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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:
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.
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.
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- Ocean view
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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 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.

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 labelled.
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
Verified
21 May, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in May 2024
Verified
10/10 Excellent
Laura S.
17 Aug, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Luxury Property
Laura S.
Stayed 4 nights in Aug 2024
Verified
10/10 Excellent
Isaac G.
18 Nov, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Isaac G.
Stayed 5 nights in Nov 2025
Verified
10/10 Excellent
Todd G.
23 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome house in St John
Todd G.
Stayed 4 nights in May 2023
Verified
10/10 Excellent
Michael W.
27 Jul, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house
Michael W.
Stayed 4 nights in Jul 2023
Verified
10/10 Excellent
Chris W.
30 Jan, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
40th Birthday trip
Chris W.
Stayed 4 nights in Jan 2025
Verified
10/10 Excellent
Joseph S.
8 Jul, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Trip
Joseph S.
Stayed 7 nights in Jun 2024
Verified
10/10 Excellent
Chris H.
3 Dec, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous Week at Riley's Retreat
Chris H.
Stayed 6 nights in Nov 2023
Verified
10/10 Excellent
Chris F.
22 Dec, 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
Verified
10/10 Excellent
Gina G.
2 Jun, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything and more
Gina G.
Stayed 4 nights in May 2023
Verified
10/10 Excellent
DEBORAH L F.
18 Mar, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise
DEBORAH L F.
Stayed 6 nights in Mar 2024
Verified
10/10 Excellent
Meredith C.
28 Jan, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Villa in Paradise
Meredith C.
Stayed 4 nights in Jan 2023
Verified
10/10 Excellent
William M.
24 Jul, 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
Verified
10/10 Excellent
Laura D.
25 Jan, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Unforgettable Stay at Riley's Retreat
Laura D.
Stayed 4 nights in Jan 2024
Verified
10/10 Excellent
Michael K.
13 Jan, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Experience
Michael K.
Stayed 7 nights in Jan 2024
Verified
10/10 Excellent
Madeline S.
15 Aug, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing experience
Madeline S.
Stayed 4 nights in Aug 2022
Verified
10/10 Excellent
sergio t.
9 Aug, 2022
Liked: Cleanliness, check-in, location, listing accuracy
Wedding!
sergio t.
Stayed 5 nights in Aug 2022
Verified
10/10 Excellent
Verified traveller
18 May, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place!
Verified traveller
Stayed 9 nights in May 2022
Verified
10/10 Excellent
Meghen B.
10 Apr, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely gorgeous!
Meghen B.
Stayed 5 nights in Apr 2022
Verified
10/10 Excellent
Richard W.
31 Mar, 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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