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

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361 Vacation rentals

(1) Excellent 

19

Vacation apartment in Caroni

Trinidad / Caroni

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 25 mi
  • Child friendly
  • Car not necessary
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 $110 / night

$770 / week

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from $110 / night

5

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 - $1,050 / week

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from $100 / night

(7) Excellent 

Certificate of Excellence

26

Trinidad and Tobago Vacation villa rental

Tobago / Lowlands

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.48 mi
  • Swimming pool
This luxurious villa is situated on an 18-hole PGA championship golf course in the Hilton International Beach, Golf & SPA Resort, Tobago. The colonial style architecture and furniture create a unique tropical ambience. Large living areas with unique wooden furnishings …see more

Certificate of Excellence

from $295 / night

$2,065 / week

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Responds fast!
avg. 2 hours 36 minutes

from $295 / night

(3) Excellent 

17

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

from $105 / night

$731 - $1,005 / week

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from $105 / night

(9) 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, whirlpool, balconies and manicured garden l …see more

from $295 / night

$2,065 / week

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Responds fast!
avg. 2 hours 36 minutes

from $295 / night

(1) Excellent 

14

Caroni Vacation apartment rental

Trinidad / Caroni

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 25 mi
  • Child friendly
  • Car not necessary
Spacious 3 bed apt, located in the breezy, serene plains of east/central Trinidad. Only 15 minutes to the airport, to 4 major shopping malls, educational district of universities and colleges, 5 minutes from the famous Caroni bird sanctuary and other attractions. 700sq …see more

from $150 / night

$1,050 / week

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from $150 / night

(12) 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 the Car …see more

from $99 / night

$693 / week

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from $99 / night

18

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

from $301 / night

$2,039 / week

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from $301 / night

(1) Excellent 

24

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

Tobago / Mount Irvine

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • 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 $300 / night

$2,100 / week

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from $300 / night

(21) Excellent 

24

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

from $262 / night

$1,568 / week

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from $262 / night

(18) 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 $50 / night

$350 - $1,050 / week

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from $50 / night

(33) Very Good 

23

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

from $236 / night

$1,699 - $1,830 / week

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Responds fast!
avg. 1 hour 17 minutes

from $236 / night

(23) Very Good 

18

Vacation villa with swimming pool in Trinidad and Tobago

Tobago / Mount Irvine

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • 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 $301 / night

$2,105 / week

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from $301 / night

(2) Excellent 

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

$490 - $910 / week

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from $70 / night

(20) Excellent 

0

Trinidad and Tobago Vacation villa rental

Castara / Englishman's Bay

4 8 min stay varies

  • 4 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. In bet …see more

from $149 / night

$1,046 - $1,895 / week

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from $149 / night

(2) Excellent 

12

Vacation villa rental

Tobago / Black Rock

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Located on Tobago's Caribbean coast, the spacious villas are nestled in the Grafton Bird Sanctuary with views of the sea through the beautiful landscaping. Walking distance to top restaurants and Bars. Daily Villa Attendant service allows total relaxation. Our friendly …see more

from $536 / night

$3,752 / week

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from $536 / night

(3) Very Good 

23

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 $497 / night

$3,476 / week

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from $497 / night

(3) Very Good 

14

Vacation apartment in Castara

Tobago / Castara

1 3 5 nights min

  • 1 bedroom
  • sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
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 $66 / night

$457 - $639 / week

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from $66 / night

(8) Excellent 

43

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

from $275 / night

$1,850 - $2,180 / week

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Responds fast!
avg. 1 hour 59 minutes

from $275 / night

(22) Very Good 

20

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 $183 / night

$1,111 / week

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from $183 / night

15

Vacation home rental

Tobago / Goodwood, Tobago

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Suitable for children age 5+
Lovell House is a two-storey modern house in the quiet part of the island. All rooms are balconies with stunning views of the sea. In only a few minutes walk you reach the beach on a gravel road... The House offers a pleasant comfort and is attached to the House of the …see more

from $127 / night

$861 / week

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from $127 / night

8

Vacation private room in Trinidad and Tobago

Tobago / Scarborough

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
We are perfectly located a mere few minutes drive away from the main transport hub and the Ferry Terminal (in the Island's Capital) and just about 15 drive minutes from the International Airport. Beaches, restaurants, bars and nightlife are all only a short distance awa …see more

from $17 / night

$119 / week

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Responds fast!
avg. 58 minutes

from $17 / night

(3) Very Good 

19

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

from $1,157 / night

$8,099 / week

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from $1,157 / night

(1) Excellent 

13

Vacation apartment in Carnbee

Tobago / Carnbee

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Beautiful, newly built apartments on suite bathroom, living room/kitchen, attached to a private residential house situated in a quiet green area. New furniture, full kitchen, spacious bathroom, cable TV, WiFi, AC in bedroom, poarch. Tropical garden with many fruits tree …see more

