Air conditioned apartments and villas to rent in Caribbean

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14,934 Holiday homes

Filters applied: Air conditioning

(12) Excellent 

29

Caribbean holiday villa rental

Jolly Harbour / Jolly Harbour Villas

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“The best holiday ever” Coco House was the perfect place to stay with everything we could have wished for. Very spacious but homely and the pool a must. The villa was very well equipped and comfortable. Shops, bars and restaurants all within easy re
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from £170 / night

£1190 / week

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Responds fast!
avg. 1 hour 56 minutes

from £170 / night

8

Holiday apartment with shared pool in Caribbean

Saint-Martin / Marigot

1 4 5 nights min

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

from £79 / night

£492 - £746 / week

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Responds fast!
avg. 2 hours 4 minutes

from £79 / night

(20) Excellent 

33

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

(14) Excellent 

36

Holiday villa with swimming pool, golf nearby in Antigua and Barbuda

Antigua / Saint Mary's

4 8 Min stay varies

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

from £250 / night

£1750 - £2780 / week

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Responds fast!
avg. 1 hour 56 minutes

from £250 / night

(19) Excellent 

Certificate of Excellence

16

Studio rental in Martinique with shared pool

Arrondissement of Le Marin / Sainte-Luce

Studio 2 7 nights min

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

Certificate of Excellence

from £53 / night

£308 - £351 / week

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Responds fast!
avg. 2 hours 42 minutes

from £53 / night

(21) Excellent 

35

Holiday apartment with swimming pool in Caribbean

Saint Peter Parish / Mullins

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Fantastic - paradise by the sea!” What an amazing place to stay! We went for Christmas with our 7 year old and can't wait to go back. Ive been to Barbados 7 times before and this is simply the best holiday Ive ever had. The apartment was spacious, b
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from £165 / night

£1150 - £2475 / week

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Responds fast!
avg. 3 hours 2 minutes

from £165 / night

(10) Excellent 

20

Holiday villa with shared pool in Guadeloupe

Guadeloupe / Saint Anne

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £276 / night

£1930 - £5185 / week

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from £276 / night

(5) Very Good 

37

Villa rental in Antigua and Barbuda with shared pool, golf nearby

Saint Mary Parish / Jolly Harbour

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“NICE AND QUIET PLACE” We stayed almost two months in the villa and really appreciate it. The villa is very clean and updated. We specially appreciated having all our meals outside looking at the very nice view. The extended deck is fantastic and th
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from £107 / night

£745 / week

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from £107 / night

(9) Excellent 

24

Caribbean holiday villa rental

Antigua / Dickenson Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Impressive villa with stunning views” We have just returned from a fabulous holiday at Silk Cotton House. The villa owner was extremely responsive from the outset and clearly has considered everything to ensure guests have a comfortable stay.The villa
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from £286 / night

£2000 - £4000 / week

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Responds fast!
avg. 1 hour 45 minutes

from £286 / night

(12) Excellent 

14

Apartment rental in Antigua and Barbuda with shared pool, golf nearby

Antigua / Friars Hill

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“Great place to stay” Nice and easy transfer by taxi to the accommodation complex. Friendly reception staff on arrival. Very attractive and clean appartment, with a lovely balcony with sun loungers, table and chairs. Just a few hundred yards from a lo
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from £100 / night

£700 - £1100 / week

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Responds fast!
avg. 3 hours 48 minutes

from £100 / night

(21) Very Good 

23

Holiday townhouse with shared pool in Caribbean

Saint James Parish / Fitts

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Swimming pool
“Perfect family friendly villa” Ajoupa villa is set in a quiet and peaceful location, with easy access to the nearby beach and restaurants. The pool was a great place to cool off in after days spent on the beach. Their was a welcome pack on arrival whi
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from £70 / night

£490 - £590 / week

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Responds fast!
avg. 3 hours 23 minutes

from £70 / night

(24) Excellent 

17

Holiday townhouse with swimming pool in Caribbean

Saint James Parish / Holetown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“If you really want to feel at home on holiday, look no further.” After a fantastic stay last year we returned here for 2 weeks in April/May (this time 5 of us). Yet again despite its size and very modern feel we immediately felt at home – definitely a
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from £280 / night

£1960 - £3990 / week

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Responds fast!
avg. 3 hours 35 minutes

from £280 / night

(11) Excellent 

21

Antigua and Barbuda holiday villa rental

Saint Phillip Parish / Long Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“A fantastic holiday destination, where nothing more can be asked for” Brightside is an amazing place to stay on holiday - clean, spacious, wonderful views and perfect for a relaxing time away. I stayed out there with some friends and we had an excelle
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from £454 / night

£3175 - £5000 / week

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from £454 / 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
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from £235 / night

