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Riley's Retreat - Spacious Villa with Private Pool

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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.
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

Reviews

10 out of 10
Exceptional
5 bedrooms4 bathroomsSleeps 143400 sq ft

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washing machine
  • Dryer

Explore the area

View in a map
Cruz Bay, St John
  • Place, Virgin Islands National Park
    ‪11 min walk‬
  • Place, Caneel Bay Beach
    ‪16 min walk‬
  • Place, Honeymoon Beach
    ‪7 min drive‬
  • Airport, St. Thomas (STT-Cyril E. King)
    ‪55 min drive‬

Rooms & beds

5 bedrooms (sleeps 14)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 King 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
Garden
Dining area

About this property

Riley's Retreat - Spacious Villa with Private Pool

Summary:
Riley's Retreat: Your Caribbean Paradise Awaits!

Overview:
Escape to Riley's Retreat, a stunning 5-bedroom, 4-bathroom villa nestled on the serene hillside of St. John, offering panoramic views, tranquil breezes, and vibrant sunsets. This spacious haven is perfect for families and friends, blending modern amenities with the timeless charm of Old St. John.

The Space:
Immerse yourself in the luxury of Riley's Retreat, a beautifully updated villa that combines ornate stonework and custom mahogany details with contemporary conveniences. Wake up to the gentle island breeze on the expansive decks, sip tropical cocktails by the private pool, or challenge loved ones to a game of billiards in the game room. After a sun-soaked day at the beach, indulge in a gourmet dinner prepared by one of the island’s private chefs, and enjoy it on the outdoor dining terrace as the sun sets over the horizon.

Main Level:
• Open-Concept Living Area: Flooded with natural light, perfect for gatherings.
• Gourmet Kitchen: Fully equipped with modern appliances and stocked spices.
• Dining Areas: Both indoor and outdoor options to suit any mood.
• Bedrooms: Three spacious rooms with AC, ceiling fans, and comfortable beds.
o Master Suite: King-sized bed, ensuite bathroom with a stone walk-in shower, an outdoor shower and steps leading to the pool.
o Guest Bedrooms: Two rooms with queen-sized beds and ample closet space.
• Wrap-Around Porches: Offering easy access and stunning views from every angle.

Lower Level:
• Private Apartment: Two bedrooms with queen-sized beds, a full bath, and a fully equipped kitchen.
• Outdoor Deck: Furnished living and dining area for intimate gatherings.

Outdoor Amenities:
• Private Pool Area: Featuring a 14’ x 21’ in-ground pool and a 8-person hot tub.
• Clubhouse Bar: Open-air bar with a pool table and various family games.
• Underwater Mural: Guests can embark on an underwater scavenger hunt in the pool room, experiencing the many species of St. John they might encounter while snorkeling.
• Bluetooth Sound System: Enjoy your favorite music inside and around the pool.
• Laundry Room: 3 Large capacity washers, dryers, and ironing facilities for your convenience.

Guest Access:
Guests have access to the entire villa, including ample parking for up to 4 vehicles. Safari-style taxis can also easily navigate and turn around in the driveway. For the best island experience, we recommend renting a jeep, and we can assist with rental recommendations.

The Neighborhood:
Located just a mile above Cruz Bay, Riley's Retreat offers privacy and breathtaking views of the ocean and valley below. Despite its secluded feel, the villa is only minutes away from dining, dancing, and shopping. The nearest beach is just 1.5 miles away, and the Caneel hiking trail is accessible right from the base of the property.

Getting Around:
Renting a jeep is highly recommended to fully explore the island. We also have connections with reliable safari-style taxi drivers who know the property well and can accommodate large groups.

Additional Amenities:
We provide beach towels, beach chairs, coolers, beach toys, and snorkel gear for your daily excursions.

Special Services:
To make your stay even more memorable, we can help schedule and coordinate a variety of activities and services, including:
Private Chef: Indulge in gourmet meals prepared by a private chef, featuring local seafood and island flavors.
Boat Trips: Explore the surrounding waters and nearby islands.
Fishing Charters: Experience the thrill of Caribbean fishing.
Poolside Yoga: Start your day with a relaxing yoga session by the pool.
Hiking Tours: Discover the natural beauty of St. John on guided hikes.
Poolside Spa Services: Indulge in massages and other spa treatments without leaving the villa.

Interaction with Guests:
Our on-island property manager is available to assist with any questions or issues during your stay. You can be greeted at the docks and escorted to the villa or met directly at the house for a brief tour and settling in. Additional services like babysitting, grocery delivery, and tour recommendations can be arranged upon request.
Our prices include all fees. No hidden fees.

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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

Events allowed
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Pets

Pets allowed
Charge may apply
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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...

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 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 Trunk Bay and Virgin Islands National Park. Explore all the area has to offer with horse riding and mountain climbing.
View more Villas in St. JohnOpens in a new window
Map
Cruz Bay, St John

What's nearby

  • Virgin Islands National Park - 11 min walk - 1.0 km
  • Caneel Bay Beach - 16 min walk - 1.4 km
  • Cruz Bay Beach - 2 min drive - 1.6 km
  • Great Cruz Bay - 3 min drive - 1.9 km
  • Honeymoon Beach - 7 min drive - 2.4 km

Getting around

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

Restaurants

  • ‪High Tide Bar & Seafood Grill - ‬4 min drive
  • ‪Shambles - ‬3 min drive
  • ‪Cruz Bay Landing - ‬4 min drive
  • ‪Woody's Seafood Saloon - ‬4 min drive
  • ‪Greengo’s - ‬4 min drive

Frequently asked questions

Does Riley's Retreat - Spacious Villa with Private Pool have a pool?

