50 Best Trinidad and Tobago Vacation rentals on Holiday Lettings

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

Tobago / Lowlands

2 8 3 nights min

2 bedrooms
Sleeps 8
3 nights min

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

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from $180 / night

$1260 / week

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avg. 3 hours 50 minutes

from $180 / night

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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

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from $293 / night

$2045 / week

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from $293 / night

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Caroni Vacation apartment rental

Trinidad / Caroni

4 10 1 night min

4 bedrooms
Sleeps 10
1 night min

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

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from $200 / night

$1400 / week

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from $200 / night

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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

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from $60 / night

$420 - $1050 / week

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from $60 / night

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Vacation villa with swimming pool, golf nearby in Mount Irvine

Tobago / Mount Irvine

3 7 Min stay varies

3 bedrooms
Sleeps 7
Min stay varies

Beach/lakeside relaxation
Nearest beach 2 mi
Swimming pool

Eternity is a superb 3-bed Caribbean villa, nestled in 1/2 acre of beautiful grounds offering absolute privacy and spectacular panoramic views to the Caribbean. This tastefully decorated villa offers a complete outdoor living experience, combining traditional Caribbean …see more

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from $240 / night

$1600 - $2500 / week

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from $240 / night

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Vacation villa accommodation

Tobago / Goodwood, Tobago

4 8 1 night min

4 bedrooms
Sleeps 8
1 night min

Beach/lakeside relaxation
Swimming pool
Child friendly

Picture yourself on the veranda with a long, cool drink, looking down at your family and friends playing in the pool below you. This is what you can experience if you stay at Hummingbird Villa. It's a four-bedroom luxury accommodation within minutes of some of Tobago's …see more

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from $293 / night

$1982 / week

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from $293 / night

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Trinidad and Tobago Vacation villa rental

Tobago / Scarborough

4 8 Min stay varies

4 bedrooms
Sleeps 8
Min stay varies

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 garden …see more

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from $275 / night

$1925 - $2766 / week

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avg. 3 hours 3 minutes

from $275 / night

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Castara Vacation apartment rental

Tobago / Castara

5 10 3 nights min

5 bedrooms
Sleeps 10
3 nights min

Child friendly
Private garden

Castara Cottage is a bright, airy and charming traditional wooden house located on a headland only two minutes walk away Castara's two beautiful white sand beaches. The house is divided into three spacious and well-equipped apartments that offer a variety of accommodat …see more

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from $70 / night

$490 / week

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from $70 / night

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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

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from $178 / night

$1080 - $1270 / week

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from $178 / night

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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

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from $65 / night

$435 / week

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from $65 / night

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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

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from $100 / night

$700 - $1050 / week

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from $100 / night

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

Tobago / Prospect, Tobago

4 12 2 nights min

4 bedrooms
Sleeps 12
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

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from $280 / night

$1778 / week

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avg. 1 hour 31 minutes

from $280 / night

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“Perfect - Very spacious and excellent views”

Reviewed 9 Mar 2012

We have just returned from our trip to Tobago and stayed in Plantation View Villa which is very spacious and has outstanding views over the Lowlands and Atlantic side of the island. the villa is set w… More

Thank you for letting me know that you enjoyed your stay please come again

“The perfect holiday hideaway”

Reviewed 8 Nov 2011

In September we had a fabulous holiday at Plantation View, there were 4 in our party although the Villa could easily have taken 8 as it was very spacious. Situated on a hillside overlooking the lowlan… More

I am very happy that you enjoyed your vacation at my villa please come again.

“A fabulous relaxing holiday in a spectacular part of the world.”

Reviewed 7 Oct 2014

Villa in fabulous elevated private location, with fantastic views out over the Atlantic Coast line during the day time, and constantly changing night time views of the low lands. The villa is spaciou… More

Hi thank you for your review . I am glad you enjoyed your stay and the villa . I would look forward to you retuning for another stay . Regards Barry

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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

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from $197 / night

$1378 / week

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Responds fast!
avg. 3 hours 16 minutes

from $197 / night

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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

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from $400 / night

$2800 / week

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from $400 / night

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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 mins walk …see more

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from $191 / night

$1143 - $1677 / week

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avg. 3 hours 19 minutes

from $191 / night

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Vacation home with swimming pool in Trinidad and Tobago

Tobago / Scarborough

5 10 2 nights min

5 bedrooms
Sleeps 10
2 nights min

Beach/lakeside relaxation
Nearest beach 3 mi
Swimming pool

Windy Edge was designed and built by a former US ambassador to Japan and it is still known on the island as the Ambassador's House. Set on the top of Cinnamon Hill, it has sensational views over the Caribbean and Atlantic seas and catches the cooling breezes, unlike man …see more

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from $254 / night

$1524 / week

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from $254 / night

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“An ideal family getaway that isn't far away”

Reviewed 3 Sep 2013

Spacious yet cozy, a place where you can be noisy without disturbing the peace or find a secluded spot whilst everyone else is partying. We had a large group and everyone was comfortably accommodated.… More

Glad to hear you enjoyed your stay, sadly Goldie is no longer with us. Come back soon.

