See all properties
Entire home·Private host

Riley's Retreat - Spacious Villa with Private Pool

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

Beach nearby
Pool
Property grounds
TV, books, stereo, offices
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 14316 sq m

Popular amenities

  • Parking available
  • Pet-friendly
  • Pool
  • Dryer
  • Washer

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

Property manager

Brian and Dorothy Pitt

Languages

English

Add dates for prices

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Hot tub
  • Private pool

Internet

  • Available in the villa: WiFi

Parking and transport

  • Parking on site

Kitchen

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

Bedrooms

  • 5 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 4 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

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

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the mountains
  • Near the sea

Things to do

  • Arcade/game room
  • Casino nearby
  • Horseback riding nearby
  • Mountain 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

  • At least 10% of profits reinvested in community and sustainability
  • At least 80% lighting from LEDs
  • Cleaning products are eco-friendly
  • Energy-saving switches in guestrooms
  • Garden
  • Local artist showcase
  • Locally-owned and organised tours and activities
  • Solar energy
  • Unit size: 3,400 square feet
  • Water-efficient showers

Similar properties

5 bedrooms, WiFi, bed sheets

Sapphire Breeze, Majestic Views & Island Vibes w/ Infinity Pool, Waterfall & Covered Porches

  • Sea view
  • Pool
  • Kitchen
  • Washer
9.6 out of 10, Exceptional, 15 reviews
Sapphire Breeze, Majestic Views & Island Vibes w/ Infinity Pool, Waterfall & Covered Porches

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

Pets

Pets are allowed
Note from host: Charge may apply

Children and extra beds

Children are welcome

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
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

Property is also known as

65dcf3d26da3560012b666eb

About the area

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
  • Honeymoon Beach - 7 min drive - 2.4 km
  • Trunk Bay - 13 min drive - 6.3 km

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
  • ‪The Windmill Bar - ‬3 min drive

Frequently asked questions

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

Yes, this property has a pool.

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?

Checkout is at 10:00 AM.

Where is Riley's Retreat - Spacious Villa with Private Pool located?

Situated by the sea, this villa is 0.5 mi (0.8 km) from Virgin Islands National Park and 3 mi (4.8 km) from Trunk Bay. Caneel Bay Beach and Honeymoon Beach are also within 1 mile (2 km).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Riley's Retreat - Spacious Villa with Private Pool Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 19 out of 19 reviews
Rating 8 - Good. 0 out of 19 reviews
Rating 6 - Okay. 0 out of 19 reviews
Rating 4 - Poor. 0 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

10/10

Cleanliness

Reviews

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

10/10 Excellent

Laura S.

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

Luxury Property

Absolutely stunning place!
Stayed 4 nights in Aug 2024

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

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

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

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

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

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

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

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

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

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

Richard W.

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

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

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

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

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

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