Walking holiday villas and apartments Caribbean | Holiday Lettings

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1,865 Holiday homes

Filters applied: Walking holidays (1,865)

Travellers going to Caribbean are booking December dates now. Secure your holiday home today and have the perfect trip.

(4) Excellent 

1 / 27

Holiday apartment rental

Saint Michael Parish / Bridgetown

2 bedroomsSleeps 46 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min stay

from $150 / night

$1051 - $1855 / week

Book Book View

from $150 / night

(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

$1226 / week

Book Book View

from $211 / 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 $190 / night

$1420 - $4100 / week

Book Book View

from $190 / night

Featured properties

(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

(4) Excellent 

1 / 36

Luquillo holiday condo rental

Puerto Rico / Luquillo

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $126 / night

$750 - $1600 / week

Book Book View

from $126 / 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

(5) Excellent 

1 / 38

Holiday villa rental

Aruba / Noord

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $161 / night

$1086 - $1716 / week

Book Book View

from $161 / night

(3) Excellent 

1 / 12

Home rental in Island Harbour

Anguilla / Island Harbour

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $301 / night

$2000 / week

Book Book View

from $301 / night

(9) Excellent 

1 / 25

Noord holiday villa rental

Aruba / Noord

3 bedroomsSleeps 10Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies

from $196 / night

$1365 - $2975 / week

Book Book View

from $196 / night

(8) Very Good 

1 / 17

Holiday condo with shared pool in Negril

Negril / Negril Beach

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $211 / night

$1650 - $2000 / week

Book Book View

from $211 / night

(6) Excellent 

1 / 57

Apartment rental in Boca Chica with swimming pool

Santo Domingo Province / Boca Chica

3 bedroomsSleeps 123 nights min stay

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min stay

from $176 / night

$1226 / week

Book Book View

from $176 / night

(9) Excellent 

1 / 20

St. George's holiday villa rental

Saint George Parish / St. George's

5 bedroomsSleeps 91 night min stay

  • 5 bedrooms
  • Sleeps 9
  • 1 night min stay

from $501 / night

$2501 / week

Book Book View

from $501 / night

(1) Excellent 

1 / 21

Holiday home with swimming pool in Palm Beach Town

Eagle Beach / Palm Beach Town

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $190 / night

$1600 - $3500 / week

Book Book View

from $190 / night

(6) Excellent 

1 / 14

St Thomas East holiday condo rental

St. Thomas / St Thomas East

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $176 / night

$0 / week

Book Book View

from $176 / night

(4) Excellent 

1 / 50

Holiday apartment with shared pool in Seven Mile Beach

Grand Cayman / Seven Mile Beach

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $135 / night

$945 - $3221 / week

Book Book View

from $135 / night

(12) Excellent 

1 / 13

Castle accommodation in Petite Calivigny with swimming pool

St. George's / Petite Calivigny

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from $290 / night

$1885 / week

Book Book View

from $290 / night

(1) Very Good 

1 / 38

Luquillo holiday condo rental

Puerto Rico / Luquillo

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $126 / night

$750 - $1600 / week

Book Book View

from $126 / night

(6) Excellent 

1 / 28

Christiansted holiday apartment rental

St. Croix / Christiansted

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $158 / night

$1101 - $1806 / week

Book Book View

from $158 / 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 $100 / night

$674 - $1724 / week

Book Book View

from $100 / night

(7) Very Good 

1 / 36

Holiday bungalow in Negril

Negril / Negril Beach

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $142 / night

$1000 / week

Book Book View

from $142 / night

(3) Very Good 

1 / 20

Holiday villa with swimming pool in Soto

Curacao / Soto

3 bedroomsSleeps 86 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min stay

from $237 / night

$1653 - $2125 / week

Book Book View

from $237 / night

(8) Very Good 

1 / 10

Villa rental in Jolly Harbour with swimming pool, golf nearby

Jolly Harbour / Harbour View

4 bedroomsSleeps 81 night min stay

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay

from $276 / night

$1929 / week

Book Book View

from $276 / night

(25) Very Good 

1 / 30

Holiday villa with swimming pool, golf nearby in Ocho Rios

Saint Ann Parish / Ocho Rios

3 bedroomsSleeps 81 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay

from $174 / night

$1160 / week

Book Book View

from $174 / 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 $161 / night

$1121 - $1960 / week

Book Book View

from $161 / night

(6) Excellent 

1 / 37

Curacao holiday villa rental

Caribbean / Curacao

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $202 / night

$1251 - $1530 / week

Book Book View

from $202 / night

(2) Excellent 

1 / 41

Holiday villa with shared pool in Bavaro

Punta Cana / Bavaro

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from $145 / night

$1501 - $6501 / week

Book Book View

from $145 / night

(1) Excellent 

1 / 20

Luquillo holiday home rental

Puerto Rico / Luquillo

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $200 / night

$0 / week

Book Book View

from $200 / 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

$3700 - $6200 / week

Book Book View

from $529 / night

(2) Excellent 

1 / 18

Holiday guest house rental

Westmoreland Parish / Negril

4 bedroomsSleeps 102 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min stay

from $251 / night

$1501 - $1780 / week

Book Book View

from $251 / night

(10) Very Good 

1 / 28

Holiday apartment with shared pool, golf nearby in Noord

Aruba / Noord

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $75 / night

$800 - $1287 / week

Book Book View

from $75 / night

(2) Excellent 

1 / 24

Home rental in North Side with shared pool

Grand Cayman / North Side

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $236 / night

$1650 - $2000 / week

Book Book View

from $236 / night

(1) Excellent 

1 / 28

Villa rental in Marisule with swimming pool

Castries / Marisule

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $301 / night

$2101 - $2800 / week

Book Book View

from $301 / night

(1) Excellent 

1 / 17

Condo rental in Turtle Cove with indoor pool, golf nearby

Providenciales / Turtle Cove

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from $301 / night

$2000 / week

Book Book View

from $301 / night

(4) Excellent 

1 / 21

Sosua holiday home rental

Puerto Plata Province / Sosua

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $361 / night

$2501 / week

Book Book View

from $361 / night

(2) Excellent 

1 / 34

Holiday villa with swimming pool in Las Terrenas

Las Terrenas / El Portillo

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies

from $290 / night

$1600 - $5401 / week

Book Book View

from $290 / night

(5) Very Good 

1 / 41

Malmok Beach holiday villa rental

Aruba / Malmok Beach

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $451 / night

$2800 - $3500 / week

Book Book View

from $451 / night

(5) Excellent 

1 / 19

Holiday apartment with shared pool, golf nearby in Palm Beach Town

Eagle Beach / Palm Beach Town

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay

from $100 / night

$0 / week

Book Book View

from $100 / night

(3) Very Good 

1 / 41

Holiday villa with swimming pool in Soto

Curacao / Soto

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies

from $270 / night

$1889 - $4328 / week

Book Book View

from $270 / night

(5) Excellent 

1 / 29

Holiday apartment rental

Punta Cana / Bavaro

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from $350 / night

$1899 / week

Book Book View

from $350 / night

(7) Excellent 

1 / 31

Holiday apartment in Las Terrenas

Samana Province / Las Terrenas

6 bedroomsSleeps 16Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies

from $451 / night

$3300 - $6000 / week

Book Book View

from $451 / night

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