Entire home
Riley's Retreat - Spacious Villa with Private Pool
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Reviews
10 out of 10
Exceptional
5 bedrooms4 bathroomsSleeps 143400 sq ft
Popular amenities
Explore the area

Cruz Bay, St John
- Place, Virgin Islands National Park11 min walk
- Place, Caneel Bay Beach16 min walk
- Place, Honeymoon Beach7 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:
The Villa is a spacious 5 bedroom, 4 bath home with pool, hot tub, game room & gourmet kitchen. Plenty of room for friends & family &privacy/quiet time.
Panoramic views, tranquil breezes, & colorful sunsets are a few of the perks that 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 let us host you in paradise!
The Space:
Riley's Retreat is a bright and beautiful, newly updated villa that retains all the charm of Old St. John with ornate stonework and custom mahogany details, while also providing the modern conveniences you would expect from a vacation home. Enjoy morning coffee on the breezy decks, tropical cocktails by the pool in the afternoon. Challenge friends and family to a billiards tournament in the game room after a sunny beach day, or relish in a slow dance at the water’s edge while one of the island’s private chefs prepares a local seafood dinner. If you're lucky, the resident iguanas will join you for a starfruit snack in the groves surrounding the property. A beautiful sunset over the isles awaits every night, followed by a canopy of a million stars to gaze.
The two-level design of this spacious home offers plenty of room to gather, yet it also includes private areas for you to relax and enjoy some alone time. The upper living area is an open concept to capitalize on the natural light. Complete with a gourmet kitchen and furnished indoor and outdoor dining areas, the space is meant to accommodate large groups and families. There are three spacious bedrooms upstairs and 2 full bathrooms. Each bedroom has an AC unit with individual temperature controls and ceiling fans. The Master has a king-sized bed, private ensuite bathroom with a stone walk in shower. From the bathroom, you can walk out to the outdoor shower and down private steps to the pool area. There are 2 more large guest bedrooms, with new queen-sized beds and full closet. From any room, enjoy the peaceful sounds of tree frogs floating on the soft breezes to lull you to sleep at night. Wrap-around porches make it easy to navigate and explore the property from every angle.
The lower level is equally well designed and newly refurnished as its own apartment, with 2 bedrooms, both with queen-sized beds, 1 full bath and a fully equipped kitchen. The outdoor deck has a fully furnished living and dining area as well.
The pool area is very private and features an in-ground 14’ x 21’ pool and 6-person hot tub. There is a club house bar area with a pool table, ‘open air’ bar and many family games, where guests can enjoy snacks, cold beverages and a little competition. There is also a full bathroom with shower. A Bluetooth sound system is also wired inside and around the pool, so you can enjoy your playlist anywhere.
The laundry room on-site is equipped with large capacity washers and dryers, clothing iron and steamer, for your convenience.
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. Other convenient accommodations can also be arranged, to ensure your stay is stress free. Babysitting, grocery delivery, taxi services, and tour recommendations can all be arranged, don’t hesitate to ask!
Guest Access:
There is plenty of parking in the driveway to accomodate 4 vehicles and space for safari style taxis to access and turn around. We highly recommend you rent a jeep to experience all that the island of St John has to offer. We can also recommend several great safari style taxis that can accomodate large parties.
The Neighborhood:
The Villa is located a mile above 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.
Other Things to Note:
We have plenty of beach chairs and coolers to take with you when you explore St John's stunning beaches. Beach toys and snorkel gear are also available.
Interaction with Guests:
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.
The Villa is a spacious 5 bedroom, 4 bath home with pool, hot tub, game room & gourmet kitchen. Plenty of room for friends & family &privacy/quiet time.
Panoramic views, tranquil breezes, & colorful sunsets are a few of the perks that 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 let us host you in paradise!
The Space:
Riley's Retreat is a bright and beautiful, newly updated villa that retains all the charm of Old St. John with ornate stonework and custom mahogany details, while also providing the modern conveniences you would expect from a vacation home. Enjoy morning coffee on the breezy decks, tropical cocktails by the pool in the afternoon. Challenge friends and family to a billiards tournament in the game room after a sunny beach day, or relish in a slow dance at the water’s edge while one of the island’s private chefs prepares a local seafood dinner. If you're lucky, the resident iguanas will join you for a starfruit snack in the groves surrounding the property. A beautiful sunset over the isles awaits every night, followed by a canopy of a million stars to gaze.
