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Riley's Retreat + Cottage

Photo gallery for Riley's Retreat + Cottage

A beach with clear turquoise water, white sand, and small green islands in the distance. - Riley's Retreat + Cottage (Cruz Bay)
A spacious dining area with a large wooden table set for six, surrounded by teal chairs. - Riley's Retreat + Cottage (Cruz Bay)
A cozy room with a stone wall, a wooden ceiling, a desk with a lamp, and comfortable seating. - Riley's Retreat + Cottage (Cruz Bay)
A two-story building with a pool, outdoor seating, and a hot tub. - Riley's Retreat + Cottage (Cruz Bay)
A poolside dining area with a table set for four, surrounded by chairs, and a pool with a fence. - Riley's Retreat + Cottage (Cruz Bay)
Escape to Riley's Retreat on St John, where panoramic views and tranquil breezes greet you. Unwind in the pool or hot tub, challenge friends in the game room, or savor a meal prepared in the gourmet kitchen.

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms5 bathroomsSleeps 16

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Add dates for prices

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.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Hot tub
  • Private pool

Internet

  • Available in the villa: WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 6 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 5 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Books
  • Stereo
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the mountains
  • Near the bay
  • Near the sea

Things to do

  • Arcade/game room
  • Casino nearby
  • Horseback riding nearby
  • Rock climbing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden

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  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
8.4 out of 10, Very good, 493 reviews
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includes taxes & fees
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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 24

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

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...

Pets

Pets are allowed
Welcoming dogs only
1 total pets
Note from host: Charge may apply

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

About the area

Located in St. John, this villa is in the mountains and near the beach. Blackbeard's Castle is a notable landmark, and the area's natural beauty can be seen at Virgin Islands National Park and Trunk Bay. The Virgin Islands Children's Museum and JR O’Neal Botanic Gardens are also worth visiting. Explore all the area has to offer with rock climbing and horse riding. Visit our St. John travel guide
View more Villas in St. John
Map
Cruz Bay, St. John

What's nearby

  • A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.
    Virgin Islands National Park
    9 min walk - 0.8 km
  • A coastal town with buildings, a harbor filled with boats, and a mountainous backdrop.
    Cruz Bay Beach
    2 min drive - 1.8 km
  • St. John Spice
    2 min drive - 1.8 km
  • Battery
    2 min drive - 1.8 km
  • Great Cruz Bay
    2 min drive - 1.6 km

Getting around

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

Restaurants

  • Shambles
    2 min drive
  • The Windmill Bar
    2 min drive
  • High Tide Bar & Seafood Grill
    3 min drive
  • Woody's Seafood Saloon
    3 min drive
  • The Longboard
    3 min drive

Frequently asked questions

Does Riley's Retreat + Cottage have a pool?

Yes, this property has a pool.

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 mile (2 km) of Caneel Bay Beach, Virgin Islands National Park and Honeymoon Beach. Trunk Bay is 2.6 mi (4.2 km) away.

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Riley's Retreat + Cottage Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

Cleanliness

9.6

Location

Reviews

Verified

10/10 Excellent

Tyler R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding

The villa was beautiful and have everything from fun to relaxation. Our family and friends all stayed comfortably for a week! This vacation was perfect and my wife and I got married around the pool!
Stayed 5 nights in May 2025
Verified

10/10 Excellent

Daniel Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wow ! What a great week we had at Riley’s Retreat. 2 family’s with 11 people. So many large great entertaining areas throughout the house and a number a quiet spots if you needed a little time away. Anything you needed for large dinner parties, days at the beach and snorkeling the beautiful waters are provided at the house ! The views are spectacular from sunrise to sunset and can’t be truly reflected m pictures . Easy access to all the beaches am Cruz bay. The owners and property managers were fantastic and communicated quickly with any questions we had and even provided a Christmas Tree and decorations for us to set up and enjoy throughout the week . Will be coming back again! Thank you !
Sunrise Coffee
Sunset pool side
Sunset top deck
View of house Night time at the pool
Stayed 6 nights in Dec 2025
Verified

10/10 Excellent

Emily W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
You will not find a more welcoming host than Dorothy. At every step of the way, she made sure our stay was comfortable. The home was beautiful and had a very well appointed kitchen that our group of 12 easily prepared dinners in. The property was clean and spacious. We had a minor issue with water pressure and within a few minutes of reaching out to the house manager (Kim, who is equally amazing) was at our door to correct with ease. On the day we were to check out, countless flights were cancelled in the area and Dorothy graciously allowed us to stay an extra night in her home. New renters arrived the next day so she continued to exhibit unparalleled hospitality and found us another rental to get us through the next day. Our party of 12 couldn’t have picked a better home, and we couldn’t have asked for a better host!!! Thank you Dorothy!!!
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Christine B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Met all our expectations!

Beautiful spot tucked up outside of town but still conveniently located. The property was clean, well maintained. The management staff was attentive and helpful. We stayed with 6 couples and each of the spaces worked perfectly for our group. The pool was cleaned mid-week which was nice. Laundry on-site was perfect for towels and bathing suits. Plenty of amenities including pool floats, coolers, and beach chairs. We look forward to staying again.
Stayed 7 nights in Nov 2023
Verified

10/10 Excellent

Elaine D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

Beautiful and perfect for large family. Very responsive staff. Would stay again.
Stayed 8 nights in Jun 2023
Verified

10/10 Excellent

Bob S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic family getaway.

This property had everything we needed for our family. The rooms were spacious for our family of 11 adults. Kitchen fully stocked, a variety of areas to relax inside and outside. We enjoyed our early morning coffee on the comfy outdoor furniture soaking in the beautiful views surrounding us.
Stayed 8 nights in Apr 2023
Verified

10/10 Excellent

Ruth K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay

The view is gorgeous! Come for the view, stay for the amenities. There are fully stocked kitchens, bathrooms, and cold AC in all of the bedrooms. Lots of nice touches like ergo-mats, beach towels and chairs, spices in the cabinets, extra toilet paper, etc. The pool is great as is the hot tub, with the added fun of iguanas coming up for a visit at least once a day. The coordination and communication was excellent and our stay was wonderful -highly recommend Riley's Retreat.
Stayed 5 nights in Jul 2023
Verified

10/10 Excellent

Sarah C.

Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Paul M.

Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Joanie G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Jan 2025