Walking holiday villas and apartments Caribbean | Holiday Lettings

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1,870 Holiday homes

Filters applied: Walking holidays (1,870)

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

(4) Excellent 

1 / 36

Luquillo holiday condo rental

Puerto Rico / Luquillo

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £86 / night

£514 - £1096 / week

Book Book View

from £86 / night

(10) Excellent 

1 / 12

Holiday villa with swimming pool, golf nearby in New Castle

Nevis / New Castle

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £124 / night

£696 / week

Book Book View

from £124 / night

(6) Excellent 

1 / 57

Apartment rental in Boca Chica with swimming pool

Santo Domingo Province / Boca Chica

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min stay

from £120 / night

£840 / week

Book Book View

from £120 / night

(26) Very Good 

1 / 45

Villa rental in Sosua with swimming pool

Puerto Plata Province / Sosua

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min stay

from £131 / night

£801 / week

Book Book View

from £131 / night

(3) Excellent 

1 / 12

Home rental in Island Harbour

Anguilla / Island Harbour

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay

from £206 / night

£1370 / week

Book Book View

from £206 / night

(5) Excellent 

1 / 31

Apartment rental in Grand Case

Saint-Martin / Grand Case

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £131 / night

£973 - £2809 / week

Book Book View

from £131 / night

(4) Very Good 

1 / 41

Malmok Beach holiday villa rental

Aruba / Malmok Beach

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £309 / night

£1918 - £2398 / week

Book Book View

from £309 / night

(6) Excellent 

1 / 28

Christiansted holiday apartment rental

St. Croix / Christiansted

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £108 / night

£754 - £1237 / week

Book Book View

from £108 / night

(3) Excellent 

1 / 27

Holiday apartment rental

Saint Michael Parish / Bridgetown

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min stay

from £103 / night

£720 - £1271 / week

Book Book View

from £103 / night

(15) Excellent 

1 / 80

Villa rental in Soufriere with indoor pool

Soufriere Quarter / Soufriere

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £110 / night

£768 - £1343 / week

Book Book View

from £110 / night

(8) Very Good 

1 / 10

Villa rental in Jolly Harbour with swimming pool, golf nearby

Jolly Harbour / Harbour View

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay

from £190 / night

£1330 / week

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from £190 / night

(3) Excellent 

1 / 19

Villa rental in Eagle Beach with swimming pool, golf nearby

Aruba / Eagle Beach

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £137 / night

£908 - £1679 / week

Book Book View

from £137 / night

(9) Excellent 

1 / 37

Noord holiday villa rental

Aruba / Noord

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies

from £134 / night

£935 - £2038 / week

Book Book View

from £134 / night

(11) Excellent 

1 / 40

Freeport holiday apartment rental

Grand Bahama Island / Freeport

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £86 / night

£576 - £710 / week

Book Book View

from £86 / night

(8) Very Good 

1 / 17

Holiday condo with shared pool in Negril

Negril / Negril Beach

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £144 / night

£987 - £1370 / week

Book Book View

from £144 / night

(5) Excellent 

1 / 38

Holiday villa rental

Aruba / Noord

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from £110 / night

£744 - £1175 / week

Book Book View

from £110 / night

(1) Very Good 

1 / 38

Luquillo holiday condo rental

Puerto Rico / Luquillo

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £86 / night

£514 - £1096 / week

Book Book View

from £86 / night

(1) Excellent 

1 / 17

Condo rental in Turtle Cove with indoor pool, golf nearby

Providenciales / Turtle Cove

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from £206 / night

£1370 / week

Book Book View

from £206 / night

(5) Excellent 

1 / 19

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

Eagle Beach / Palm Beach Town

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay

from £82 / night

£571 / week

Book Book View

from £82 / night

(1) Excellent 

1 / 24

Villa rental in Noord with swimming pool

Aruba / Noord

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £161 / night

£1127 - £1357 / week

Book Book View

from £161 / night

(7) Excellent 

1 / 31

Holiday apartment in Las Terrenas

Samana Province / Las Terrenas

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies

from £309 / night

£2261 - £4110 / week

Book Book View

from £309 / night

(6) Excellent 

1 / 14

St Thomas East holiday condo rental

St. Thomas / St Thomas East

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £120 / night

£840 / week

Book Book View

from £120 / night

(8) Excellent 

1 / 12

St. George's holiday apartment accommodation

Saint George Parish / St. George's

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £67 / night

£400 - £688 / week

Book Book View

from £67 / night

(6) Excellent 

1 / 37

Curacao holiday villa rental

Caribbean / Curacao

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £139 / night

£857 - £1048 / week

Book Book View

from £139 / night

(1) Excellent 

1 / 16

Holiday b&b rental

Saint Ann Parish / Ocho Rios

  • 7 bedrooms
  • Sleeps 18
  • 2 nights min stay

from £24 / night

£168 - £2546 / week

Book Book View

from £24 / night

(2) Excellent 

1 / 41

Holiday villa with shared pool in Bavaro

Punta Cana / Bavaro

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from £100 / night

£1028 - £4453 / week

Book Book View

from £100 / night

(1) Excellent 

1 / 28

Villa rental in Marisule with swimming pool

Castries / Marisule

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from £206 / night

£1439 - £1918 / week

Book Book View

from £206 / night

(24) Very Good 

1 / 30

Holiday villa with swimming pool, golf nearby in Ocho Rios

Saint Ann Parish / Ocho Rios

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay

from £120 / night

£800 / week

Book Book View

from £120 / night

(2) Excellent 

1 / 15

Villa rental in Hull Bay with swimming pool

St. Thomas / Hull Bay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £363 / night

