Air conditioned apartments and villas to rent in Caribbean

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15,359 Holiday homes

Filters applied: Air conditioning

(2) Excellent 

14

Holiday villa in Barbados

Christ Church Parish / Rockley

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £250 / night

£1750 / week

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from £250 / 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 £333 / night

£2326 - £2714 / week

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Responds fast!
avg. 2 hours 17 minutes

from £333 / night

(4) Excellent 

13

Penthouse accommodation in Caribbean

Saint Peter Parish / Speightstown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £150 / night

£1050 - £1750 / week

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Responds fast!
avg. 2 hours 45 minutes

from £150 / night

(5) Very Good 

19

Grande-Terre Island / Le Gosier

1 4 7 nights min

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

from £68 / night

£475 / week

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from £68 / night

31

Holiday villa in Jamaica

Saint James Parish / Montego Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Private garden

from £250 / night

£1700 / week

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Responds fast!
avg. 2 hours 42 minutes

from £250 / night

(1) Excellent 

20

Basse-Terre Island / Deshaies

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £97 / night

£678 / week

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from £97 / night

(4) Very Good 

16

Arrondissement of La Trinite / Le Robert

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £36 / night

£255 / week

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Responds fast!
avg. 43 minutes

from £36 / 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 £274 / night

£1915 / week

Enquire View

Responds fast!
avg. 3 hours 27 minutes

from £274 / night

(12) Excellent 

24

Caribbean holiday villa rental

Saint James Parish / Holetown

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £550 / night

£3850 / week

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from £550 / night

(1) Excellent 

22

Holiday apartment with shared pool in Caribbean

Saint Peter Parish / Mullins

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool

from £94 / night

£569 - £743 / week

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Responds fast!
avg. 3 hours 5 minutes

from £94 / night

(3) Very Good 

10

Holiday apartment rental

Maxwell / Fairholme Gardens

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £45 / night

£315 / week

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from £45 / night

(7) Very Good 

21

Holiday villa in Caribbean

Holetown / Queens Fort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“Great place to stay with fantastic hosts” 7 of us stayed at the villa for a week back in April, we were catered for perfectly by Tony and Rose who really made our trip. Tony's gravy is worth the trip alone. The villa was ideal for us, loads of outsi
…see more

from £300 / night

£2100 - £3500 / week

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from £300 / night

(1) Excellent 

14

Holiday apartment in Caribbean

San Pedro de Macoris Province / San Pedro de Macoris

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning

from £41 / night

£250 / week

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from £41 / night

(1) Very Good 

16

Saint-Martin / Marigot

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 3 km
  • Child friendly
  • Car not necessary

from £34 / night

£221 / week

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from £34 / night

(3) Very Good 

34

Bahamas holiday home rental

Great Abaco Island / Marsh Harbour

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly

from £79 / night

£547 / week

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from £79 / night

24

Caribbean holiday townhouse rental

Saint Michael Parish / Garrison

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £128 / night

£896 / week

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Responds fast!
avg. 2 hours 38 minutes

from £128 / night

6

Basse-Terre Island / Sainte Rose

1 2 Min stay varies

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

from £39 / night

£246 - £450 / week

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from £39 / night

(15) Excellent 

16

Holiday apartment with swimming pool in Caribbean

Mullins / Beacon Hill

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Condo is kept at a very high specification and standard” Had a very relaxing 9 days in a lovely garden apartment with pool. John & Sheila who own it helped a great deal before we went. Kerry the local manager was also very professional & helpful, as
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from £150 / night

£1050 - £2295 / week

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from £150 / night

24

Grande-Terre Island / Le Moule

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 5 km
  • Swimming pool
  • Child friendly

from £73 / night

£511 / week

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Responds fast!
avg. 1 hour 30 minutes

from £73 / night

(2) Excellent 

24

Holiday home in Caribbean

Saint James Parish / Holetown

3 6 Min stay varies

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

from £250 / night

£1700 - £1910 / week

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from £250 / night

(8) Excellent 

13

Grande-Terre Island / Saint Francois

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.1 km
  • Swimming pool
  • Child friendly

from £51 / night

£356 - £717 / week

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from £51 / night

(3) Excellent 

13

Basse-Terre Island / Deshaies

2 6 Min stay varies

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

from £77 / night

£467 - £2272 / week

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from £77 / night

(3) Excellent 

22

Arrondissement of Fort-de-France / Le Lamentin

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £85 / night

£594 / week

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from £85 / night

(9) Very Good 

24

Holiday bungalow with shared pool in Caribbean

Saint James Parish / Holetown

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
“Brilliant holiday in glorious sunshine!” Ellie's apartment is spotlessly clean and very convenient for local facilities. There's no need to cook as so many restaurants are within walking distance, all price ranges catered for. It's great to have the
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from £50 / night

