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Description
Betsy
Know Before You Go...®
Island Rider overlooks some of the clearest Caribbean water you’ve ever seen. You can spend hours just relaxing on the covered patio enjoying the sun. You can entertain friends in the large open living area that opens onto the deck, or take a quiet stroll in the garden to gather your thoughts and unwind. If you want to squeeze in a little shopping, Cruz Bay is just minutes away.
Perfect getaway for friends or families with older children.
Island Rider is located in the exclusive Point Rendezvous community on St. John’s south shore. This villa sits on a hillside above Klein Bay overlooking Rendezvous Bay and Ditliff Point.
This well-appointed home holds all of the charm of old St. John without sacrificing modern amenities. The octagonal, solar-heated swimming pool faces the sea and small islands. A surrounding terrace holds loungers and stairs that lead to the deck’s various levels. The lower and upper levels has dining tables with umbrellas, and there’s a stainless steel BBQ grill under the veranda. Plus, there’s a hammock to sleep in, a sand shower to rinse off in, and a covered courtyard to relax in. The home’s entrance is at the back of the house for extra privacy and security. The open plan Great Room opens to views on one side and the covered patio on the other. It incorporates the lounge, gourmet kitchen, and dining room into one open space with vaulted ceilings and stone walls. A media room sits opposite with a flatscreen TV, entertainment system, balcony access, ocean views, and tons of seating. There are four air-conditioned king suites, all on the lower level. Each suite has exterior access, a TV, seating, and an ensuite bathroom. The fourth suite is on the main level next to the media room.
Island Rider is an ideal 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 seclusion.
Rates
| Dates | People | Nightly | Weekly |
|---|---|---|---|
| Dec 17, 2024 to Jan 6, 2025 7 Night Minimum | 1-8 people | $2,171 USD | $15,200 USD |
| Jan 7, 2025 to May 2, 2025 5 Night Minimum | 1-2 people | $1,343 USD | $9,400 USD |
| 3-4 people | $1,514 USD | $10,600 USD | |
| 5-6 people | $1,686 USD | $11,800 USD | |
| 7-8 people | $1,857 USD | $13,000 USD | |
| May 3, 2025 to Nov 21, 2025 5 Night Minimum | 1-2 people | $1,171 USD | $8,200 USD |
| 3-4 people | $1,343 USD | $9,400 USD | |
| 5-6 people | $1,514 USD | $10,600 USD | |
| 7-8 people | $1,686 USD | $11,800 USD | |
| Nov 22, 2025 to Nov 29, 2025 7 Night Minimum | 1-8 people Thanksgiving |
$1,686 USD | $11,800 USD |
| Nov 30, 2025 to Dec 16, 2025 5 Night Minimum | 1-2 people | $1,171 USD | $8,200 USD |
| 3-4 people | $1,343 USD | $9,400 USD | |
| 5-6 people | $1,514 USD | $10,600 USD | |
| 7-8 people | $1,686 USD | $11,800 USD | |
| Dec 17, 2025 to Jan 4, 2026 7 Night Minimum | 1-8 people | $2,171 USD | $15,200 USD |
Rates shown in
Notes on Rates:
- Rates range from $1,100 to $2,171/night.
- All rental rates are based on two persons per bedroom.
- This property charges rates in US Dollars (USD).
- Rates do not include: tax of 12.5%, damage waiver fee of $50.00.
- Rates are subject to change.
- Holiday bookings may require longer stays or whole house rate.
Personal Concierge Services
Choosing the right villa is just the first step in creating the perfect vacation experience. We help you plan every element of your villa vacation, from rental cars to spa treatments, completely personalized to you.
