Sheppy's Den - a myTobago guide to Tobago holiday accommodation

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Sheppy's Den, Tobago

Sheppy's Den

5-bedroom Holiday Rental Villa

Sheppy's Den is a very individual house that offers visitors a unique experience packed with local flavour. With five very well-furnished and colourful bedrooms,... this lovely house absolutely bursts with character. Fully air-conditioned and furnished and equipped to the highest standards, the vibrant colour schemes and furnishings offer visitors a unique experience and a comfortable holiday 'home from home'.

The property is owned, designed and managed by Colin 'Sheppy' Shepherd, who's popular car rental business has an enviable reputation for excellent service.
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from US $250

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Sheppy's Den

5-bedroom Holiday Rental Villa

Sheppy's Den is a very individual house that offers visitors a unique experience packed with local flavour. With five very well-furnished and colourful bedrooms, this lovely house absolutely bursts with character. Fully air-conditioned and furnished and equipped to the highest standards, the vibrant colour schemes and furnishings offer visitors a unique experience and a comfortable holiday 'home from home'.

The property is owned, designed and managed by Colin 'Sheppy' Shepherd, who's popular car rental business has an enviable reputation for excellent service.

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Property Description

Provided by the property, or taken from their website

Sheppy’s Den is a highly individual and comfortable four-bedroom vacation rental villa on the sun-kissed island of Tobago, the jewel in the Caribbean crown.

Owned and managed by Colin Shepherd, whose unsurpassed standards of service has made his auto rental business one of the largest on the island, Sheppy’s Den will provide visitors with an unrivalled holiday experience.

Located in Bacolet Park, a new and sought-after development on the outskirts of capital, Scarborough, the villa offers a wonderful base from which to explore our beautiful island. Gorgeous Bacolet Bay and beach is just a 2-minute drive away and the centre of Scarborough just a few minutes more. The airport and all of Tobago’s most popular beaches are within 15-20 minutes drive. No worries about a car – you are guaranteed a perfect specimen from Sheppy’s ever-expanding rental stock.

Completed in 2008, Sheppy’s Den has all the character and vibrancy of the Caribbean. Furnished and equipped to the very highest standards, you will lack for nothing. The air-conditioned main house offers four double bedrooms and the very highest standards of living comfort. In addition, the house also features a separate self-contained studio apartment, although this is only available for rental when the main house is not occupied.

myTobago Review

Our reviews are devoid of marketing hype. We aim to provide concise, unbiased factual information that will help you find Tobago holiday accommodation that perfectly matches your hopes, requirements and expectations.

The following review was produced during a 7-night stay at Sheppy's Den in February 2016.


Regular visitors to Tobago will be familiar with the name Colin Shepherd. Best-known for his highly-regarded auto rental service, 'Sheppy' has expanded his business activities in recent years and now has a portfolio that includes one of the best small hotels and restaurants on the island and two, very different, holiday rental villas.

Sheppy's first foray into the hospitality industry was the sujbect of this review - a charming 5-bedroom vacation rental villa, Sheppy's Den. This colourful property was very much more than a business project to Sheppy. He may have justified the build on commercial grounds, but the bottom line was that he built the house because he could and wanted to. It also became his private retreat from the pressures of business. The name, Sheppy's Den, says it all.

There are over 200 holiday rental villas on Tobago and the vast majority offer high levels of accommodation. However, most of these properties have no real sense of identity or any distinguishable association with Tobago. You could be anywhere in the world. Villas with true character are much harder to find. Every aspect of Sheppy's Den screams Tobago. There is nothing subtle about this house. From the location to the violent colour scheme and décor, you are guaranteed a fairly unique Tobagonian experience.


Sheppy's Den is located in Bacolet Park, a relatively new development next to the Dwight York Stadium, at the eastern end of the Claude Noel Highway that bypasses Scarborough.

