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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Classic 1-3 Bdrm Chocolate Hole on Secluded Hart Bay w/ Private Path Beach Path

Bedrooms 3
Property type house
Minimum Stay 5 - 7 nights


About the property

Beachfront, Pool, Spa, 1-3 Bdrms, 3 Baths, Sleeps up to 9*, Kids 1/2 Price

Owner usually responds directly via phone and email so please disregard response rate.

Kids 6 -18 1/2 price

Great for families or for couples seeking a secluded getaway, Odessa nestles on a hillside that flows into multi textured Hart Bay in Chocolate Hole.

The private beach is shared with only a few other houses - no public parking to this beach.

A stone path leads down to excellent hiking and sunning, on Hart Bay Beach.

RECENTLY REMODELED, stone walls with arched windows, blue and white clapboard, lattice and gingerbread detailing convey classic West Indian charm. Folding French Doors open the entire front of the house to a panorama of sights and sounds of the sea. Gentle off-shore waves and rocks texture the bay. Dine at the indoor bar or at the outside table.

Odessa is located on the southwest corner of St. John in the Chocolate Hole area on Hart Bay. It is about five minutes from the village of Cruz Bay. The house has a full kitchen, living room, three bedrooms (lower two with A/C and upper with ceiling fans) with queen-sized beds, TV and VCR, three full baths, spacious decks, a Jacuzzi and a swimming pool.

Enjoy the natural beauty surrounding Odessa: The private lower level offers two bedrooms with queen-size beds, full bathrooms and a spacious deck. All three bedrooms have queen sized beds and a sleeper sofa in the living room plus two roll away beds are available.

Every room faces the ocean and has open air verandas with screens. At night you hear only the surf and tree frogs.

Upon arrival, we escort you from the ferry dock to your rental car and then to the house. There is also a 2 hour mid-week light cleaning included.

(No kids under 6 for safety reasons)

We accept checks and credit cards and online payments.

More Details

Property Manager
Rachel Langosch
Member since: 2006
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
March 6, 2017

Guestbook comments from the manager

The view from the decks and pool are breathtaking. Our favorite was sitting on the lower deck listening to the waves crash and falling asleep to the pound of them.If we make it back to St. John we will find ourselves here again.
Aug 2012
  • 1 of 7


Estate Chocolate Hole and Great Cruz Bay House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
House Rules:
  • Max. occupancy: 9
  • non smoking only
  • pets not allowed
  • Minimum Age Limit for Renters ...
  • children welcome ...
Location Type:
  • Beach ...
  • Beach View ...
  • Beachfront ...
  • Village ...
  • Water View
  • Waterfront
  • Adventure
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Air Conditioning
  • Alarm Clock
  • Basic Soaps
  • Broadband Access
  • Ceiling Fans
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Parking Off Street
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • 4 Ring Stove
  • Blender
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Freezer
  • Grill
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 4 people
  • 3 Bathrooms
  • Bathroom - toilet , shower
    Bathroom - toilet , shower
    Bathroom - toilet , shower
  • The newly remodeled bathroom on the top floor has an outdoor shower
  • 3 Bedrooms, Sleeps 9
  • Bedroom - 1 queen
    Bedroom - 1 queen
    Bedroom - 1 queen
  • All three bedrooms are Queen sized beds plus sleeper sofa in Living Room and two roll away beds available.
  • Books
  • CD Player
  • DVD Player
  • Satellite / Cable
  • Stereo
  • VCR
  • Balcony
  • Barbecue
  • Beach Towels
  • Deck / Patio ...
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Tennis ...
  • Walkway to Water
  • Wood Deck
  • 4 garden chairs
  • unsuitable for elderly or infirm
  • wheelchair inaccessible
Pool / Spa:
  • Hot Tub ...
  • Jacuzzi
  • Outdoor Hot Tub
  • Outdoor Pool
  • Private Pool ...
  • Whirlpool
  • bay/sound
  • duty free shops
  • forests
  • library
  • marina
  • playground
  • reefs
  • restaurants
  • ruins
Leisure Activities:
  • beachcombing
  • bird watching
  • eco tourism
  • gambling casinos
  • horseback riding
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • golf
  • hiking
  • jet skiing
  • mountain biking
  • paragliding
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Mid week, 2 hour cleaning also included for weekly stays. for more information:


Very Good! 4.2/5 -
(6 traveler reviews)

Classic 1-3 Bdrm Chocolate Hole on Secluded Hart Bay w/ Private Path Beach Path
average rating of 4.1666665 based on 13 reviews

Beware of this rental-nice location but...

