Air conditioned apartments and villas to rent in Caribbean

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Caribbean

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15,378 Holiday homes

Filters applied: Air conditioning

17

Trinidad and Tobago holiday apartment rental

Trinidad / Caroni

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
  • Air conditioning

from £154 / night

£1077 / week

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from £154 / night

(4) Excellent 

35

Holiday villa rental

Puerto Plata / Playa Cofresi

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £220 / night

£1539 - £4948 / week

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from £220 / night

(4) Excellent 

14

Holiday villa rental

Isla de Vieques / Isabel Segunda

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £212 / night

£1385 - £2385 / week

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from £212 / night

6

Holiday studio with shared pool, golf nearby in Caribbean

Grande-Terre Island / Saint Francois

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £50 / night

£345 - £518 / week

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from £50 / night

(4) Excellent 

16

Holiday studio in Caribbean

Arrondissement of Le Marin / Les Anses d'Arlet

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Air conditioning

from £53 / night

£371 - £492 / week

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from £53 / night

(5) Very Good 

12

Caribbean holiday apartment rental

Grande-Terre Island / Le Moule

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £32 / night

£220 - £268 / week

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from £32 / night

37

Holiday home in Caribbean

Warrens / Arthur Seat

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £80 / night

£450 - £490 / week

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from £80 / night

(5) Excellent 

20

Guadeloupe holiday gite rental

Basse-Terre Island / Capesterre-Belle-Eau

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Air conditioning

from £65 / night

£449 / week

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from £65 / night

(18) Very Good 

32

Holiday penthouse with golf nearby in Barbados

Saint Peter Parish / Speightstown

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for children age 5+
“Caribbean Dreamin'” My girlfriend and I enjoyed the absolute BEST week we could have hoped for at this apartment. Both Trisha and her housekeeper, Marva, could not have been more helpful and accommodating. And the apartment was a perfect base to en
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from £150 / night

£1000 - £1600 / week

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from £150 / night

(1) Excellent 

42

Holiday apartment with shared pool in Caribbean

Nevis / Charlestown

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very enjoyable week on Pinneys Beach” Just arrived back from a week’s stay at Hamilton Beach. We booked a 2 bedroom beachfront villa which was bright modern and overlooked the beach and ocean. Waking up in the morning and looking across at St Kitts wa
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from £270 / night

£1885 / week

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from £270 / night

(7) Very Good 

23

Holiday villa with swimming pool in Caribbean

Saint James Parish / Weston

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Definitely the place to stay.” We spent an amazing, relaxing week at this beautiful beach villa in St. James. The house is tucked away behind an electronic gate down a private drive. The beach is on your door step and the views from the veranda are br
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from £616 / night

£4308 / week

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from £616 / night

(1) Excellent 

16

Guadeloupe holiday villa rental

Iles des Saintes / Terre-de-Haut

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £100 / night

£604 - £1298 / week

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from £100 / night

(16) Very Good 

26

Holiday villa rental

Gros Islet / La Brolette

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.6 km
  • Swimming pool

from £330 / night

£2308 - £2693 / week

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from £330 / night

(4) Excellent 

13

Holiday apartment accommodation

Basse-Terre Island / Deshaies

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £78 / night

£475 - £2311 / week

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from £78 / night

(4) Excellent 

21

Caribbean holiday villa rental

Vieux Fort Quarter / Vieux Fort

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
“A-M-A-Z-I-N-G-!” The pictures speak for themselves: the beauty, style and comfort of Villa Pierre are undeniable. It took me two days to get over the fabulous views sprawling before my eyes... But then, I got it: the views are not just beautiful ; the
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from £270 / night

£1885 - £3770 / week

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from £270 / night

(4) Excellent 

11

Caribbean holiday apartment rental

Arrondissement of La Trinite / Le Robert

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning

from £44 / night

£302 / week

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from £44 / night

(8) Very Good 

36

Holiday villa letting

St. Lucia / Soufriere Quarter

6 12 5 nights min

  • 6 bedrooms
  • Sleeps 12
  • 5 nights min
  • Nearest beach 2 km
  • Swimming pool
  • Suitable for children age 5+

from £770 / night

£4616 / week

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from £770 / night

5

Barbados holiday apartment rental

Christ Church Parish / Hastings

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning

from £66 / night

£458 - £674 / week

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from £66 / night

25

Holiday apartment with shared pool in Caribbean

Saint-Martin / Orient Bay

1 7 5 nights min

  • 1 bedroom
  • Sleeps 7
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £62 / night