Bacolet Park overlooks Minster Bay. Intervening scrubland inhibits sea views from the house. Beautiful Bacolet Bay beach is a three-minute drive from the villa. Upper Scarborough is a minute or two more and you can be in downtown Scarborough within ten minutes of leaving the house.

Bacolet Park is very popular with Tobagonian business and professional families. It is not a vacation rental villa development, where most of the properties remain vacant for all but a few weeks of the year. Bacolet Park currently boasts about 50 completed houses. A similar number of plots are available for future development. In truth, not much seemed to have changed since our last visit in 2010. Development is very low key. Even though the main Atlantic coast road passes just 75m behind the house, it is one of the quietest locations we have stayed in. No early-morning roosters, Chachalacas or boom boxes. Nada!

One thing that we particularly like about Bacolet Park is the fact that it is very much a 'local' neighbourhood. Most of the houses are owned by local professionals and business people. We were particularly taken with the friendliness of the neighbours and genuinely felt that they would 'watch out' for visitors.

It has to be said that there are no shops, bars, restaurants or other facilities within walking distance of Bacolet Park. Having your own transport is essential. In fairness, given Sheppy's primary business activities, this is hardly likely to be an issue. In fact, Sheppy offers particularly good deals when renting both the house and a car or jeep.

From this location, the island is your oyster. The journey from the airport takes little more than 20 minutes. You can drive to any of popular Crown Point/Lower Caribbean beaches in much the same time. In fact, every point of the most populated Crown Point-Plymouth-Scarborough triangle is within a 20-minute drive.

Living Room & Kitchen

From the road, Sheppy's Den looks like a compact two or three-bedroom cottage. The house actually offers a gross accommodation area of around 1700ft2 (156m2). Looks can be so deceptive.

That aside, the first thing to strike you is undoubtedly going to be the vibrant exterior colour scheme of the property. You will either love or hate the violent purple and green mix. Either way, there is no mistaking that you are in the Caribbean. Those wanting minimalist under-statement should look elsewhere. This property doesn't believe in subtlety – it socks you between the eyes and attempts to wrap you in a thick cosy duvet of opulence. This is the lifestyle to which most Tobagonians aspire. Like their music, cars, worship and partying, it is loud, unabashed and distinctive.

The wide front doors of the single-storey house lead into a large living area. The strong colours of the exterior become softer pastel tones of dusky pink and light apple green; colours that act as an interesting foil to the ornate stained wood kitchen cabinets and dining table. Sheppy claims total responsibility for the exterior and interior design, including all soft furnishings. His choices may not be to everyone's taste, but the décor often shows a sensitive side and interesting eye for colour; at other times the masculine side dominates.

The lounge occupies the shorter leg of the L-shaped open-plan living area. Two large sofas and an armchair in matching chocolate velour, with white lace antimacassars, are just so different to the cane and rattan furniture found in most holiday rental villas. And that's before we mention the intricately embroidered beige and gold lace curtains and swags, or the three ornate chandeliers. Then, suddenly you are hit by the boy's toys: a 55-inch Sony LCD television with DVD player and a linked hi-fi system with 7.1 cinema surround sound system. What a pity that the leads and wires associated with such systems cannot be easily hidden. Not having brought any CDs or DVDs we can't vouch for the quality of the impressive-looking audio system, but I suspect that it is loud enough to wake the neighbourhood. It should certainly be enough to satisfy Trinidadian guests. As if that is not enough, there is also an iPod player unit with wireless speakers.

The dining area lies in the centre of the living area, between the kitchen and lounge, and consists of a decorative partially-glass-topped 7ft 6in wooden dining table with six matching cushioned chairs.

The solid teak cabinets in the kitchen must have consumed half a rainforest. There's no cheap MDF here. If anything, the kitchen is somewhat over the top for a holiday rental property. But, that's not the point. Sheppy wants his guests to have the best.