£350 - £399 / week

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Responds fast!
avg. 3 hours 56 minutes

from £50 / night

(3) Very Good 

17

Basse-Terre Island / Deshaies

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 0.4 km
  • Swimming pool
  • Child friendly

from £80 / night

£463 - £832 / week

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from £80 / night

(14) Excellent 

23

Apartment rental in Caribbean

Speightstown / Port St Charles

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary
“The most beautiful condo you will ever stay in!” I don't know where to begin other than to say this condo is the most beautiful condo I have ever seen. The entire place is top notch and nothing could be better. The kitchen is state of the art if you
…see more

from £280 / night

£1960 - £6870 / week

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Responds fast!
avg. 3 hours 36 minutes

from £280 / night

(4) Excellent 

16

Grande-Terre Island / Sainte-Anne

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £43 / night

£297 - £382 / week

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Responds fast!
avg. 2 hours 39 minutes

from £43 / night

(9) Very Good 

15

Caribbean holiday villa rental

Tobago / Scarborough

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £214 / night

£1493 - £2144 / week

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Responds fast!
avg. 3 hours 6 minutes

from £214 / night

23

Basse-Terre Island / Deshaies

Studio 4 6 nights min

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

from £60 / night

£416 / week

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Responds fast!
avg. 2 hours 19 minutes

from £60 / night

(48) Excellent 

23

Villa rental in St. Lucia with swimming pool, golf nearby

Castries / La Toc

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“It was a magical experience and we were reluctant to return home” We had a wonderful five night stay at this impressive newly built villa in a stunning location overlooking the Caribbean Sea, with the sandy beach of La Toc a short stroll away. The
…see more

from £235 / night

£1641 - £3719 / week

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from £235 / night

(15) Very Good 

18

Holiday villa with swimming pool in Caribbean

Tobago / Mount Irvine

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £230 / night

£1610 / week

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from £230 / night

(26) Excellent 

12

Holiday b&b in St. Kitts and Nevis

Nevis / Gingerland

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 7 km
  • Child friendly
  • Air conditioning
“Beautiful house and grounds on Nevis” My wife, myself, and our young child enjoyed a wonderful two night stay at this great little house. It had everything that we needed to make our time enjoyable. The owners were very friendly and made sure that all
…see more

from £63 / night

£388 / week

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from £63 / night

(9) Excellent 

29

Samana Province / Las Terrenas

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.15 km
  • Child friendly

from £34 / night

£212 - £272 / week

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Responds fast!
avg. 1 hour 45 minutes

from £34 / night

(6) Excellent 

19

Apartment rental in Caribbean with golf nearby

Saint James Parish / Paynes Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
“Relaxation in luxury” If you're looking to get away from your hectic daily life then Life's a Beach - Coral Cove 8 is the perfect place to unwind and relax in luxury surroundings. The beach front location is spectacular and also practical, as it's on
…see more

from £427 / night

£2714 - £4187 / week

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from £427 / night

(14) Excellent 

24

Grande-Terre Island / Sainte-Anne

3 6 7 nights min

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

from £116 / night

£806 - £1272 / week

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Responds fast!
avg. 2 hours 8 minutes

from £116 / night

13

Grande-Terre Island / Saint Francois

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £51 / night

£356 - £382 / week

Book View

Responds fast!
avg. 1 hour 30 minutes

from £51 / night

(20) Excellent 

20

Home rental in Caribbean with swimming pool

Saint Peter Parish / Maynards

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Lovely Villa, great location” Our party of family and friends had a lovely time at Palm Villa. The facilities are excellent, it was plenty big enough for all ten of us and Beverley was helpful and went out of her way to make our stay comfortable. We
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from £125 / night

£875 - £2555 / week

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from £125 / night

(1) Very Good 

18

Grande-Terre Island / Le Gosier

5 8 1 night min

  • 5 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £80 / night

£559 / week

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from £80 / night

(2) Average 

11

Basse-Terre Island / Bouillante

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £47 / night

£339 - £424 / week

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from £47 / night

13

Holiday home with shared pool in Caribbean

Saint Ann Parish / St. Ann's Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 13 km
  • Swimming pool
  • Child friendly

from £94 / night

£621 / week

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Responds fast!
avg. 56 minutes

from £94 / night

1