Allesandra - Chocolate Hole

4 Bedrooms | 4 Baths | 8 Max. Guests

Beds Baths Location High Season
1/2/24 - 4/17/24
Low Season
4/18/24 - 12/18/24
Max Guests
4 4 Chocolate Hole $4,900 (1-2)
$5,600 (3-4)
$6,300 (5-6)
$7,000 (7-8)
$3,500 (1-2)
$4,200 (3-4)
$4,900 (5-6)
$5,600 (7-8)

High and Low Season rates listed for 1 - 4 guests are for the Main House. 5 - 8 guests include Cottage & Upper level bedroom.

Thanksgiving Week $7000 1- 8 pp

Christmas / New Year's Week $8400

Request a Reservation for Allesandra

A/C Internet - Main House and Cottage IPod Base Station Kids allowed
Yes Yes Audio Sound System Cable TVs
Washer/Dryer Ocean view

Welcome to the amazing Allesandra located in upper Estate Chocolate Hole fully equipped with all the amenities for the vacationing traveler.

Villa Allesandra is a 4 bedroom 4 bath villa. Two bedroom suites in the main house with a separate cottage suite on the ground level and small upper 4th bedroom accessed by a stairway.

All air-conditioned.

Expansive pool deck

Expansive panoramic views of Cruz Bay, Great Cruz Bay, Chocolate Hole, St Thomas, Little St James and the surronding cays.

Panoramic views off of the pool deck

This sophisticated 4 bedroom, 4 bath villa affords guests panoramic views only possible from one of St John's premiere hilltop locations.

Outside dining with a view!

View from pool deck a few steps up to outdoor dining area and villa.

Deck Trellis

The expansive driveway allows for plenty of parking. From the driveway a separate staircase leads you down to the Citrus Garden Cottage where you will find a quiet retreat from the main house.

Driveway offers plenty of room for everyone!

Allesandra is surrounded by lush tropical gardens with an abundance of trees and orchids.

Just a five minute drive to the town of Cruz Bay, where you can enjoy dining at one of the many casual or classic restaurants or stroll to the many small and unique shops this charming town has to offer.

Lush tropical plants greet you at your door

Allesandra Main entrance. One step into villa from driveway!

Main entrance

Allesandra is surrounded by lush tropical gardens with an abundance of specimans trees and orchids. Bay Rum, Allspice, Avocados, Mangos, Key lime, Bananas and Mandarin Orange trees just to name a few. Small path from driveway meanders the property and the wonderful flora.

Allesandra is surrounded by lush tropical gardens.

Oh what a beautiful day!

Flamboyant trees abound

Allesandra's view of a heavenly rainbow.

Caribbean Rainbow

Allesandra at Sunset

Allesandra at Sunset

The Air-Conditioned Great room features an expansive living and diningroom area. Cathedral ceilings with two large windows and four sets of sliding glass doors that open out to the spacious pool deck.

Living, dining and entertainment areas are open and inviting, a perfect reflection of typical island living.

The living space has comfortable rattan furniture including two love seats, a large chair with ottoman and a recliner. Enjoy reading or watching TV on the 42' Samsung Plasma TV wall mounted flat screen LSD with expanded digital cable. A sony 5 disc DVD/CD Changer with 5 Direct reflecting BOSE speakers, Onkyo Receiver and outdoor speakers for your listening and viewing pleasures as well as a LG I Pad/Phone/Pod Sound Dock. A mahogany desk and chair are available for reading, writing or using your lap top. A glass top dining table for six is located in the main living area as well as a table for six just outside under the gazebo.

Air conditioned great room with cathedral ceilings

Great room.

Living room offers many ways to relax!

Plenty of room for relaxing!

Living room/dining room is wonderful to entertain!

Every window and door has a wonderful view!

Relax after a wonderful beach day!

The fully equipped gourmet kitchen including all major and minor appliances that will please any chef. A Whirlpool side by side refrigerator with water and ice dispenser including UV water filter system for added convenience. A four burner gas stove / oven, dish washer, microwave, blender, Kerig coffeemaker, toaster and all the necessary gadgets for the gourmet chef.

An island counter and bar with seating for four separates the kitchen from the dining / living areas.