A central kitchen island offers a central work area and features a four-ring gas hob. Kitchen cabinets surround the island, with a small breakfast bar and three matching teak stools separating the kitchen from the dining area. Built into the kitchen units are a large fridge-freezer, electric oven with grill/broiler, a dishwasher and a microwave oven. Smaller items include an electric kettle, blender, coffee filter machine and toaster. A range of kitchen utensils, pots, pan and other kitchen and barbeque tools help to fill some of the cabinets, leaving ample space for groceries.

Discretely located at the far end of the kitchen is a small utility area equipped with a washer and dryer, plus iron and board. Housekeeping services are provided six days a week.

The house is fully air-conditioned, with individual split units servicing each of the bedrooms and two units in the living area. The house faces north, so the sun passes over the roof during the course of the day, rather than constantly shining on, and warming, any particular aspect. The front of the house is in shade at all times of the day, meaning that it is possible to sit outside at any time without being in the direct sun. While writing this review I experienced perfectly equitable working conditions, without resorting to air-conditioning, simply by keeping the front doors open and setting the living room air-con units to 'fan' operation. A very swish looking remotely-controlled floor-standing ionizing tower fan is also available.


The hugely spacious 235ft2 (5.6x3.9m) master bedroom is impressive enough, even before mentioning the attached 125ft2 (4.75x2.5m) en suite bathroom. The room is dominated by a charming reproduction upholstered chaise longue and romantic four poster queen bed with twisted decorative posts. There is no canopy, but this would probably have been overkill anyway. The intricately embroidered ivory and gold bedding add a distinctive finishing touch. Few guests are likely to fill the ten-feet of floor to ceiling solid teak wardrobes.

When we first stayed at Sheppy's Den, there was no separation between this bedroom and its huge lime-green tiled en suite bathroom. However, since that visit, half-height wooden double doors have been installed, overcoming any privacy concerns.

A large single washbasin is inset into an attractive vanity unit, which in turn is part of an extensive range of bathroom units offering more storage for cosmetics and toiletries than most people are likely to carry. Every bedroom features a wall-mounted electric hair-dryer.

In our last review, we made favourable comment about the master bedroom's impressive shower stall with its twin shower heads and double wall jets. Sadly, only one of the shower heads was working during our latest visit. Still, water pressure was good and there always seemed to be lots of hot water.

With a nice gentle shower taking care of sensitive sun-burnt shoulders, it would be a shame if the effect was spoiled by scratchy towels. No fear! The towels are thick and soft and fluffy. Like the bed linen, everything is of excellent quality and beautifully clean and well-laundered.

Although not quite as luxuriously appointed, the other bedrooms do not disappoint. Bedrooms two and three are on the far side of the kitchen/dining area and separated by a single shared bathroom with pedestal washbasin, toilet and large fully-tiled shower. The location of this bathroom means that is also ideally located as a general washroom for villa guests.

Bedrooms two and three are adequately spacious (4.2x3m). Both are furnished with a double bed, bedside tables and lamps and built-in wardrobes offering 1.2m of full and half-length hanging space, plus shelving and a large mirrored dressing table. The only difference between the two rooms is that one has windows (with elaborate and colourful drapery) on two aspects, whereas the other has only a single window.

Bedroom four is located to the rear of the property and is smaller than the others at 2.9x2.85m. It is a very cosy room, possibly due to its attractive 2.9x1.9m en suite bathroom. Like the other bedrooms, it is fully air-conditioned and furnished with a double bed plus bedside tables with reading lamps. The en suite bathroom features a large fully-tiled shower cubicle and a range of floor-to-ceiling cabinets offering dressing table and storage facilities, including 0.75m of full and half-length hanging space. Both an electric hairdryer and a liquid soap dispenser are installed.

The fifth bedroom is also located to the rear of the property and was originally designed as a self-contained studio apartment. It offers a gross floor area of 4.5x4.4m and should perhaps be described as cosy, rather than spacious. However, it is very attractively furnished with a double bed, wardrobe, 26-inch LCD television and a small kitchenette equipped with a four-ring gas oven, small fridge-freezer, microwave oven, kettle and blender. The attached en suite bathroom is small but immaculately equipped and maintained and features a pedestal washbasin, toilet and a good-sized fully-tiled walk-in shower.