The two-level design of this spacious home offers plenty of room to gather, yet it also includes private areas for you to relax and enjoy some alone time. The upper living area is an open concept to capitalize on the natural light. Complete with a gourmet kitchen and furnished indoor and outdoor dining areas, the space is meant to accommodate large groups and families. There are three spacious bedrooms upstairs and 2 full bathrooms. Each bedroom has an AC unit with individual temperature controls and ceiling fans. The Master has a king-sized bed, private ensuite bathroom with a stone walk in shower. From the bathroom, you can walk out to the outdoor shower and down private steps to the pool area. There are 2 more large guest bedrooms, with new queen-sized beds and full closet. From any room, enjoy the peaceful sounds of tree frogs floating on the soft breezes to lull you to sleep at night. Wrap-around porches make it easy to navigate and explore the property from every angle.
The lower level is equally well designed and newly refurnished as its own apartment, with 2 bedrooms, both with queen-sized beds, 1 full bath and a fully equipped kitchen. The outdoor deck has a fully furnished living and dining area as well.
The pool area is very private and features an in-ground 14’ x 21’ pool and 6-person hot tub. There is a club house bar area with a pool table, ‘open air’ bar and many family games, where guests can enjoy snacks, cold beverages and a little competition. There is also a full bathroom with shower. A Bluetooth sound system is also wired inside and around the pool, so you can enjoy your playlist anywhere.
The laundry room on-site is equipped with large capacity washers and dryers, clothing iron and steamer, for your convenience.
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. Other convenient accommodations can also be arranged, to ensure your stay is stress free. Babysitting, grocery delivery, taxi services, and tour recommendations can all be arranged, don’t hesitate to ask!
Guest Access:
There is plenty of parking in the driveway to accomodate 4 vehicles and space for safari style taxis to access and turn around. We highly recommend you rent a jeep to experience all that the island of St John has to offer. We can also recommend several great safari style taxis that can accomodate large parties.
The Neighborhood:
The Villa is located a mile above 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.
Other Things to Note:
We have plenty of beach chairs and coolers to take with you when you explore St John's stunning beaches. Beach toys and snorkel gear are also available.
Interaction with Guests:
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.
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Pool
Hot Tub
Kitchen
Washer
Dryer
Pet friendly
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10.0 out of 10, Exceptional, (68 reviews)
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
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 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 horse riding and mountain climbing.

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
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
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window9.8/10
Cleanliness
10/10
Check-in
9.8/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
May 21, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in May 2024
10/10 Excellent
Isaac G.
Nov 18, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Isaac G.
Stayed 5 nights in Nov 2025
10/10 Excellent
Laura S.
Aug 17, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Luxury Property
Laura S.
Stayed 4 nights in Aug 2024
10/10 Excellent
Todd G.
May 23, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome house in St John
Todd G.
Stayed 4 nights in May 2023
10/10 Excellent
Chris W.
Jan 30, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
40th Birthday trip
Chris W.
Stayed 4 nights in Jan 2025
10/10 Excellent
Michael W.
Jul 27, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house
Michael W.
Stayed 4 nights in Jul 2023
10/10 Excellent
Joseph S.
Jul 8, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Trip
Joseph S.
Stayed 7 nights in Jun 2024
10/10 Excellent
Chris H.
Dec 3, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous Week at Riley's Retreat
Chris H.
Stayed 6 nights in Nov 2023
10/10 Excellent
Chris F.
Dec 22, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
What a wonderful place to stay on St John!
Chris F.
Stayed 7 nights in Dec 2024
10/10 Excellent
Gina G.
Jun 2, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything and more
Gina G.
Stayed 4 nights in May 2023
10/10 Excellent
DEBORAH L F.
Mar 18, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise
DEBORAH L F.
Stayed 6 nights in Mar 2024
10/10 Excellent
Meredith C.
Jan 28, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Villa in Paradise
Meredith C.
Stayed 4 nights in Jan 2023
10/10 Excellent
William M.
Jul 24, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
A Great Property Spoiled by St. John's Power Issues
William M.
Stayed 5 nights in Jul 2024
10/10 Excellent
Laura D.
Jan 25, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Unforgettable Stay at Riley's Retreat
Laura D.
Stayed 4 nights in Jan 2024
10/10 Excellent
Michael K.
Jan 13, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Experience
Michael K.
Stayed 7 nights in Jan 2024
10/10 Excellent
Madeline S.
Aug 15, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing experience
Madeline S.
Stayed 4 nights in Aug 2022
10/10 Excellent
sergio t.
Aug 9, 2022
Liked: Cleanliness, check-in, location, listing accuracy
Wedding!
sergio t.
Stayed 5 nights in Aug 2022
10/10 Excellent
Verified traveler
May 18, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place!
Verified traveler
Stayed 9 nights in May 2022
10/10 Excellent
Meghen B.
Apr 10, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely gorgeous!
Meghen B.
Stayed 5 nights in Apr 2022
10/10 Excellent
Richard W.
Mar 31, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Richard W.
Stayed 7 nights in Feb 2025
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.
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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