Air conditioned apartments and villas to rent in Caribbean

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15,264 Holiday homes

Filters applied: Air conditioning (15,264)

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1 / 5

Hotel apartment letting in Philipsburg with swimming pool

Sint Maarten / Philipsburg

3 8 7 nights min stay

Hotel apartment / 3 bedrooms / sleeps 8 / 7 nights min stay

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from £449 / night

£2759 / week

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from £449 / night

1 / 8

Holiday apartment accommodation

Gros Islet Quarter / Gros Islet

3 5 1 night min stay

Apartment / 3 bedrooms / sleeps 5 / 1 night min stay

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from £207 / night

£1380 / week

Book

from £207 / night

1 / 14

Vieux Fort holiday home rental

Vieux Fort Quarter / Vieux Fort

4 10 Min stay varies

House / 4 bedrooms / sleeps 10 / Min stay varies

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from £249 / night

£1738 - £1859 / week

Book

from £249 / night

Featured properties

(5) Excellent 

1 / 24

Holiday villa with swimming pool in Jan Thiel

Curacao / Jan Thiel

5 10 Min stay varies

Villa / 5 bedrooms / sleeps 10 / Min stay varies

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from £220 / night

£1535 - £2424 / week

Book

from £220 / night

1 / 18

Las Terrenas holiday condo rental

Las Terrenas / Playa Bonita

5 8 Min stay varies

Condo / 5 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £273 / night

£1621 - £2173 / week

Book

from £273 / night

1 / 4

English Harbour holiday villa rental

Saint Paul Parish / English Harbour

3 6 2 nights min stay

Villa / 3 bedrooms / sleeps 6 / 2 nights min stay

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from £173 / night

£1207 - £1932 / week

Book

from £173 / night

(1) Excellent 

1 / 17

Kralendijk holiday villa rental

Bonaire / Kralendijk

5 9 7 nights min stay

Villa / 5 bedrooms / sleeps 9 / 7 nights min stay

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from £352 / night

£2462 - £8924 / week

Book

from £352 / night

(1) Excellent 

1 / 49

Holiday villa with swimming pool in Cul de Sac

Saint-Martin / Cul de Sac

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

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from £145 / night

£1207 - £1521 / week

Book

from £145 / night

(6) Excellent 

1 / 32

Holiday villa with indoor pool in Tower Isle

Saint Mary Parish / Tower Isle

3 6 2 nights min stay

Villa / 3 bedrooms / sleeps 6 / 2 nights min stay

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from £249 / night

£1725 / week

Book

from £249 / night

1 / 10

Holiday villa with shared pool in George Town

Great Exuma / George Town

3 8 Min stay varies

Villa / 3 bedrooms / sleeps 8 / Min stay varies

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from £345 / night

£2311 - £4345 / week

Book

from £345 / night

(9) Excellent 

1 / 32

Holiday villa with swimming pool, tennis court in Punta Cana

La Altagracia Province / Punta Cana

3 8 Min stay varies

Villa / 3 bedrooms / sleeps 8 / Min stay varies

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from £345 / night

£2138 / week

Book

from £345 / night

(2) Excellent 

1 / 24

Holiday apartment rental

Punta Cana / Bavaro Beach

2 4 3 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 3 nights min stay

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from £111 / night

£973 / week

Book

from £111 / night

(2) Excellent 

1 / 12

Holiday villa in Marsh Harbour

Great Abaco Island / Marsh Harbour

4 9 7 nights min stay

Villa / 4 bedrooms / sleeps 9 / 7 nights min stay

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from £365 / night

£2552 / week

Book

from £365 / night

(1) Very Good 

1 / 31

Villa rental in Rif St. Marie with swimming pool

Banda Bou / Rif St. Marie

4 10 6 nights min stay

Villa / 4 bedrooms / sleeps 10 / 6 nights min stay

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from £177 / night

£1239 - £2359 / week

Book

from £177 / night

(2) Very Good 

1 / 18

Holiday villa with swimming pool, golf nearby in La Romana

La Romana Province / La Romana

5 12 Min stay varies

Villa / 5 bedrooms / sleeps 12 / Min stay varies

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from £276 / night

£1932 - £3163 / week