Gourmet kitchen with seats for all!

The ideal great room for everyone.

kit 2

The 20' x 16' swimming pool with jackknife edge and bench seating. Depths from 5' to 6' 6".

What a wonderful to watch the sunset or enjoy your breakfast!

An ideal floor plan! The lower level also has a separate laundry room and a covered 20' x 20" area with built in benches, ping pong table, checkerss and lots more. Hammock and hanging chiars invite you to relax in a fine breeze with a wonderful view of surrounding islands. Great for children of all ages. This is accessed from the pool deck stairway or from the Citrus Garden cottage.

The floorplan!

Beautiful views from the pool deck.

Whether it is shade or sun you crave, we have it!

Game deck for relaxing and entertainment.


Game deck with a view. Chess, Ping-Pong and more.


As you enter the main house through the mahogany front door, the Master Suite is located to the West. A lovely mahogany King sized sleigh bed with Tempur-pedic mattress awaits you. A large mahogany armoire is available for all your Caribbean attire. Enjoy the cozy sitting area with two comfortable wicker barrel chairs and mahogany side table for reading or watching TV. Air conditioning, ceiling fan, telephone, 32" RCA LCD TV wall mounted flat screen with expanded digital cable and built in DVD player are included. The screened sliding glass doors open onto the expansive coral tiled deck.

En-suite Bathroom with shower, double Basins & W/C.

Walk-in wardrobe.

Luxurious master suite!

Bright and spacious Master opens onto pool deck.

Master bedroom opens directly onto your pooldeck!

Master bedroom deck.

Master bedroom deck

Master bath.

Master bathroom fit for royalty!

Spacious baths.

Spacious bathrooms!

The Flamboyant Suite is also air conditioned and features a mahogany, four poster canopied, King sized bed with a chocolate colored tropical spread featuring bold philodendron & fern leaves in soothing shades of green with vibrant red heliconia flowers. Two euro and king decorative pillow shams with sheer organza panels behind, invite one to a cozy space for napping or gazing out to the beautiful flamboyant tree.

A full size futon in the suite is available for small children with extendable wall lamp for reading. This suite features a full size dresser with large oval shaped wicker mirror, a writing desk, and closet to store all your personal items. FDouble sliding glass doors give easy access to the pool deck. A 19" Sanui LCD TV wall mounted flat screen and a I Pad/Phone Sound Dock await you for relaxing. There is also a mahogany desk and chair for working or writing.

The Master Suite and the Flamoyant Suite are on opposite sides of the kitchen/living areas making this villa ideal for families with small children.

En-Suite Bathroom with Shower, Basin & WC.

Flamboyant second bedroom!

Bed set in alcove in bedroom.

Beautiful canopied bed!

Flamboyant Suite


This Second Master also has a Queen futon.

mounted TV

Additional sleeping futon in bedroom.


Bedroom hall desk.

bedroom hall desk



Desk study area.

Desk study

View from Allesandra deck to Citrus Cottage a few steps away where the 3rd and 4th bedroom are located.


View from Main house to Cottage.


View from Citrus Cottage to Main house. (No internet service in Cottage)

View from Main House to Cottage

The Citrus Suite contains a deluxe country cottage queen sized bed with wicker night stands on either side including reading lamps for each guest. This room features air conditioning, ceiling fans, cordless telephone and large closets. A large armoire holds the 36' Toshiba TV with expanded digital cable and DVD player. There is a lovely hand painted glass top table with seating for two and a small refrigerator for drinks or snacks. The cottage can be entered from a gated staircase off the pool deck or from the driveway.

En-suite Bathroom with Shower, Double Basins & WC.

14 citrus

Ground level Citrus Suite

Citrus room

Citrus Suite.


The 4th Air-conditioned bedroom called the "Coral Room" with private bath and balcony accessed by exterior stairway.


4th bedroom


View and deck from fourth bedroom.

new 4th bedroom

Deck view from fourth bedroom.

new bedroom view

Upper Cottage Bedroom

4th bdrm



4th bedroom private bath



Heavenly sunsets....


Our quiet, breathtaking Caribbean sunsets.....

15 sunset

View of the night lights of St Thomas from Allesandra.

Night view

The perfect villa for you on St John.

