Reefside Villa

Chocolate Hole Harbor

  • Reefside Villa – viewed from your pool

  • The view from the deck off the living room

  • The deck off the livingroom overlooking your inviting pool. Is it time for a swim?

  • Two paths diverged, I took the one to the beach. And that made all the difference

  • Reefside Villa

  • Reefside Villa viewed from the beach

  • Imagine yourself
    relaxing by your
    private pool

  • The living room, looking out at the harbor

  • Looking into the living room

  • This is an elegant setting for formal dinners

  • Enjoy morning coffee or an evening dinner on your outside table

  • Relax on the deck outside the dining room

  • This view shows only half of the kitchen

  • A comfortable and private workplace

  • The upper left bedroom

  • The upper right bedroom

  • The view from the upper bedrooms

  • The master bedroom

  • Another view of the master bedroom

  • The poolside bedroom in the main house

  • The poolside cabana bedroom

  • This photo shows the poolside cabana bedroom (in the middle of the photo) and the main house poolside bedroom on the right

  • A path has been cleared for easy access to snorkeling


Reefside Villa is a spacious and elegant multi level villa where all the bedrooms are on different levels from the living areas, thereby providing a very distinct sense of privacy for multiple guests. Another design feature that differentiates Reefside Villa is that each living space is in a distinct room with its own individual style and personality, unlike most island homes where the living spaces are combined into a great room. To enter Reefside Villa, you park on the upper (3rd) level and enter through a gated entrance. A well landscaped walkway leads past the two upper level bedrooms and down to the main (2nd) level, which contains the living room dining room, the kitchen and a 500 sq/ft covered deck that runs the length of the living and dining rooms. A private exterior stairway located off the living and dining rooms leads up the master bedroom, located on the 3rd level in a very private setting above the kitchen. From the living areas on the 2nd level, exterior stairs lead down a half level to the poolside cabana bedroom and then down another half level to the main house bedroom and the handsome office. The oversized pool and spacious sun deck are three steps below the main house bedroom and the office. The path to the beach is accessed from the pool deck and it is an easy walk to the man made private beach that offers very good sunning, swimming and snorkeling.


  • Bedrooms: 5
  • Beds: 5
  • Bed Description: 5 kings
  • Bathrooms: 5.5
  • Property Location: Chocolate Hole Harbor
  • Proximity: Waterfront
  • Property Size: 7600+ sq. ft.
  • Year Property Complete: 1999
  • Beach: Chocolate Hole Harbor
  • Pool: Yes
  • Pool Dimensions: N/A
  • Hot Tub: No
  • Air Conditioning: Yes, all rooms
  • Children: Welcome
  • Wifi: Yes
  • Housekeeping: No
  • Ipod Connectivity: Yes
  • Damage Deposit: $50 non-refundable damage waiver
  • Distance To Town: It's a 5-6 minute drive in to the shops, restaurants and grocery stores in Cruz Bay.
  • Living And Dining: Terra cotta tiled floors, a 17 foot beamed cathedral ceiling and gorgeous arched mahogany doors and windows create a classic Caribbean ambiance in the rich living room. This traditional setting is enhanced by handsome and comfortable mahogany cushioned furniture, and artifacts and works of art from around the world, with an emphasis on Africa art. The living room includes comfortable seating for 10, a 36” Sony satellite TV/DVD with four speaker surround sound, high speed DSL internet and an iPod dock.

    The centerpiece of the formal dining room is an elegant chandelier and a mahogany table that seats 8 – 10 persons on cushioned chairs. There is a built in bar with a mini fridge and arched mahogany doors open to a covered deck that runs the length of the dining room. A gas barbeque grill is outside the dining room.
  • Kitchen: This chef’s kitchen combines both beauty and functionality. Black polished granite countertops, mahogany cabinets and terra cotta tiled floors provide the beauty. The functionality is provided by a 6-burner gas range with griddle in the middle and double ovens and hood, side by side s/s refrigerator, dishwasher, microwave, double sink, blender, toaster, coffeemaker, food processor and an island/bar that seats four.

