Air conditioned apartments and villas to rent in Caribbean

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19,928 Holiday homes

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(8) Excellent 

24

Caribbean holiday villa rental

New Providence Island / Nassau

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
WE INVITE YOU TO STAY AT WINDFALL FOR A RARE OPPORTUNITY TO ENJOY AN UNFORGETTABLE ISLAND HOLIDAY IN EXCEPTIONALLY GENEROUS ACCOMMODATIONS INSIDE A PRIVATE BAHAMIAN ESTATE.  …see more

from £300 / night

£2100 / week

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from £300 / night

(8) Excellent 

27

Holiday apartment with golf nearby in Kingston Parish

Kingston Parish / Kingston

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
The Pentwood is close Constant Spring Golf Course, Bob Marley Museum, Devon House, Sabina Park, The National Stadium, Half Way Tree Transport Centre, University of Technology, University of the West Indies, New Kingston, Barbican, Mona, USA British Canadian EmbassyDownt  …see more

from £60 / night

£381 / week

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from £60 / night

25

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
Welcome to Golfers Glory, a lovely 2 bedroom 1580 sq foot Caribean-style villa with private plunge pool and stunning views of the golf course and Nevis peak. This luxury Nevis vacation rental has the perfect location right beside the Four Seasons resort and the first te  …see more

from £917 / night

£6417 - £12473 / week

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from £917 / night

(3) Excellent 

9

Guadeloupe / Saint Anne

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Air conditioning

 …see more

from £170 / night

£1187 / week

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from £170 / night

(2) Excellent 

19

Saint-Martin / Cul de Sac

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £509 / night

£3560 / week

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from £509 / night

(2) Excellent 

14

Holiday apartment with golf nearby in Caribbean

Grande-Terre Island / Saint Francois

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
UNUSUAL LOCATION: FEET ON GREEN ... AIRFIELD, CASINO, MARINA, RESTAURANTS, BEACHES, NATURE, ALL ... IN THE HEART OF ST FRANCIS, THE STATION ALL SMILE !  …see more

from £73 / night

£509 - £636 / week

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from £73 / night

(1) Excellent 

10

Grande-Terre Island / Saint Francois

2 6 2 nights min

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

 …see more

from £43 / night

£255 - £433 / week

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from £43 / night

17

Holiday villa rental

Saint Francois / Anse des Rochers

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Location saisonnière d'une villa créole donnant sur un magnifique parc et piscine privative.Saint François - Guadeloupe - belles plages de sable blancVacation rental of a Creole Villa over a wonderful park with a secured swimming pool.  …see more

from £255 / night

£839 / week

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from £255 / night

17

Martinique / Sainte Anne

Studio 5 1 night min

  • Studio
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £30 / night

£149 - £297 / week

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from £30 / night

(12) Excellent 

18

Holiday villa with pool in Casuarina Estate

Bottom Bay / Casuarina Estate

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
“FANTASTIC” My wife and I stayed at the villa from 02/09/2013 to 30/09/2013, of all the places we have stayed in Barbados this is the first place we have re-booked for the following year. First of all the photographs do not do the place justice, it  …see more

from £96 / night

£650 - £675 / week

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from £96 / night

(5) Excellent 

21

Saint-Martin / Marigot

1 6 Min stay varies

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

 …see more

from £71 / night

£467 - £806 / week

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from £71 / night

10

Saint-Martin / Baie Nettle

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £102 / night

£712 - £1484 / week

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from £102 / night

15

Home rental in St. Barthelemy with swimming pool

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
Located on glitzy St. Barthélemy, this modern house offers the perfect base for exploring the everything the island has to offer. It can easily accommodate 4 sun-loving holidaymakers. Set just 100 metres from the sea and 500 metres from local shops, sights and restau  …see more

from £494 / night

£2998 - £8043 / week

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from £494 / night

16

Arrondissement of Le Marin / Le Francois

Studio 2 4 nights min

  • Studio
  • Sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £77 / night

£534 / week

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from £77 / night

(1) Excellent 

9

Bermuda / Smith's Parish

1 2 Min stay varies

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

 …see more

from £96 / night

£612 - £862 / week

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from £96 / night

(2) Excellent 

29

Saint-Martin / Orient Bay

2 4 Min stay varies

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

 …see more

from £43 / night

£297 - £1128 / week

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from £43 / night

(2) Very Good 

24

Marigot / Nettle Bay Beach Club

Studio 4 5 nights min

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

 …see more

from £50 / night

£350 - £789 / week

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from £50 / night

(1) Very Good 

21

Christ Church Parish / Oistins

2 6 Min stay varies

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

 …see more

from £60 / night

£477 - £810 / week

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from £60 / night

(14) Very Good 

19

Holiday apartment with shared pool, golf nearby in Antigua and Barbuda

Jolly Harbour / Hamilton Estate

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great Apartment in a Fabulous Location” This apartment really does have it all !! Nicely furnished well equipped very comfortable and in a lovely location near to 4 great beaches on the best side of the island Pool is wonderfully clean and a great pla  …see more

from £92 / night

£645 - £995 / week

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from £92 / night

(26) Excellent 

31

Turks and Caicos Islands / Providenciales

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £179 / night

£1250 / week

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from £179 / night

(5) Excellent 

16

Barbados holiday villa rental

Black Rock / Brighton Beach, Barbados

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Paradies does exist and its in Barbados...!” Four of us rented Sea Turtle for a bit of pre-Christmas sunshine and it was fantastic. The bungalow has clearly been refurbished to a high standard along with the grace of air con in all the bedrooms. The o  …see more

