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Book Online or call HomeAway Booking Assistance 888-829-7076
Book Online or call HomeAway Booking Assistance 888-829-7076

Air Conditioned Deluxe Villa w/Pool in Chocolate Hole. Panoramic Ocean Views!

Bedrooms 5
Space 2,071 sq. ft.
Property type villa
Minimum Stay 5 - 7 nights


About the property

5 bedrooms, 5 bathrooms

Villa Serendipity is a beautifully appointed 5 bedroom/5 bath villa located high above Chocolate Hole Bay featuring a gorgeous full length pool and sun deck with built in swimming pool.  The pool deck also features numerous seating and lounging areas, including the unique 'surfboard bar', from to enjoy the fabulous panoramic views of Chocolate Hole and the Caribbean Sea beyond! Villa Serendipity is a deluxe vacation rental villa which is conveniently located in the upscale community of Chocolate Hole. This fabulous villa is a short 8-10 minute drive to the village of Cruz Bay where guests can enjoy an assortment of fine dining options and a vast selection of duty free shopping options. There is a nearby beach located within 5-10 minutes walk and the world famous beaches in the VI National Park are only 10-20 minutes from Cruz Bay.

Arriving at Villa Serendipity, guests will find off-street private parking adjacent to the upper level of the villa. Entry to the villa is through a privacy gate from the parking areas into the covered breezeway where you will be 'swept away' by the panoramic views of Chocolate Hole Bay, St. Thomas and the incredible Caribbean Sea. The breezeway area features a solar shower for rinsing bodies and chairs coming from the beach, a casual seating area overlooking the fantastic views, a tiled table with seating for four and breakfast bar with pass through opening to the kitchen. The gas BBQ grill is also located adjacent to the breezeway a short distance from the kitchen area.

The entrance to the main house is through a beautiful sliding glass and screen door which opens to the dramatic domed ceiling and air conditioned great room. Immediately inside the entrance is the fully equipped gourmet 'chefs' kitchen featuring stainless steel appliances and all the necessary amenities to prepare snacks to full meals. The formal dining area with elegant glass topped table has seating for up to eight and a wine cooler built into the cabinetry of the kitchen provides quick access to wine for the evening meals. The comfortable living room area offers several chairs and an overstuffed queen sleeper sofa surrounding the armoire containing a flat screen HDTV, DVD Player and eclectic DVD video library. The open and spacious design of the great room is complimented by the full wall sliding glass and screen doors which allow the breathtaking ocean views and cooling tradewinds unrestricted entry to the living spaces.

There are two bedrooms with individually controlled air conditioning systems located adjacent to the great room. Next to the living room area is a queen bedroom with en suite garden bath and large tiled, open air walk-in shower. Closer to the kitchen is a king bedroom suite with a reading alcove and en suite bath featuring a beautiful dual sink vanity and tiled, walk-in shower. A third air conditioned guest bedroom on the main level is located across the entry breezeway from the main house and features a queen sized bed, a dual sink vanity and a beautiful tiled, walk-in shower. The southwest facing wall contains a full wall sliding glass and screen door which provides a fantastic view of Chocolate Hole Bay, St. Thomas Island and the Caribbean Sea.

Descending a short stairway from the full length, wrap around deck surrounding the upper living areas will bring you to the pool deck with the inviting in-deck pool and outdoor lounge areas. There is also an umbrella covered deck table with seating for six and the unique one-of-a-kind 'Surfboard Bar' located on either end of the pool. The Surfboard Bar features an ice maker, mini-fridge, a flat screen HDTV, DVD player and audio sound system with dual docking and streaming capability. For lounging and sunbathing or lying in the shade with a good book there is an expansive side deck attached to the pool deck which offers several loungers, a unique cushioned rattan seating area and a large arching umbrella.

There are two additional bedrooms located adjacent to the pool and sun decks. The first guest bedroom is located directly off the pool deck and is a fully air conditioned bedroom suite featuring a queen size bed and a queen futon bed plus an en suite bathroom with tiled walk-in shower. There is also a wall mounted flat screen HDTV with cable service and a DVD Player. Direct access to the pool deck from this lower bedroom suite is provided through a large sliding glass doorway. The guest laundry facilities are conveniently located directly behind this bedroom in another breezeway. The fully air conditioned master bedroom suite is located adjacent to the sun deck and features a king size bed, exotic en suite bathroom with a dual sink vanity and an enormous tiled walk-in shower. Full wall sliding glass and screen doors allow panoramic views of Chocolate Hole and the Caribbean Sea as well as allowing the ever present cooling trade wind breezes to permeate this bedroom suite.