16 deck


Driveway fro Allesandra.


Main pool deck with covered dining area and villa.

house 6

View of pool deck with Citrus Cottage in background.

house 7 cottage in background

View with faint rainbow.

view with small rainbow

Cactus Rose.

Cactus Rose

The end of a perfect day!


Welcome to our island of St John.


Allesandra Great Room

Al-Main room

Allesandra Great Room

Al-Main room

Allesandra Great Room

Allesandra is a non-smoking villa.

Al-Main room

Our family of seven, ages 18 and up, had a fabulous week here. The house had everything we needed and we spent quite a bit of time lounging by the pool or in the hot tub. The location is great for access to Cruz Bay and the beaches. The beds were comfortable and the kitchen had everything we needed for preparing meals at home. Best of all is the view! Wow! We have rented houses in St John several times, and Allesandra has by far and away the best and most panoramic view we’ve experienced. Highly recommended!

Date of arrival August 9, 2023.


This property exceeded our expectations. It was clean, comfortable, and very well equipped. The views were breathtaking from every room. We totally enjoyed our stay at Alessandra and look forward to staying there again in the future.

Date of arrival - April 29, 2023

Reviewer location - Birmingham, AL (USA)


Sunset views of Chocolate Hole at night and the harbor during the day. The house was everything and more than we could have hoped for. Well-stocked kitchen, comfortable beds, lots of beach chairs and snorkeling equipment. The pool and hot tub were in use all the time. We spent most of our time at the outdoor table which overlooks the pool. Lounge chairs at the pool were comfortable in both sun and shade.

Date of arrival - February 4, 2023


Allesandra checked all the boxes for us and our adult children! Very well stocked kitchen, pool floats, snorkel gear, coolers, linens, etc. Loved every minute of our time in St. John, & the house exceeded our expectations

Date of arrival - January 14, 2023


Our family of 5 had a wonderful vacation! The house was exactly as listed, and the view was breathtaking. Clean, convenient, well-appointed kitchen, comfy beds, plenty of linens, and more! I would love to return again next year!

Date off arrival December 19, 2022

Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool & Spa!

















The Allesandra property was beautiful with the absolute best views! It was very well stocked and had everything you might need and then some. Our trip was a family vacation with multiple adults so the availability of the cottage with 2 extra rooms was very convenient. The property management team at Carefree Getaways was fabulous! Cindy truly made our trip Carefree; when we had an issue at the property she took care of it immediately and did not let it interfere with our good time! I would recommend this property and team to anyone looking for a beautiful home with incredible views from every balcony, a great indoor space, an even better outoor space, and a property management team who will do everything possible to give you the best experience on their amazing island!!





Reviewer location - Ft Myers, Fl



Date of arrival - December 10, 2022

Additional Images
Allesandra Great room 2 Main level Master Bedroom
Beds Baths Location High Season
1/2/24 - 4/17/24
Low Season
4/18/24 - 12/18/24
Max Guests
4 4 Chocolate Hole $4,900 (1-2)
$5,600 (3-4)
$6,300 (5-6)
$7,000 (7-8)
$3,500 (1-2)
$4,200 (3-4)
$4,900 (5-6)
$5,600 (7-8)

High and Low Season rates listed for 1 - 4 guests are for the Main House. 5 - 8 guests include Cottage & Upper level bedroom.

Thanksgiving Week $7000 1- 8 pp

Christmas / New Year's Week $8400

Call for Holiday Rates

*Rates shown are weekly.

2024 Dates
High Season: January 2, 2024 - April 17, 2024
Low Season: April 18, 2024 - December 18, 2024
Thanksgiving Week: November 21 - November 28, 2024
Holiday Season: December 19, 2024 - January 2, 2025

2025 Dates
High Season: January 2, 2025 - April 20, 2025
Low Season: April 20, 2025 - November 23, 2025
Thanksgiving Week: November 23 - November 30, 2025
Low Season: November 30, 2025 - December 19, 2025
Holiday Season: December 19, 2025 - January 2, 2026

All rates subject to 12.5% USVI Hotel Tax. A $35 non-refundable security deposit and $35 reservation fee are required.
Rates are subject to change without notice.

Request a Reservation for Allesandra

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