from £358 / night

£2500 - £5556 / week

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from £358 / night

19

Holiday apartment with shared pool in Caribbean

Gros Islet Quarter / Gros Islet

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Blue Skies Apartments with Swimming Pool and Heated Spa Tub. Situated in a quiet leafy road in the Tourist Mecca of Rodney Bay, close to the Shopping Malls, Stylish Restaurants, Bars and Beautiful Beaches. A few minutes walk to Rodney Bay Marina and close to Beausejour  …see more

from £100 / night

£695 / week

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from £100 / night

(4) Excellent 

21

Caribbean holiday cottage rental

Aruba / Palm - Eagle Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Welcome to Paradise” This is our first holidays in the Caribbean and we had a great time there thanks to our hosts Kiki and Frans at the Mango Casita. We had a warm welcome from our hosts and settled very well in this spacious villa and nice pool and  …see more

from £91 / night

£636 - £954 / week

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from £91 / night

24

St. Vincent and the Grenadines holiday villa rental

Bequia / Spring Bay

9 20 Min stay varies

  • 9 bedrooms
  • Sleeps 20
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
Exclusive, private, luxury Caribbean resort on Bequia in the Grenadines. More like a private resort than just a villa .Up to 20 guests can be accommodated in 10 air-conditioned suites with 4 poster beds, 40 ft. pool, full staff and more. Individual room rates also avail  …see more

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Pricing unknown

22

Holiday home letting

Saint George Parish / Roseau

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 13 km
  • Child friendly
  • Air conditioning
Welcome to Bluemoon Cottage, our cozy family cottage and studio. We’re located in expansive tropical gardens, 300 meters (1,000 ft) above the Roseau Valley—a world away and just ten minutes from the capital city of Roseau, with easy access to hiking trails and hot s  …see more

from £44 / night

£245 - £342 / week

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from £44 / night

(2) Very Good 

11

Arrondissement of La Trinite / Le Robert

1 4 Min stay varies

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

 …see more

from £34 / night

£238 / week

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from £34 / night

(4) Excellent 

29

Caribbean holiday cottage rental

Bonaire / Kralendijk

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden
This small resort is situated south of Kralendijk: the capitol of Bonaire.The territory of Bonaire is the most easterly island of the bottom Caribbean archipelago.Bonaire recently became part of the special municipality of the Netherlands called the "bes islands&qu  …see more

from £120 / night

£794 / week

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from £120 / night

4

Tobago / Mount Irvine

4 2 2 nights min

  • 4 bedrooms
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £48 / night

£286 / week

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from £48 / night

(4) Excellent 

29

Grande-Terre Island / Sainte-Anne

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 2 km
  • Child friendly
  • Air conditioning

 …see more

from £40 / night

£267 / week

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from £40 / night

(1) Excellent 

4

Guadeloupe / Terre-de-Bas

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Ask owner if suitable for children

 …see more

from £94 / night

£636 / week

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from £94 / night

(2) Excellent 

49

Saint-Martin / Cul de Sac

3 6 Min stay varies

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

 …see more

from £171 / night

£1389 - £1612 / week

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from £171 / night

24

Holiday apartment in Caribbean

Puerto Plata / Lifestyle Hacienda Resort

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
These units are truly PRESIDENTIAL ! Sleek, modern and very exclusive. Members/guests who are staying in any of the 3 available size Presidential Suite units will have exclusive access to the private presidential poolin the 2 bedroom Presidential Suite you get 8 people&  …see more

from £120 / night

£754 / week

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from £120 / night

(1) Excellent 

30

Holiday apartment accommodation

La Romana / La Romana Downtown, Dominican Republic

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly
At about 15 minutes by car you can find the lovely town of Bayahibe, it is a popular seaside area, full of white sandy beaches, coconut trees, and the warm and clear waters of the Caribbean Sea.  …see more

from £36 / night

£239 / week

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from £36 / night

(5) Average 

16

Ski apartment to rent in Caribbean

Saint Ann Parish / Ocho Rios

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski
FREE WIFIBeautiful beachfront apartment, villa, condo, vacation rental Ocho rios, Jamaica, cheap, affordable sea, sun, sunshine, fun, family, getawayFREE WIFI, NETFLIX  …see more

from £68 / night

£473 / week

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from £68 / night

(9) Excellent 

24

Basse-Terre Island / Deshaies

2 4 Min stay varies

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

 …see more

from £51 / night

£356 / week

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from £51 / night

(27) Excellent 

26

Holiday apartment in Caribbean

Saint Peter Parish / Mullins

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Just Beautiful, I wish it was mine!!” This is the second time I have stayed at Ocean View and it's just perfect. The apartment is immaculate and is extremely well equipped, has wifi and also a docking station/speakers for your i-pod. I fell in love w  …see more

from £150 / night

£1050 - £3220 / week

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from £150 / night

23

Grand Cayman / Seven Mile Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £235 / night

£1639 / week

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from £235 / night

15

Sint Maarten / Oyster Pond

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

 …see more

from £97 / night

£678 - £1077 / week

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from £97 / night

18

Las Terrenas / El Portillo

3 6 Min stay varies

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

 …see more

from £104 / night

£715 - £1112 / week

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from £104 / night

(3) Very Good 

35

Holiday apartment rental

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
Fishermans point resort is a one Bedroom beach apartment (living room, bedroom, kitchen, bath room), beach 3 minutes walk, with ocean view, located in Ocho Rios Turtle Street Mahogany Beach. The spacious apartments sleeps 4, Cable TV. The living and dining area a  …see more

from £70 / night

£350 - £520 / week

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from £70 / night