    Office: The 300 sq/ft air conditioned office is on the pool level and is the finest home office we have seen in an island rental home. It includes a large mahogany desk and comfortable seating for six, plus a copier/fax machine and telephone. Definitely a great place to work and you’re just steps from the pool.
  • Bedroom Details: All five bedrooms are private and quiet because each is located in a separate building. All the bedrooms have king beds and air conditioning, and each includes a tasteful, and distinctive décor, and all include terra cotta tiled floors, a TV/DVD and a handsome bathroom with mahogany cabinets and marble tiles accented by antique brick. The two upper level guest bedrooms are on the third (uppermost) level and are separated by a tiled breakfast patio. Both are oversized (260 sq/ft) with a 15 ft beamed cathedral ceiling and a small balcony with harbor views. The very private master bedroom is also on the 3rd level, but you must enter the main house to access the master. The master bedroom is also larger than the guest bedrooms and naturally it has the best views. The pool cabana bedroom is located in a separate building (cabana) a half level above the pool. It also has a beamed cathedral ceiling and a small balcony. The fourth bedroom is the largest of all the guest bedrooms and is located 3 steps above the pool deck on the ground level of the main house.


Reefside Villa is located on a lushly landscaped waterfront lot on Chocolate Hole Harbor, on the same side of the harbor as its neighbor, Ciellodonna. Reefside Villa occupies a one plus acre lot and has a very unique feature; a sand beach. This is a peaceful and seemingly away-from-it-all location where the mature landscaping and large lot offers great privacy, peace and quiet. A private path (a very easy 1-2 minute walk) leads to good snorkeling, swimming and kayaking in the calm 82 degree waters of Chocolate Hole Harbor. Your view looks to the east- southeast with sailboats floating peacefully in the harbor. This is a sun lover’s villa with sun on your spacious pool deck most of the day. It’s an easy 5 minute drive into Cruz Bay, and the spa, restaurants and beach at the Westin Resort are a 10 minute walk or a 2 minute drive.

Additional Information

All Payments are non-refundable

This villa has a $50 non-refundable security deposit waiver which covers up to the first $500 in accidental damage. Damage must be reported to the local office while you are on island, otherwise it will not be covered.

There is a $55 check-in fee for all arrivals on 9pm to midnight boat.

Vehicle Information: A 4 Wheel Drive vehicle is needed for travel on St John

Rates, Printing Errors, Changes and Omissions: Caribbean Villas is not responsible for printing errors and inadvertent omissions. All rates and villa details are subject to change without prior notice.

PHONE SERVICE/CELL PHONES: Local phone service is interrupted regularly and in spite of our efforts to reinstate service it can some times take weeks. AT&T is the only cell service we find operates efficiently on the island. If you do not have AT&T we strongly suggest you bring a pay as you go AT&T cell phone with you as we do not provide cell phones should the local phone service be interrupted.

Internet Service: The internet service is subject to frequent interruption. We cannot guarantee internet quality or speed. Renters might find it convenient to travel with a cellular carrier MiFi – a couple of examples are AT&T and Virgin Mobile. There will be no refunds due to the internet not working.

Pool Floats: Pool floats are not guaranteed with your villa rental. If you want access to them, please bring them with you.

Privacy Policy: All photos are the property of Caribbean Villas and Resorts Management Company (unless otherwise indicated) and may not be reproduced or used for commercial purposes without the express written consent of Caribbean Villas and Resorts.


Reservation Policies

Caribbean Villas Reservation Policies for: Reefside Villa, La Bella Vita, Colibri, Francis Bay Estates, Sunset Beach, Vista Caribe and Terrahawk. After making your villa/condo reservation with us, you have 7 days to send us your rental deposit. Your sending us your payment constitutes your acceptance and agreement to these terms, conditions, limitations and restrictions as printed below. If you have any problems or questions with any of the following, please phone us for discussion and explanation before you send us your rental deposit monies.

PAYMENT: Caribbean Villas requires 50% down within 7 days of making your reservation. Payments are by check only. Failure to make this payment subjects your reservation to automatic cancellation. The balance of your reservation including tax/service charge, and security deposit where applicable; is due 60 days prior to arrival. Please make checks payable to Caribbean Villas and mail them to Caribbean Villas, 89 Mussey Rd, Suite 103, Scarborough, ME 04074. All cancellations and any requests for changes to your reservation (such as date changes or changes in the number of persons) must be made IN WRITING. Rates are based on Cash Prices – To pay with a visa/mastercard there is a 3% service fee.

