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Riley's Retreat + Cottage

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A two-story building with a pool, outdoor seating, and a hot tub.
A kitchen with wooden cabinets, stainless steel appliances, granite countertops, and a ceiling fan.
A rooftop pool area with lounge chairs, a hot tub, and a view of the surrounding landscape.
A cozy room with a stone wall, a wooden ceiling, a desk with a lamp, and comfortable seating.
A spacious dining area with a large wooden table set for six, surrounded by teal chairs.

Reviews

10 out of 10
Exceptional

Highlights

  • Room to gather
    Guests love the top-rated, spacious living areas.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Discover nearby landmarks
    Close to Virgin Islands National Park
6 bedrooms5 bathroomsSleeps 16

Popular amenities

  • Private pool
  • Hot tub on site
  • Garage parking available
  • Dog-friendly
  • Kitchen
  • Washing machine

Explore the area

View in a map
Cruz Bay, St. John
  • Place, Virgin Islands National Park
    ‪9 min walk‬
  • Place, Cruz Bay Beach
    ‪2 min drive‬
  • Place, Battery
    ‪2 min drive‬
  • Airport, St. Thomas (STT-Cyril E. King)
    ‪57 min drive‬

Rooms & beds

6 bedrooms (sleeps 16)

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

Bedroom 6

1 Queen Bed

Living Room 1

2 Double Sofa Beds

5 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Office
Balcony
Number of living rooms
Garden
Dining area

About this property

Riley's Retreat + Cottage

Summary:
Spacious 6 bedroom, 5 bath estate with pool, hot tub, game room and gourmet kitchen. Plenty of room for family, friends, privacy/quiet time.

Panoramic views, tranquil breezes, and colorful sunsets 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 explore! Let us host you in paradise!

Guest Access:
They will have access to the full property with the exception of the private storage in the garage and couple locked owners closets.

The Neighborhood:
The Villa is located a mile uphill from 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.

Interaction with Guests:
Our property manager is on island to show you the house, answer questions and generally be available if there is an issue. Otherwise, you will have complete privacy.

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 1 total)
Charge may apply
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Smoking

Smoking is not permitted
In the event of a hurricane you must leave the property and the island for your own safety. Travel insurance is highly recommended, especially dur...

Important information

You need to know

Property # 3894199vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

St. John

Located in St. John, this villa is in the mountains and near the beach. The area's natural beauty can be seen at Virgin Islands National Park and Cruz Bay Beach. The Virgin Islands Children's Museum and JR O’Neal Botanic Gardens are also worth visiting. Explore all the area has to offer with horse riding and rock climbing.
Map
Cruz Bay, St. John

What's nearby

  • Virgin Islands National Park - 9 min walk - 0.8 km
  • Cruz Bay Beach - 2 min drive - 1.8 km
  • Battery - 2 min drive - 1.8 km
  • St. John Spice - 2 min drive - 1.8 km
  • Mongoose Junction - 2 min drive - 2.2 km

Getting around

  • St. Thomas (STT-Cyril E. King) - 64 min drive

Restaurants

  • ‪Trunk Bay Beach Bar - ‬12 min drive
  • ‪Maho Crossroads - ‬20 min drive
  • ‪Shambles - ‬2 min drive
  • ‪Woody's Seafood Saloon - ‬3 min drive
  • ‪Cruz Bay Landing - ‬3 min drive

Frequently asked questions

Does Riley's Retreat + Cottage have a pool?

Yes, this property has a pool.

How much does it cost to stay at Riley's Retreat + Cottage?

As of 5 Sept, 2026, prices found for a 1-night stay for 2 adults at Riley's Retreat + Cottage on 11 Sept, 2026 start from S$10,068, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Riley's Retreat + Cottage pet-friendly?

Yes, this property allows dogs (limit 1 total).

How much is parking at Riley's Retreat + Cottage?

On-site parking is available at the property.

What time is check-in at Riley's Retreat + Cottage?

Check-in begins at 4:00 PM.

What time is check-out at Riley's Retreat + Cottage?

Checkout is at 10:00 AM.

Where is Riley's Retreat + Cottage located?

Situated by the sea, this villa is within 1 mi (2 km) of Virgin Islands National Park and Cruz Bay Beach. Trunk Bay is 2.6 mi (4.2 km) away.

About the host

Hosted by Brian and Dorothy Pitt

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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