Book

from £276 / night

1 / 20

Kralendijk holiday condo rental

Bonaire / Kralendijk

2 6 Min stay varies

Condo / 2 bedrooms / sleeps 6 / Min stay varies

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from £138 / night

£966 - £1135 / week

Book

from £138 / night

(2) Excellent 

1 / 16

Black Rock holiday home rental

Saint Michael Parish / Black Rock

5 10 Min stay varies

House / 5 bedrooms / sleeps 10 / Min stay varies

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from £587 / night

£587 - £9656 / week

Book

from £587 / night

(5) Very Good 

1 / 19

Villa rental in Las Galeras with swimming pool

Samana Province / Las Galeras

4 10 3 nights min stay

Villa / 4 bedrooms / sleeps 10 / 3 nights min stay

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from £242 / night

£1690 / week

Book

from £242 / night

1 / 8

St. John holiday villa rental

US Virgin Isles / St. John

3 10 7 nights min stay

Villa / 3 bedrooms / sleeps 10 / 7 nights min stay

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from £670 / night

£4690 / week

Book

from £670 / night

(5) Excellent 

1 / 17

Holiday condo with shared pool in Negril

Negril / Negril Beach

3 6 5 nights min stay

Condo / 3 bedrooms / sleeps 6 / 5 nights min stay

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from £145 / night

£994 - £1383 / week

Book

from £145 / night

1 / 62

Apartment rental in East End with shared pool

St. Thomas / East End

2 8 Min stay varies

Apartment / 2 bedrooms / sleeps 8 / Min stay varies

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from £138 / night

£966 / week

Book

from £138 / night

(1) Excellent 

1 / 52

Holiday apartment with golf nearby in Eagle Beach

Aruba / Eagle Beach

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

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from £173 / night

£1207 - £2366 / week

Book

from £173 / night

(5) Excellent 

1 / 22

Holiday villa in Rincon

Puerto Rico / Rincon

11 22 Min stay varies

Villa / 11 bedrooms / sleeps 22 / Min stay varies

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from £1725 / night

£12069 - £31380 / week

Book

from £1725 / night

1 / 26

Holiday apartment with swimming pool in Seven Mile Beach

Grand Cayman / Seven Mile Beach

2 7 3 nights min stay

Apartment / 2 bedrooms / sleeps 7 / 3 nights min stay

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from £296 / night

£1772 / week

Book

from £296 / night

1 / 21

Holiday villa rental

Puerto Plata / Playa Cofresi

7 15 3 nights min stay

Villa / 7 bedrooms / sleeps 15 / 3 nights min stay

Add to shortlist

from £276 / night

£1725 / week

Book

from £276 / night

(3) Excellent 

1 / 19

Holiday home in Tar Bay

Great Exuma / Tar Bay

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

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from £242 / night

£1725 - £1863 / week

Book

from £242 / night

(1) Very Good 

1 / 21

Holiday villa with swimming pool, golf nearby in Puerto Plata

Puerto Plata Province / Puerto Plata

4 8 3 nights min stay

Villa / 4 bedrooms / sleeps 8 / 3 nights min stay

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from £242 / night

£1311 / week

Book

from £242 / night

1 / 21

Holiday home with swimming pool in Palm Beach Town

Eagle Beach / Palm Beach Town

4 8 Min stay varies

House / 4 bedrooms / sleeps 8 / Min stay varies

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from £158 / night

£1104 - £2414 / week

Book

from £158 / night

(1) Excellent 

1 / 30

Holiday villa rental

Providenciales / Chalk Sound National Park

4 8 5 nights min stay

Villa / 4 bedrooms / sleeps 8 / 5 nights min stay

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from £828 / night

£5794 / week

Book

from £828 / night

1 / 15

Holiday villa with swimming pool in Dawn Beach

Sint Maarten / Dawn Beach

3 8 5 nights min stay

Villa / 3 bedrooms / sleeps 8 / 5 nights min stay

Add to shortlist

from £483 / night

£2069 - £5311 / week

Book

from £483 / night

(2) Excellent 

1 / 11

Holiday apartment in Sainte-Anne

Grande-Terre Island / Sainte-Anne

2 4 7 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 7 nights min stay

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from £124 / night

£862 / week

Book

from £124 / night

(5) Excellent 

1 / 40

Holiday yacht in West End

Grand Bahama Island / West End

