50 Best Trinidad and Tobago Vacation rentals on Holiday Lettings - Villas

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Trinidad
99 properties

Trinidad and Tobago

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229 Vacation rentals

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(18) Excellent 

20

Trinidad and Tobago Vacation villa rental

Castara / Englishman's Bay

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
A 5 minute drive from Englishman's Bay, this is a secluded yet comfortable villa that is perfect for anyone wishing for a holiday in beautiful surroundings close to nature. It is set amongst a thriving jungle with one of the world's largest variety of birdlife  …see more

from $145 / night

$1016 - $1842 / week

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from $145 / night

(10) Excellent 

18

Vacation villa with swimming pool in Trinidad and Tobago

Tobago / Mount Irvine

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
As soon as you walk through the front door you are struck by the sheer tranquillity and elegance of your surroundings. Mot Mot Lodge is beautifully appointed with everything you could wish for to make your stay a relaxing and rejuvenating experience. A short walk throug  …see more

from $293 / night

$2045 / week

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from $293 / night

(9) Excellent 

19

Vacation cottage in Trinidad and Tobago

Trinidad / Maracas Bay

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Private garden
La Vapeur Estate is located at the summit at the third highest point in Trinidad, which is located in the southern Caribbean. With stunning sea and mountain views, the property's wood cabin offers a private, luxurious and serene getaway with spectacular views of th  …see more

from $100 / night

$693 / week

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from $100 / night

(20) Very Good 

28

Vacation villa with swimming pool, golf nearby in Trinidad and Tobago

Tobago / Prospect, Tobago

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
This fantastic secluded 4 bedroomed all with en-suite family villa comes with private pool and spa. It can be rented either as two apartments (both with separate entrances) or as a large villa. Both apartments are fitted with full working kitchens and dining areas. ai  …see more

from $248 / night

$1778 / week

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from $248 / night

17

Caroni Vacation apartment rental

Trinidad / Caroni

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Welcome to our largest apartment. This five(5) bedroom, 2 bathroom beauty is the perfect apartment for a larger family coming on vacation. It can host up to 10 persons. 1200 sq ft of living space is more than enough for a comfortable short stay. ADDITIONAL SERVICES (  …see more

from $200 / night

$1400 / week

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from $200 / night

(3) Very Good 

25

Trinidad / Chaguanas

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 40 mi
  • Air conditioning

 …see more

from $80 / night

$501 - $551 / week

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from $80 / night

(12) Excellent 

12

Vacation villa in Buccoo

Tobago / Buccoo

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Oleander Villa is situated on the hillside near Mt.Irvine with views overlooking Pigeon Point and Buccoo Reef. The villa has four air conditioned double bedrooms, three ensuite, with an additional queen size sofa. There is a spacious sitting room with cable TV and fren  …see more

from $401 / night

$2800 / week

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from $401 / night

(15) Very Good 

21

Bacolet Bay Vacation villa rental

Tobago / Bacolet Bay

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Bougain-villa is a charming luxury detached air-conditioned villa with a swimming pool, set in a tropical garden with fruit bearing trees. The property is light and very welcoming with tall ceilings, cool floor tiles, ceiling fans, and furniture of a high quality. The v  …see more

from $178 / night

$1080 - $1270 / week

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from $178 / night

(2) Excellent 

18

Condo rental in Trinidad and Tobago with shared pool, golf nearby

Tobago / Lowlands

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
It's a ground floor condo overlooking the Tobago Plantations golf course. tranquil and peaceful surroundings. Access to 3 separate pools on compound and Lowlands beach. Sleeps 8 comfortably. Perfect for small families with young children. Cable television and wifi at n  …see more

from $180 / night

$1260 / week

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from $180 / night

(1) Very Good 

22

Vacation apartment in Mayaro

Trinidad / Mayaro

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Castle 'J' offers fully serviced executive accommodation for clients who expect bit more. Situated in the picturesque town of St. Joseph, Mayaro. The accommodation is fully air-conditioned and furnished to modern international standards. It is located within 5  …see more

from $150 / night

$900 - $1320 / week

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from $150 / night

24

Vacation villa in Trinidad and Tobago

Tobago / Arnos Vale

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
A beautifully presented one bedroom villa situated in an acre of orchard land in a semi rural area on the outskirts of Plymouth, Arnos Vale being just a 20 minute drive from the airport. A bird watchers paradise as the land is home to parrots, mot mots - better known a  …see more

from $51 / night

$356 / week

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from $51 / night

19

Vacation apartment in Caroni

Trinidad / Caroni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Spacious 2 bedroom apartment, located in the breezy, serene plains of east/central Trinidad. Only 10 minutes to the airport, to 4 major shopping malls, educational district of universities and colleges, famous Caroni Bird Sanctuary and other attractions. There is also a  …see more

