Riley's Retreat - Spacious Villa with Private Pool

Top rated by guests
Privacy, gorgeous ocean views overlooking the harbour of Cruz Bay and the islands in Pillsbury Sound. Amazing 14 x 21 pool with steps, sitting ledge and deep end.  Plenty of room for gatherings with friends and family or quiet time.
Spacious open floor plan with ocean views
What's for dinner?  Plenty of space to get creative with food in the chef inspired gourmet kitchen.
Plenty of space to cook in our chef inspired gormet kitchen.
Kitchen and dining second level
review stars
10.0Outstanding
(20 Ratings)
"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 ..."
Isaac G.
Don't miss out! Price and availability may change
10.0 / 10.0
Outstanding(20 Ratings)

Villa in Cruz Bay

14 guests · 5 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this villa rental

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.

Amenities at Riley's Retreat - Spacious Villa with Private Pool

Air conditioning
Pool
Non-smoking
Pets allowed
TV
Coffee/tea maker
Refridgerator
Kitchen
Balcony/Terrace
WiFi/Internet
Private pool access
Microwave
Dishwasher
Washing machine
Dryer
Patio
Kitchenware
Garden
Oven
Stove
Laundry services
Sofa bed
Ironing facilities
Towels
Desk
Hairdryer

Map of Cruz Bay


Ratings and reviews

10.0 / 10.0
Outstanding(20 Ratings)
10.0 / 10.0Outstanding·Nov 2025
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.
10.0 / 10.0Outstanding·Jan 2025
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.
10.0 / 10.0Outstanding·Dec 2024
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
10.0 / 10.0Outstanding·Aug 2024
Absolutely stunning place!

$$$$
vrbo logo

FAQs

Is parking included with this villa?

Parking is not specified as an available amenity at Riley's Retreat - Spacious Villa with Private Pool. For more information, we encourage you to contact the property about where to park.

Is there a pool at this villa?

Yes, a swimming pool is available for use at Riley's Retreat - Spacious Villa with Private Pool. Enjoy the water!

Is Riley's Retreat - Spacious Villa with Private Pool pet friendly?

Yes! This villa is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Riley's Retreat - Spacious Villa with Private Pool?

We found 26 amenities for this rental. This includes air conditioning, pool, non-smoking, pets allowed, and tv.


Explore similar stays in Cruz Bay

Explore all stays