“Stunning location”

Reviewed 3 Jan 2013

Fantastic garden and so many beautiful plants and flowers. I learnt a lot about palm trees and their magnificent fronds as well as all the exotic plants. The housekepper is simply superb and really c… More

These guests obviously had a great time, their comments were complimentary, they genuinely seem to have loved the place and would recommend it to others; I am disappointed that they only gave us 3 stars, where did we go wrong?

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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

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from $100 / night

$700 - $1050 / week

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from $100 / night

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

Tobago / Prospect, Tobago

7 14 2 nights min

7 bedrooms
Sleeps 14
2 nights min

Beach/lakeside relaxation
Nearest beach 1 mi
Swimming pool

Villa Petrus is a luxury Caribbean villa in Tobago, built in the plantation style, with outstanding facilities that accommodate up to 14 with ease, set in beautiful 2-acre grounds that include a 22 metre pool. Villa Petrus provides a luxurious serviced venue for family …see more

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from $1157 / night

$8099 / week

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from $1157 / night

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Villa rental in Trinidad and Tobago

Tobago / Buccoo

4 12 3 nights min

4 bedrooms
Sleeps 12
3 nights min

Nearest beach 0.2 mi
Child friendly
Car not necessary

Ocean View villa is a two story 3000 square foot charming villa located at the end of a quiet street overlooking the Caribbean sea.The ground floor is built on the open area concept and has a kitchen complete with fridge,stove,toaster,microwave, coffee maker,cutlery and …see more

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from $155 / night

$1000 / week

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Responds fast!
avg. 1 hour 11 minutes

from $155 / night

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Vacation apartment rental

Tobago / Black Rock

1 2 Min stay varies

1 bedroom
Sleeps 2
Min stay varies

Beach/lakeside relaxation
Nearest beach 0.5 mi
Air conditioning

Clair Matin has a spacious air conditioned bedroom with a large king size bed and an equally spacious en suite shower room with a hairdryer. Living and kitchen/dining room with fully equipped kitchen. Laundry area with washer and dryer, remote control a/c unit and ce …see more

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from $102 / night

$635 / week

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Responds fast!
avg. 3 hours 1 minutes

from $102 / night

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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 mins walk o …see more

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from $191 / night

$1143 - $1677 / week

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Responds fast!
avg. 3 hours 19 minutes

from $191 / night

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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
Child friendly

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

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from $50 / night

$700 - $1050 / week

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from $50 / night

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Vacation villa with swimming pool in Trinidad and Tobago

Tobago / Bon Accord

4 10 Min stay varies

4 bedrooms
Sleeps 10
Min stay varies

Beach/lakeside relaxation
Nearest beach 0.7 mi
Swimming pool

ANGELFISHTOBAGO 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 …see more

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from $255 / night

$1400 - $2000 / week

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Responds fast!
avg. 39 minutes

from $255 / night

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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

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from $483 / night

$3379 / week

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from $483 / night

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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 the Car …see more

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from $99 / night

$693 / week

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from $99 / night

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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

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from $73 / night

$507 - $641 / week

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Responds fast!
avg. 2 hours 39 minutes

from $73 / night

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Vacation home in Trinidad and Tobago

Trinidad / Port of Spain

1 3 4 nights min

1 bedroom
Sleeps 3
4 nights min

Air conditioning

no thing to say, Travellers look for specific criteria when searching for a home, so take the time to fill out as many details here as you canTravellers look for specific criteria when searching for a home, so take the time to fill out as many details here as you canTra …see more

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from $299 / night

$2090 / week

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from $299 / night

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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

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from $40 / night

$250 - $346 / week

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Responds fast!
avg. 2 hours 55 minutes

from $40 / night

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Caroni Vacation apartment rental

Trinidad / Caroni

2 6 1 night min

2 bedrooms
Sleeps 6
1 night min

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

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from $100 / night

$700 / week

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from $100 / night

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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
Child friendly

Situated next to Heavenly Bay (the smaller of Castara's two beaches), our apartments offer you an escape to paradise. Our apartment Raster Man is on our 2nd floor. Locals and tourists share the restaurants, cafes and bars, and there are many shops in the village selling …see more

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from $100 / night

$700 - $1050 / week

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from $100 / night

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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

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from $45 / night

$285 / week

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Responds fast!
avg. 2 hours 55 minutes

from $45 / night

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Vacation villa with swimming pool in Trinidad and Tobago

Tobago / Bon Accord

3 8 Min stay varies

3 bedrooms
Sleeps 8
Min stay varies

Beach/lakeside relaxation
Nearest beach 0.5 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

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from $185 / night

$1300 - $1800 / week

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from $185 / night

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“What a Gem!”

