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Riley's Retreat - Spacious Villa with Private Pool

Villa in Cruz Bay, U.S. Virgin Islands

14 guests·5 bedrooms·4 bathrooms
5.0 · 50 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Stunning private pool, hot tub, and decks with panoramic Cruz Bay views.

Entertainment & Amenities

Entertainment & Amenities

Well equipped gourmet kitchen and game room elevate expansive group gatherings.

Location & Accessibility

Location & Accessibility

Easy access to Cruz Bay with jeep friendly hillside setting.

Property details

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! Pets: Allowed (maximum 1). Smoking: Not allowed. Events: Allowed. Suitable for: children and infants. Additional 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 predicted and St John will be closing the ports as a result, the guest must leave the property and the island for their own safety. Travel insurance is recommended, especially during hurricane season. Pets: Only dogs - no cats allowed. Additional cleaning and/or damage fees will be charged if the pet damages the home in any way. 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! 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. 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 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. 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.

Sleeping arrangements

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

Livingroom

2 Sofa Beds

What’s included

  • Parking

    Parking

  • Hot tub

    Hot tub

  • Pool

    Pool

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Kitchen

    Kitchen

Guest reviews

Star icon 5.0 | 50 reviews
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Andrea

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June 2026

The home is easy to get to, excellent location, beautiful views, and well thought out for large families. There were plenty of items to cook with, and more than enough beach/pool gear. Will definitely consider staying again!

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Daniel

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May 2026

Dorothy and her team did a great job. They were very accommodating getting us in a little earlier than normal check in time. Riley’s Retreat was the perfect spot for our crew. Private, with plenty of room to spread out. The swimming pool, pool table and grill areas were big hits! Incredible laundry room on top of everything else. I highly recommend this property and we will definitely be back!

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Cory

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March 2026

The host greeted us and did a full walk through for us when we arrived. They were in touch with us from when we landed until we walked into the house. The house was perfect for our group and the setup was perfect for multiple groups. We enjoyed the house for our wedding week there and it had everything we needed. They had plenty of chairs, floaties and even snorkel gear for the people who didn't bring any. The view from all of the levels was amazing! We loved it and highly recommend this property and hosts.

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Kendall

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March 2026

This is a beautiful place with everything you need. The views are amazing, and there is plenty of space to relax. The pool and hot tub were great and there is plenty of seating around for lounging outside. The location is very convenient to Cruz Bay restaurants, National Park dock, and all of the north shore beaches. Cinnamon Bay was our favorite beach to visit with the kids, and there is more parking compared to other beaches. Everything you need for a beach day is at the house which was very convenient. We rented vehicles which were great for visiting the beaches and driving over to Coral Bay. When going into Cruz Bay for dinner as a group of 12, we found it easier to just take a taxi to and from the house ($8/person each way) rather than trying to find parking for 3-4 vehicles in the busy area with very limited and expensive parking. We lost power a few times (entire island out), so the back up solar power was great. House managers were super helpful and responsive!

Know before you go

House rules

Check-in: 4:00pm

Checkout: 10:00am

Pets allowed

No smoking

No parties

Have a question about this property?

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