Allesandra - Chocolate Hole

4 Bedrooms | 4 Baths | 8 Max. Guests

Beds Baths Location High Season
1/2/23 - 4/16/23
Low Season
4/17/22 - 12/18/22
Max Guests
4 4 Chocolate Hole $4,900 (1-2)
$5,400 (3-4)
$5,900 (5-6)
$6,300 (7-8)
$2,900 (1-2)
$3,500 (3-4)
$4,200 (5-6)
$5,400 (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 is a non-smoking villa.



Pack n' play crib

Linens & Bath towels

Swimming Pool 20' x 16' - depth 5' - 6' 6" with bench seating

Air-conditioned Great room

Air-conditoned bedrooms with Energy Eye System

Fully equipped kitchen

Kerig & Mr. Coffee machines

Triple water filtration system

Weber gas grill

Whirlpool washer/dryer

Iron/ironing board

Great room contains a 42'  Samsung Plasma TV

Sony 5 disc DVD/CD Changer

5 Direct reflecting Bose speakers

Onkyo Receiver

LG I Pad/Phone/Pod SoundDock

Wireless DSL

Master suite contains a 32" RCA LCD TV with built in DVD Player and expanded Digital Cable

Flamboyant suite contains a 19" Sansui LCD TV with built in DVD Player and expanded Digital Cable.

I Pad/Pod/Phone Sound Dock

Citrius Suite contains a 36" toshiba TV with Expanded Digital Cable, CyberHome DVd Player and Portable Stereo Cassette Player


Beach chairs, beach towels and beach coolers.

Safe for your valuables

A "Ping Pong" deck with Ping Pong table, Checkers and much more...

Hammock and hanging chairs for cocktails and relaxing


We had a fantastic family gathering lasting 8 nights at the gorgeous Allesandra! This house has everything you need for groups as large as 8 adults and the pool area , overlooking Cruz Bay, is a real beauty. Carefree Getaways, the managers of the property, were great to work with. Highest recommendation!



Date of arrival - August 8, 2022



May 14 - 22, 2022; ..."This was an amazing rental more than equipped with everything you would need to make your stay wonderful! So much room and the beds gave us the best nights sleep! The view was breath taking, the sunsets from the balcony was spectacular. The property managers responded very fast with any need also". Tina

July 17 - 24; ......"Outstanding Property" My wife and I stayed here for a week on our honeymoon, and it exceeded our expectations. The pictures don't do the view justice, it is absolutely stunning and didn't lose any of it's impact as the week went on. The amenities were also impressive for being on the top of a hill in an isolated Caribbean paradise; solid internet, A/C, fairly large pool, hot tub. wireless speakers, and an entertainment center (which we didn't use, but nice to have). Definitely recommended. There were only two of us, but the property is definitely large enough to accommodate larger groups. It also has another small deck underneath the main deck with hammocks, chairs, and a ping pong table. Carefree Getaways did a great job communicating with us and getting us settled in. It's also worth noting that the pool, hot tub, tec. are private and not shared with any other units. The property is quite private, except for some sight lines to the neighboring house through the trees. Bonus; fresh limes in the surrounding trees"...Dan....

Date of arrival - July 9, 2021-Great view over Cruz Bay, located close to supermarkets and restaurants/bars. Beautiful pool and the house had everything you need. 10-15 minute drive to the north shore beaches. Everything you are looking for from an amenity and location perspective.

Sept. 30 - Nov. 7;

....."Cindy, Mo and Elly,  I, along with my wife, daughter and son-in-law, recently visited St. John and stayed as your guests at Allesandra.  I wanted to get back to you to let you know how pleased we were with the villa as well as the service provided by the Carefree Getaways staff.  For my wife and I, I believe this was our 10th visit to the island (and certainly not our last!).  So we consider  ourselves “veterans”, and don’t need much attention, but what we did need was cheerfully provided!  Though we’ve enjoyed each of the villas we’ve stayed in, they sometimes have items that could use attention (broken screens, so-so appliances, general up-keep, etc.).  Allesandra was everything we expected and more.  The villa is in excellent condition, well provisioned and worked out perfectly for our party of four.  Elly was prompt, friendly, and very helpful.  And though we didn’t have the pleasure of meeting you ,Cindy and Mo, it was obvious when visiting with you on the phone that you care about your clients, and were the kind of people I enjoy doing business with.  By the way – a big “Thank You!” for allowing us to push checkout back an hour – the trip home is hard enough without having to worry about rushing to beat the cleaning crew.  On the flip-side, I hope we left the villa in appropriate condition and will be welcome the next time we visit!  We try to respect each property, be mindful of water/electricity use, etc.  Please let us know if we were negligent in any way.  Thank you so much to all of you at Carefree Getaways, and I hope we’ll be able to see you again soon!  Dave & Kim"......

....."My family stayed at Allesandra August 8th - 15, 2017. From the minute we walked in we were in love. This home is perfect in every way! The main living space is perfect with plenty of seating and wonderful air conditioning. The kitchen works great and has everything you could need. The Webber grill was great and we used it a few nights for dinner! The two master bedrooms in the main house are perfect and private. The beds were very confortable with tempurpedic mattresses. We had plenty of towels and the showers were great! Everything was clean and updated! The Pool and pool deck with the hot tub and views were beyond our wildest dreams! I think this is the best location on the island! Chocolate Hole, Cruz Bay and the night time views of St Thomas...beautiful! We also used the Cottage, which was also updated and air conditioned. The 4th bedroom which is on the top floor of the cottage is brand new, and also has amazing views!!! Also not to miss, the deck under the pool, this was an extra fun space! There is a ping pong table and a hammock and two hanging chairs! The Laundry was perfect for drying wet beach towels, which were provided along with beach chairs and coolers! We used them everyday to explore the beautiful beaches! Which brings me to location! 5 minutes to town, 10 minutes to the beaches, perfect! Also convienient St John Market and deli! We stopped often for ice for our cooler and the deli was great too.

Now I want to talk about Carefree Getaways and the office staff! They are amazing! Call them!!! They are all so easy to talk to and beyond helpful! The services they provided were amazing! Mo, Cindy and the rest of the staff not only greeted us at the ferry and drove us to the car rental, but they also escorted us to the villa and provided a wonderful tour of the property. Carefree helped with booking our car for us, booking our taxi service for us, (Ed and Ivan were the nicest men) and also arranged a meeting for food delivery for us. Starfish Market was great and delivered and stocked the house for our arrival! Carefree Getaways is doing everything right!


Beds Baths Location High Season
1/2/23 - 4/16/23
Low Season
4/17/22 - 12/18/22
Max Guests
4 4 Chocolate Hole $4,900 (1-2)
$5,400 (3-4)
$5,900 (5-6)
$6,300 (7-8)
$2,900 (1-2)
$3,500 (3-4)
$4,200 (5-6)
$5,400 (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.

2022 Dates
High Season: January 2, 2022 - April 16, 2022
Low Season: April 17, 2022 - December 18, 2022
Thanksgiving Week: November 20 - November 27, 2022
Holiday Season: December 19, 2022 - January 1, 2023

2023 Dates
High Season: January 2, 2023 - April 17, 2023
Low Season: April 18, 2023 - December 18, 2023
Thanksgiving Week: November 21 - November 28, 2023
Holiday Season: December 19, 2023 - January 2, 2024

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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