50 Best Tobago Villas on Holiday Lettings - Vacation rentals

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Castara
37 properties
Estates Black Rock
30 properties
Crown Point
25 properties
Scarborough
19 properties
Buccoo
12 properties
Villas Bon Accord
10 properties
Mount Irvine
10 properties
Lowlands
9 properties
Canaan
7 properties
Signal Hill
7 properties
Black Rock
5 properties

Tobago

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218 Vacation rentals

(19) Excellent 

20

Castara 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. …see more

from $152 / night

$1,063 - $1,927 / week

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from $152 / night

(1) Very Good 

17

Villa rental in Buccoo

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

from $155 / night

$1,000 / week

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Responds fast!
avg. 3 hours 33 minutes

from $155 / night

(33) Very Good 

23

Vacation villa with swimming pool, golf nearby in Prospect, 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 $293 / night

$1,860 / week

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Responds fast!
avg. 2 hours 5 minutes

from $293 / 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 $505 / night

$3,534 / week

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from $505 / night

(21) Excellent 

24

Vacation home with swimming pool in Scarborough

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 $266 / night

$1,595 / week

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from $266 / night

(21) Very Good 

18

Vacation villa with swimming pool in Mount Irvine

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 $305 / night

$2,134 / week

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from $305 / night

(19) Excellent 

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 $186 / night

$1,130 / week

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from $186 / night

(18) Excellent 

12

Vacation villa with swimming pool in Bon Accord

Tobago / Bon Accord

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • 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

from $185 / night

$1,300 - $2,030 / week

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from $185 / night

(8) Excellent 

43

Vacation villa with swimming pool in Bon Accord

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 - $2,150 / week

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Responds fast!
avg. 1 hour 59 minutes

from $275 / night

(3) Excellent 

16

Condo rental in Arnos Vale

Tobago / Arnos Vale

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 4 mi
  • Child friendly
  • Air conditioning
Le Caprice is a bright and sunny condominium located away from the hustle and bustle yet within easy reach of Tobago's tourist stretch in the Bon Accord area. It is 5 minutes away from Turtle Beach which offers turtle watching activiites and 7 minutes away from Mt. Irvi …see more

from $75 / night

$525 / week

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Responds fast!
avg. 3 hours 16 minutes

from $75 / night

17

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

from $140 / night

$976 / week

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from $140 / night

(2) Excellent 

12

Vacation villa rental

Tobago / Black Rock

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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 $550 / night

$3,850 / week

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from $550 / night

(5) Excellent 

26

Lowlands 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

from $295 / night

$2,065 / week

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Responds fast!
avg. 2 hours 22 minutes

from $295 / 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

5

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 - $1,050 / week

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from $100 / 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 $206 / night

$1,442 / week

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from $206 / night

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

(2) Good 

9

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
  • 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

(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 $67 / night

$465 - $651 / week

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from $67 / 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 $128 / night

$871 / week

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from $128 / night

(8) Excellent 

25

Vacation villa with golf nearby in Mount Irvine

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 $240 / night

$1,329 - $2,325 / week

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from $240 / 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

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 $306 / night

$2,073 / week

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from $306 / 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 $100 / night

$700 - $1,050 / week

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from $100 / night

(14) 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 $380 / night

$2,130 / week

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from $380 / 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 $106 / night

$743 - $1,021 / week

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from $106 / night

(7) Excellent 

13

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

from $350 / night

$2,126 / week

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from $350 / night

7

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
  • 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

(1) Excellent 

24

Villa rental in Mount Irvine 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

(9) Very Good 

15

Scarborough 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 22 minutes

from $295 / night

10

Vacation private room in Scarborough

Tobago / Scarborough

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
We are perfectly located 5 minutes away from the Ferry Terminal (in the Island's Capital) and 15 minutes from the International Airport. Beaches, restaurants, bars and nightlife are all only a short distance away. You’ll love our place which we refer to as our Sanctuary …see more

from $23 / night

$158 / week

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from $23 / night

9

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

from $150 / night

$1,050 / week

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from $150 / night

(1) Excellent 

23

Vacation apartment in Castara

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 …see more

from $110 / night

$770 / week

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from $110 / night

(2) Very Good 

19

Vacation villa with swimming pool, golf nearby in Prospect, 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

11

Vacation private room in Signal Hill

Tobago / Signal Hill

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
We are perfectly located 5 minutes away from the Ferry Terminal (in the Island's Capital) and 15 minutes from the International Airport. Beaches, restaurants, bars and nightlife are all only a short distance away. You’ll love our place which we refer to as our Sanctuary …see more

from $26 / night

$177 / week

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from $26 / night

12

Villa rental in Black Rock with shared pool

Tobago / Black Rock

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A well-equipped and spacious modern colonial design house, light and airy, with views to the sea. The villa sleeps 6 people in 3 air-conditioned double bedrooms all en-suite. There are living and dining areas inside and outside on the terraces. All rooms have ceiling …see more

from $113 / night

$791 / week

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from $113 / night

10

Vacation private room accommodation

Tobago / Signal Hill

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
We are perfectly located 5 minutes away from the Ferry Terminal (in the Island's Capital) and 15 minutes from the International Airport. Beaches, restaurants, bars and nightlife are all only a short distance away. You’ll love our place which we refer to as our Sanctuary …see more

from $34 / night

$232 / week

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from $34 / night

(5) Excellent 

14

Castara Vacation apartment rental

Tobago / Castara

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
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 $67 / night

$468 - $655 / week

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from $67 / night

9

Vacation private room in Signal Hill

Tobago / Signal Hill

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
We are perfectly located 5 minutes away from the Ferry Terminal (in the Island's Capital) and 15 minutes from the International Airport. Beaches, restaurants, bars and nightlife are all only a short distance away. You’ll love our place which we refer to as our Sanctuary …see more

from $26 / night

$177 / week

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from $26 / night