Virgin Islands National Park is a short stroll from this villa, and other popular attractions like Cruz Bay Beach are within a mile (2 km). The villa includes a private pool, a kitchen, and a balcony.
Virgin Islands National Park - 11 min walk - 0.6 miles
Caneel Bay Beach - 16 min walk - 0.9 miles
Cruz Bay Beach - 2 min drive - 1.0 mile
Battery - 2 min drive - 1.0 mile
Honeymoon Beach - 7 min drive - 1.5 miles
Getting around
St. Thomas (SPB-St. Thomas Seaplane Base) - 59 min drive
Restaurants
Cruz Bay Landing - 4 min drive
Woody's Seafood Saloon - 4 min drive
Upstairs Bar & Grill - 4 min drive
Sun Dog Cafe - 4 min drive
The Longboard - 4 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Riley's Retreat - Spacious Villa with Private Pool
Summary: The Villa is a spacious 5 bedroom, 4 bath home with pool, hot tub, game room & gourmet kitchen. Plenty of room for friends & family &privacy/quiet time.
Panoramic views, tranquil breezes, & colorful sunsets are a few of the perks that await at Riley's Retreat on the island of St John. Nestled on the hillside in a private neighborhood, this villa provides relaxation with numerous on-site amenities to enjoy, while remaining conveniently close to Cruz Bay.
Come let us host you in paradise!
The Space: Riley's Retreat is a bright and beautiful, newly updated villa that retains all the charm of Old St. John with ornate stonework and custom mahogany details, while also providing the modern conveniences you would expect from a vacation home. Enjoy morning coffee on the breezy decks, tropical cocktails by the pool in the afternoon. Challenge friends and family to a billiards tournament in the game room after a sunny beach day, or relish in a slow dance at the water’s edge while one of the island’s private chefs prepares a local seafood dinner. If you're lucky, the resident iguanas will join you for a starfruit snack in the groves surrounding the property. A beautiful sunset over the isles awaits every night, followed by a canopy of a million stars to gaze.
The two-level design of this spacious home offers plenty of room to gather, yet it also includes private areas for you to relax and enjoy some alone time. The upper living area is an open concept to capitalize on the natural light. Complete with a gourmet kitchen and furnished indoor and outdoor dining areas, the space is meant to accommodate large groups and families. There are three spacious bedrooms upstairs and 2 full bathrooms. Each bedroom has an AC unit with individual temperature controls and ceiling fans. The Master has a king-sized bed, private ensuite bathroom with a stone walk in shower. From the bathroom, you can walk out to the outdoor shower and down private steps to the pool area. There are 2 more large guest bedrooms, with new queen-sized beds and full closet. From any room, enjoy the peaceful sounds of tree frogs floating on the soft breezes to lull you to sleep at night. Wrap-around porches make it easy to navigate and explore the property from every angle.
The lower level is equally well designed and newly refurnished as its own apartment, with 2 bedrooms, both with queen-sized beds, 1 full bath and a fully equipped kitchen. The outdoor deck has a fully furnished living and dining area as well.
The pool area is very private and features an in-ground 14’ x 21’ pool and 6-person hot tub. There is a club house bar area with a pool table, ‘open air’ bar and many family games, where guests can enjoy snacks, cold beverages and a little competition. There is also a full bathroom with shower. A Bluetooth sound system is also wired inside and around the pool, so you can enjoy your playlist anywhere.
The laundry room on-site is equipped with large capacity washers and dryers, clothing iron and steamer, for your convenience.
Our property manager is on island and available to assist with questions or issues as needed during your stay. You can be greeted at the docks and escorted to the house or we can meet you at the house, give you a brief tour and get you settled in. Other convenient accommodations can also be arranged, to ensure your stay is stress free. Babysitting, grocery delivery, taxi services, and tour recommendations can all be arranged, don’t hesitate to ask!
Guest Access: There is plenty of parking in the driveway to accomodate 4 vehicles and space for safari style taxis to access and turn around. We highly recommend you rent a jeep to experience all that the island of St John has to offer. We can also recommend several great safari style taxis that can accomodate large parties.
The Neighborhood: The Villa is located a mile above Cruz Bay at the end of a private road. It is a very private property overlooking the ocean and the valley below. Just minutes to dining, dancing & shopping. 1.5 Miles to the nearest beach. Caneel hiking trail accessible at base of property.
Getting Around: We recommend you rent a jeep to explore and experience the island to its fullest. We can recommend several safari style taxi drivers who also know the property well and take great care of you in your palnning, especially when staying with a large group. The Villa can easily accomododate multiple vehicles parked at the property.
Other Things to Note: We have plenty of beach chairs and coolers to take with you when you explore St John's stunning beaches. Beach toys and snorkel gear are also available.
Interaction with Guests: Our property manager is on Island and available to assist with questions or issues as needed during your stay. You can be greeted at the docks and escorted to the house or we can meet you at the house, give you a brief tour and get you settled in.
The villa is air-conditioned and features a kitchen, 4 bathrooms, and a balcony, and there's space to spread out with 5 bedrooms. Other standard amenities include a private pool, a washing machine, and a sofa bed.
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Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
General
At least 10% of profits reinvested in community and sustainability
At least 80% lighting from LEDs
Cleaning products are eco-friendly
Energy-saving switches in guestrooms
Garden
Local artist showcase
Locally-owned and organized tours and activities
Solar energy
Unit size: 3,400 square feet
Water-efficient showers
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 24
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
Events: All events must be approved by the property owner. Additional fees may apply depending on the event.
In the event that a hurricane is pre...