  • 1 of 5

BAD EXPERIENCE AT ODESSA!!! First of all, after we carried all of our luggage and groceries (with not an offering of help from the free-handed Nemisy-property manager) down the 60 steps to the house, were we told that there would be no keys issued to us, because the house has no locks, but, the rental agreement states that if you lose the keys, they will charge you $75!!! So, we got to sleep with unlocked doors, left the house to explore the island while anyone could enter and steal. We were not told this when we inquired about booking the place and if we had been told this, we would have declined the opportunity to rent this house. We were also not told (until we paid and received the house rules) that we would be charged $75 if we did not haul away our garbage at the end of our stay. The gap between the bedroom air conditioner (only two rooms in the entire house both downstairs bedrooms have air conditioning) allowed mosquitoes in and so I was eaten alive while trying to sleep. We were initially told (by th homeowner, I believe) that we could swim at the beach below the house-not true, you cannot enter the water there. We chose the house because we were told we could swim from that beach. I specifically stated during my initial inquiry that I wanted to rent a house on the beach so I could walk from the house to the beach and swim. So, we were lied to, duped, and disappointed overall with the house, its condition (old, run down). Also, if you use the bathroom, you are told not to flush toilet paper! So your poopy toilet paper gets to sit in a waste basket until you haul it off yourself!!!!! Also, the signs in the bathrooms tell you not to flush if all you do is pee, only flush when you poop! So, the bathrooms stunk to high heaven, not to mention the flies that it attracted! We had to call the property manager on the day before we left, as when we awoke, there was no water! It took several hours to have someone come out and fill the tank. Another annoyance. All in all, we loved St. John, but not the house we stayed at. We cannot recommend this house due to all of the problems, dishonesty and annoyances (and it is over priced for the house condition and problems we faced). Also, some of the photos are misleading. We will definitely be more careful by asking many more questions for our next stay at this beautiful island.

  • Submitted: Oct 10, 2016
  • Stayed: Sep 2016
  • Source: HomeAway
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9 4

Private getaway with amazing view

  • 4 of 5

We enjoyed our stay on beautiful St. John. Odessa is very private, surrounded by cactus and scrub vegetation typical of the island. We loved watching iguanas lazing in the trees and land crabs crawling the hillside. The ocean view was gorgeous, and a manta ray came every late afternoon to feed in the cove.

The home is comfortable but not fancy, so we felt like we were living like typical islanders. You can see the water from every room in the house. Truly an amazing property on an amazing island.

  • Submitted: Sep 26, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
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2 0

The property at Odessa is breathtaking!

  • 5 of 5

Odessa was the perfect home base from which to travel around St. John. While we weren't on the beach or having a great meal at a restaurant, we were relaxing by the pool on the upper Deck of Odessa or hanging in the comfortable and beautifully decorated Odessa home. I would recommend this hideaway in the hills of St. John to anyone who wants peace and tranquility.

  • Submitted: Mar 7, 2016
  • Stayed: Feb 2016
  • Source: HomeAway
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1 0
Earleton, Florida

Relax with Great Views!

  • 5 of 5

My husband and I recently met our daughter, who lives in Tortola, at Odessa for a week vacation. The home was very comfortable, has a great pool and hot tub, and fantastic ocean views with breezes! We loved the outdoor eating area, the gas grill was very convenient, and the location fantastic! We were met at the ferry dock with our rental Jeep from Aqua Blue Rentals. The sisters there were very helpful and answered ALL our questions. A housekeeper checked on us as well as the pool maintenance guy. The pool was crystal clear and great to relax in after a day visiting a beach on St. John. Loved the home!!!

