Air conditioned apartments and villas to rent in Caribbean

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13,990 Holiday homes

Filters applied: Air conditioning

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

15

Holiday apartment with shared pool, golf nearby in Caribbean

Christ Church Parish / Hastings

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £245 / night

£1715 / week

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from £245 / night

(6) Excellent 

23

Arrondissement of Le Marin / Le Diamant

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0.8 km
  • Swimming pool
  • Child friendly

from £130 / night

£906 / week

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from £130 / night

(8) Very Good 

37

Caribbean holiday tower rental

Saint George Parish / Lance aux Epines

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £295 / night

£2100 - £4100 / week

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from £295 / night

25

Holiday villa with swimming pool, golf nearby in Caribbean

Sint Maarten / Beacon Hill, Sint Maarten

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £794 / night

£5556 - £5953 / week

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from £794 / night

(4) Very Good 

24

Caribbean holiday apartment rental

Jolly Harbour / Hamilton Estate

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
“Loved it” Lovely apartment, had everything we need and spacious. Walking distance to valley church beach ( which you have to yourself if you get there early enough!) it is worth hiring a car though, which we did after one day of lugging water back fro
…see more

from £92 / night

£645 - £995 / week

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from £92 / night

(16) Excellent 

37

Barbados holiday apartment rental

Speightstown / Heywoods

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Comfortable, convenient and safe villa with a first class agent adjacent able to resove issues.” Fantastic property within a short walk of the beach and facilities. Friendly shop keepers and restauranteers. Ideal location for visiting all areas on the
…see more

from £68 / night

£476 - £756 / week

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from £68 / 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 £341 / night

£2381 - £2778 / week

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from £341 / night

9

Basse-Terre Island / Sainte Rose

1 2 Min stay varies

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

from £65 / night

£302 - £518 / week

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from £65 / night

(6) Very Good 

14

Holiday villa with swimming pool, golf nearby in Caribbean

Saint James Parish / Sunset Crest

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £278 / night

£1945 - £2143 / week

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from £278 / night

(1) Excellent 

24

Barbados holiday apartment rental

Saint James Parish / Paynes Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £516 / night

£3612 - £5278 / week

Enquire View

from £516 / night

(13) Very Good 

18

Holiday villa with swimming pool in Caribbean

Tobago / Mount Irvine

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £230 / night

£1610 / week

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from £230 / night

21

Basse-Terre Island / Deshaies

Studio 4 6 nights min

  • Studio
  • Sleeps 4
  • 6 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £65 / night

£453 / week

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from £65 / night

(5) Excellent 

23

Caribbean holiday apartment rental

Saint James Parish / Paynes Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
“There is NO PLACE like Coral Cove #12” Coral Cove never fails...fully equipped kitchen...beautifully appointed and incredibly roomy. Simon the owner is a pleasure to deal with, Dena who sees to the apartment, the security and Deborah the property mana
…see more

from £370 / night

£2590 / week

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from £370 / night

25

Grande-Terre Island / Le Moule

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 5 km
  • Air conditioning
  • Private garden

from £57 / night

£393 / week

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from £57 / night

(2) Very Good 

23

Saint-Martin / Baie Nettle

1 4 Min stay varies

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

from £69 / night

£414 - £725 / week

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from £69 / night

8

Saint-Martin / Marigot

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £78 / night

£483 - £733 / week

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from £78 / night

(6) Excellent 

30

Holiday villa with swimming pool in Barbados

Christ Church Parish / Six Cross Roads

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
“Lovely house” The house was well presented, clean and spacious. There was always a nice breeze which was always welcome and the pool was a good size. Communication was very good with the owner and the booking was stress free. Would stay here again.
…see more

from £100 / night

£700 - £750 / week

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from £100 / night

(2) Very Good 

23

Holiday apartment in Barbados

Saint Peter Parish / Speightstown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £90 / night

£499 - £914 / week

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from £90 / night

25

Holiday villa with swimming pool, golf nearby in Caribbean

Saint James Parish / Royal Westmoreland Golf Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £477 / night

