50 Best Trinidad and Tobago Houses and Villas – Holiday Lettings - Holiday Rentals Trinidad and Tobago

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197 Holiday homes

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(7) Excellent 

1 / 12

Holiday chalet with swimming pool in Trinidad and Tobago

Tobago / Parlatuvier

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay

from $177 / night

$1108 / week

Book Book View

from $177 / night

(1) Excellent 

1 / 6

Trinidad and Tobago holiday b&b rental

Trinidad / Port of Spain

5 bedroomsSleeps 153 nights min stay

  • 5 bedrooms
  • Sleeps 15
  • 3 nights min stay

from $126 / night

$882 - $8282 / week

Book Book View

from $126 / night

(12) Excellent 

1 / 7

Trinidad and Tobago holiday villa rental

Tobago / Charlotteville

5 bedroomsSleeps 83 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $303 / night

$2014 / week

Book Book View

from $303 / night

(1) Excellent 

1 / 5

Holiday b&b in Trinidad

Trinidad / Port of Spain

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay

from $126 / night

$882 - $1410 / week

Book Book View

from $126 / night

(2) Excellent 

1 / 24

Holiday villa with swimming pool in Trinidad and Tobago

Tobago / Scarborough

4 bedroomsSleeps 85 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min stay

from $882 / night

$6168 - $10199 / week

Book Book View

from $882 / night

(2) Very Good 

1 / 13

Holiday b&b in Trinidad

Trinidad / Port of Spain

5 bedroomsSleeps 201 night min stay

  • 5 bedrooms
  • Sleeps 20
  • 1 night min stay

from $66 / night

$459 - $5146 / week

Book Book View

from $66 / night

(2) Very Good 

1 / 10

Apartment letting in Trinidad and Tobago

Caribbean / Trinidad and Tobago

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $111 / night

$677 / week

Book Book View

from $111 / night

(2) Very Good 

1 / 28

Apartment rental in Trinidad

Trinidad / Chaguanas

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $91 / night

$655 - $1410 / week

Book Book View

from $91 / night

(1) Excellent 

1 / 31

Holiday apartment in Trinidad and Tobago

Trinidad / Arima

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $101 / night

$705 - $1974 / week

Book Book View

from $101 / night

(6) Excellent 

1 / 96

Villa accommodation in Trinidad and Tobago with swimming pool

Tobago / Arnos Vale

3 bedroomsSleeps 103 nights min stay

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min stay

from $745 / night

$3721 / week

Book Book View

from $745 / night

(3) Excellent 

1 / 14

Trinidad holiday apartment rental

Trinidad / Port of Spain

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $91 / night

$705 / week

Book Book View

from $91 / night

(7) Excellent 

1 / 12

Holiday villa with swimming pool in Trinidad and Tobago

Tobago / Bacolet Bay

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $554 / night

$3021 - $4229 / week

Book Book View

from $554 / night

(3) Excellent 

1 / 19

Holiday villa rental

Tobago / Lambeau

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $303 / night

$2115 - $2820 / week

Book Book View

from $303 / night

1 / 47

Holiday home rental

Trinidad / Chaguanas

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $81 / night

$705 - $1058 / week

Book Book View

from $81 / night

(7) Very Good 

1 / 75

Villa rental in Tobago with swimming pool

Trinidad and Tobago / Tobago

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $212 / night

$1410 - $1561 / week

Book Book View

from $212 / night

1 / 32

Trinidad and Tobago holiday apartment rental

Trinidad / San Fernando

3 bedroomsSleeps 102 nights min stay

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min stay

from $174 / night

$0 / week

Book Book View

from $174 / night

(1) Excellent 

1 / 9

Holiday apartment in Trinidad

Trinidad / Port of Spain

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $96 / night

$705 / week

Book Book View

from $96 / night

(2) Very Good 

1 / 8

Holiday apartment in Trinidad and Tobago

Tobago / Castara

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $125 / night

$869 / week

Book Book View

from $125 / night

(16) Excellent 

1 / 20

Trinidad and Tobago holiday villa rental

Castara / Englishman's Bay

5 bedroomsSleeps 84 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 4 nights min stay

from $249 / night

$1752 / week

Book Book View

from $249 / night

(3) Excellent 

1 / 47

Holiday villa in Trinidad

Trinidad / Diego Martin

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $292 / night

$2014 / week

Book Book View

from $292 / night

1 / 21

Holiday apartment in Trinidad

Trinidad / Woodbrook

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $101 / night

$705 - $1763 / week

Book Book View

from $101 / night

(3) Very Good 

1 / 51

Tobago holiday apartment rental

Tobago / Castara

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $121 / night

$846 / week

Book Book View

from $121 / night

(7) Very Good 

1 / 15

Trinidad and Tobago holiday villa rental

Tobago / Scarborough

4 bedroomsSleeps 82 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $277 / night