from $65 / night

$455 / week

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from $65 / night

(18) Excellent 

12

Vacation villa with swimming pool in Trinidad and Tobago

Tobago / Bacolet Bay

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sea Breeze is a stunning private villa situated by the sea in one of the most sought after locations on the island of Tobago with outstanding views and a peaceful sense of space. A wide veranda along two sides of the house provides a scenic 180° view of the ocean. The v …see more

from $346 / night

$2,419 - $3,023 / week

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from $346 / night

(9) Very Good 

32

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

from $220 / night

$1,450 - $2,350 / week

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from $220 / night

7

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

from $100 / night

$700 - $1,050 / week

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from $100 / night

(16) Excellent 

15

Vacation villa in Mount Pleasant

Tobago / Mount Pleasant

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • 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 en-suites. There is a spacious sitting room with cable TV and french doors leading onto the veranda. …see more

from $350 / night

$2,130 / week

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from $350 / night

(2) Very Good 

12

Vacation apartment in Caroni

Trinidad / Caroni

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 25 mi
  • Child friendly
  • Car not necessary
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 $110 / night

$770 / week

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from $110 / night

6

Trinidad and Tobago Vacation guest house rental

Port of Spain / St. Ann's

4 2 3 nights min

  • 4 bedrooms
  • sleeps 2
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Tennille's Guest House has a large bar beneath the property that serves food and drinks. There are many eateries and bars nearby if you want other cuisines. St Ann's road is very close to the Carnival Road and is popular for Carnival goers. We have a housekeeper availab …see more

from $111 / night

$778 / week

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from $111 / night

33

Vacation apartment rental

Trinidad / Couva

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Brand new apartment inside the gated community of Savonetta Estate, just completed in March 2018. There are 3 apartments, all of them are 1600sqft, 2 bedrooms, 2 1/2 bathrooms, fully furnished, stainless steel appliances, washer/dryer, storage, cable, high speed interne …see more

from $90 / night

$630 / week

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from $90 / night

(2) Very Good 

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 - $1,050 / week

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from $100 / night

9

Vacation private room in Trinidad and Tobago

Tobago / Signal Hill

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
We are perfectly located a mere few minutes drive away from the main transport hub and the Ferry Terminal (in the Island's Capital) and just about 15 drive minutes from the International Airport. Beaches, restaurants, bars and nightlife are all only a short distance awa …see more

from $25 / night

$174 / week

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Responds fast!
avg. 58 minutes

from $25 / night

25

Vacation apartment in Couva

Trinidad / Couva

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Air conditioning
Brand new apartment, just completed in March 2018..... There are 3 apartments, all of them are 1600sqft, 2 storeys, 2 bedrooms, 2 1/2 bathrooms, fully furnished, stainless steel appliance, bose speaker, (2) 50inch flat screen TV's, swimming pool, keypad entry, washer/dr …see more

from $90 / night

$630 / week

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from $90 / night

(2) Good 

9

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

from $100 / night

$700 - $1,050 / week

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from $100 / night

9

Vacation apartment in Trinidad and Tobago

Trinidad / Piarco

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
Piarco Studio Apartment furnished A/C Hot water, WIFI Laundry room, ample parking gated compound very close to the Airport. 5 minutes from Trincity Mall and 1 minute to the Airport. Ask for our Special rates for longer stays. Car rental, taxi service and site seen …see more

from $70 / night

$490 / week

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from $70 / night

(1) Excellent 

26

Vacation apartment accommodation

Tobago / Castara

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Private garden
Castara Cottage is an open, natural style Caribbean house situated in Castara, Tobago. The split-level house offers flexible and comfortable, holiday rental accommodation in three private self-catering apartments - Tamarind, Saffron and Cinnamon. Each apartment is d …see more

from $90 / night

$630 / week

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from $90 / night

(10) Excellent 

25

Vacation villa with golf nearby in Trinidad and Tobago

Tobago / Mount Irvine

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
Mahogany Villa is situated at the prime location of 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 …see more

from $151 / night

$1,046 - $2,287 / week

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Responds fast!
avg. 3 hours 45 minutes

from $151 / night

(3) Excellent 

18

Mayaro Vacation home rental

Trinidad / Mayaro

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 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

from $98 / night

$654 - $928 / week

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Responds fast!
avg. 1 hour 4 minutes

from $98 / night

(2) Good 

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 $203 / night

$1,418 / week

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Responds fast!
avg. 3 hours 17 minutes

from $203 / night