Yes, this property has a pool.

How much does it cost to stay at Riley's Retreat - Spacious Villa with Private Pool?

As of 27 Mar 2026, prices found for a 1-night stay for 2 adults at Riley's Retreat - Spacious Villa with Private Pool on 10 Apr 2026 start from £1,181, 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 - Spacious Villa with Private Pool pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Riley's Retreat - Spacious Villa with Private Pool?

On-site parking is available at the 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?

Checkout 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 mile (2 km) of Virgin Islands National Park, Honeymoon Beach and Cruz Bay 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 labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 20 out of 20 reviews
Rating 8 - Good. 0 out of 20 reviews
Rating 6 - Okay. 0 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Kevin M.

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

Wonderful stay

I’d stay here again. Wonderful accommodations.
Stayed 5 nights in May 2024
Verified

10/10 Excellent

Laura S.

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

Luxury Property

Absolutely stunning place!
Stayed 4 nights in Aug 2024
Verified

10/10 Excellent

Isaac G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Nov 2025
Verified

10/10 Excellent

Todd G.

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

Awesome house in St John

This was a wonderful place in St John. The views and the house was amazing
Stayed 4 nights in May 2023
Verified

10/10 Excellent

Michael W.

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
Verified

10/10 Excellent

Chris W.

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

40th Birthday trip

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.
Stayed 4 nights in Jan 2025
Verified

10/10 Excellent

Joseph S.

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

Family Trip

St John is an idyllic destination. Riley’s Retreat was the perfect home base for our island experience. Well equipped and handsomely appointed with a spectacular view, having a most enjoyable pool with ideal size and cleanliness, Riley’s Retreat perfectly fit the needs of our three generational family When we encountered some difficulties with appliances, the staff did everything they could to rectify problems This was one location that my wife and I agreed that we would visit again
Stayed 7 nights in Jun 2024
Verified

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
Verified

10/10 Excellent

Chris F.

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

What a wonderful place to stay on St John!

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
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Gina G.

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

Everything and more

This property was amazing beautiful view’s very comfortable there were 8 in our group it’s spacious well stocked kitchen with everything you’ll need. Our stay here was amazing you won’t be disappointed The property manager was great very responsive. Gina G
Stayed 4 nights in May 2023
Verified

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
Verified

10/10 Excellent

Meredith C.

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

Perfect Villa in Paradise

Riley‘s retreat is an absolutely gorgeous villa with incredible views and space enough for a group of 10. Dorothy and her property managers made planning this trip and enjoying this villa absolutely seamless comfortable and easy. They are all extremely responsive and helpful. Everything you need is included. The pictures don’t even do it justice. I had a beautiful girls trip and can’t wait to go back.
Stayed 4 nights in Jan 2023
Verified

10/10 Excellent

William M.

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

A Great Property Spoiled by St. John's Power Issues

This house is a great property. It is spacious and tastefully furnished with conveniences and comforts. However, the island of St. John is experiencing troubling interruptions to their power supply that caused us to lose electricity (and therefore water) for several hours every day that we were there. This interrupted lighting, air conditioning, and bathroom access for extended periods of time for our entire abbreviated stay. A backup power supply would help, but there will still be issues with the commercial properties on the island that do not have electrical backup. It is very unfortunate.
Stayed 5 nights in Jul 2024
Verified

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
Verified

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
Verified

10/10 Excellent

Madeline S.

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

Amazing experience

We loved our stay here. We had the most amazing time. The location was easy to navigate to and from, and the property manager and coordinators were incredible. We’d happily come back again for another stay!
Stayed 4 nights in Aug 2022
Verified

10/10 Excellent

sergio t.

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

Wedding!

The property delivered all that we wanted! The view was better than expected. ! Does need a little maintenance.
Stayed 5 nights in Aug 2022
Verified

10/10 Excellent

Verified traveller

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

Great place!

Good communication with owner and property manager. Lots of space. Convenient location. Hope to return soon.
Stayed 9 nights in May 2022
Verified

10/10 Excellent

Meghen B.

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

Absolutely gorgeous!

Fantastic house. Has everything you need with an amazing host. Communication was good. House had everything and more needed for a great vacation. We were paired with a taxi driver (Ricky) during our stay who took care of everything. Any issues were immediately handled with a smile. We went to Oppenheimer beach which was fantastic. Great restaurants nearby were Lime Inn and Dave and Jerry’s. Pool and hot tub were wonderful. House is only minutes to town. I recommend a taxi driver unless you are comfortable on island roads. Bedrooms all have AC. Great for traveling with families or large groups. Can’t say enough about the property.
Stayed 5 nights in Apr 2022
Verified

10/10 Excellent

Richard W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Feb 2025

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

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