- grocery provisioning
- car rental
- spa services
- chef/cook services
- butler service
- restaurant reservations
- activities and sightseeing
- ferry/airport transfers
- laundry service
Details
Beds & Baths
Main House
- Bedroom 1: Main level
- 1 King, Air Conditioning, Exterior Access Only, TV
- Ensuite Full Bath with Shower
- Bedroom 2: Lower level
- 1 King, Air Conditioning, Exterior Access Only, TV
- Ensuite Full Bath with Shower
- Bedroom 3: Lower level
- 1 King, Air Conditioning, Exterior Access Only, TV
- Ensuite Full Bath with Shower
- Bedroom 4: Lower level
- 1 King, Air Conditioning, Exterior Access Only, TV
- Ensuite Full Bath with Shower
Other Bathrooms
- Bathroom 5: Half bath
- Bathroom 6: Half bath
Features
Interior
- Big Screen Television
- Ceiling Fans
- Coffee Maker - Drip style
- Dishwasher
- Docking Station
- DVD Player
- Hair Dryers
- Ice maker
- Internet Access/WiFi
- Iron/Ironing Board
- Microwave
- Safe
- Satellite
- Stereo System
- Washer/Dryer
Exterior
- BBQ Outside (Gas)
- Beach Chairs
- Beach Towels
- Cooler
- Pool at Villa
| Check In | 15:00:00 |
|---|---|
| Check Out | 10:00:00 |
| Pool | 17 x 17 Depth 4'; solar heated pool |
| Location | Point Rendezvous |
| Beach | 5 minutes from Great Cruz Bay |
| Transfers | You will be greeted at the Cruz Bay ferry dock on St. John, accompanied to pick up your rental car and then led to the villa. One arrival greeting is included. You may schedule additional arrivals as needed at an additional cost. |
| Children | Welcome over 8 years of age or under 8 months. |
| Additional | A fee for arrivals after 7 pm. |
Calendar
Reviews
5.00/11
(11 reviews)
100% traveler satisfaction
One word: Paradise
Island Rider Villa, St. John villa review
We recently stayed at Island Rider Villa and it far exceeded our expectations. The Villa has so many breathtaking views; you could just stay here and never leave to explore the island but please do it is equally breathtaking. We loved how all 4 bedrooms had their own exits that did not go to the “main” part of the Villa. Some of us like to sleep late and we were not interrupted. Plenty of space in the common areas (kitchen, living room, and media room) as well as so many spaces outside (pool area, hot tub area, porches and back patio). We used a grocery service and had our food delivered before we arrived which was awesome. House was very clean as well as the pool and hot tub. We had 4 teenagers and 4 adults- plenty of space in the pool and all around the house. Water in showers was always hot and the air conditioning was perfect. The ride up to the Villa is a steep one! After the first couple of times we got used to it as well as driving on the left side of the road. You really are not too far from the grocery stores and some of the beaches. Also, if you ferry your car over from St. Thomas -Red Ferry Hook Marina is super close. I am not sure how we could come back to St. John’s and not rent this Villa again. If you are hesitant- just do it- you won’t regret it!
Great- Betsy called me a few of the mornings to check in and ask how it was going. She also called to let me know that the Pool Lady was coming to service the hot tub and pool.
Posted by Nicole V
Absolutely PERFECT!!
Island Rider Villa, St. John villa review
The Island Rider Villa was absolutely perfect, gorgeous views, & Betsy & the entire team were fabulous, so nice, & so helpful!! I HIGHLY recommend the beautiful Island Rider Villa, & the Where to Stay team is the best… they truly go above & beyond!! Our entire St. John vacay was absolutely PERFECT!! Loved everything about our stay!!
Betsy is the BEST!!! She is so very sweet, helpful, answered all our questions / emails promptly & thoroughly, gave us so much valuable information, and truly made sure we had the BEST experience!! We are so thankful for her, she made sure our entire vacay was perfect … she goes above & beyond!!
Posted by Stephanie C
Fantastic villa.
Island Rider Villa, St. John villa review
Wonderful experience. Gorgeous views. Would definitely book again.
Very helpful
Posted by Sue S
Very hard to beat this place.
Island Rider Villa, St. John villa review
We loved our stay at Island Rider. The pictures online were a perfect representation of what you get. There’s A/C everywhere (which you can’t say of all Villas). The views from the pool and jacuzzi were phenomenal. Had washer/dryer with soap already there, so you really only need to being a few dates worth of clothes. Very reasonable drive into Cruz Bay. Only small negative was the hot water. Have to wait a very long time for it, and sometimes it seemed to run out a little soon. Otherwise, this place is an absolute dream. Good chance we’ll stay here again whenever we can get back to St John.
Betsy and everyone was great to work with. Absolutely loved out greeter Winnie when we arrived.
Posted by Deryll S
Wonderful paradise!