$1939 - $2785 / week

Book Book View

from $277 / night

(1) Very Good 

1 / 15

Trinidad and Tobago holiday villa accommodation

Trinidad / Chaguanas

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $76 / night

$504 - $882 / week

Book Book View

from $76 / night

(8) Very Good 

1 / 32

Holiday villa with swimming pool, golf nearby in Tobago

Tobago / Mount Irvine

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $242 / night

$1612 - $2820 / week

Book Book View

from $242 / night

(6) Very Good 

1 / 23

Holiday home in Tobago

Tobago / Crown Point

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $86 / night

$0 / week

Book Book View

from $86 / night

(1) Excellent 

1 / 12

Trinidad and Tobago holiday apartment rental

Trinidad / Port of Spain

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $91 / night

$635 / week

Book Book View

from $91 / night

(2) Excellent 

1 / 18

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

Tobago / Grafton

4 bedroomsSleeps 81 night min stay

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay

from $333 / night

$2211 / week

Book Book View

from $333 / night

1 / 7

Trinidad and Tobago holiday home rental

Port of Spain / St. Ann's

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $150 / night

$939 / week

Book Book View

from $150 / night

(5) Excellent 

1 / 10

Townhouse rental in Tobago with shared pool

Tobago / Bon Accord

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay

from $162 / night

$907 / week

Book Book View

from $162 / night

1 / 20

Apartment rental in Trinidad

Trinidad / San Fernando

3 bedroomsSleeps 102 nights min stay

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min stay

from $174 / night

$0 / week

Book Book View

from $174 / night

(1) Excellent 

1 / 10

Holiday villa in Trinidad and Tobago

Tobago / Prospect, Tobago

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $219 / night

$1314 - $1898 / week

Book Book View

from $219 / night

1 / 11

Holiday guest house in Trinidad and Tobago

Tobago / Bon Accord

8 bedroomsSleeps 292 nights min stay

  • 8 bedrooms
  • Sleeps 29
  • 2 nights min stay

from $66 / night

$459 - $6168 / week

Book Book View

from $66 / night

(1) Excellent 

1 / 16

Trinidad and Tobago holiday villa rental

Trinidad / Matura

4 bedroomsSleeps 84 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min stay

from $511 / night

$3066 / week

Book Book View

from $511 / night

(15) Very Good 

1 / 21

Tobago holiday villa rental

Tobago / Bacolet Bay

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $205 / night

$1241 - $1460 / week

Enquire Enquire View

from $205 / night

(11) Excellent 

1 / 12

Holiday villa in Tobago

Tobago / Buccoo

4 bedroomsSleeps 82 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $403 / night

$2518 / week

Enquire Enquire View

from $403 / night

(12) Very Good 

1 / 24

Holiday villa with swimming pool in Trinidad and Tobago

Tobago / Lambeau

3 bedroomsSleeps 10Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies

from $252 / night

$1612 - $2216 / week

Book Book View

from $252 / night

(7) Excellent 

1 / 18

Holiday villa with swimming pool in Trinidad and Tobago

Tobago / Mount Irvine

4 bedroomsSleeps 12Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies

from $336 / night

$2351 / week

Book Book View

from $336 / night

(9) Excellent 

1 / 14

Holiday home in Tobago

Tobago / Scarborough

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $91 / night

$564 - $705 / week

Book Book View

from $91 / night

1 / 53

Trinidad holiday villa rental

Trinidad / Arouca

4 bedroomsSleeps 101 night min stay

  • 4 bedrooms
  • Sleeps 10
  • 1 night min stay

from $177 / night

$0 / week

Book Book View

from $177 / night

Trinidad and Tobago offer completely different experiences of the Caribbean, small Tobago is laid back and scarcely developed, often called the pearl of the Caribbean, while Trinidad is thriving and busy. Both islands have wonderful beaches, while cosmopolitan Trinidad buzzes with festivals, mostly centred on the capital Port of Spain, Tobago is unspoilt and tranquil.

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