£431 - £523 / week

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from £62 / night

15

Holiday condo in Caribbean

Samana Province / Las Terrenas

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £76 / night

£524 / week

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from £76 / night

(55) Very Good 

29

Caribbean holiday cottage let

Iles des Saintes / Terre-de-Haut

4 5 1 night min

  • 4 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £76 / night

£501 - £682 / week

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from £76 / night

(5) Excellent 

41

Holiday bungalow in Guadeloupe

Grande-Terre Island / Saint Francois

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £100 / night

£604 / week

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from £100 / night

(1) Excellent 

13

Caribbean holiday apartment rental

Saint James Parish / Holetown

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Car not necessary

from £85 / night

£593 / week

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from £85 / night

(4) Excellent 

16

Holiday apartment in Martinique

Arrondissement of Le Marin / Riviere-Salee

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £35 / night

£242 / week

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from £35 / night

(7) Excellent 

16

Holiday villa with swimming pool in Caribbean

Grande-Terre Island / Sainte-Anne

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 3 km
  • Swimming pool
  • Child friendly

from £52 / night

£363 / week

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from £52 / night

13

Apartment rental in Caribbean

Christ Church Parish / Hastings

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning

from £154 / night

£1077 - £1562 / week

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from £154 / night

(15) Very Good 

17

Caribbean holiday villa rental

Iles des Saintes / Terre-de-Haut

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £100 / night

£604 - £1298 / week

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from £100 / night

30

Villa rental in Dominican Republic

Samana Province / Las Galeras

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

from £108 / night

£679 - £1757 / week

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from £108 / night

(17) Excellent 

20

Caribbean holiday villa rental

St. Kitts / Frigate Bay

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Beautiful place and view!!!” Beautiful place - one of the best places we have stayed at - location was great!! We would go go back! One concern was that there was no hot water ion the kitchen until the last day.
…see more

from £330 / night

£2308 - £3039 / week

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from £330 / night

(27) Excellent 

21

Home rental in Caribbean with shared pool

Grande-Terre Island / Sainte-Anne

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £100 / night

£690 - £1371 / week

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from £100 / night

17

Holiday villa in Caribbean

St. Vincent / Penniston

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £85 / night

£600 / week

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from £85 / night

(6) Excellent 

22

Bungalow rental in Guadeloupe with shared pool

Grande-Terre Island / Le Moule

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Swimming pool

from £31 / night

£190 - £475 / week

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from £31 / night

(3) Excellent 

20

Caribbean holiday bungalow let

Curacao / Willemstad

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

from £55 / night

£380 / week

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from £55 / night

(18) Very Good 

26

Bungalow rental in Guadeloupe with shared pool

Grande-Terre Island / Saint Francois

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 4 km
  • Swimming pool
  • Child friendly

from £69 / night

£363 - £725 / week

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from £69 / night

4

Guadeloupe holiday b&b rental

Basse-Terre Island / Basse-Terre

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

from £43 / night

£296 / week

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from £43 / night

36

Caribbean holiday villa rental

Grande-Terre Island / Sainte-Anne

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £154 / night

£1078 - £1716 / week

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from £154 / night

(8) Excellent 

23

Holiday villa with swimming pool in St. Kitts and Nevis

Nevis / Barnes Ghaut

4 6 1 night min

  • 4 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool
“Large spacious house with beautiful scenery” The house for just beautiful, great scenery and what a view! The staff was wonderful. The road is horrible and it is getting worse everyone says. Pretty dangerous in some spots. It takes 15 minutes to get t
…see more

from £185 / night

£1270 - £1385 / week

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from £185 / night

(4) Very Good 

8

Holiday apartment with shared pool in Caribbean

Arrondissement of Le Marin / Trois-Ilets

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £35 / night

£233 - £242 / week

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from £35 / night

(3) Excellent 

18

Condo letting in Caribbean with shared pool, golf nearby

Tobago / Lowlands

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly

from £139 / night

£970 / week

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from £139 / night

26

Home rental in Caribbean

Enterprise / Enterprise

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £100 / night

£600 - £1500 / week

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from £100 / night

1