£2535 - £4247 / week

Book Book View

from £363 / night

(3) Excellent 

1 / 12

St. George's holiday apartment accommodation

Saint George Parish / St. George's

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £67 / night

£400 - £688 / week

Book Book View

from £67 / night

(10) Excellent 

1 / 51

Holiday villa with swimming pool, golf nearby in La Romana

La Romana Province / La Romana

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies

from £257 / night

£1644 - £4932 / week

Book Book View

from £257 / night

(9) Excellent 

1 / 20

St. George's holiday villa rental

Saint George Parish / St. George's

  • 5 bedrooms
  • Sleeps 9
  • 1 night min stay

from £343 / night

£1713 / week

Book Book View

from £343 / night

(3) Very Good 

1 / 11

Cabo Rojo holiday condo rental

Puerto Rico / Cabo Rojo

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from £103 / night

£720 / week

Book Book View

from £103 / night

(5) Excellent 

1 / 17

Holiday villa with shared pool, tennis court in Las Terrenas

Samana Province / Las Terrenas

  • 4 bedrooms
  • Sleeps 10
  • 1 night min stay

from £257 / night

£1507 - £2946 / week

Book Book View

from £257 / night

(11) Excellent 

1 / 33

Las Terrenas holiday apartment rental

Samana Province / Las Terrenas

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from £240 / night

£1576 - £2398 / week

Book Book View

from £240 / night

(3) Excellent 

1 / 75

Holiday home in Frederiksted

St. Croix / Frederiksted

  • 3 bedrooms
  • Sleeps 11
  • Min stay varies

from £155 / night

£959 - £1096 / week

Book Book View

from £155 / night

(2) Excellent 

1 / 24

Holiday condo in East End

St. Thomas / East End

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from £205 / night

£1370 - £2603 / week

Book Book View

from £205 / night

(4) Excellent 

1 / 25

Rincon holiday apartment rental

Rincon / Barrio Puntas

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay

from £93 / night

£648 / week

Book Book View

from £93 / night

(1) Excellent 

1 / 20

Luquillo holiday home rental

Puerto Rico / Luquillo

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from £137 / night

£959 / week

Book Book View

from £137 / night

(2) Very Good 

1 / 20

Holiday villa with swimming pool in Soto

Curacao / Soto

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min stay

from £166 / night

£1158 - £1489 / week

Book Book View

from £166 / night

(3) Very Good 

1 / 41

Holiday villa with swimming pool in Soto

Curacao / Soto

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies

from £189 / night

£1323 - £3032 / week

Book Book View

from £189 / night

(13) Excellent 

1 / 27

Holiday apartment with shared pool, golf nearby in Cabo Rojo

Puerto Rico / Cabo Rojo

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £79 / night

£446 - £535 / week

Book Book View

from £79 / night

(8) Excellent 

1 / 23

Holiday villa in Coral Bay

St. John / Coral Bay

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £137 / night

£955 - £2518 / week

Book Book View

from £137 / night

(4) Excellent 

1 / 21

Sosua holiday home rental

Puerto Plata Province / Sosua

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay

from £247 / night

£1713 / week

Book Book View

from £247 / night

(4) Excellent 

1 / 50

Holiday apartment with shared pool in Seven Mile Beach

Grand Cayman / Seven Mile Beach

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £93 / night

£648 - £2206 / week

Book Book View

from £93 / night

(1) Excellent 

1 / 31

Holiday villa with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £89 / night

£583 - £973 / week

Book Book View

from £89 / night

(1) Excellent 

1 / 22

Jan Sofat holiday villa rental

Spanish Water / Jan Sofat

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from £165 / night

£1151 - £2038 / week

Book Book View

from £165 / night

(1) Excellent 

1 / 21

Holiday home with swimming pool in Palm Beach Town

Eagle Beach / Palm Beach Town

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from £164 / night

£1096 - £2398 / week

Book Book View

from £164 / night

(5) Very Good 

1 / 35

Merricks holiday home rental

Saint Philip Parish / Merricks

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from £52 / night

£360 - £648 / week

Book Book View

from £52 / night

(3) Excellent 

1 / 34

Holiday villa with shared pool in Bavaro

Punta Cana / Bavaro

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £38 / night

£309 - £2055 / week

Book Book View

from £38 / night

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