£1641 - £3719 / week

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from £235 / night

(2) Very Good 

23

Holiday villa in Caribbean

Saint Mary Parish / Jolly Harbour

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £171 / night

£1024 - £1378 / week

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from £171 / night

(9) Very Good 

27

Holiday condo in Caribbean

Saint James Parish / Sunset Crest

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Ask owner if suitable for children

from £35 / night

£240 - £325 / week

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from £35 / night

33

Holiday bungalow in Martinique

Arrondissement of Le Marin / Trois-Ilets

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 0.5 km
  • Car not necessary
  • Air conditioning

from £34 / night

£229 - £255 / week

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from £34 / night

(6) 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 £142 / night

£993 / week

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Responds fast!
avg. 3 hours 50 minutes

from £142 / night

(2) Excellent 

31

Caribbean holiday villa rental

Saint James Parish / Holetown

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £190 / night

£1330 - £1540 / week

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Responds fast!
avg. 1 hour 30 minutes

from £190 / 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

£254 / week

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from £41 / 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 £276 / night

£1930 / week

Enquire View

from £276 / night

(8) Excellent 

19

Holiday apartment with shared pool in Barbados

Saint Peter Parish / Gibbes

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Perfect holiday, perfect place - relaxation, sun and calm” We spent 2 weeks at Ashanti, staying in one of the larger 3 bed appartments. Our lift from the airport had been arranged with Collis, the fantastically helpful site manager, so the transfer wa
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from £115 / night

£800 - £960 / week

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from £115 / night

(11) Very Good 

10

Caribbean holiday bungalow rental

Guadeloupe / Saint Anne

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning

from £101 / night

£707 / week

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Responds fast!
avg. 1 hour 59 minutes

from £101 / night

(7) Very Good 

23

Holiday villa with swimming pool in Caribbean

Saint James Parish / Weston

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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 £749 / night

£5237 / week

Enquire View

from £749 / night

(3) Very Good 

8

Holiday gite in Caribbean

Basse-Terre Island / Capesterre-Belle-Eau

1 4 1 night min

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

from £45 / night

£239 - £425 / week

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Responds fast!
avg. 3 hours 46 minutes

from £45 / night

(1) Excellent 

31

Apartment rental in Dominican Republic

Samana Province / Las Terrenas

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.15 km
  • Child friendly

from £27 / night

£176 - £237 / week

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Responds fast!
avg. 2 hours 27 minutes

from £27 / night

(20) Very Good 

Certificate of Excellence

18

Holiday bungalow with shared pool in Caribbean

Grande-Terre Island / Sainte-Anne

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Can't find anything to fault” This is a lovely bungalow set within mango and starfruit trees. It is well equipped and the pool is within the grounds. The owners, Christine and Jean-Marc are friendly and helpful without being intrusive. When the a
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Certificate of Excellence

from £36 / night

£246 - £400 / week

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Responds fast!
avg. 1 hour 7 minutes

from £36 / night

24

Holiday villa with swimming pool, golf nearby in Caribbean

Saint Phillip Parish / Long Bay

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £630 / night

£4410 / week

Enquire View

from £630 / night

(3) Very Good 

12

Holiday apartment in Caribbean

Holetown / Lascelles

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Swimming pool

from £85 / night

£600 - £2600 / week

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from £85 / night

14

Holiday apartment rental

South Coast / Grand Anse

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Car not necessary

from £78 / night

£544 / week

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Responds fast!
avg. 3 hours 57 minutes

from £78 / night

12

Holiday studio with shared pool in Caribbean

Saint-Martin / Marigot, Saint Martin

Studio 4 Min stay varies

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

Pricing unknown

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Pricing unknown

(6) Very Good 

19

Holiday bungalow with shared pool in Caribbean

Grande-Terre Island / Sainte-Anne

1 4 3 nights min

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

from £36 / night

£246 - £400 / week

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Responds fast!
avg. 1 hour 7 minutes

from £36 / night

(3) Very Good 

20

St. Maarten-St. Martin holiday villa rental

Sint Maarten / Oyster Pond

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £172 / night

£1198 - £2426 / week

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Responds fast!
avg. 2 hours 29 minutes

from £172 / night

(5) Very Good 

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 - £1225 / week

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Responds fast!
avg. 2 hours 57 minutes

from £150 / night

(18) 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
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from £68 / night

£476 - £756 / week

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Responds fast!
avg. 1 hour 1 minutes

from £68 / night

(1) Excellent 

14

Apartment rental in Curaçao with shared pool

Willemstad / Mambo Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £203 / night

£1417 - £2299 / week

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from £203 / night

(16) 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

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 £159 / night

£1107 - £1762 / week

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from £159 / 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
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from £300 / night

£2100 - £3500 / week

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from £300 / night

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 £158 / night

£1103 / week

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from £158 / night

1