Riley's Retreat - Spacious Villa with Private Pool | Villa in Cruz Bay

10.0 (19 Reviews) |   Pet Friendly   5 Bedrooms  4 Bathrooms  14 Guests
Estate Pastory Villa | Riley's Retreat - Spacious Villa with Private Pool

5 Bedroom Villa in Estate Pastory, Cruz Bay

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.

This 5 Bedrooms Villa provides accommodation with Oceanfront, Guest Services, Private Pool, for your convenience. This Villa features many amenities for guests who want to stay for a few days, a weekend or probably a longer vacation with family, friends or group. The rental Villa has 5 Bedrooms and 4 Bathrooms to make you feel right at home.

Check to see if this Villa has the amenities you need and a location that makes this a great choice to stay in Estate Pastory. Enjoy your stay in Estate Pastory at this Villa.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • Pool
  • TV
  • View
  • Private Pool
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Guest Services
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Hot Tub
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy Events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 24
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Note from host: charge may apply pets allowed
Smoking Policy Smoking is not permitted
Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property parties and events are allowed on site safety features at this property include a fire extinguisher and a first aid kit special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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 this property uses solar energy
 
Cruz Bay, 00830, U.S. Virgin Islands

What Our Guests say 500 + Reviews

Jan 30, 2025 10:38:11 PM
Summary: 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. Chris W.
Dec 22, 2024 09:31:07 PM
Summary: 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. Chris F.
Aug 18, 2024 05:54:41 AM
Summary: Absolutely stunning place!
Laura S. Laura S.
Jul 24, 2024 07:33:47 AM
Summary: 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. William M.
Jul 8, 2024 10:13:19 PM
Summary: 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. Joseph S.
May 21, 2024 09:26:42 PM
Summary: I’d stay here again. Wonderful accommodations.
Kevin M. Kevin M.
Mar 19, 2024 05:00:45 AM
Summary: 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. DEBORAH L F.
Jan 26, 2024 01:10:32 AM
Summary: 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. Laura D.
Jan 14, 2024 02:49:25 AM
Summary: 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. Michael K.
Dec 6, 2023 04:01:01 PM
Summary: 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. Chris H.

FAQ's

Is this Estate Pastory villa pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Estate Pastory villa have a swimming pool?

Yes, this Estate Pastory villa has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Estate Pastory villa?

Best-rates for the Estate Pastory villa starts from $1,571 per night with includes Sports/Activities, Bedding/Linens, Air Conditioner, Pet Friendly, Pool, Security/Safety, Entertainment, Hot Tub, Parking, View, Fireplace/Heating, Barbecue/Outdoor Cooking, Child Friendly, Internet, Kitchen, Wellness Facilities, TV, Ocean View, Balcony/Terrace, Oceanfront, Guest Services, Private Pool, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Estate Pastory villa a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this villa Good or guests have recommended them suitable for families. As reported by the owner or manager, the villa has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Estate Pastory villa wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Estate Pastory villa has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Estate Pastory villa?

Based on the information reported by the owner or manager, the Estate Pastory villa indicates 1 day stay policy at this villa. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Estate Pastory villa?

Based on the information reported by the owner or manager, details for the cancellation policy for the Estate Pastory villa are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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