Air conditioned apartments and villas to rent in Caribbean

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19,734 Holiday homes

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(44) Very Good 

21

Grande-Terre Island / Saint Francois

1 3 Min stay varies

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

 …see more

from £61 / night

£337 - £432 / week

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from £61 / night

(7) Very Good 

16

Arrondissement of Le Marin / Le Marin

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Swimming pool

 …see more

from £74 / night

£513 / week

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from £74 / night

(1) Very Good 

11

Iles des Saintes / Terre-de-Haut

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

 …see more

from £87 / night

£518 / week

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from £87 / night

Featured properties

(2) Excellent 

26

Samana Province / Las Terrenas

2 4 7 nights min

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

 …see more

from £40 / night

£284 / week

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from £40 / night

(1) Very Good 

24

Barahona Province / Paraiso

11 28 1 night min

  • 11 bedrooms
  • Sleeps 28
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

 …see more

from £35 / night

£216 - £1785 / week

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from £35 / night

16

Arrondissement of Le Marin / Les Anses d'Arlet

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £87 / night

£604 / week

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from £87 / night

(2) Very Good 

22

Villa rental in Caribbean with swimming pool, golf nearby

Antigua / Dickenson Bay

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
“Lots of activities on Antigua” This is a beautiful house located on the northwest part of the island...It has a large pool and great views from every room. It is nicely furnished. We found good beaches a short drive from this location and more. The s  …see more

from £370 / night

£1725 / week

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from £370 / night

(2) Excellent 

36

Grande-Terre Island / Le Gosier

1 4 3 nights min

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

 …see more

from £57 / night

£393 / week

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from £57 / night

(11) Very Good 

23

Holiday villa accommodation

Saint James Parish / Holder's Hill

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Beautiful Villa with that personal touch from the cleaner” Prior to arrival the owner was very helpful with car hiring and attention to detail as we needed a divider in one of the rooms as we had brother and sister teenagers of different sexes sharing  …see more

from £105 / night

£735 - £900 / week

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from £105 / night

26

Holiday villa rental

Arrondissement of La Trinite / Le Robert

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Villa for up to 6 people on an exceptional site Ideal for holidays at several while preserving the privacy of each! In Martinique, the end of the Pointe Sable Blanc in the town of Robert, the site of Lucy's Bay is breathtaking. It offers a privileged and unique 360  …see more

from £87 / night

£604 - £1164 / week

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from £87 / night

(17) Excellent 

12

Holiday villa with swimming pool in Caribbean

Tobago / Bon Accord

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Just what we needed” Superb location within walking distance of great beach. Also close to airport - we were in the villa within 40 minutes of landing. The villa is in a good residential area and security is excellent. It has everything you need fo  …see more

from £151 / night

£1057 - £1464 / week

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from £151 / night

(15) Very Good 

21

Trinidad and Tobago holiday villa rental

Tobago / Bacolet Bay

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
Luxury villa with swimming pool just 5 minutes from the beach. Ideal for family holidays, couples getting away for a break, honeymooners or friends wanting a good time.  …see more

from £140 / night

£850 / week

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from £140 / night

(1) Excellent 

43

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £216 / night

£1509 / week

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from £216 / night

(1) Very Good 

21

Grande-Terre Island / Le Gosier

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning

 …see more

from £35 / night

£225 / week

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from £35 / night

9

Arrondissement of Le Marin / Le Marin

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly

 …see more

from £57 / night

£380 / week

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from £57 / night

(6) Excellent 

24

Caribbean holiday villa rental

Saint Paul Parish / Mamora Bay

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
The villa is privately owned, recently renovated and very well maintained. It has terracotta tiled floors and large patio doors to all living rooms, and the cooling Caribbean trade winds blow throughout, so although there is air conditioning to all rooms, there is rarel  …see more

from £142 / night

£1000 / week

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from £142 / night

(11) 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
Mot Mot Lodge has an open plan living, dining and kitchen area, with double hight ceilings and full width sliding doors, opening out on to a large upper patio,with outdoor dining facilities. This dining area links the interior and the garden seamlessly.  …see more

from £230 / night

£1610 / week

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from £230 / night

(3) 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

 …see more

from £89 / night

£617 - £1282 / week

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from £89 / night

(1) Excellent 

29

Villa rental in Caribbean

Port Antonio / Williamsfield

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
The Fan is a great holiday villa with one of the most magnificent views of Turtle Crawl Bay, Trident Castle and the Blue Mountains. !5 minutes drive from the main beaches and the Blue Lagoon it consists of two elegant 1-bedroom apartments in villa.  …see more

from £163 / night

£1139 / week

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from £163 / 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

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from £93 / 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