The villa and all bedrooms are fully air conditioned and there are ceiling fans throughout the villa. Free WiFi service is also available on both levels of the villa and beach chairs and coolers are provided for use at our many world class beaches.

VILLA SERENDIPITY is an ideal location for large or small family gatherings and couples vacations. It is conveniently located a short drive from Cruz Bay and all of its eclectic duty free shopping venues and varied dining options. Come 'Live the Dream' on St. John at beautiful Villa Serendipity where you can relax and enjoy the visual beauty of Chocolate Hole and the breathtaking vistas of the Caribbean Sea!

Villa Serendipity is professionally managed and maintained by a duly licensed and insured on-island Property Management Agency. Our staff are 'locals' who live on St. John year around who intimately know the island of St. John and specialize in providing unparalleled hospitality services for our guests. We are the experts on St. John and are best equipped to provide knowledgeable, up-to-date advice about all relevant activities, features and amenities which are available to enhance our guests vacation experience.

More Details

Property Manager
Cimmaron St. John
Speaks: english
Manager indicates their response time is:
Within an hour
Calendar last updated:
September 17, 2017

About Cimmaron St. John



Telephone: 340-715-2666

Fax: 340-774-1440

Guestbook comments from the manager

Stayed at villa serendipity for 8 days and found it to be a very nice home and in a very nice location. A few thoughts about the villa:

1 - The drive up to the house is interesting and would highly suggest a 4 wheel drive vehicle because the last 1/8th of a mile is pretty rough.

2 - The master bedroom of the house is located on the lower level. If you want to go between the master and the kitchen/living area you need to go outside and use the stairs. The master bedroom does not have a television.

3 - The living/kitchen area is very nice and has all of the utensils you need to cook at home.

4 - The pool area is wonderful and the view is awesome.

Overall, I would go back to this home. It is very nice.
Mar 2012
  • 1 of 2


Estate Chocolate Hole and Great Cruz Bay Villa Accommodation and Amenities

Property Type:
  • villa
  • Catering available
  • Housekeeper Included ...
  • Housekeeper Optional ...
Floor Area:
  • 2071 sq. ft.
House Rules:
  • Max. occupancy: 13
  • Minimum Age Limit for Renters ...
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Beach View
  • Near The Ocean
  • Ocean View
  • Rural
  • Water View
  • Adventure
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine
  • Free Wifi
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator
  • Stove
  • Toaster
  • Child's Highchair ...
  • Dining Room
  • 5 Bathrooms
  • Master Bedroom Bath - toilet , shower , en suite
    Pool Deck Bedroom Bath - toilet , shower , En Suite
    Breezeway Bedroom Bath - toilet , shower , en suite
    Main Queen Bedroom Bath - toilet , shower , en suite
    Main King Bedroom Bath - toilet , shower , en suite
  • 5 Bedrooms, Sleeps 13
  • Master Bedroom - 1 king , 1 twin/ single , Air Conditioned
    Pool Deck Bedroom - 2 queen , Also has a Queen sized Futon Bed en suite Air Conditioned
    Breezeway Bedroom - 1 queen , Air Conditioned
    Main Queen Bedroom - 1 queen , Air Conditioned
    Main King Bedroom - 1 king , Air Conditioned
  • One twin roll-away bed available.
  • DVD Player
  • Satellite / Cable
  • Stereo
  • Television
  • Video Library
  • Balcony
  • Deck / Patio ...
  • Lanai / Gazebo ...
  • Outdoor Grill ...
  • Water Sports Gear ...
  • 12 beach chairs
  • wheelchair inaccessible
Pool / Spa:
  • Private Pool ...
Onsite Services:
  • Concierge ...
  • Massage ...
  • Private Chef ...
  • bay/sound
  • duty free shops
  • playground ...
  • pond
  • reefs
  • restaurants
  • ruins
Leisure Activities:
  • beachcombing
  • bird watching
  • gambling casinos ...
  • horseback riding ...
  • photography
  • scenic drives
  • sight seeing
  • walking
  • whale watching ...
Local Services & Businesses:
  • ATM/bank ...
  • Babysitter ...
  • fitness center ...
  • groceries ...
  • hospital ...
  • massage therapist ...
  • medical services ...
Sports & Adventure Activities:
  • basketball court ...
  • deepsea fishing
  • fishing
  • golf ...
  • hiking
  • jet skiing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • surfing
  • swimming
  • tennis ...
  • wind-surfing
St. John is a small island approximately 4 miles wide by 9 miles long and is the home of the Virgin Islands National Park and the Coral Reef National Monument. Together these National treasures comprise more than 2/3 of the total land area and a significant amount of coastal waters surrounding St. John. Within the borders of the National Park, visitors will enjoy numerous hiking trails, visiting ruins, snorkeling and of course, sunbathing on a beautiful white sand beach. Commonly called 'The Jewel of the Caribbean' St. John boasts of its numerous world class beaches, duty free shopping venues and eclectic collection of dining options sure to satisfy the most discerning palates. Dare to 'Live the Dream' on beautiful St. John!


