Unwind in the top-rated pool, your perfect spot for relaxation.
Arcade/game room
A rare find - fun for all ages with on-site arcade and game room.
Centrally-located
You're never far from where you need to be with this convenient location.
Discover nearby landmarks
Close to Virgin Islands National Park
5 bedrooms4 bathroomsSleeps 14
Popular amenities
Balcony
Hot tub on site
Private pool
Toys
Barbecue grill
Pet-friendly
Explore the area
Cruz Bay, St John
Virgin Islands National Park
Place, Virgin Islands National Park
13 min walk
Cruz Bay Beach
Place, Cruz Bay Beach
2 min drive
Honeymoon Beach
Place, Honeymoon Beach
8 min drive
St. Thomas (STT-Cyril E. King)
Airport, St. Thomas (STT-Cyril E. King)
55 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
About this property
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.
Our prices include all fees. No hidden fees.
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Important information
You need to know
Property # 2741818
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 some 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
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 Trunk Bay and Virgin Islands National Park. Explore all the area has to offer with horse riding and mountain climbing.
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 - 8 min drive - 3.7 km
Caneel Bay Beach - 8 min drive - 5.2 km
Getting around
St. Thomas (SPB-St. Thomas Seaplane Base) - 59 min drive
Restaurants
Shambles - 3 min drive
High Tide Bar & Seafood Grill - 4 min drive
Woody's Seafood Saloon - 4 min drive
Cruz Bay Landing - 4 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 Jun 11, 2026, prices found for a 1-night stay for 2 adults at Riley's Retreat - Spacious Villa with Private Pool on Aug 12, 2026 start from $2,117, 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 Virgin Islands National Park, Honeymoon Beach, 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.
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
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.
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.
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!
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
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.
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
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
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.
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.
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
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
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.
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.
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
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.
Good communication with owner and property manager. Lots of space. Convenient location. Hope to return soon.
Verified traveler
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.
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.
Let us introduce ourselves, new owners Brian and Dorothy. We have had a lifelong love of St. John. Brian has been visiting family and friends here since he was a young child and introduced me to this beautiful place at the start of our 28 year marriage. We have been fortunate enough to have continued to share our love of the island with our three girls and are blessed to have made a dream come true, after purchasing Riley's Retreat this summer. Our wish is to share our love of St. John and this home with our friends and family and yours too.
Why they chose this property
This Villa and its location is hard to match. Cruz Bay and all it has to offer is conveniently only one mile down the hill from Riley’ Retreat, so shopping, restaurants, bars and the ferry are a quick drive. The house is nestled at the end of a private road, overlooking Cruz Bay and Pillsbury sound....so lots of privacy and convenience. Additionally, the Windmill bar, Shambles, Shambles Sweet treats, Coco Jim’s and more are just a short trip up the hill. Our location makes accessing the beaches and all St John has to offer easy.
What makes this property unique
For those adventurers and hikers, the Caneel Hill trail can be accessed from the base of the property. The Caneel Hill outlook is just a short hike from the property and is a great place to watch the sunset. Pack a picnic basket, some wine and sit on top of the world while the sun sets. Return and cool off in the pool or tend to your muscles with a long relaxing soak in the hot tub. Our favorite is a late night skinny dip, watching all the stars twinkling in the night sky.
Languages:
English
Premier Host
They consistently provide great experiences for their guests