Allesandra - Chocolate Hole

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

20% Discount October & November!

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

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

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

After a long day at the beach relax in your private spa ...with a view.

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.

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.

Allesandra Main entrance. One step into villa from driveway!

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.

Oh what a beautiful day!

Allesandra's view of a heavenly rainbow.

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.

Great room.

Plenty of room for relaxing!

Every window and door has a wonderful view!

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.

The ideal great room for everyone.

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

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.

Beautiful views from the pool deck.

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.

Bright and spacious Master opens onto pool deck.

Master bedroom deck.

Master bath.

Spacious baths.

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.

Bed set in alcove in bedroom.

Flamboyant Suite

This Second Master also has a Queen futon.

Additional sleeping futon in bedroom.

Bedroom hall desk.

Bedroom

Desk study area.

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)

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.

Ground level Citrus Suite

Citrus Suite.

The 4th Air-conditioned bedroom called the "Coral Room" with private bath and balcony accessed by exterior stairway. This bedroom has WiFi TV only. No cable.

4th bedroom

View and deck from fourth bedroom.

Deck view from fourth bedroom.

Upper Cottage Bedroom

4th bedroom private bath

Heavenly sunsets....

Our quiet, breathtaking Caribbean sunsets.....

View of the night lights of St Thomas from Allesandra.

The perfect villa for you on St John.

Driveway fro Allesandra.

Main pool deck with covered dining area and villa.

View of pool deck with Citrus Cottage in background.

View with faint rainbow.

Cactus Rose.

The end of a perfect day!

Welcome to our island of St John.

Allesandra Great Room

Allesandra Great Room

Allesandra Great Room

Spa

Sunset view from spa.

Allesandra is a non-smoking villa.

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

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

20% Discount October & November!

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.