 …see more

from £49 / night

£302 - £388 / week

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from £49 / night

(3) Very Good 

24

Holiday apartment in Caribbean

Castries Quarter / Marigot Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Amazing time at your condo” My wife, my son and I had an amazing time at this condo. The apartments is fantastically positioned for everything we wanted to do. We dived, snorkelled, sailed and swam in the beautiful caribbean sea. Thank you so much  …see more

from £150 / night

£1050 / week

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from £150 / night

(6) Excellent 

11

Apartment rental in Caribbean

Saint James Parish / Paynes Bay

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“The Perfect Getaway” We had an absolutely amazing stay at The Ivy. The apartment is beautifully furnished and really does look as it is online. An added bonus was the proximity of some of the island's best restaurants with The Cliff within staggering  …see more

from £448 / night

£3131 - £4838 / week

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from £448 / night

(2) Excellent 

26

Arrondissement of Le Marin / Les Anses d'Arlet

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £57 / night

£393 - £694 / week

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from £57 / night

(2) Very Good 

31

Caribbean holiday villa rental

Saint James Parish / Paynes Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Lovely 2 Bedroom House, fully enclosed, directly on the Beach in Paynes Bay with beautiful views on the Caribbean sea.<br />The perfect beach home for all who like swim, snorkeling and dive.  …see more

from £236 / night

£1651 / week

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from £236 / night

8

Arrondissement of Le Marin / Sainte-Anne

Studio 2 5 nights min

  • Studio
  • Sleeps 2
  • 5 nights min
  • Child friendly
  • Air conditioning

 …see more

from £33 / night

£230 / week

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from £33 / night

24

Caribbean holiday apartment rental

La Altagracia Province / Punta Cana

3 2 4 nights min

  • 3 bedrooms
  • Sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
One, two and three bed room suites in this luxurious resort is set within the lush tropical area of Punta Cana, with a Caribbean hideaway vibe. Fully furnished living and kitchen area, with stainless steel appliances and designer furnishings set the standard for lavish  …see more

from £163 / night

£1142 / week

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from £163 / night

20

Holiday villa in Caribbean

Saint Mary Parish / Jolly Harbour

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden
The villa is set on the water's edge with a spectacular view of the rolling hills. Located at the end of a quiet street in the Jolly Harbour Marina, the villa captures a refreshing breeze thought the day. This contemporary villa will be your perfect vacation home t  …see more

from £163 / night

£1139 / week

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from £163 / night

(1) Excellent 

27

Holiday condo with shared pool in U.S. Virgin Islands

St. Thomas / St Thomas East

1 7 Min stay varies

  • 1 bedroom
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
WELCOME to the one of the most amazing condos at the Sapphire Beach! Book with us and you will not be disappointed - we treat our guests with the respect they deserve. We are online and ready to help you with any questions before and during your stay. Many of our guests  …see more

from £205 / night

£4065 / week

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from £205 / night

11

Caribbean holiday villa rental

Saint James Parish / Royal Westmoreland Golf Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
Luxury Royal Westmoreland Golf Resort - Elegant 3 BR villa on the West Coast close to all amenities and excellent restaurants. Pool, Golf, Tennis, Spa, Excellent Gym, Restaurant, shuttle to RWM's private beach, beach chairs, towels and umbrellas and Spa facility.  …see more

from £185 / night

£1610 - £1960 / week

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from £185 / night

6

Sint Maarten / Oyster Pond

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Air conditioning

 …see more

from £98 / night

£682 / week

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from £98 / night

(6) Very Good 

34

Caribbean holiday condo rental

Saint Ann Parish / Ocho Rios

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Most Relaxing Holiday Ever” My son & I had never been to Jamaica before... traveled with friends that were born in Jamaica. People in Jamaica are the most genuine people on earth. They are so kind, helpful and always happy. I definitely will be goi  …see more

from £90 / night

£600 / week

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from £90 / night

22

Apartment rental in Dominican Republic with shared pool

San Pedro de Macoris Province / Juan Dolio

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Our awesome two bedroom apartment is located Juan Dolio's Club Hemingway, a private residential apartment complex resorts. There are 2 bedrooms, the master bedroom has one king size bed and the other bedroom is equipped with two queen sized beds and a couc  …see more

from £224 / night

£976 / week

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from £224 / night

(2) Very Good 

29

Holiday apartment with shared pool in Caribbean

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
The Resort is situated on 19 acres of lush landscaped gardens with 90 story residences surrounding a freshwater swimming pool, swim-up bar, whirlpool and bar. There are also two tennis courts and a Spa. Beach 7 minutes walk from apartment. We also have rentals at S  …see more

from £75 / night

£350 - £590 / week

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from £75 / night

18

Santo Domingo Province / Boca Chica

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £41 / night

£285 / week

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from £41 / night

(1) Very Good 

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

 …see more

from £48 / night

£345 - £432 / week

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from £48 / night

(2) Excellent 

15

Holiday cottage in Caribbean

Saint Peter Parish / Mullins

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
A charming seaside cottage located directly on the popular Mullins Beach in a northern part of Barbados. Sandy beach, sparkling blue sea, fabulous sunsets, neighbouring beach bar,and a variety of watersports, all on your doorstep. Situated on a main bus route,to eit  …see more

from £100 / night

£700 - £850 / week

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from £100 / night

(15) Excellent 

24

Holiday villa with shared pool in Caribbean

Saint Andrew Parish / Crochu

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Beautiful sweeping views” Absolutely gorgeous location on the less touristy side of the island. Our favorite part was opening up all the French doors and having the sea breeze blow through the villa. We love to cook, so having the kitchen was a major  …see more

from £163 / night

£976 - £1224 / week

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from £163 / night

10

Holiday apartment in Trinidad and Tobago

Trinidad / Caroni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Spacious 2 bedroom apartment, located in the breezy, serene plains of east/central Trinidad. Only 10 minutes to the airport, to 4 major shopping malls, educational district of universities and colleges, famous Caroni Bird Sanctuary and other attractions. There is also a  …see more

from £82 / night

£570 / week

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from £82 / night

(1) Excellent 

22

Arrondissement of Le Marin / Le Francois

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool

 …see more

from £216 / night

£949 - £1423 / week

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from £216 / night