CANCELLATION POLICIES: All payments for the following homes are NON-REFUNDABLE/NON-CHANGEABLE: Reefside Villa, Vista Caribe, Francis Bay Estates, La Bella Vita, Sunset Beach and Terrahawk.

TRIP CANCELLATION INSURANCE:  If you do not have a source for cancellation insurance there is a web site with suggestions and reviews –Consumer Advocates – Trip Cancellation Insurance.   Please verify all terms and conditions of coverage with the trip cancellation insurance company.  It is the guests responsibility to cover themselves in the event they need to cancel or change their vacation plans.

PASSPORT REQUIREMENTS: If you are a U.S. Citizen traveling to the U.S. Virgin Islands (St Thomas, St John, St Croix) you will need Proof of Citizenship; this is a Photo ID and a birth certificate with a raised seal (photo copies are not allowed). For further information: If you are traveling to the U.S. Virgin Islands and are planning to do any day trips/day sails to the British Virgin Islands or any other Caribbean country you will need a valid passport.

HURRICANE CANCELLATIONS: Hurricane season is from June 1-November 30. Caribbean Villas highly recommends you purchase trip cancellation insurance. This insurance will cover you in case of a natural disaster (please verify all terms and conditions with the insurance company). In the unlikely event that we should experience a hurricane this season, there are several things you should know:
1. WE DO NOT ALLOW GUESTS TO REMAIN IN OUR VILLAS DURING HURRICANES! We will be available to make recommendations for hotel accommodation on St. Thomas or St. John which will have generators and running water.
2. In the case of a hurricane while you are on island you will not receive a refund of your rental and hotel tax from the day you vacate the villa. We highly recommend that you purchase trip cancellation insurance to cover other canceled expenses. Check with your travel professional or contact a provider for more information.
3. If predictions indicate a hurricane is headed our way and there is enough warning time you need to make every effort to fly out of St. Thomas before the storm is upon us. Delaying your departure plans may trap you on the island when no space is available on departing flights and after the storm you can expect to wait several days before normal airline travel is restored.
4. The Catered To staff will be monitoring the storm’s progress. If we feel strongly that we may be in the path of an approaching hurricane, we will notify you and advise you to fly off the island or to check into a St. Thomas hotel that is equipped with an emergency generator for the duration of the storm.
5. IMPORTANT: Once you make plans for a hotel or to leave the island, you MUST contact Catered To to let us know where you are and what you’re doing … we must keep track of all of our guests! Kindly make sure you call and speak with us before you depart.
6. The Catered To staff will try and assist you with advice but all guests must hurry to make their own airline or hotel reservations. In this emergency situation we will be busy supervising the shuttering and closing of all of our villas, office and preparing our own families and homes for the oncoming storm. We will appreciate your understanding and your full and willing cooperation to help yourselves under these circumstances.
7. Your villa will be shuttered up, electricity and gas will be turned off-island wide. Telephone and cable service will most likely be down also. All items from the patios and decks: furniture, grill, pool equipment, etc., will be put in your villa. There will be neither running water nor flushing toilets. Your villa will no longer be luxurious or even comfortable. Our government will impose a curfew for the day of and sometimes days after a hurricane so you will not be able to leave the property and, of course, the weather will be terrible!

In an extreme situation where there is insufficient time for you to leave the island please come by the Catered To office and we will give you a list of items you should have. This will include a flashlight and batteries, a battery operated radio, and storm preparation instructions in the unlikely situation that you must ride out the storm in one of our rental villas. YOU MUST COME TO THE OFFICE TO PICK UP YOUR HURRICANE LIST.

The Weather Channel (Channel 45) broadcasts a tropical report every hour at 48 minutes past the hour. This source and other information sources have, in the past, given us ample warning of the approach of a storm that will affect the Virgin Islands. When cable and/or TV go out, listen on FM to Isle 95 at 95.1 or on AM to WSTA Lucky 13 at 1340. HOTEL TAX: If traveling to St. John, a 12.5% hotel tax will be added to your reservation. If the hotel tax increases all reservations are subject to this increase.

