Navigation Menu+

Riley’s Retreat Villa St John

Riley's Retreat Villa, St John vacation rental



Panoramic views, tranquil breezes, and peaceful sunsets are just a few of the perks that await at Riley’s Retreat. Nestled on the hillside in a private neighborhood, this villa provides relaxation with numerous on-site amenities to enjoy, while also close to other conveniences of the island.  Just a 1 mile drive to the passenger ferry, great restaurants, local shops and entertainment in Cruz Bay.

Riley’s 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 closets. 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 of the villa is equally well designed and newly refurnished as its own apartment, with 2 bedrooms, a queen-sized bed in the first, and your choice of a king or two twin beds in the second, 1 full bath and a fully equipped kitchen. The outdoor deck has a fully furnished living and dining area as well.

The cottage is a romantic studio nestled in the garden, with a beautiful garden path to the pool and a short walk across the driveway to the main house.  This studio space boasts a queen size bed, full bathroom, kitchenette and outdoor deck space.

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 favorite playlist from anywhere.

The laundry room on-site is equipped with large capacity washers and dryers, 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!



1-6 Guests = $850/nt – Upstairs access only, full property private to you 

1-10 Guests = $1250/nt  Full house and property private to you
3 night minimum stay

Full House + Cottage and property private to you up to 12 guests = $1500/night

Additional Guests @ $50/night

Property can accomodate up to 16.  You can choose a 5 or 6 bedroom option with two extra guests on pull out couch.  Please specify.


Holiday Period

Thanksgiving Week

December 18 – January 2
7 night minimum stay

30% Premium will be applied