Island Rider Villa, St. John villa review
Overall, I cannot recommend this villa enough. It offers an unparalleled experience of luxury, comfort, and natural beauty. Whether you’re seeking a romantic getaway, a family vacation, or a serene retreat, this place has it all. So, indulge yourself and bask in the wonders of this villa overlooking the sea with its mesmerizing pool—I guarantee it will be an experience you’ll never forget!
I would highly recommend planning your trip with Andrew! He has amazing attention to detail and provides great travel tips!! he will ensure you have a special time!
He went above and beyond by sending me additional links for car, rental, sailing, groceries, and everything else. He also gave me tips on what I would experience driving on the island that was very helpful in planning my location.
Posted by Christina M
A return to Island Rider in St. John
Island Rider Villa, St. John villa review
We can’t tell you enough how much we enjoyed staying at Island Rider! The location is superb! Views are great! All the bedrooms are King beds, and very well appointed. We had to call maintenence to come show us how to turn on the A/C in the TV room, and they were very prompt. It was successfully working in no time! Mike had to come back the next day to change batteries in a small detector, and once again, he was very prompt to come!
Excellent once again!
Posted by Charlotte B
Absolutely Incredible
Island Rider Villa, St. John villa review
Photos and description do not do this home justice. Everything was amazing - furnishings, space, views, etc. Our group included four adults and three kids (ages 8-11), and everyone was beyond happy the entire time.
Betsy and team are the best. They’ve thought of every detail to make your trip perfect.
Posted by Brett W
Amazing view
Island Rider Villa, St. John villa review
This villa is beautifully done, especially love the stone work! The view out to the infinity pool was breathtaking! The kitchen is well stocked with everything you could imagine, we even had a little welcome “basket” of local beer, pop, cheese, crackers and other items which was nice. It was nice having outdoor space both in the front of the house and back overlooking the pool. The outdoor space is huge, especially loved the open area from the kitchen leading to the bar counter. Bedrooms are well done with comfortable beds. It was also nice having a hot tub even though not all the jets were working. We had one issue with not having water which didn’t happen until midnight. I called the after hour number and someone was there by 7am the next morning. Something to do with the pump, it was fixed and all was well!
Everything was great working with Shawna & WhereToStay!!
Posted by Denice S
Billion dollar paradise!!!
Island Rider Villa, St. John villa review
My fiancé and I were planning our trip to elope in St. John. We searched and searched then found this gem! We looked no further. Island Rider villa has a billion dollar view! It is very up to date, immaculate, plenty of bedrooms and living space. The kitchen was fully equipped and the pool was absolutely breath-taking to enjoy the view while floating in the pool. The hot tub was also very clean and enjoyable and of course with an amazing view! There is plenty of outside terrace to sit and have a glass of wine and enjoy the lovely weather. It is paradise! Everyone we spoke with regarding renting this was exceptionally nice and very very helpful. We got married in front of the pool and I received so many compliments about how beautiful it was! Sunrise to sunset and even in the evening sky the view is priceless! It is only minutes to Cruz Bay where all the shopping and restaurants are. We are planning on returning with our children the next time! I cannot say enough about Island Rider! So many memories and gorgeous pictures and romantic villa that will meet all your needs.
Shawna is excellent. She was helpful on day 1 and was there for every question and helped us with recommendations. She is a 5 star representative! Excellent and appreciated all her time with us answering our questions about restaurants, car rentals, beaches and many other things. Very responsive and professional. Highly recommended working with her. Thank you Shawna!!!
Posted by Robyn C
Great stay!
Island Rider Villa, St. John villa review
We had a wonderful time at Island Rider Villa!
Shawna was awesome and helped us every step of the way. She answered all of our questions and her recommendations were great!
Posted by Electra M
Amazing views Amazing house!
Island Rider Villa, St. John villa review
Island Rider Villa is everything we thought it would be! The pictures were spot on. The villa is beautiful and very well appointed. The sunrise and sunset views are nothing short of spectacular. If you’ve never stayed on St. John, the villa is really well situated for quick trips to Cruz Bay and easy drives to all of the north shore beaches. We will absolutely plan to stay at Island Rider again!!
Shawna and Sharon were great to work with. They provided great communication leading up to our trip and were very helpful with check in information and taxi transfers to and from the ferry/airport. We will absolutely book through whereto stay.com for our future trips!! Thanks Ladies, for helping to make this a memorable trip!!
Posted by Renee P