Wonderful! 4.8/5 -
(6 traveler reviews)

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Air Conditioned Deluxe Villa w/Pool in Chocolate Hole. Panoramic Ocean Views!
average rating of 4.8333335 based on 8 reviews
Bridgewater, MA

This villa is spectacular, can't wait to go back!

  • 5 of 5

My wife and I stayed in Villa Serendipity last week with 3 other couples and had a fabulous time on St. John. The pictures on the website are accurate, but do not do justice to how spacious the villa is, or the views from the deck over Chocolate Hole & looking west toward Cruz Bay and St. Thomas.

The great room & newly renovated kitchen provide plenty of space. The villa easily accomodated the 8 adults in our group.

As nice as it is indoors, the outdoor areas of Villa Serendipity are what makes it really special. The outdoor breakfast bar, sitting area in the breezeway, and the 2 tier deck with pool are where we spent our time when not sightseeing on St. John - the views across the water & hills cannot be beat. The location of the villa is great too, only about 10 minutes by car from the ferry in Cruz Bay, but near the end of a side road up the hillside - very private location.

Check out Villa Serendipity, you will not be disappointed. Our only regret was that we had to leave!

  • Submitted: Aug 15, 2006
  • Stayed: Jul 2006
  • Source: HomeAway
During this stay the property was under previous owner or management.
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36 5
Dillsburg, PA

Perfect for our family getaway!

  • 5 of 5

Our family of 11 had a wonderful time in the villa! It was the perfect place for us! Well-maintained and gorgeous views. I could not have asked for a better place to spend the week in St. John!

  • Submitted: Jun 25, 2017
  • Stayed: Jun 2017
  • Source: HomeAway
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0 0
Ashburn, VA

Phenomenal Week at Villa Serendipity

  • 5 of 5

Villa Serendipity was just perfect for our vacation...we were two families, 4 adults and 5 teenagers! We had visited St. John before and stayed at the Westin, but our friends had never experienced the island before and neither had our kids! Our arrival went really smoothly and we had our rental cars and our luggage transported up to the villa before we knew it! Checkout was really easy too as the management office is right by the ferry dock. We had one issue w/a circuit breaker being tripped that wasn't quite obvious and they came right over and fixed it for us when we called!

The views from the house and deck are just unreal and now that I am home, I really miss them! We had rainbows over Chocolate Hole for several mornings! The layout of the villa ensures the perfect blend of privacy but also great spaces for hanging out together! The kitchen had everything we needed to cook great meals, which we definitely did and we appreciated the coolers, floats and beach chairs that we could use while there!

Such a great location to easily get to all the beaches we wanted to visit, the hiking trails we conquered and the essential St John Market for groceries. Villa is very centrally located. We even took a tour over to the British Virgin Islands w/Stormy Petrel/Pirate's Penny one day and highly recommend them! Our friends did an afternoon sail around St. John with Kekoa, which was also a great experience! We had such a great vacation and big thanks to the owner and management company for making our rental and our stay so memorable!

  • Submitted: Aug 15, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
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0 0
Bristol, Rhode Island

Family vacation

  • 5 of 5

Family came from CA, VT, DC and RI, 7 adults, 2 infants and a 3 yr old to celebrate milestones in the family. Stay was between a 4 and 5 star. Drive up the hill was difficult in spots but the view was worth it. Great house for family coming together for vacation. Each "family unit" had their own space with bath. The master bedroom/bath appeared to be very new. Enjoyed most meals outdoors. Supermarkets were very well stocked, pricey but expected. Great weather and beaches.House was extremely clean, plenty of towels. Kitchen was well stocked with several sets of dishes, silverware including many plastic dishes and glasses for outdoor use.The property management company answered all questions in a timely manner.