£3334 - £11112 / week

Enquire View

from £477 / night

(4) Excellent 

17

Basse-Terre Island / Bouillante

2 4 5 nights min

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

from £87 / night

£518 / week

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from £87 / night

(2) Average 

24

Caribbean holiday villa rental

Saint George Parish / St. George's

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

from £62 / night

£437 - £497 / week

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from £62 / night

36

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

(1) Excellent 

36

Arrondissement of Le Marin / Sainte-Anne

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 0.5 km
  • Child friendly
  • Air conditioning

from £26 / night

£182 / week

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from £26 / night

25

Saint-Martin / Orient Bay

1 7 5 nights min

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

from £64 / night

£445 - £667 / week

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from £64 / night

(2) Excellent 

24

Villa rental in Dominican Republic with swimming pool

Las Terrenas / Las Ballenas

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £199 / night

£1008 - £2401 / week

Book View

from £199 / night

(4) Excellent 

15

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

24

Holiday home rental

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £1043 / night

£7302 - £15794 / week

Enquire View

from £1043 / night

(7) Very Good 

15

Saint Francois / Anse des Rochers

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £56 / night

£388 - £475 / week

Book View

from £56 / night

(1) Excellent 

32

Holiday villa with golf nearby in Caribbean

St. Kitts / Basseterre

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“An Oasis Of Relaxation” We just arrived back from a truly wonderful stay at the new Belle Mont Farm in St Kitts. My wife organised a little family gathering in one of the resorts 4 bedroom guesthouses and it was amazing!! The views from our villa were
…see more

from £1191 / night

£8334 - £14445 / week

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from £1191 / night

8

Arrondissement of Fort-de-France / Saint-Joseph

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £121 / night

£845 / week

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from £121 / night

(1) Excellent 

12

Saint-Martin / Bellevue

Studio 4 5 nights min

  • Studio
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £52 / night

£363 - £604 / week

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from £52 / night

31

Holiday villa with swimming pool in Caribbean

Guadeloupe / Saint Anne

3 8 6 nights min

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £114 / night

£798 - £1720 / week

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from £114 / night

(4) Very Good 

21

Guadeloupe / Saint Anne

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £89 / night

£617 - £1282 / week

Book View

from £89 / night

(3) Very Good 

24

Marie-Galante / Capesterre

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £173 / night

£1207 - £1690 / week

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from £173 / night

24

Holiday villa with golf nearby in Caribbean

Saint James Parish / James Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £635 / night

£4445 - £16667 / week

Enquire View

from £635 / night

(18) Very Good 

22

Self-catering villa with private pool in Bottom Bay, Barbados

Bottom Bay / Apple Hall

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Lovely Villa, quiet location” Hideaway was a lovely villa to stay in for a week. It is new, so in very good condition, everything you need is provided and the manager is on hand for anything you require. Only drawback for some may be it's relatively r
…see more

from £97 / night

£675 - £843 / week

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from £97 / night

(21) Excellent 

24

Holiday villa with swimming pool in Caribbean

Porters / Porters Gate

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Swimming pool
“The perfect location for chilling out and enjoying local hospitality” Actually this was my second trip to the property, I love being near to Hole Town's excellent shops and night life ( especially Friday night and Sundays on 2nd Street). I feel the
…see more

from £100 / night

£700 - £2500 / week

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from £100 / night

(2) Excellent 

20

Arrondissement of Le Marin / Trois-Ilets

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £49 / night

£302 - £388 / week

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from £49 / night

26

Barbados holiday condo rental

Saint James Parish / Holetown

3 6 Min stay varies

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

from £735 / night

£5139 - £9334 / week

Enquire View

from £735 / night

(1) Excellent 

24

Holiday villa with swimming pool, golf nearby in Caribbean

Nevis / Charlestown

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Amazing stay in Nevis” My fiancé and I spent 5 nights at this villa in early December. They offered us a free night when we booked 4 nights which was a huge saving. Utopia is a very modern and peaceful villa and boasts a wonderful infinity pool. Hou
…see more

from £924 / night

£6468 - £12572 / week

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from £924 / night

1