Island Rider

Located in the exclusive enclave of Point Rendezvous on the south shore of St. John, Island Rider is a fully renovated villa that sits upon the open breezy hillside above Klein Bay. Island Rider's sprawling verandas overlook the gentle curves of Rendezvous Bay and Ditliff Point. This beautifully appointed four bedroom home holds all of the charm of the old St. John with beautiful stone work while providing all of the modern amenities one could expect in a luxury home including a fabulous solar heated pool.

This villa sets the standards in modern vacation accommodations with a state of the art gourmet kitchen and open dining room for entertaining, as well as a separate media room to relax in for a night of watching movies. The spacious open plan living area opens to spectacular views south on one side and an expansive covered patio for grilling in back. There are four distinct outdoor seating areas that accommodate 8 guests for meals: The Veranda, Courtyard, Pool Deck and Lower Deck.

Designed to be the ultimate personal retreat, Island Rider is the perfect getaway for friends or families with adult children. Located just five minutes from Cruz Bay, it has convenient access to town and the North Shore beaches but still provides the seclusion you want for your island getaway. Island Rider will offer you a vacation you will never forget.

Vacation Rental Reviews

• Great House. Great View. Great Location

  Stayed 7 days ending in December, 2025

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  Scott S from West Newton, MA recommends this vacation rental

  Awesome house. Catered To was super helpful and responsive. Highly recommend this house.

  • Manager Responded on 1/12/2026

    Thank you for sharing your review of your recent stay at Island Rider. We certainly look forward to having you again.

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• Wedding Vacay

  Stayed 5 days ending in April, 2024

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  a guest from Chicago, IL recommends this vacation rental

  The Island Rider experience was better than we could’ve ever imagined and definitely exceeded expectations! From the incredible views, sunsets and sunrises, this home was second to none. Awesome updated kitchen! We cooked multiple dinners and brunches and were able to thoroughly enjoy our meals on the huge deck overlooking the Sea. The pool was incredible and the hottub was a nice amenity! Everything was 5-Star and we will certainly be back for our next time on St. John, USVI! Special mention to our greeter/conceirge Jehlisa! ⭐️⭐️⭐️⭐️⭐️

  • Manager Responded on 5/13/2024

    Thank you for sharing your stay at Island Rider. We are so happy you enjoyed the villa and that the greeter assisted you greatly. We look forward to your return.

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• Beautiful villa with stunning views!

  Stayed 7 days ending in December, 2023

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  a guest from Dover, Massachusetts recommends this vacation rental

  This was our 4th time renting a villa on St John and Island Rider was the most beautiful (hard to achieve among many beautiful villas!) The photos don't do it justice. The villa is beautifully decorated with a large comfortable sectional in the main living space and nice sturdy outdoor furniture. The bedrooms are all en suite with very comfortable king beds. The view is nearly a 180 degree water view - absolutely gorgeous with views of both sunrise and sunset. The pool is small and cool but refreshing and we enjoyed the hot tub too. We had not stayed as far from Cruz Bay before but it was only about 10 mins to town. Overall, a beautiful and well appointed villa and the caretakers (Catered To) were excellent and very responsive.

  • Manager Responded on 1/16/2024

    Thank you very much for your feedback on your recent stay at Island Rider! We are so happy you enjoyed everything about this villa. We certainly look forward to your next visit!

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• Cateredto - Island Rider Review

  Stayed 7 days ending in May, 2023

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  Tim C from Glenmoore, PA recommends this vacation rental

  Our experience with Catered was excellent. Everyone we dealt with was very professional and pleasant. It was clear they wanted our stay to be as positive as possible. The property was beautiful and in excellent condition. We have been using Catered To for 20 years and have never been disappointed. Highly recommend.

  • Manager Responded on 5/15/2023

    Thank you so much for your feedback of your recent stay at island Rider and with Catered To! It was a pleasure having you and we certainly look forward to your return!

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• Top-Notch Villa

  Stayed 7 days ending in November, 2022

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  a guest from Commerce Twp, MI recommends this vacation rental

  Our experience staying at Island Rider was excellent! The villa was clean, well-appointed, had a fabulous view in a convenient location on the island, and just plain delightful. Catered To was helpful with our questions, really friendly and quick to respond when we needed anything. The villa is even more beautiful in person! We would stay here again!

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• Perfect Villa for us!

  Stayed 7 days ending in March, 2021

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  Jane B recommends this vacation rental

  Our Island Rider Villa was perfect for our group of 3 couples for our week in St. John VI. The villa has gorgeous bedrooms with ensuite bathrooms and privacy. The pool and hot tub has amazing views and was so relaxing after a day at the beaches. We cooked breakfast at home, made picnic lunch for the beach during the day and enjoyed the beautiful kitchen and porches in the evenings. Catered to You was so professional and helped us every step of the way. You will love the house too :)

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• SPECTACULAR VILLA AND VIEW!

  Stayed 10 days ending in December, 2020

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  Hirschinger S recommends this vacation rental

  We had a great time!! The view from this villa does not disappoint!! The villa was so nice and well kept and Catered To did a great job of solving any issues we had. Vernesta and Vicky were great and answered tons of questions for us while booking and while there. We did not want to leave. Nothing better than waking up to that view every day!! It is located far enough away for privacy but close enough to Cruz Bay for shopping, eating and groceries! WE LOVED IT AND ONLY HOPE WE CAN COME BACK SOMEDAY. WE FEEL VERY LUCKY TO BE ABLE TO HAVE GONE! THANKS AGAIN!! Shelly Hirschinger & family.

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