Tobago Holiday Accommodation Guide

Holiday Accommodation

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Tobago Vacation Rental Villas

Showing estimated rates per night in US Dollars  

Black Rock Dreams, Tobago

Black Rock Dreams

3 Holiday Rental Villas

Black Rock Dreams is a prestigious up-market development at the Black Rock end of Grafton Beach in Stonehaven Bay. The building comprises of eight 3-bedroom... condominiums on two levels. The four villa-apartment units at either end of the building are particularly spacious, light and desirable. We recommend three of these units. The fourth is now in private hands and no longer available for rental.

The stunning beach-front location, superb facilities and high levels of accommodation put these units firmly in the upper tier of Tobago holiday accommodation. We describe Black Rock Dreams as villa-apartments because these luxurious accommodations are in many ways more suited to holidaymakers who would normally be considering a holiday rental villa.
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from $300

Kapinjala, Tobago


4-bedroom Holiday Rental Villa

Kapinjala is an immensely striking 4-bedroom luxury villa situated on a hillside in beautiful Arnos Vale. The villa offers the most stunning views over the... surrounding hills and out to sea. This is one of the most tranquil properties that we have ever stayed at in Tobago and the villa offers the very highest standards of accommodation. The views from the house, deck and infinity pool are almost impossible to describe. We can only summarise our feelings by saying that we think it will be some time before any other property impresses us quite as much as Kapinjala. [read more]

Mahogany Villa, Tobago

Mahogany Villa

3-bedroom Holiday Rental Villa

Mahogany Villa is a spacious 3-bedroom villa located on the attractive and desirable Villas On The Green development, set in a lovely two-acre valley... setting adjacent to and overlooking the Mount Irvine golf course. Mahogany Villa has direct access onto the golf course and the clubhouse is within easy walking distance, making the villa ideal for golfing holidaymakers.

The development comprises of just 5 privately-owned villas built around a large central swimming pool. These villas make a great holiday accommodation base and could be an ideal solution for large wedding, family or corporate events.
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from $228

SeaBreeze, Tobago


6-bedroom Holiday Rental Villa

SeaBreeze is a spacious six-bedroom clifftop villa located in Bacolet, an upscale residential area of Scarborough. This tranquil villa is set in more than an... acre of mature tropical gardens and offers 180-degree views of the ocean. It is constantly blessed with cooling breezes being on the Atlantic side of the island. The villa is just a short walk away from picturesque Bacolet Bay beach and would make a great holiday base for larger parties or groups. [read more]

Shepherd's House, Tobago

Shepherd's House

3-bedroom Holiday Rental Villa

New for 2019, Shepherd's House is a fully-refurbished grand colonial 3-bedroom villa sleeping up to 8 adults in comfort. Nestled on a quiet hillside in Bacolet,... the villa catches the best of the cooling trade winds whilst offering stunning views over the Atlantic Sea and Bacolet Point. This hugely impressive villa is just a short walk from glorious Bacolet Bay beach. [read more]


from $300

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 $250

Soleil, Tobago


5-bedroom Holiday Rental Villa

Soleil is undoubtedly the most stunning villa on Tobago and yet few visitors will ever even be aware of its existence or ever have the pleasure of seeing it.... Located beside the Caribbean Sea at the end of a discrete cul-de-sac on the Arnos Vale plantation, this amazing villa is straight off the pages of a glossy 'Amazing Homes'-type publication. With five hugely spacious bedrooms, this property drips tasteful luxury devoid of ostentation. [read more]


from $550

Tosca, Tobago


3-bedroom Holiday Rental Villa

Tosca is a quaint three-bedroom villa located in the grounds of the Sanctuary Villa Resort at Pleasant Prospect. Beautiful Grafton beach is within... walking distance and this homely comfortable property makes an ideal holiday home for those wishing to tour the island.

Full development of the Sanctuary Villa Resort was never completed. Tosca is largely unaffected and avoids views of many of the uncompleted buildings that blight some properties on the development.
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from $162

7 Samaan Grove, Tobago

7 Samaan Grove

3-bedroom Holiday Rental Villa

7 Samaan Grove is a modern 3-bedroom holiday rental villa with swimming pool, located on the gated Samaan Grove development in Golden Grove, Canaan.

Ambassador's House, Tobago

Ambassador's House

5-bedroom Holiday Rental Villa

Ambassador's House is an established 5-bedroom family house set in extensive mature tropical grounds with private pool and located high in the hills of... Concordia, between Scarborough and Mason Hall. The property is secluded, but not isolated. Your own transport is fairly essential, however. [read more]


from $350

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