50 Best Caribbean Villas and Estates – Holiday Lettings - Holiday Rentals Caribbean

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20,469 Holiday homes

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(26) Very Good 

1 / 45

Villa rental in Sosua with swimming pool

Puerto Plata Province / Sosua

5 bedroomsSleeps 123 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min stay

from $211 / night

$1225 / week

Book Book View

from $211 / night

(8) Excellent 

1 / 32

Holiday villa in Ocho Rios

Saint Ann Parish / Ocho Rios

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $151 / night

$1050 - $1400 / week

Book Book View

from $151 / night

(18) Excellent 

1 / 27

Holiday apartment with shared pool in Grand Cayman

Cayman Islands / Grand Cayman

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $191 / night

$1331 - $1925 / week

Book Book View

from $191 / night

Featured properties

(6) Excellent 

1 / 38

Holiday villa in St. John

US Virgin Isles / St. John

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $343 / night

$2401 - $3240 / week

Book Book View

from $343 / night

(4) Excellent 

1 / 19

Holiday beach hut rental

Puerto Rico / Naguabo

4 bedroomsSleeps 107 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay

from $300 / night

$2100 / week

Book Book View

from $300 / night

(26) Excellent 

1 / 23

Holiday villa rental

Puerto Rico / Rincon

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $296 / night

$2000 - $3250 / week

Book Book View

from $296 / night

(6) Excellent 

1 / 26

Holiday apartment with golf nearby in Rio Grande

Puerto Rico / Rio Grande

2 bedroomsSleeps 64 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min stay

from $300 / night

$2000 / week

Book Book View

from $300 / night

(11) Excellent 

1 / 17

Holiday home with swimming pool in Willikies

Willikies / The Peninsula

3 bedroomsSleeps 65 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min stay

from $256 / night

$2592 - $2913 / week

Book Book View

from $256 / night

(1) Excellent 

1 / 27

Bavaro holiday apartment rental

Punta Cana / Bavaro

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $296 / night

$2066 / week

Book Book View

from $296 / night

(6) Excellent 

1 / 73

Villa rental in Ocho Rios with shared pool

Saint Ann Parish / Ocho Rios

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $119 / night

$0 / week

Book Book View

from $119 / night

(6) Excellent 

1 / 22

The Valley holiday home rental

Anguilla / The Valley

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $226 / night

$1309 - $1975 / week

Book Book View

from $226 / night

(5) Excellent 

1 / 11

Holiday apartment in Sainte-Anne

Grande-Terre Island / Sainte-Anne

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $177 / night

$1239 / week

Book Book View

from $177 / night

(20) Very Good 

1 / 93

Holiday villa in Ocho Rios

Saint Ann Parish / Ocho Rios

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $151 / night

$951 - $1001 / week

Book Book View

from $151 / night

(22) Excellent 

1 / 32

Bequia holiday villa rental

St. Vincent and the Grenadines / Bequia

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies

from $200 / night

$1400 - $18000 / week

Book Book View

from $200 / night

(16) Excellent 

1 / 18

Home rental in Sainte-Anne with shared pool

Grande-Terre Island / Sainte-Anne

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $177 / night

$1206 - $1759 / week

Book Book View

from $177 / night

(18) Very Good 

1 / 23

Holiday home in Santa Barbara de Samana

Samana Province / Santa Barbara de Samana

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $175 / night

$1050 - $1470 / week

Book Book View

from $175 / night

(3) Excellent 

1 / 12

Home rental in Island Harbour

Anguilla / Island Harbour

4 bedroomsSleeps 103 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay

from $326 / night

$0 / week

Book Book View

from $326 / night

(4) Excellent 

1 / 27

Holiday apartment rental

Saint Michael Parish / Bridgetown

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $151 / night

$1050 - $1856 / week

Book Book View

from $151 / night

1 / 71

Holiday apartment with shared pool in Montego Bay

Saint James Parish / Montego Bay

3 bedroomsSleeps 82 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $501 / night