DAMAGE (security) Waiver: We require a $50 non-refundable Security Deposit Waiver fee for all reservations. This Peace of Mind fee is in lieu of a damage deposit and covers all minor accidental damage or breakage up to $500. If damage occurs during your stay, please let us know immediately and it will be paid for by Catered To Vacation Homes. This privilege is offered to you as our way of saying thank you for your business. This policy does not cover intentional acts that results in damage, gross negligence, willful and wanton conduct, or any cause if the guest fails to report the damage to Catered To Vacation Homes before departure. Coverage does not apply to theft or damage of any property owned by or brought onto the premises by a guest. In cases of abuse and malicious damage to rental property the guest will reimburse Agent and/or Owner the amount of all damage including attorney’s fees.

LIABILITY: Caribbean Villas/Catered To, is acting hereunder as an agent for accommodations, and assumes no liability for property loss or damages, nor liability for injury, accident, delay, or irregularity which may be occasioned either by reason of defect in any vehicle or the acts of any company or persons engaged in conveying passengers to or from their villa. Transportation (airlines, ferries, charter vessels, rental cars and taxis) is supplied by providers who operate independently of Caribbean Villas. We assume no responsibility, therefore, for any loss, injury, or damage to person or property because of the acts of those providers. Furthermore, Guests are responsible for their villa during occupancy, and must lock villa windows and doors securely at all times when not on the premises, and must observe all cautions as given in our blue guest book and/or by your local contact. All Caribbean Villa’s/Catered To properties are privately owned. The Owner and Caribbean Villas/Catered To reserve the right to refuse service to anyone at their complete discretion. Any and all disputes will be subject to jurisdiction only in the USVI.

INDEMNIFICATION/HOLD HARMLESS: The tenant and guests agree to defend, indemnify and hold harmless Caribbean Villas/Catered To Vacation Homes and represented property owners from and against all claims, demands, loss, liability of any kind and character, including cost of defense, arising out of or in any way connected with the tenant’s use of the property: in the event tenants or guests suffer personal/physical/property damage, injury, or loss. Caribbean Villas/Catered To Vacation Homes and property owners are not responsible for lost or stolen items or physical security. The duty to defend arises when the claim or demand is first made and is not waived by a delayed tender of defense.
You agree to indemnify, defend, and hold harmless Caribbean Villas/Catered To Vacation Homes and its directors, employees, sponsors, licensors, independent contractors, providers, subsidiaries and affiliates (collectively, the “Indemnified”), from and against any and all liability costs (including attorney’s fees and costs) incurred by the Indemnified in connection with any claim arising out of any breach by you of any provision of this User Agreement.
You agree to cooperate as fully as reasonably required in defense of any such claims. Caribbean Villas/Catered To Vacation Homes reserves the right, at its own expense, to assume the exclusive defense and control of any matter otherwise subject to indemnification by you and you shall not in any event settle any claim without the written consent of Caribbean Villas/Catered To Vacation Homes.

LEGAL RECOURSE – Any dispute arising out of these rental terms shall be construed and interpreted in accordance with the laws of the Territory of the US Virgin Islands without resort to the conflicts or choice of law principles thereof. The Courts of the United States Virgin Islands, Division of St. Thomas and St. John, shall be the exclusive venue for all judicial disputes and the prevailing party shall recover its costs, expenses and reasonable attorneys’ fees. Your sending a signed rental form and payment in response to an invoice constitutes your acceptance and agreement to these terms, conditions, limitations and restrictions as printed upon the signed rental agreement.

CHECK-IN TIME: St. John-3:00pm forward. This allows the house-keepers to complete their cleaning duties.

CHECK-OUT TIME: 10 AM is the required check-out time. Late checkouts are not available. If there are guests arriving that day the housekeeper will be there at 9 AM to begin cleaning. If the property is not vacated by 10 am, Catered To Vacation Homes is authorized to remove Guest belongings from the property at the guest’s expense. The minimum charge of $60 will be charged to the credit card on file.

ARRIVALS: For St. John there is one complimentary arrival that brings the arriving guests to the car rental to pick up their reserved vehicle and then escorts the party to their villa. For 9 pm – Midnight arrivals there is a $55 check-in fee. You may schedule additional arrivals as needed for $75 per arrival. There is a $100 check-in fee for arrivals on a holiday.

