Riley's Retreat - Spacious Villa with Private Pool

Photo gallery for Riley's Retreat - Spacious Villa with Private Pool

A two-story house with a swimming pool, surrounded by lush greenery.
A kitchen with wooden cabinets, stainless steel appliances, granite countertops, and a ceiling fan.
A cozy room with a stone wall, a wooden ceiling, a desk with a lamp, and comfortable seating.
A multi-story house with a pool, surrounded by dense vegetation.
A spacious dining area with a large wooden table set for six, surrounded by teal chairs.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • At the center of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Close to Virgin Islands National Park

Popular amenities

  • Balcony
  • Hot tub on site
  • Private pool
  • Toys
  • Barbecue grill
  • Pet-friendly

Explore the area

View in a map
Cruz Bay, St John
  • Place, Virgin Islands National Park
    ‪13 min walk‬
  • Place, Cruz Bay Beach
    ‪2 min drive‬
  • Place, Honeymoon Beach
    ‪9 min drive‬
  • Airport, St. Thomas (STT-Cyril E. King)
    ‪56 min drive‬

Rooms & beds

5 bedrooms (sleeps 14)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 King Bed

Living Room 1

2 Double Sofa Beds

4 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Office
Balcony
Garden
Dining area

Add dates for prices

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About the neighborhood

St. John

Located in St. John, this villa is in the mountains and near the beach. Blackbeard's Castle is a notable landmark, and the area's natural beauty can be seen at Virgin Islands National Park and Cruz Bay Beach. Explore all the area has to offer with mountain climbing and horse riding.
View more Villas in St. JohnOpens in a new window
Map
Cruz Bay, St John

What's nearby

  • Virgin Islands National Park - 13 min walk - 1.2 km
  • Cruz Bay Beach - 2 min drive - 1.6 km
  • Battery - 2 min drive - 1.6 km
  • Honeymoon Beach - 9 min drive - 3.7 km
  • Caneel Bay Beach - 11 min drive - 5.2 km

Getting around

  • St. Thomas (SPB-St. Thomas Seaplane Base) - 59 min drive

Restaurants

  • ‪Trunk Bay Beach Bar - ‬12 min drive
  • ‪Maho Crossroads - ‬21 min drive
  • ‪Cruz Bay Landing - ‬4 min drive
  • ‪Shambles - ‬3 min drive
  • ‪The Longboard - ‬4 min drive

Frequently asked questions

Does Riley's Retreat - Spacious Villa with Private Pool have a pool?

Yes, this property has a pool.

How much does it cost to stay at Riley's Retreat - Spacious Villa with Private Pool?

As of Nov 3, 2026, prices found for a 1-night stay for 2 adults at Riley's Retreat - Spacious Villa with Private Pool on Nov 15, 2026 start from $1,589, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Riley's Retreat - Spacious Villa with Private Pool pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Riley's Retreat - Spacious Villa with Private Pool?

Check-in begins at 4:00 PM.

What time is check-out at Riley's Retreat - Spacious Villa with Private Pool?

Check-out is at 10:00 AM.

Where is Riley's Retreat - Spacious Villa with Private Pool located?

Situated by the sea, this villa is within 1 mi (2 km) of Caneel Bay Beach, Virgin Islands National Park, and Cruz Bay Beach. Trunk Bay is 3 mi (4.8 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 21 reviews
Rating 8 - Good. 0 out of 21 reviews
Rating 6 - Okay. 0 out of 21 reviews
Rating 4 - Poor. 0 out of 21 reviews
Rating 2 - Terrible. 0 out of 21 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Huge accomodations, great location, very clean and well stocked.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay

I’d stay here again. Wonderful accommodations.
Stayed 5 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Luxury Property

Absolutely stunning place!
Stayed 4 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome house in St John

This was a wonderful place in St John. The views and the house was amazing
Stayed 4 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house

The house was perfect form our group. It was my wife’s 40th birthday and we stayed on St John with a group of friends. The house, house managers and amenities couldn’t have been better. I’d recommend this home to anyone.
Stayed 4 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous Week at Riley's Retreat

We had a group of friends here to celebrate a couple of 50th Birthdays and honestly, the week could not have gone any better. The views from this house, it's convenience to the rest of the island and all of the included amenities made for a trip that was just about perfect. Thanks to the whole team involved with this house for making everything amazing!
Stayed 6 nights in Nov 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Trip

St John is an idyllic destination. Riley’s Retreat was the perfect home base for our island experience. Well equipped and handsomely appointed with a spectacular view, having a most enjoyable pool with ideal size and cleanliness, Riley’s Retreat perfectly fit the needs of our three generational family When we encountered some difficulties with appliances, the staff did everything they could to rectify problems This was one location that my wife and I agreed that we would visit again
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Everything and more

This property was amazing beautiful view’s very comfortable there were 8 in our group it’s spacious well stocked kitchen with everything you’ll need. Our stay here was amazing you won’t be disappointed The property manager was great very responsive. Gina G
Stayed 4 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

40th Birthday trip

Riley's Retreat was AMAZING. 10 of us went to St. John for my wife's 40th birthday trip and it was perfect. The listing hardly scratches the surface on how great this property actually is. All of the amenities, the space, the character and style of the house were fantastic. We really enjoyed our stay here. As a party of 10 it can be overwhelming for some properties regarding space and furniture, never once an issue.
Stayed 4 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Dorothy was very easy to work with and was very prompt to our questions we had, and patient, which we appreciate. Everyone involved was so accommodating and welcoming. Home was in great shape, except for a nasty smell outside the home that kept us from being able to hang out by the pool, but sometimes those things are uncontrollable from the hosts to solve.
Stayed 5 nights in Nov 2025
Response from VrboOwner on Nov 19, 2025
Happy you enjoyed the place and our support. We would love an opportunity to host you again. It’s unfortunate that an animal died near the property and despite searching we were unable to locate it to remove it. Cycle of life in the vast nature around us unfortunately, appreciate your understanding and thankful it’s a first in our four years of hosting.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a wonderful place to stay on St John!