from $100 / night

$700 / week

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from $100 / night

(1) Excellent 

19

Mayaro Vacation home rental

Trinidad / Mayaro

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Child friendly
Castle 'J' offers fully serviced executive accommodation for clients who expect bit more. Situated in the picturesque town of St Joseph Mayaro. The accommodation is fully air-conditioned and furnished to modern international standards. It is located within 5 m  …see more

from $150 / night

$900 - $1320 / week

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from $150 / night

(1) Excellent 

15

Vacation villa with shared pool, golf nearby in Mount Irvine

Tobago / Mount Irvine

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Mahogany Villa is located at Mount Irvine in 2.5 acres of landscaped tropical gardens shared with just four other villas. With lovely views across the award winning golf course and through palm trees to the Caribbean Sea, guests at Mahogany will enjoy the peaceful, secl  …see more

from $293 / night

$2045 / week

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from $293 / night

(8) Very Good 

15

Trinidad and Tobago Vacation villa rental

Tobago / Scarborough

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Villa Sans-Souci is located in the Tobago Plantations Golf, Beach & SPA Resort with its entry and exists controlled by manned security gates.The villa is situated on the 12th fairway of the golf course with its swimming pool, jacuzzi, balconies and manicured gar  …see more

from $275 / night

$1925 - $2765 / week

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from $275 / night

5

Vacation apartment in Castara

Tobago / Castara

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Ask about children
Sunset 2 is a bright & airy self catering studio apartment set in the heart of the fishing village of Castara. Just a short walk from either of the 2 beaches The studio has Caribbean sea views from the queen size double bed & most days you hear the waves kiss the shore  …see more

from $92 / night

$641 / week

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from $92 / night

(1) Excellent 

6

Vacation apartment rental

Tobago / Castara

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Situated next to Heavenly Bay (the smaller of Castara's two beaches), our apartments offer you an escape to paradise. Angel Retreat has eight apartments - each apartment has a two queen size beds with mosquito net, fitted air-conditioning, a large bathroom (with shower)  …see more

from $100 / night

$700 - $1051 / week

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from $100 / night

(12) Very Good 

16

Vacation apartment with swimming pool in Castara

Tobago / Castara

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Situated next to Heavenly Bay (the smaller of Castara's two beaches), our apartments offer you an escape to paradise. Angel Retreat has eight apartments - each apartment has a two queen size beds with mosquito net, fitted air-conditioning, a large bathroom (with shower)  …see more

from $100 / night

$700 - $1051 / week

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from $100 / night

(1) Excellent 

16

Caroni Vacation apartment rental

Trinidad / Caroni

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Spacious 2 bed apt, located in the breezy, serene plains of east/central Trinidad. Only 15 tothe airport, to 4 major shopping malls, educational district of universities and colleges, famous Caroni bird sanctuary and other attractions. 700sq ft. ADDITIONAL SERVICES (Su  …see more

from $100 / night

$700 / week

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from $100 / night

23

Villa rental in Scarborough with swimming pool

Tobago / Scarborough

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Moonlight Mountain is built along traditional lines, it is what is called in the Caribbean a gingerbread house - a reference to the decorative fretwork which adorns the outside. Set in what used to be agricultural land and designed to catch the sea breezes, it has its o  …see more

from $197 / night

$1378 / week

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from $197 / night

(17) Excellent 

12

Vacation villa with swimming pool in Trinidad and Tobago

Tobago / Bon Accord

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Villa Kiskadee has an open-plan sitting room with cable TV, telephone, wifi, CD/radio, well equipped kitchen and a dining area. There is a shaded patio area with additional seating, an outside BBQ area, a utility room (with washing and drying facilities) and a private 3  …see more

from $153 / night

$1080 - $1397 / week

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from $153 / night

20

Vacation apartment in Trinidad and Tobago

Trinidad / Port of Spain

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Car not necessary
Bayville Holiday Apartment is a Tastefully Appointed Self-Contained Apartment and can sleep up to 5 persons, it is fully furnished to a high standard and features One Spacious Air-Conditioned Bedroom, furnished with 2 double beds and one twin bed. The kitchen has 7pc  …see more

from $70 / night

$491 - $1051 / week

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from $70 / night

(2) Excellent 

8

Trinidad / Point Fortin

5 9 2 nights min

  • 5 bedrooms
  • Sleeps 9
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $150 / night

$1050 / week

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from $150 / night

(7) Excellent 

12

Tobago / Parlatuvier

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $175 / night

$1101 / week

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from $175 / night

13

Woodbrook Vacation studio rental

Trinidad / Woodbrook

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Car not necessary
  • Air conditioning
Located in Woodbrook, a historic suburb west of the capital, Port of Spain, Secret Haven TnT is a new, self-catering guest house suitable for business or pleasure. Enjoy independent living in a safe, pleasant, comfortable environment, with en-suite bathroom, kitchenette  …see more

from $45 / night

$280 - $351 / week

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from $45 / night

(2) Excellent 

12

Trinidad / Port of Spain

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from $90 / night

$631 / week

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from $90 / night

4

Tobago / Mount Irvine

4 2 2 nights min

  • 4 bedrooms
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $60 / night

$361 / week

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from $60 / night

(2) Excellent 

21

Trinidad / Arouca

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 39 mi
  • Ask about children

