Air conditioned apartments and villas to rent in Caribbean

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12,760 Holiday homes

Filters applied: Air conditioning (12,760)

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

(5) Excellent 

1 / 19

Jolly Harbour holiday villa rental

Jolly Harbour / Ffryes Beach

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £305 / night

£2055 - £3699 / week

Book Book View

from £305 / night

(36) Very Good 

1 / 8

Noord holiday villa rental

Aruba / Noord

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £66 / night

£411 - £682 / week

Book Book View

from £66 / night

(2) Excellent 

1 / 39

Santo Domingo holiday apartment rental

Santo Domingo Province / Santo Domingo

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay

from £164 / night

£1164 / week

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from £164 / night

(15) Excellent 

1 / 21

Freeport holiday apartment rental

Grand Bahama Island / Freeport

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from £89 / night

£599 / week

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from £89 / night

(3) Good 

1 / 17

Holiday condo in Freeport

Grand Bahama Island / Freeport

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £120 / night

£840 / week

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from £120 / night

(4) Excellent 

1 / 14

Holiday apartment with shared pool in West Bay

Grand Cayman / West Bay

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £137 / night

£959 - £1798 / week

Book Book View

from £137 / night

(7) Excellent 

1 / 26

Holiday apartment with shared pool in Kralendijk

Bonaire / Kralendijk

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min stay

from £145 / night

£1012 - £1362 / week

Book Book View

from £145 / night

(4) Excellent 

1 / 8

Providenciales holiday home rental

Turks and Caicos Islands / Providenciales

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from £79 / night

£617 / week

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from £79 / night

(7) Very Good 

1 / 25

Holetown holiday villa rental

Saint James Parish / Holetown

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay

from £59 / night

£411 - £480 / week

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from £59 / night

(6) Very Good 

1 / 14

Holiday condo with shared pool in West Bay

Grand Cayman / West Bay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £109 / night

£737 / week

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from £109 / night

(15) Excellent 

1 / 20

Villa rental in Peterborg with shared pool

St. Thomas / Peterborg

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £257 / night

£1798 - £2038 / week

Book Book View

from £257 / night

(2) Very Good 

1 / 26

Holiday apartment with shared pool in Christiansted

St. Croix / Christiansted

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay

from £120 / night

£788 - £1117 / week

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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

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from £67 / night

1 / 34

Holiday home with swimming pool in Dorado

Puerto Rico / Dorado

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay

from £158 / night

£959 - £1216 / week

Book Book View

from £158 / night

(3) Poor 

1 / 21

Holiday villa in Savaneta

Aruba / Savaneta

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay

from £446 / night

£2877 - £4042 / week

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from £446 / night

(17) Excellent 

1 / 48

Holiday home with shared pool in Grand Cayman

Cayman Islands / Grand Cayman

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min stay

from £189 / night

£1319 - £2494 / week

Book Book View

from £189 / 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

(10) Excellent 

1 / 63

St. Ann's Bay holiday home rental

Saint Ann Parish / St. Ann's Bay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from £68 / night

£466 / week

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from £68 / night

(4) Very Good 

1 / 23

Holiday home in Oistins

Christ Church Parish / Oistins

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from £172 / night

£1199 / week

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from £172 / night

1 / 5

Hotel apartment rental in Boca Chica with shared pool, golf nearby

Santo Domingo Province / Boca Chica

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from £96 / night

£672 / week

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from £96 / night

(4) Excellent 

1 / 16

Holiday home with swimming pool in Willemstad

Curacao / Willemstad

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min stay

from £137 / night

£959 / week

Book Book View

from £137 / night

(2) Excellent 

1 / 24

Villa letting in Bavaro with swimming pool, golf nearby

Punta Cana / Bavaro

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from £178 / night

£1164 / week

Book Book View

from £178 / night

(2) Very Good 

1 / 26

West Bay holiday apartment rental

Grand Cayman / West Bay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay

from £127 / night

£887 - £1703 / week

Book Book View

from £127 / night

(6) Excellent 

1 / 151

Holiday apartment with swimming pool in Bavaro

Punta Cana / Bavaro

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £137 / night

£576 - £959 / week

Book Book View

from £137 / 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

(16) Very Good 

1 / 63

Holiday apartment in Christiansted

St. Croix / Christiansted

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay

from £93 / night

£648 / week

Book Book View

from £93 / night

(1) Good 

1 / 38

Holiday apartment with shared pool in Guaynabo

Puerto Rico / Guaynabo

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min stay

from £86 / night

£514 / week

Book Book View

from £86 / night

(4) Excellent 

1 / 21

Seven Mile Beach holiday apartment rental

Grand Cayman / Seven Mile Beach

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £137 / night

£864 - £3333 / week

Book Book View

from £137 / night

(9) Excellent 

1 / 28

Holiday villa in Aruba

Caribbean / Aruba

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min stay

from £211 / night

£1473 - £2398 / week

Book Book View

from £211 / 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

(5) Excellent 

1 / 6

Townhouse letting in Jolly Harbour with swimming pool, golf nearby

Jolly Harbour / Ffryes Beach

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £305 / night

£2398 - £3699 / week

Book Book View

from £305 / 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

(7) Very Good 

1 / 9

Apartment rental in Luquillo

Puerto Rico / Luquillo

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay

from £69 / night

£480 / week

Book Book View

from £69 / night

(2) Excellent 

1 / 21

Holiday villa with shared pool in Oranjestad

Aruba / Oranjestad

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min stay

from £109 / night

£685 - £989 / week

Book Book View

from £109 / 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

(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

(7) Very Good 

1 / 24

Holiday home in Hope Town

Elbow Cay / Hope Town

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £196 / night

£1370 / week

Book Book View

from £196 / night

(3) Very Good 

1 / 35

Holiday studio with shared pool in Isla Verde

Carolina / Isla Verde

  • Studio
  • Sleeps 4
  • 5 nights min stay

from £83 / night

£569 / week

Book Book View

from £83 / night

(2) Very Good 

1 / 21

Paynes Bay holiday villa rental

Saint James Parish / Paynes Bay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £192 / night

£1343 / week

Book Book View

from £192 / night

(13) Excellent 

1 / 17

Home rental in Sainte-Anne with shared pool

Grande-Terre Island / Sainte-Anne

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £125 / night

£852 - £1243 / week

Book Book View

from £125 / night

(5) Excellent 

1 / 13

San Juan holiday apartment rental

Puerto Rico / San Juan

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from £137 / night

£891 - £1028 / week

Book Book View

from £137 / 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

(1) Excellent 

1 / 24

Holiday villa rental

Puerto Rico / Dorado

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £103 / night

£685 - £753 / week

Book Book View

from £103 / 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

(15) Very Good 

1 / 32

Holiday penthouse with golf nearby in Speightstown

Saint Peter Parish / Speightstown

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £140 / night

£995 - £1600 / week

Book Book View

from £140 / night

(1) Excellent 

1 / 19

Holiday home with swimming pool in Freeport

Grand Bahama Island / Freeport

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min stay

from £103 / night

£617 - £822 / week

Book Book View

from £103 / 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

(3) Excellent 

1 / 12

Bouillante holiday b&b rental

Basse-Terre Island / Bouillante

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from £110 / night

£766 / week

Book Book View

from £110 / night

(4) Excellent 

1 / 15

Holiday apartment in Las Terrenas

Samana Province / Las Terrenas

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from £199 / night

£1302 / week

Book Book View

from £199 / night

(6) Excellent 

1 / 25

Baie Nettle holiday villa rental

Saint-Martin / Baie Nettle

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £56 / night

£959 - £1583 / week

Book Book View

from £56 / night

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