  • Submitted: Nov 25, 2014
  • Stayed: Oct 2014
  • Source: VRBO, from HomeAway
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3 0

Amazing Tropical Breezes

  • 5 of 5

We just got back from Odessa and I wish I could have stayed another week. The owner is very concerned his guests are happy at this classic beach home. He called mid week to see if we had any concerns and then we had a nice conversation about what the islands has to offer and the beautiful landscape at the home. My one comment to him was he needs to emphasize the amazing breezes even more on his website. The concierge that delivered our provisions to the home said there are very few houses on the islands with such spectacular breezes.

The house has everything you want in a tropical rental: pool, jacuzzi, deck space, outdoor shower and beach access. You can spend hours on the beach looking at the shells and coral or just hang out at the spacious pool space and look at the amazing ocean view.

  • Submitted: Mar 30, 2014
  • Stayed: Mar 2014
  • Source: HomeAway
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5 0
Fort Lauderdale, Florida

Nice Place Private!

  • 5 of 5

My boyfriend and I recently stayed at Odessa. We had a wonderfully peaceful time there, with a beautiful open view of Hart Bay and further along St John’s south coast. It really felt like we were “living on St. John” and enjoyed getting the fresh ocean breezes. The owner’s description calling it a “classic rental” is very appropriate, and the pictures posted are good– it had everything we needed, beach towels, all kitchen items, etc. The kitchen is separated from the living area with a bar, so it was great when I was cooking and my boyfriend was reading on the couch - and the views from there are beautiful. The upstairs (main) bedroom is behind the kitchen and the outside deck runs the entire length of the upper floor (we only used the top bedroom, there are two bedrooms below). There is even an outdoor stone shower, which was a real vacation treat! (We understand there are many of these at homes on St. John) The house is situated down a few steps from where we parked on a dead end road, so it is very private. We walked down to Hart Bay beach each morning on a little private path, and were usually the only two there. The pool and deck look very new, and we spent allot of time up there –it is very peaceful. The house is close to Cruz Bay so easy to go to in for groceries or shopping. Just go to any bar and they will give you dining and shopping ideas based on what you like! Hiking and beaches are great here!

  • Submitted: Jul 21, 2012
  • Stayed: Mar 2012
  • Source: HomeAway
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14 0


Nearest Airport
15 Miles
St Thomas/St John
Nearest Barpub
1 Miles
Westin, The Marketplace and Cruz Bay Bar
Nearest Ferry
3 Miles
Cruz Bay
Nearest Golf
10 Miles
Mahogany Run on St Thomas
Nearest Restaurant
1 Miles
Westin, The Marketplace and Cruz Bay Restaurants
Car: necessary

Only 6 minutes from Cruz Bay with craft shops, groceries, excellent dining, dancing or exploring, Odessa feels like worlds away from civilization. Considered to be a part of Chocolate Hole, Odessa faces east and has a private path down to secluded Hart Bay, one of the few beaches on St John with no public parking nearby.

Resident cat on the property keeps the critters down!


Rates & Availability

Estate Chocolate Hole and Great Cruz Bay House Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Apr 16 - Sept 8 2 ppl
Apr 16 2017 - Sep 8 2017
5 night minimum stay
Sept 9 - Dec 15 2 ppl
Sep 9 2017 - Dec 15 2017
5 night minimum stay
Dec 16 - Dec 22 2 ppl
Dec 16 2017 - Dec 22 2017
7 night minimum stay
Dec 23 - Jan 6
Dec 23 2017 - Jan 6 2018
7 night minimum stay
Jan 7 - April 14 2 ppl
Jan 7 2018 - Apr 14 2018
7 night minimum stay

Additional information about rental rates

Tax Rate 10.0%

now - April 17 '17: 2 = 4000, 4 = 4500, 6 = $5000
April 17 - Dec 17 '17 2 = $3500, 4 = $4000, 6 = $4500
Includes 2 hour mid-week cleaning for weekly stays Please see website for Last Minute Specials and Availability
Children 6- 18 1/2 price (no kids under 6 for safety reasons), max 9 guests at any ti

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.

Enter dates for accurate pricing


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