 …see more

from $55 / night

$385 / week

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from $55 / night

22

Vacation villa with swimming pool in Trinidad and Tobago

Tobago / Bon Accord

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.7 mi
  • Swimming pool
Tropical Luxury is located in the beautiful caribbean island of Tobago. Boasting 4 bedrooms, 3 toilet/baths, fully air-conditioned, private pool and jacuzzi, 40" HD LED TV with premium cable, High speed wifi, comfortably accommodating ten persons. On the ground floor o  …see more

from $275 / night

$1801 - $2150 / week

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from $275 / night

(1) Excellent 

24

Villa rental in Trinidad and Tobago with swimming pool, golf nearby

Tobago / Mount Irvine

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
This superb mexican style villa on 3 levels has stunning views over the palm trees to the Golf Course, Pigeon Point, Nylon Pool, Buccoo Reef and the Caribbean Sea. One of just four private villas set in a secluded cul-de-sac above the Mt. Irvine Golf Course it has a l  …see more

from $351 / night

$2451 - $3151 / week

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from $351 / night

(5) Very Good 

19

Tobago / Lambeau

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $300 / night

$2100 - $2800 / week

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from $300 / night

10

Trinidad and Tobago Vacation studio rental

Trinidad / Woodbrook

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 14 mi
  • Car not necessary
  • Air conditioning
Located in Woodbrook, a historic suburb west of the capital, Port of Spain, Secret Haven TnT is a new, self-catering guest house suitable for business or pleasure. Enjoy independent living in a safe, pleasant, comfortable environment, with en-suite bathroom, kitchenette  …see more

from $55 / night

$346 / week

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from $55 / night

(1) Excellent 

10

Villa rental in Black Rock with swimming pool

Tobago / Black Rock

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
RIDGE HOUSE VILLA SITS ON HORSE SHOE RIDGE ABOVE THE VILLAGE OF PLEASANT PROSPECT,WHICH HAS A RESTAURANT,BAR,AND SMALL SUPERMARKET. A SHORT WALK TO THE PALM TREE LINED SANDY BEACH WHERE LEATHERBACK TURTLES COME TO LAY THERE EGGS. IT ALSO HAS A BAR FOR FOOD AND DRINK,B  …see more

from $445 / night

$2667 / week

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from $445 / night

4

Vacation apartment with swimming pool in Trinidad and Tobago

Tobago / Castara

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Situated next to Heavenly Bay (the smaller of Castara's two beaches), our apartments offer you an escape to paradise. Angel Retreat has eight apartments - each apartment has a two queen size beds with mosquito net, fitted air-conditioning, a large bathroom (with shower)  …see more

from $100 / night

$700 - $1051 / week

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from $100 / night

17

Trinidad / Port of Spain

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 22 mi
  • Swimming pool
  • Child friendly

 …see more

from $65 / night

$455 / week

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from $65 / night

(1) Excellent 

5

Trinidad and Tobago Vacation apartment rental

Tobago / Castara

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
Sunset 1 is a bright & airy self catering studio apartment set in the heart of the fishing village of Castara. Just a short walk from either of the 2 beaches The studio has Caribbean sea views from the queen size double bed & most days you hear the waves kiss the shore  …see more

from $92 / night

$641 / week

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from $92 / night

18

Vacation apartment in Trinidad and Tobago

Tobago / Castara

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Tobago is a small paradise! Far away from industry and the usual hustle and bustle, you can enjoy the pure Caribbean joie de vivre. With a rain forest, small and large waterfalls, secluded bays, beautiful beaches, mysterious caves, as well as one of the oldest nature re  …see more

from $65 / night

$436 / week

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from $65 / night

20

Trinidad / Woodbrook

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 19 mi
  • Suitable for children age 5+
  • Car not necessary

 …see more

from $80 / night

$560 / week

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from $80 / night

(2) Excellent 

13

Apartment rental in Black Rock with shared pool

Tobago / Black Rock

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
With fantastic uninterrupted Caribbean sea views, Chaconia is an extremely well furnished, upscale apartment offering immediate access to one of the top beaches on the Island. While sitting on your patio and listening to the sound of the waves, you can enjoy having brea  …see more

from $296 / night

$2032 - $2223 / week

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from $296 / night

8

Woodbrook Vacation studio rental

Trinidad / Woodbrook

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 14 mi
  • Car not necessary
  • Air conditioning
Located in Woodbrook, a historic suburb west of the capital, Port of Spain, Secret Haven TnT is a new, self-catering guest house suitable for business or pleasure. Enjoy independent living in a safe, pleasant, comfortable environment, with en-suite bathroom, kitchenette  …see more

from $45 / night

$285 / week

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from $45 / night