  • Submitted: Jan 27, 2014
  • Stayed: Jan 2014
  • Source: HomeAway
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4 0
Raleigh, NC

Better than advertised!

  • 4 of 5

WE read all the reviews, studied hard, had choices and were very pleased we stayed at Serendipity. We wanted to rent from an owner with a property mgt company for a number of reasons-peace of mind, etc., and Crystal from Cimmaron was not only prompt at the ferry dock but had our rental car ready as well! Took just a few minutes from Courtesy Car rental(highly recommend them) to reach the villa. The villa is very convenient just 5 minutes to the main food market on the island, Starfish, and passes the Weston Hotel and garbage dump. The home is very EASY to drive to including the last 1/8 miles of where pavement has broken away, not a problem. We felt very safe with our 3 children, each staying in their own room, which helped us not to look at their lack of daily housekeeping. The kitchen had everything- great coffee maker, plastic glassware, oversize refrigerator and large dishwasher. Living area with plenty of space, dvd collection, dimmer lighting, sliding glass doors, and comfortable dining table. Outside we enjoyed 3 times the gas weber grill outside and would recommend to anyone to order Omaha Steaks ahead of time and have them shipped to the Villa saving on time and money. The pool was positioned perfectly to start receiving morning sun by 9:30am and continuous until sunset. It was refreshing and clean with plenty of pool deck. The outside bar area with stereo was just a huge addition to our experience. With an outside refrigerator, neon and led lighting and stereo we plugged our iphone into for endless hours of Pandora mix music. Many properties advertise to be in Chocolate Hole but Serendipity is about 1/3 of the way into the bay, the wind and waves were soothing sounds and welcomed 24/7! The home actually with 4 bedrooms also has an office in its own separate room with internet and printer, a 5th bathroom outside near the front load washer/dryers, and a quiet room with TV and futon could actually fold open for a person to sleep in if necessary. Lastly the view (webcam if you want to see), but we could see St. Thomas/Red Hook Bay area with the Ritz Carlton, the St. James Islands, and St. Croix on a very clear day, and Cruise Ships passing in and out of Charlotte Amalie. You would be hard pressed to find a villa or view equal anywhere - (there are some buildings at the bottom of Chocolate Hole that look vacant and are eye sores, but easily overlooked). We would stay again if wondering and hope this helps you with your decision.

  • Submitted: Apr 5, 2013
  • Stayed: Mar 2013
  • Source: HomeAway
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13 0
southold n.y.

we loved it!!!!

  • 5 of 5

we were 8 adults celebrating my best friends 60th birthday.It could not have been more comfortable for all of us. there are so many choices of seating areas you can't decide were to lounge .The views are spectacular .The downstairs bedroom is like being in a grand hotel.(only better).The kitchen was to die for .We cooked in most of the nights. The location to Cruz Bay was great, a short 10 min.ride. We also took a snorkel trip from the Weston and that is only a 5 min. car ride from the villa I look forward to returning some time with my family.

  • Submitted: Jan 21, 2008
  • Stayed: Dec 2007
  • Source: HomeAway
During this stay the property was under previous owner or management.
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33 4


Nearest Airport
13 Miles
St. Thomas Airport
Nearest Barpub
1 Miles
Westin Hotel
Nearest Ferry
2.5 Miles
Cruz Bay
Nearest Golf
9 Miles
Mahogany Run, St. Thomas
Nearest Restaurant
1 Miles
Westin Hotel
Nearest Beach
0.5 Miles
Chocolate Hole Beach
Car: recommended

Villa Serendipity in Estate Chocolate Hole is a 10-minute drive from the Cruz Bay ferry dock. For beaches and outdoor activities, you can find no better place to spend your vacation than the island of St. John! Choose from every water sport imaginable - swimming, snorkeling, diving, boating, para-sailing, windsurfing, kite surfing, kayaking, etc. Or, enjoy nature walks, hiking, tennis, mountain biking or horseback riding.

Other Activities: Recharging your batteries.

Golf: Golfing is available on the island of St. Thomas, a 20 minute ferry ride and a 20 minute cab ride. There are also additional courses on the island of St. Croix, 40 miles away via seaplane from St. Thomas.





  • Rates from $785 to $1240 per night


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