House is in very good condition and unbelievable views, nice pool and hot tub but it also has lots of space for a big group! This house is in a great location only about a half a mile from downtown Cruz Bay. Property manager was easy to get hold of and check out was very easy. There is plenty of pots and pans and kitchen needs for cooking and feet nice appliances. Don’t forget the pool table and gameroom w bar top by the pool. Overall a great place and would consider again
Stayed 7 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise

Absolutely beautiful! Everything you need and more. Loved all the space. Pool area was great for everyone hanging together. Spacious kitchen was great for gathering too. All the comforts of home. We all slept great. Beach chairs were much appreciated at the beaches and pool floats at the house. Gorgeous views from the balconies and pool.
Stayed 6 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Villa in Paradise

Riley‘s retreat is an absolutely gorgeous villa with incredible views and space enough for a group of 10. Dorothy and her property managers made planning this trip and enjoying this villa absolutely seamless comfortable and easy. They are all extremely responsive and helpful. Everything you need is included. The pictures don’t even do it justice. I had a beautiful girls trip and can’t wait to go back.
Stayed 4 nights in Jan 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Great Property Spoiled by St. John's Power Issues

This house is a great property. It is spacious and tastefully furnished with conveniences and comforts. However, the island of St. John is experiencing troubling interruptions to their power supply that caused us to lose electricity (and therefore water) for several hours every day that we were there. This interrupted lighting, air conditioning, and bathroom access for extended periods of time for our entire abbreviated stay. A backup power supply would help, but there will still be issues with the commercial properties on the island that do not have electrical backup. It is very unfortunate.
Stayed 5 nights in Jul 2024
Response from VrboOwner on Jul 24, 2024
William, We hope to have an opportunity to welcome you back. Riley’s Retreat will have full solar, battery back-up and automatic generator installed Fall 2024. Thank you for your understanding, Dor
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unforgettable Stay at Riley's Retreat

We visited St. John and stayed at Riley's Retreat for my 40th birthday celebration - I can't say enough wonderful things about both! If you've never been to St. John, go now! It's such a peaceful and laid back place, much less touristy than any island in the Caribbean I've been to before. The villa is amazing with stunning views and plenty of space for all 12 of us to relax and unwind. Loved all the unique touches, pool, hot tub, outdoor shower and all of the amenities you could possibly need. It really felt like home for a few days. The villa is in a very convenient location, a quick ride away from the Cruz Bay ferry and "downtown" area, but you'll feel like you're miles away when gazing out over the water from the villa's beautiful deck. Dorothy was a fantastic host, always very responsive and provided some great recommendations. The on-island property manager was also super helpful. I have no complaints other than we wish we had stayed longer! Will definitely be back and would definitely recommend Dorothy and Brian's place for a large group.
Stayed 4 nights in Jan 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Experience

Riley’s Retreat was a wonderful home base for our family vacation. It is close to the car ferry but yet high up enough to have an amazing view. If anyone tells you to go somewhere else for the best sunsets, you’ll probably find that they’re better at the house. The house had everything we needed for our 11 person, week long vacation, and we spent most of our time at the house, in the pool, making meals together. There were some maintenance issues. Both apartment level air conditioners stopped working or leaked at times during our stay. In each case, the management team responded quickly to address the problems. The dishwasher leaked but we found that the drain was clogged and we were able to fix it on our own. Overall though, we loved Riley’s Retreat, and we were very happy with the service.
Stayed 7 nights in Jan 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing experience

We loved our stay here. We had the most amazing time. The location was easy to navigate to and from, and the property manager and coordinators were incredible. We’d happily come back again for another stay!
Stayed 4 nights in Aug 2022
Response from VrboOwner on Aug 15, 2022
Madeline you were amazing guests! We’d be blessed if all guests were like you and your group. Appreciate your kind words and look forward to an opportunity to host you again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, location, listing accuracy

Wedding!

The property delivered all that we wanted! The view was better than expected. ! Does need a little maintenance.
Stayed 5 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

Good communication with owner and property manager. Lots of space. Convenient location. Hope to return soon.
Stayed 9 nights in May 2022
Response from VrboOwner on May 24, 2022
We look forward to hosting you again! Glad you enjoyed the space with your large group and the convenience to Cruz Bay, the restaurants, bars and beaches.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely gorgeous!

Fantastic house. Has everything you need with an amazing host. Communication was good. House had everything and more needed for a great vacation. We were paired with a taxi driver (Ricky) during our stay who took care of everything. Any issues were immediately handled with a smile. We went to Oppenheimer beach which was fantastic. Great restaurants nearby were Lime Inn and Dave and Jerry’s. Pool and hot tub were wonderful. House is only minutes to town. I recommend a taxi driver unless you are comfortable on island roads. Bedrooms all have AC. Great for traveling with families or large groups. Can’t say enough about the property.
Stayed 5 nights in Apr 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Feb 2025
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