover, Checks