Air conditioned apartments and villas to rent in Caribbean

Close

View larger map

Also consider

North America Holidays
167837 properties
Caribbean Holidays
23144 properties
Villas St. Barts
3,320 properties
Villas Dominican Republic
3,299 properties
Villas Barbados
2,505 properties
Villas Jamaica
2,463 properties
Villas St. Maarten - Saint Martin
2,460 properties
Apartments Puerto Rico
1,826 properties
Villas Guadeloupe
980 properties
Villas Bahamas
844 properties
US Virgin Isles
779 properties
Villas Aruba
571 properties
Villas Antigua and Barbuda
535 properties
Villas St. Lucia
518 properties
Apartments Martinique
515 properties
Villas Curacao
350 properties
Villas Anguilla
344 properties
Villas British Virgin Isles
323 properties
Holiday rentals Turks and Caicos Islands
323 properties
Houses Cayman Islands
245 properties
Houses Trinidad and Tobago
228 properties
Apartments Bonaire
169 properties

Caribbean

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

15,362 Holiday homes

Filters applied: Air conditioning

(1) Excellent 

5

Grande-Terre Island / Sainte-Anne

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £51 / night

£356 / week

Book View

from £51 / night

(13) 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

Book View

from £250 / night

(3) Very Good 

8

Basse-Terre Island / Capesterre-Belle-Eau

1 4 1 night min

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

from £43 / night

£229 - £407 / week

Book View

from £43 / night

(4) Excellent 

16

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 £34 / night

£238 / week

Book View

from £34 / night

(11) 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
…see more

from £170 / night

£1610 / week

Book View

from £170 / 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 £166 / night

£1157 - £2344 / week

Book View

from £166 / night

(19) Excellent 

35

Holiday apartment with swimming pool in Caribbean

Saint Peter Parish / Mullins

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • 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
…see more

from £165 / night

£1150 - £2475 / week

Book View

from £165 / 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

Book View

from £85 / night

(23) Excellent 

24

Villa rental in Caribbean with swimming pool, golf nearby

Jolly Harbour / Jolly Harbour Villas

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Good Place to relax” Great location well appointed with good backup staff. Ideal for forgetting the world exists. Great fun to have the golf buggy to get arround Jolly Harbour.
…see more

from £150 / night

£900 - £1250 / week

Book View

from £150 / 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
…see more

from £106 / night

£739 / week

Book View

from £106 / night

(2) 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

£178 / week

Book View

from £26 / 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

Book View

from £150 / night

(22) 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 £130 / night

£840 - £2500 / week

Book View

from £130 / 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
…see more

from £150 / night

£1050 - £2295 / week

Book View

from £150 / night

(19) Very Good 

18

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 £34 / night

£238 - £386 / week

Book View

from £34 / 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 £77 / night

£475 - £721 / week

Book View

from £77 / night

(5) Very Good 

20

Barbados holiday apartment rental

Saint James Parish / Holetown

1 2 7 nights min

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

from £75 / night

£520 - £800 / week

Book View

from £75 / night

(5) Very Good 

19

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 £34 / night

£238 - £386 / week

Book View

from £34 / night

5

Apartment rental in Barbados with shared pool, golf nearby

Saint Peter Parish / Mullins

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £120 / night

£840 / week

Book View

from £120 / night

(20) Excellent 

27

Grande-Terre Island / Port-Louis

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from £40 / night

£280 / week

Book View

from £40 / night

(26) Excellent 

24

Holiday villa in Caribbean

Speightstown / Heywoods

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“a fantastic family rental !” The house was fantastic and would definitely rent again. Everything you saw and had was like the pictures. The walk in shower was brilliant especially after the beach with two children. The beach was just across the road.
…see more

from £100 / night

£575 - £968 / week

Book View

from £100 / night

10

Guadeloupe / Saint Anne

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £176 / night

£1229 - £1484 / week

Book View

from £176 / night

(7) Very Good 

19

Holiday villa with shared pool, golf nearby in Caribbean

Jolly Harbour / Hamilton Estate

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Jolly Harbour south finger villa” Perfect location 2 mins walk from jolly beach. Lovely villa with air con and all the useful things in the villa that you need or use when your at home. Great for the price! Will definitely be staying in the villa agai
…see more

from £100 / night

£400 - £550 / week

Book View

from £100 / 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 £267 / night

£1865 - £5009 / week

Book View

from £267 / 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
…see more

from £125 / night

£875 - £2555 / week

Book View

from £125 / night

(8) Excellent 

25

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

Saint Mary Parish / Jolly Harbour

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Tropical home from home” We were delayed at the airport sorting out a car rental and so were late arriving at our villa but we're greeted with a warm Antiguan welcome. have stayed at Jolly Harbour twice before this, so was already knowledgable of the
…see more

from £110 / night

£766 / week

Book View

from £110 / night

(9) Very Good 

26

Saint-Martin / Anse Marcel

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £51 / night

£356 - £1128 / week

Book View

from £51 / 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

£391 / week

Book View

from £63 / 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

£625 / week

Book View

from £94 / 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

Book View

from £34 / night

(18) 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
“Lovely accommodation in a quiet, well maintained complex close to the beach.” Fitts is a small quiet village with a lovely beach between Bridgetown and Holetown both of which are easily accessed by frequent buses, There is a well stocked supermarket,
…see more

from £70 / night

£490 - £590 / week

Book View

from £70 / night

(4) Very Good 

25

Holiday apartment with shared pool, golf nearby in Caribbean

Jolly Harbour / Hamilton Estate

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Lovely property” We participated in a family reunion and this was the perfect property for that. 2b 2b condos just outside Jolly Harbour. Good facilities very nearby, numerous restaurants and market. TV is old as is stove and washing machine. No coffe
…see more

from £93 / night

£645 - £995 / week

Book View

from £93 / night

(9) Excellent 

16

Caribbean holiday apartment accommodation

Speightstown / Heywoods

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary

from £97 / night

£675 - £900 / week

Book View

from £97 / night

(2) Very Good 

11

Basse-Terre Island / Basse-Terre

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £119 / night

£589 - £1145 / week

Book View

from £119 / night

(9) Excellent 

19

Caribbean holiday apartment rental

Saint Peter Parish / Gibbes

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

from £151 / night

£800 - £960 / week

Book View

from £151 / night

(6) Excellent 

16

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 £51 / night

£356 / week

Book View

from £51 / 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 £152 / night

£1060 - £1687 / week

Book View

from £152 / night

(14) 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

Book View

from £230 / night

(10) Very Good 

22

Apartment rental in Antigua and Barbuda

Saint Phillip Parish / Saint Philip

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £47 / night

£325 - £489 / week

Book View

from £47 / night

(3) Excellent 

22

Arrondissement of Le Marin / Le Francois

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £60 / night

£416 - £742 / week

Book View

from £60 / night

1