MAID SERVICE: Our homes/condos do not include maid service. Maid Service may be arranged at an additional cost. Towels, linens, beach towels and paper products are provided for your stay. Any additional supplies will need to be purchased by the guest.

CABLE/SATELLITE TELEVISION: For St. John, most of the homes have expanded cable, with a few exceptions. Occasionally there is a problem with the cable television service. Caribbean Villas does not have any control over the cable service and repairs are currently taking between 8-14 days to complete.

PHONE SERVICE: All long distance phone calls are restricted. We ask all guests to use a calling card to make long distance phone calls. Local calls are free. Occasionally there is a problem with the telephone lines for the villa and condo rentals. Caribbean Villas does not have any control over the telephone company and repairs are currently taking up to 30 days to complete. Rapture and Kalorama only have cell phone service.

CELL PHONE USAGE ALONG THE NORTH SHORE: If you use your cell phone on the north side of the island there is a good chance you will pick up the cell tower on Tortola (British Virgin Islands). If this happens you will be charged for an international call on your cell phone plan.

NO PETS: Pets are NOT allowed in Caribbean Villas/Catered To properties. A pet or evidence of a pet found on premises will cause immediate eviction and forfeiture of Guest’s entire rent and deposit.

COMPLAINTS AND MAINTENANCE: Caribbean Villas/Catered To shall make every effort to keep all villas and their inventories in good working order. In case of a maintenance problem, they will strive to repair the problem as soon as possible after being notified. However, NO refund or rate adjustment shall be made for unforeseen mechanical failures such as the supply of electricity, telephone service, water, pool filtration systems, hot tubs, air-conditioning, television, internet service or cable service, appliances, etc. It is the Guest’s obligation to report any problems or damage to their villa IMMEDIATELY to us. No refunds will be considered unless problems are reported and reviewed by our Staff during your stay on island.

ENTRY INTO VILLA: Caribbean Villas/Catered To or its staff may enter your villa to perform any repairs as necessary. If your villa is on the market for sale, we reserve the right to allow the villa to be shown, but only by advance appointment made with Guests. We will make every effort to schedule such brief showings at a time convenient to you, to respect your privacy, and not interrupt your stay.

SUBSTITUTION: Caribbean Villas/Catered To reserves the right to substitute comparable or better accommodations without liability, should the villa reserved be sold, be out of order or be deemed substandard by us for any reason. If comparable accommodations are not available, Guest may receive a complete refund of all pro-rated rent and Hotel Tax paid for the original villa.

DRUGS AND HAZARDOUS MATERIALS: Guest and members of his party shall not use or permit to be brought into any villa any illegal substances, inflammable fluids (e.g., gasoline, kerosene, naphtha or benzene), or other explosives or articles deemed hazardous to life, limb or property.

VILLA, SAFE AND GATE KEYS: Caribbean villas/Catered To shall charge Guest $175 for each set of lost or mishandled keys; gate remote controls will be charged at replacement cost. Guest is required to follow all instructions precisely on where to leave your villa keys and gate remote controls when you depart—call if you are unsure!

CAPACITY OF VILLAS: The total number of persons allowed in the villa at any one time is restricted to the number of persons scheduled and paid for, based on two persons per bedroom. Should a group misrepresent themselves, they will be required to pay for the excess immediately, or shall vacate the villa without refund. Gatherings/Meetings: No groups larger than those renting a house are allowed in our villas without written permission. Additional fees may apply.

QUIET ENJOYMENT AND PARTIES: Caribbean Villas/Catered To wishes to maintain a family atmosphere for the quiet enjoyment of Guests. We rent to family groups and responsible adults only; absolutely NO house parties or functions such as weddings are allowed at the villas. Guests shall be sufficiently quiet and peaceful, so as not to disturb other residents of the neighborhood.

RATES AND PRINTING ERRORS: Caribbean Villas/Catered To is not responsible for printing errors and inadvertent omissions. All rates and villa details are subject to change without prior notice.

CONSTRUCTION NOISE: Due to the amount of new villa construction on St. John, it is a possibility that construction may occur near your villa rental. Any construction and the possibility of new construction is outside the control of Caribbean Villas.

SMOKING: All Villas are non-smoking. Guests may be fined up to $150 for smoking violations.