Throughout the property, all windows and doors have secure, but discrete, security grills. Guests are large unaware of these as they tend to be hidden by the curtains, which are best left closed to aid cooling. The only entry to the grounds is via the entrance to the driveway, which has a large and easily-operated sliding gate.

Despite this, visitors should observe all normal 'sensible' precautions and ensure that doors and windows are locked before retiring at night, or when leaving the property. A large (13x11 inch) waterproof and fireproof security safe is provided. This is large enough for all valuables, including items like cameras and iPods, etc.

Complimentary Wi-Fi access is available throughout the property.

Swimming Pool & Gardens

The fenced perimeter of Sheppy's Den is attractively landscaped and planted with colourful bougainvillea and other vibrant tropical flowering bushes and plants. The gardens have matured well since our last visit and are now a riot of colour.

The house is built on a gentle hillside, with the land sloping down from road. The pool is a metre or so above house level and separated from it by an attractive rockery. The pool itself is roughly 8.6x3.7m with steps leading from one corner of the shallow end and depths ranging from about 33 inches to a little over 5 feet.

The six-foot-wide pool surround is furnished with half a dozen comfortable cushioned sun recliners. A small patio area in front of the house has three all-weather tables and chairs. Although neighbouring houses overlook the property, one never felt any real lack of privacy.

Needless to say, no villa in Tobago would be complete without a gas barbeque. It is such a pity that the salty sea air takes such a toll on metal-based objects. In our last review, we commented that the large stainless steel gas barbeque would not look out of place in a professional kitchen. Sadly, this is no longer the case. Whilst the appearance has suffered, it seemed to work adequately.

The house features a large viewing deck on the roof. From this vantage point one gets a great perspective of the surroundings and across the brush land out towards Minster Bay.


One cannot deny that Sheppy's Den is a unique property. The house absolutely shouts character and unquestionably offers highly comfortable holiday accommodation. It is located in an environment very different from the somewhat sterile and often deserted holiday home developments that represent much of Tobago's vacation rental stock.

As a guest of Sheppy's Den, you are also the guest of someone whose commercial success is the result of offering the highest levels of personal, friendly service and goodwill - characteristics that you are sure to experience and endorse for yourself.

Reader Reports

This property has a weighted Reader Satisfaction Rating of 97.5%   . Click below to read the 16 reader reports that this rating is based on.

Aamir from Trinidad visited in August 2013 and awarded   

My family and I returned to stay at Sheppy's one year later and the place has remained extremely well kept and beautiful. The new housekeeper was most welcoming and helpful. I really like the added lights outside surrounding the villa. All the amenities were working perfectly. I would recommend this villa to anyone, it truly is a paradise of its own. See you soon Sheppy's Den :)

Roger Bentley from U.K. visited in November 2012 and awarded   

Wonderful accommodation in quiet select part of east Scarborough just after Dweight Yorker stadium with 4 -5 double bedrooms swimming pool and full services ( wifi was not working while we were there). Monique the housekeeper cooked us delicious coconut bake and we felt very safe ans secure.

No sound of dogs barking all night plus 3 am cockerels which was a bonus, I would recommend unreservedly.

Location Map

To view a detailed interactive map showing the location of this property relative to restaurants, shops and sightseeing features, click this link  

Full Villa:US$250 - US$300
Minimum Nights:1 night + 1
Property Type:Holiday Rental Villa
Maximum Guests:10
Bathrooms:3 (ensuite)
Air-Conditioning:Fully air-conditioned
Children:Children welcome
Hair Dryers:Available
Internet Access:Yes
Safety Deposit:Yes
Wheelchair Access:No
Swimming Pool:Full pool
Catering Options:

Housekeeping:6 times per week
Personal Laundry:No
Personal Cooking:By Arrangement
Location Type:Low Density Urban
Airport:20 minutes
Beach:5 minute Drive