Riley's Retreat - Spacious Villa with Private Pool - Estate Pastory

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Entire home

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.

Overview
Amenities
Policies
Location
Host

5 bedrooms4 bathroomsSleeps 14

Popular amenities

Pet-friendly

Outdoor space

Enjoy the area

Cruz Bay, St John

Cruz Bay Beach8 min drive
Honeymoon Beach9 min drive
Trunk Bay17 min drive

Rooms & beds

5 bedrooms (sleeps 14)

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

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

Dining Area

About this property

Riley's Retreat - Spacious Villa with Private Pool

Looking for privacy, stunning views, pool and convenience for your tropical vacation? Look no further than Riley's Retreat on the beautiful island of St. John. Located atop Caneel Hill above Cruz Bay, with stunning views of Pillsbury Sound and St Thomas.

Our Villa is a spacious 5 bedroom, 4 bath home with a 14x21 pool, 8 person hot tub, game room with pool table, and gourmet kitchen. Plenty of room for family time and privacy/quiet time.

Come enjoy - we would love to host you in paradise!

Our property manager is on Island and available to assist with questions or issues as needed during your stay. You can be greeted at the docks and escorted to the house or we can meet you at the house, give you a brief tour and get you settled in.

We recommend you rent a jeep to explore and experience the island to its fullest.
No smoking, no events or parties without prior written authorization

Property manager

Brian and Dorothy Pitt

Premier Host

Languages

English

Amenities

Pet-friendly

Outdoor space

Pool

Hot tub

Kitchen

Free WiFi

House Rules

Check in after 4:00 PM

Minimum age to rent: 24

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

Events allowed

Pets

Pets allowed

Charge may apply

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...

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

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 by the sea. The area's natural beauty can be seen at Virgin Islands National Park and Honeymoon Beach.

Cruz Bay, St John

What's nearby

Virgin Islands National Park - 10 min walk
Caneel Bay Beach - 20 min walk
Cruz Bay Beach - 8 min drive
Honeymoon Beach - 9 min drive
Trunk Bay - 17 min drive

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
Tap & Still - 4 min drive

Frequently asked questions

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 within 1 mi (2 km) of Virgin Islands National Park and Honeymoon Beach. Caneel Bay Beach and Battery are also within 1 mile (2 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

DEBORAH L F.

18 March 2024

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

Laura D.

25 January 2024

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.

13 January 2024

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

Chris H.

3 December 2023

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

Michael W., Austin Texas

27 July 2023

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

About the host

Hosted by Brian and Dorothy Pitt

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.