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Riley's Retreat - Spacious Villa with Private Pool

Riley's Retreat - Spacious Villa with Private Pool

Photo gallery for Riley's Retreat - Spacious Villa with Private Pool

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.
Morning coffee on the deck?  Upper deck with ocean views and hilltop breezes - Large sitting and eating area - oh those views!
Romantic dinner and dancing by the pool - with our outdoor blue tooth sound system.

View overlooking islands in Pillsbury sound, including views of the caribean islands St Thomas and even St Croix on a clear day.
Spacious and Private Villa with multiple outdoor spaces with Ocean views and Hilltop breezes.  Access Caneel Trail at the base of the property to hike in the National Park.
Colorful Ocean Sunset views

Overview of Riley's Retreat - Spacious Villa with Private Pool

Reviews
10 out of 10 Exceptional
5 bedrooms4 bathroomsSleeps 143400 sq ft

Popular amenities

  • PoolPoolPool
  • Hot TubHot TubHot Tub
  • Pet friendlyPet friendlyPet friendly
  • Outdoor SpaceOutdoor SpaceOutdoor Space
  • Air conditioningAir conditioningAir conditioning
  • KitchenKitchenKitchen

Check out the area

Map
Cruz Bay, St John
  • Popular LocationVirgin Islands National Park10 min walk
  • Popular LocationHoneymoon Beach9 min drive
  • Popular LocationTrunk Bay17 min drive

Rooms & beds

5 bedrooms (sleeps 14)

Bedroom 1

1 Queen Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 King Bed

Bedroom 5

1 Queen 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
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.

Property manager

Brian and Dorothy Pitt
Premier Host
Premier Host

Languages

English

Amenities

Pool
Hot Tub
Kitchen
Washer
Dryer
Pet friendly

House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 AM

Children

Children allowed: ages 0-17

Events

Events allowed

Pets

Pets allowed
Charge may apply

Smoking

Smoking is not permitted
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 pre...

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

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 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 by the sea. The area's natural beauty can be seen at Virgin Islands National Park and Honeymoon Beach.
Map
Cruz Bay, St John

What's nearby

  • Virgin Islands National Park - 10 min walk
  • Cruz Bay Beach - 8 min drive
  • Honeymoon Beach - 9 min drive
  • Cinnamon Bay Beach - 15 min drive
  • Trunk Bay - 17 min drive

Getting around

  • St. Thomas (SPB-St. Thomas Seaplane Base) - 59 min drive

Restaurants

  • High Tide Bar & Seafood Grill - 4 min drive
  • Cruz Bay Landing - 4 min drive
  • Beach Bar - 4 min drive
  • Lovango Rum Bar - 4 min drive
  • Tap & Still - 4 min drive

Frequently asked questions

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

Yes, pets are allowed at this 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 and Honeymoon 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.
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Rating 10 - Excellent. 11 out of 11 reviews" "
Rating 8 - Good. 0 out of 11 reviews" "
Rating 6 - Okay. 0 out of 11 reviews" "
Rating 4 - Poor. 0 out of 11 reviews" "
Rating 2 - Terrible. 0 out of 11 reviews" "

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

DEBORAH L F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise
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.
Stayed 6 nights in Mar 2024

10/10 Excellent

Laura D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Unforgettable Stay at Riley's Retreat
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.
Stayed 4 nights in Jan 2024

10/10 Excellent

Michael K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Experience
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.
Stayed 7 nights in Jan 2024

10/10 Excellent

Chris H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous Week at Riley's Retreat
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!
Stayed 6 nights in Nov 2023

10/10 Excellent

Michael W., Austin Texas

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house
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.
Stayed 4 nights in Jul 2023

About the host

Hosted by Brian and Dorothy Pitt

Host profile image
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

Premier Host
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