$3001 / week

Book Book View

from $501 / night

(24) Very Good 

1 / 33

East End holiday apartment rental

St. Thomas / East End

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $226 / night

$1575 - $2066 / week

Book Book View

from $226 / night

(18) Excellent 

1 / 38

Villa rental in Christiansted with swimming pool, golf nearby

St. Croix / Christiansted

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay

from $256 / night

$1792 / week

Book Book View

from $256 / night

(10) Very Good 

1 / 12

Home rental in Ponce

Puerto Rico / Ponce

4 bedroomsSleeps 102 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min stay

from $99 / night

$674 - $1724 / week

Book Book View

from $99 / night

(29) Excellent 

1 / 47

Freeport holiday apartment rental

Grand Bahama Island / Freeport

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $196 / night

$1201 - $2051 / week

Book Book View

from $196 / night

(8) Excellent 

1 / 17

Villa rental in Gibbes with swimming pool

Saint Peter Parish / Gibbes

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies

from $431 / night

$4307 / week

Book Book View

from $431 / night

(11) Excellent 

1 / 29

Holiday villa with swimming pool in Caribbean

Anguilla / Caribbean

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $375 / night

$0 / week

Book Book View

from $375 / night

(18) Excellent 

1 / 14

Magens Bay holiday home rental

St. Thomas / Magens Bay

1 bedroomSleeps 25 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 5 nights min stay

from $110 / night

$770 - $945 / week

Book Book View

from $110 / night

(9) Excellent 

1 / 37

Holiday apartment with shared pool in Sosua

Puerto Plata Province / Sosua

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from $151 / night

$1156 / week

Book Book View

from $151 / night

(6) Very Good 

1 / 29

Holiday condo with shared pool in Montego Bay

Saint James Parish / Montego Bay

2 bedroomsSleeps 8Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies

from $189 / night

$0 / week

Book Book View

from $189 / night

(18) Excellent 

1 / 27

Las Terrenas holiday apartment rental

Samana Province / Las Terrenas

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $261 / night

$1499 - $2886 / week

Book Book View

from $261 / night

(3) Excellent 

1 / 19

Villa rental in Eagle Beach with swimming pool, golf nearby

Aruba / Eagle Beach

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $199 / night

$1325 - $2450 / week

Book Book View

from $199 / night

(40) Excellent 

1 / 11

Woodlands holiday cottage rental

Montserrat / Woodlands

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $100 / night

$1050 - $1750 / week

Book Book View

from $100 / night

(5) Excellent 

1 / 31

Apartment rental in Grand Case

Saint-Martin / Grand Case

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $191 / night

$1421 - $4100 / week

Book Book View

from $191 / night

(15) Excellent 

1 / 69

Holiday home rental

Saint Ann Parish / Ocho Rios

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $145 / night

$0 / week

Book Book View

from $145 / night

(2) Very Good 

1 / 34

Arikok National Park holiday b&b rental

Aruba / Arikok National Park

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $121 / night

$840 - $945 / week

Book Book View

from $121 / night

(32) Very Good 

1 / 11

Holiday villa rental

Aruba / Noord

2 bedroomsSleeps 8Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies

from $100 / night

$676 - $1201 / week

Book Book View

from $100 / night

(28) Excellent 

1 / 13

St. Thomas holiday villa rental

US Virgin Isles / St. Thomas

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $200 / night

$1400 - $2930 / week

Book Book View

from $200 / night

(15) Excellent 

1 / 80

Villa rental in Soufriere with indoor pool

Soufriere Quarter / Soufriere

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $160 / night

$1120 - $1961 / week

Book Book View

from $160 / night

(2) Very Good 

1 / 52

Villa rental in Ocho Rios with swimming pool

Saint Ann Parish / Ocho Rios

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $175 / night

$1201 - $1351 / week

Book Book View

from $175 / night

(2) Excellent 

1 / 15

Villa rental in Hull Bay with swimming pool

St. Thomas / Hull Bay

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $529 / night

$3701 - $6200 / week

Book Book View

from $529 / night

(5) Excellent 

1 / 38

Holiday villa rental

Aruba / Noord

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $160 / night

$1086 - $1716 / week

Book Book View

from $160 / night

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