Reviewed 4 Feb 2012

We have just arrived back from 2 weeks at Villa Kiskadee, and are already looking for dates to return! Firstly the communication between the owner Steve, and ourselves was always prompt, friendly a… More

“Great vacation at Villa kiskadee (tobago)”

Reviewed 5 Oct 2011

This is our second stay at Villa Kiskadee, stayed in 2010 & 2011. This villa exceeded our expectations, it was very clean and very safe (alarm system with rapid arm response), the property manager (Di… More

“The best villa I've rented in Tobago”

Reviewed 13 Apr 2015

The villa is situated near to Crown Point and is located close to two of Tobago's best beaches. The villa is beautifully decorated and incredibly comfortable. It suited myself, my mum and my two child… More

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Vacation apartment rental

Tobago / Castara

1 2 7 nights min

1 bedroom
Sleeps 2
7 nights min

Beach/lakeside relaxation
Nearest beach 0.2 mi
Ask about children

The Green Room is the first bedroom of "OurPlace" the 2 bedroomed apartment upstairs. When we are not in residence you have the sole use of the fully equipped kitchen, open plan lounge area & 48' x 10' veranda with an amazing view across Castara bay. Perfect for Al fres …see more

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from $120 / night

$838 - $1015 / week

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Responds fast!
avg. 2 hours 39 minutes

from $120 / night

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Vacation home in Scarborough

Tobago / Scarborough

3 6 3 nights min

3 bedrooms
Sleeps 6
3 nights min

Nearest beach 5 mi
Child friendly
Air conditioning

The Bougainville Guest-House is located in a quiet breezy cul-de-sac with open views. The property is fenced, gated and is centrally located between the main town, scarborough and some of the most popular beaches on the Island. There are also a number of restaurants …see more

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from $134 / night

$934 / week

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from $134 / night

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Vacation apartment in Caroni

Trinidad / Caroni

2 4 1 night min

2 bedrooms
Sleeps 4
1 night min

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

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from $100 / night

$700 / week

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from $100 / night

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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

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from $350 / night

$2450 - $3150 / week

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from $350 / night

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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

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from $70 / night

$490 - $910 / week

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from $70 / night

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Apartment rental in Black Rock with shared pool

Tobago / Black Rock

3 6 Min stay varies

3 bedrooms
Sleeps 6
Min stay varies

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

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from $331 / night

$2032 / week

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from $331 / night

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Vacation apartment rental

Tobago / Castara

2 4 5 nights min

2 bedrooms
Sleeps 4
5 nights min

Beach/lakeside relaxation
Nearest beach 0.2 mi
Child friendly

Sandcastles is ideally situated just above the idyllic fishing village of Castara in Tobago and is ideally suited to the discerning family, or couples with good taste. If you have an eye for beauty and a love of nature we offer the option of a 2-bedroom apartment …see more

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from $150 / night

$1050 / week

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from $150 / night

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Caroni Vacation home rental

Trinidad / Caroni

5 3 1 night min

5 bedrooms
Sleeps 3
1 night min

Child friendly
Air conditioning
Pet friendly

Hostal Groning is located in the beautiful city of Trinidad , the third village founded in Cuba by Diego Velázquez in 1514. In 1988 , UNESCO inscribed in the World Heritage List the Old Town and the “Valle de los Ingenios” . This small town, located in the heart of Cuba …see more

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from $34 / night

$201 / week

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from $34 / night

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

Price per day

Bedrooms

Bathrooms

Location

Property type

Activities

Facilities

Suitability

259 Vacation rentals

“Tranquility in Paradise”

“Perfect - Very spacious and excellent views”

“The perfect holiday hideaway”

“A fabulous relaxing holiday in a spectacular part of the world.”

“An ideal family getaway that isn't far away”

“Stunning location”

“What a Gem!”

“Great vacation at Villa kiskadee (tobago)”

“The best villa I've rented in Tobago”

What is Certificate of Excellence?