3 8 7 nights min stay

Yacht / 3 bedrooms / sleeps 8 / 7 nights min stay

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from £444 / night

£3104 - £5863 / week

Book

from £444 / night

1 / 43

Holiday villa with swimming pool in Jan Sofat

Spanish Water / Jan Sofat

5 11 Min stay varies

Villa / 5 bedrooms / sleeps 11 / Min stay varies

Add to shortlist

from £286 / night

£2000 - £2615 / week

Book

from £286 / night

1 / 31

Holiday villa rental

Puerto Plata / Playa Cofresi

6 15 1 night min stay

Villa / 6 bedrooms / sleeps 15 / 1 night min stay

Add to shortlist

from £200 / night

£1380 / week

Book

from £200 / night

(1) Excellent 

1 / 22

Holiday villa with golf nearby in Paynes Bay

Saint James Parish / Paynes Bay

2 4 7 nights min stay

Villa / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £194 / night

£1352 / week

Book

from £194 / night

1 / 24

Cabarete holiday home rental

Puerto Plata Province / Cabarete

4 8 1 night min stay

House / 4 bedrooms / sleeps 8 / 1 night min stay

Add to shortlist

from £363 / night

£1883 / week

Book

from £363 / night

1 / 10

Paradise Island holiday villa rental

New Providence Island / Paradise Island

2 8 Min stay varies

Villa / 2 bedrooms / sleeps 8 / Min stay varies

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from £449 / night

£3104 / week

Book

from £449 / night

(1) Excellent 

1 / 27

Holiday condo with shared pool in St Thomas East

St. Thomas / St Thomas East

1 7 3 nights min stay

Condo / 1 bedroom / sleeps 7 / 3 nights min stay

Add to shortlist

from £207 / night

£1444 / week

Book

from £207 / night

(5) Excellent 

1 / 10

Holiday villa in Nassau

New Providence Island / Nassau

5 10 3 nights min stay

Villa / 5 bedrooms / sleeps 10 / 3 nights min stay

Add to shortlist

from £656 / night

£4483 - £7380 / week

Book

from £656 / night

1 / 13

Home rental in Road Town with swimming pool

Tortola / Road Town

4 10 3 nights min stay

House / 4 bedrooms / sleeps 10 / 3 nights min stay

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from £518 / night

£3449 / week

Book

from £518 / night

(23) Excellent 

1 / 15

Holiday home rental

Saint George Parish / Lance aux Epines

4 8 7 nights min stay

House / 4 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £449 / night

£3138 - £4552 / week

Book

from £449 / night

1 / 49

English Harbour holiday villa rental

Saint Paul Parish / English Harbour

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £276 / night

£1932 - £4828 / week

Book

from £276 / night

1 / 21

Holiday villa with swimming pool in Noord

Aruba / Noord

3 10 Min stay varies

Villa / 3 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £138 / night

£966 / week

Book

from £138 / night

(2) Excellent 

1 / 21

West End Village holiday villa rental

Anguilla / West End Village

3 6 7 nights min stay

Villa / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £350 / night

£2450 - £3500 / week

Book

from £350 / night

1 / 19

Holiday condo rental

La Altagracia Province / Punta Cana

1 2 3 nights min stay

Condo / 1 bedroom / sleeps 2 / 3 nights min stay

Add to shortlist

from £220 / night

£1536 / week

Book

from £220 / night

1 / 16

Eagle Beach holiday condo rental

Aruba / Eagle Beach

1 4 Min stay varies

Condo / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £173 / night

£1207 - £1414 / week

Book

from £173 / night

1 / 14

Holiday villa rental

Montego Bay / Sandy Bay

6 15 4 nights min stay

Villa / 6 bedrooms / sleeps 15 / 4 nights min stay

Add to shortlist

from £987 / night

£6897 - £17242 / week

Book

from £987 / night

(7) Excellent 

1 / 30

Carriacou Island holiday home accommodation

Grenada / Carriacou Island

2 4 7 nights min stay

House / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £207 / night

£1449 / week

Book

from £207 / night

(2) Very Good 

1 / 18

Holiday apartment with shared pool in Nassau

New Providence Island / Nassau

3 7 3 nights min stay

Apartment / 3 bedrooms / sleeps 7 / 3 nights min stay

Add to shortlist

from £242 / night

£1690 / week

Book

from £242 / night

1 / 20

Villa accommodation in Sosua with swimming pool

Puerto Plata Province / Sosua

4 8 2 nights min stay

Villa / 4 bedrooms / sleeps 8 / 2 nights min stay

Add to shortlist

from £328 / night

£2064 / week

Book

from £328 / night

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