CONSERVING ELECTRICITY: Due to the cost of electricity, the air-conditioning in our villas/condos will not be turned on when you are checked in to your property. At check-in, our staff will be happy to show you how to turn the systems on and off, should you decide to use the air-conditioning. We are requesting that you turn the air-conditioning off in all rooms when not at the villa. It does not take long to cool a room down when you return to the villa. We understand this is your vacation and we want it to be enjoyable and relaxing. Anything you are willing to do will be appreciated in conserving your electrical usage.

GARBAGE REMOVAL: Guests are responsible for removal of all trash from their villa. A $75 fee will be applied to guest’s security deposit if rental agent is required to remove trash left behind. There are numerous dumpsters throughout the island for your use.

CABLE/INTERNET/TELEPHONE/ELECTRICTY: In the Virgin Islands these services may be interrupted. If an interruption occurs the rental manager will report the problem but we have no control over service repairs. There will be no rental refunds due to the interruption of these services. INTERNET SERVICE: The internet service is subject to frequent interruption. We cannot guarantee internet quality or speed. Renters might find it convenient to travel with a cellular carrier MiFi – a couple of examples are AT&T and Virgin Mobile.

    • Rates
    • In Season
      Jan. 4, 2020 – April 17, 2020
      $9000/wk for 2 people * $9500/wk 3-4 * $10,000/wk for 5-6 * $10,500/wk for 7- 8 * $11000/wk 9-10
    • Off Season
      April 16, 2019 – Dec. 16, 2019
      $5000/wk for 2 people * $5500/wk 3-4 * $6000/wk 5-6 * $6500/wk 7-8 * $7000/wk 9-10
    • Holiday Rates (Flat Rate)
    • Thanksgiving
      (Nov. 23 -30, 2019)
      $7000/wk 2-10 people

      Christmas/New Years
      (Dec 17, 2019 – Jan. 4, 2020)
      $14,000/wk 2 – 10 people

    • 12.5% Hotel Tax
    • Damage Deposit
      $50 non-refundable damage waiver
      (this covers up to the 1st $500 in accidental damage that could occur during your stay. The damage must be reported while on island for it to be covered.)

    Caribbean Villas Comments

    • Caribbean Villas Comments:

      Reefside Villa is located on an uncommonly large lot of more than one acre. This allows Reefside Villa enough land area to include a small sand beach on the calm, protected waters of Chocolate Hole Harbor. Although this beach will never be confused with Trunk Bay, it is quite a pleasant, tranquil and sunny place to relax by the water, or to launch a snorkeling or kayaking expedition, or to pull up in a dingy and come ashore for lunch. (kayaks and dinghies can be rented in Cruz Bay).

      • Other distinctive features of Reefside Villa include;
      • Zoned, a/c in all rooms,
      • A handsome traditional design where the living room, dining room and kitchen are separate and distinct rooms, each with its own attractive and discerning interior décor,
      • An oversized pool, surrounded by luxuriant landscaping that creates a beautiful and very private poolside patio,
      • Sun all day on the poolside patio and the beach, and for those who prefer to be outside in the shade, there is a 500 sq/ft covered deck with comfortable furniture, located off the living and dining rooms,
      • A very comfortable, 300 sq/ft air conditioned office, located just off the pool deck, for those who must work on vacation,
      • A very private and tranquil location, yet you’re an easy walk to the Westin Resort and a 5-minute drive from Cruz Bay.
      • Four very private and attractively furnished guest bedrooms plus a spacious master bedroom with excellent views and a top of the villa location.

      Reefside Villa is recommended for families or multiple couples who desire to vacation together while still maintaining a strong sense of privacy.

    • Guest Comments:

      We had a wonderful time. The villa and the staff exceeded expectations. Thank you very, very much!

    Request Information

    Thank you for your interest in Reefside Villa!

    Our villa consultants have 30+ years of knowledge and we look forward to helping you find your perfect villa vacation!

    To email, please complete the following information or if you prefer to speak with a “live” person, please call our sales office, 800 338-0987. We are open from 9:00 am to 5:00 pm, Monday – Friday, EST.

    You may also check availability and make a reservation on our website Reefside Villa

    We look forward to hearing from you!
    Diane, Dolores, Kris & Kim
    Caribbean Villas of St John Sales Staff

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