Pets
This property welcomes pets
Note from host: Charge may apply
Children and extra beds
Children allowed: ages 0-17
Events
Events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events are allowed on site
This property uses solar energy
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Check-in: 4:00 PM
Check-out: 10:00 AM
Minimum check-in age: 24
We should mention
Details about charges, deposits, or other important information:
This property is managed by a private host, not a professional engaged in trade or business.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
This property uses solar energy.
Parties and events are allowed on site.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit.
Property is also known as
65dcf3d26da3560012b666eb
Frequently asked questions
What can I see around this villa?
This villa is located in St. John, a short 10-minute walk from Virgin Islands National Park and also 20 minutes on foot from Caneel Bay Beach. You'll also find Trunk Bay and Cruz Bay Beach within a short drive.
Will I be able to park at this villa?
No, there isn't parking available at the villa.
Is this villa next to a casino?
No, this villa is not connected to a casino.
Will I find an indoor pool at this villa?
No, this villa doesn't have an indoor pool; however, there is a hot tub.
Is Riley's Retreat - Spacious Villa with Private Pool good for couples?
Couples will appreciate amenities at this villa, including a private pool and a kitchen in each villa with some featuring ocean views.
Does Riley's Retreat - Spacious Villa with Private Pool have a hot tub?
Yes, this villa has a spa tub.
Does this villa provide breakfast?
No, this villa doesn't offer breakfast.
Will this villa allow pets to stay for free?
Although pets can't stay for free, they are welcome at this villa.
Are there connecting rooms at this villa?
No, there aren't connecting rooms at this villa.
Where is the closest airport to this villa?
The closest major airport to this villa is St. Thomas (SPB-St. Thomas Seaplane Base), which is 13.9 mi away (59 minutes by car). Another top airport is Cyril E. King Airport (STT), which is located 16.5 mi away (67-minute drive).
Are there rooms with balconies at Riley's Retreat - Spacious Villa with Private Pool?
Yes, every villa at Riley's Retreat - Spacious Villa with Private Pool comes with a balcony with some featuring ocean views.
Riley's Retreat - Spacious Villa with Private Pool Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 20 out of 20 reviews
10 - Excellent
20
Rating 8 - Good. 0 out of 20 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 20 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 20 reviews
4 - Poor
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Rating 2 - Terrible. 0 out of 20 reviews
2 - Terrible
0
9.8/10
Cleanliness
Reviews
10/10 Excellent
Isaac G.
Nov 18, 2025
Liked: Cleanliness
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.
Isaac G.
Stayed 5 nights in Nov 2025
10/10 Excellent
Richard W.
Mar 31, 2025
Liked: Cleanliness
Richard W.
Stayed 7 nights in Feb 2025
10/10 Excellent
Chris W.
Jan 30, 2025
Liked: Cleanliness
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.
Chris W.
Stayed 4 nights in Jan 2025
10/10 Excellent
Chris F.
Dec 22, 2024
Liked: Cleanliness
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
Chris F.
Stayed 7 nights in Dec 2024
10/10 Excellent
Laura S.
Aug 17, 2024
Liked: Cleanliness
Luxury Property
Absolutely stunning place!
Laura S.
Stayed 4 nights in Aug 2024
10/10 Excellent
William M.
Jul 24, 2024
Liked: Cleanliness
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.
William M.
Stayed 5 nights in Jul 2024
10/10 Excellent
Joseph S.
Jul 8, 2024
Liked: Cleanliness
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
Joseph S.
Stayed 7 nights in Jun 2024
10/10 Excellent
Kevin M., Georgia
May 21, 2024
Liked: Cleanliness
Wonderful stay
I’d stay here again. Wonderful accommodations.
Kevin M.
Stayed 5 nights in May 2024
10/10 Excellent
DEBORAH L F.
Mar 18, 2024
Liked: Cleanliness
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.
DEBORAH L F.
Stayed 6 nights in Mar 2024
10/10 Excellent
Laura D.
Jan 25, 2024
Liked: Cleanliness
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.
Laura D.
Stayed 4 nights in Jan 2024
10/10 Excellent
Michael K.
Jan 13, 2024
Liked: Cleanliness
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.
Michael K.
Stayed 7 nights in Jan 2024
10/10 Excellent
Chris H.
Dec 3, 2023
Liked: Cleanliness
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!
Chris H.
Stayed 6 nights in Nov 2023
10/10 Excellent
Michael W., Austin Texas
Jul 27, 2023
Liked: Cleanliness
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.
Michael W.
Stayed 4 nights in Jul 2023
10/10 Excellent
Gina G.
Jun 2, 2023
Liked: Cleanliness
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
Gina G.
Stayed 4 nights in May 2023
10/10 Excellent
Todd G.
May 23, 2023
Liked: Cleanliness
Awesome house in St John
This was a wonderful place in St John. The views and the house was amazing
Todd G.
Stayed 4 nights in May 2023
10/10 Excellent
Meredith C.
Jan 28, 2023
Liked: Cleanliness
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.
Meredith C.
Stayed 4 nights in Jan 2023
10/10 Excellent
Madeline S.
Aug 15, 2022
Liked: Cleanliness
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!
Madeline S.
Stayed 4 nights in Aug 2022
10/10 Excellent
sergio t.
Aug 9, 2022
Liked: Cleanliness
Wedding!
The property delivered all that we wanted! The view was better than expected. ! Does need a little maintenance.
sergio t.
Stayed 5 nights in Aug 2022
10/10 Excellent
Verified traveler
May 18, 2022
Liked: Cleanliness
Great place!
Good communication with owner and property manager. Lots of space. Convenient location. Hope to return soon.
Verified traveler
Stayed 9 nights in May 2022
10/10 Excellent
Meghen B.
Apr 10, 2022
Liked: Cleanliness
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.