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Riley's Retreat + Cottage

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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.
Come snorkel at Trunk bay, voted worlds #1 beach in travel magazine
Gorgeous sunset views from the upper deck of Riley's Retreat.

Reviews

10 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade and game room.
  • Discover nearby landmarks
    Close to Virgin Islands National Park
6 bedrooms5 bathroomsSleeps 16

Popular amenities

  • Balcony
  • Hot tub on site
  • Private pool
  • Dog-friendly
  • Toys
  • Barbecue grill

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, St. John Spice
    ‪2 min drive‬
  • Airport, St. Thomas (STT-Cyril E. King)
    ‪55 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.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
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 # 3894199
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
Onsite parties or group events are strictly prohibited
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 in the mountains and near the beach. The area's natural beauty can be seen at Trunk Bay and Virgin Islands National Park. Explore all the area has to offer with rock climbing and horse riding.
View more Villas in St. JohnOpens in a new window
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
  • 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

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

Restaurants

  • ‪Shambles - ‬2 min drive
  • ‪High Tide Bar & Seafood Grill - ‬3 min drive
  • ‪Woody's Seafood Saloon - ‬3 min drive
  • ‪The Windmill Bar - ‬2 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 Jun 18, 2026, prices found for a 1-night stay for 2 adults at Riley's Retreat + Cottage on Aug 12, 2026 start from $2,571, 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?

Onsite 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?

Check-out 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, Honeymoon Beach, and Cruz Bay Beach. Trunk Bay is 2.6 mi (4.2 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 10 out of 10 reviews
Rating 8 - Good. 0 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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
Response from VrboOwner on Dec 28, 2025
Yeah! So happy you enjoyed your Christmas at Riley’s Retreat! You were great guests and we look forward to hosting you again!
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

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

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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