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Villas in Caribbean and Estates - Holiday Lettings - Holiday Rentals Caribbean

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17,596 Holiday homes

Dominican Republic holiday home rental

Las Galeras house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £384 / night

£2,415 - £2,670 / week

1 / 21

Caribbean holiday home rental

Las Galeras house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

from £92 / night

£543 / week

1 / 16

Caribbean holiday boathouse rental

San Juan boathouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £548 / night

£3,833 / week

1 / 7

Bungalow rental in Caribbean

Le Moule bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £50 / night

£275 / week

1 / 4

Caribbean holiday home rental

Priory house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £38 / night

£203 / week

1 / 16

Holiday studio with shared pool in Caribbean

Punta Cana studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £137 / night

£913 / week

1 / 11

Holiday villa with swimming pool in Caribbean

Le Marin villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £216 / night

£1,513 / week

1 / 56

Dominican Republic holiday condo rental

Puerto Plata condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £114 / night

£799 / week

1 / 14

Apartment rental in Caribbean

Priory apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £51 / night

£352 / week

1 / 26

Holiday apartment in Caribbean

Cabarete apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £51 / night

£352 / week

1 / 67

Caribbean holiday home rental

Enterprise house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £146 / night

£1,022 / week

1 / 16

Holiday villa in Trinidad and Tobago

Black Rock villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £165 / night

£676 - £3,359 / week

1 / 26

Villa accommodation in Caribbean

Orange Bay villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £83 / night

£466 / week

1 / 28

Holiday apartment accommodation

Grand Anse apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £174 / night

£1,214 / week

1 / 45

Holiday condo with shared pool, golf nearby in Caribbean

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £502 / night

£2,355 / week

1 / 21

Studio rental in Caribbean with shared pool

Prospect studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £172 / night

£1,203 - £2,213 / week

1 / 29

Caribbean holiday cottage let

Rainbow Bay cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £137 / night

£959 / week

1 / 21

Kingston Parish holiday home rental

Kingston house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

from £92 / night

£594 / week

1 / 27

Holiday apartment with shared pool in St Martin / St Maarten

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £411 / night

£2,875 / week

1 / 11

Caribbean holiday home rental

William's Town house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £297 / night

£2,076 / week

1 / 19

Holiday home rental

Ironshore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £60 / night

£333 / week

1 / 10

Holiday home in Caribbean

Bavaro house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £83 / night

£575 / week

1 / 7

Holiday home in Guadeloupe

Les Abymes house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £69 / night

£442 / week

1 / 29

Holiday condo with shared pool in Dominican Republic

Puerto Plata condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £273 / night

£1,910 / week

1 / 8

Dominican Republic holiday apartment rental

Santiago de los Caballeros apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £65 / night

£452 / week

1 / 17

Holiday hotel apartment with shared pool in Dominican Republic

Puerto Plata hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £59 / night

£411 / week

1 / 44

Home rental in Caribbean with shared pool, golf nearby

Portmore house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing” To start, the location is great. Being in a gated community it made my family feel extremely safe. The house was clean, both rooms are big and well decorated with A/C. The kitchen made me feel at home large and spacious with all the basic necessities. The Wi-Fi was on point, never missed an email or my connection on social media. Needless to say, Mr Henry was great to work with. I will recommend this house to all my friends and family. Thank you Mr Henry.

from £90 / night

£575 / week

1 / 34

Dominican Republic holiday apartment rental

Bavaro apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £174 / night

£1,214 / week

1 / 5

Holiday villa with swimming pool, golf nearby in Barbados

Holetown villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £219 / night

£1,533 / week

1 / 27

Caribbean holiday villa rental

Cabrera villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £160 / night

£1,118 / week

1 / 9

Holiday bungalow with shared pool in Guadeloupe

Bouillante bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £74 / night

£295 / week

1 / 10

Caribbean holiday apartment rental

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £64 / night

£448 / week

1 / 19

Dominican Republic holiday villa rental

Puerto Plata villa

  • 6 bedrooms
  • 12 bathrooms
  • sleeps 12

from £685 / night

£3,468 / week

1 / 8

Holiday home with shared pool in Guadeloupe

Petit-Bourg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £99 / night

£688 / week

1 / 14

Holiday home in U.S. Virgin Islands

Christiansted house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £260 / night

£1,821 / week

1 / 34

Aruba holiday apartment rental

Oranjestad apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £115 / night

£685 - £813 / week

1 / 12

Holiday bungalow in Martinique

Le Marin bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £69 / night

£482 / week

1 / 22

Holiday bungalow with shared pool in Caribbean

Le Marin bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £63 / night

£440 / week

1 / 22

Villa rental in U.S. Virgin Islands with shared pool

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £1,597 / night

£11,179 / week

1 / 17

Holiday apartment with shared pool in Caribbean

Black Rock apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £114 / night

£760 / week

1 / 21

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Caribbean holidays

Turquoise ocean, sun-bleached sand, peach-gold sunsets and the most easy-going people on the planet… the Caribbean is every inch the perfect tropical paradise. Saint Lucia, Antigua, Dominica, Barbuda, Hispaniola and over 700 more islands are waiting to steal your heart.

Beachside Bliss

Awarding the title of ‘best beach in the Caribbean’ is like deciding which diamond in the Crown Jewels sparkles the most. It’s a nigh-on impossible, yet dazzling experience. Grand Cayman’s seven-mile paradise is a good place to start, with water as clear as glass, and the luxurious capital of George Town a stone’s throw away. Other Caribbean beach havens include Jamaica’s Montego Bay and virtually anywhere on Saint Martin island.

Secret Treasures

But the Caribbean isn’t all beaches and blue topaz seas. If you can drag yourself away from the sand on Puerto Rico, you’ll discover the tropical rainforest of El Yunque National Forest. Explorers who venture inland on most islands will be rewarded with secluded waterfalls, like Dunn’s River Falls in Ocho Rios, Jamaica.

Sub-Marine Spectacular

Snorkelling in the azure seas of the Caribbean is incredible, not least because of the vivid colours on display. Shoals of shimmering fish dart between coral reefs beneath the waves and when you come up for air, forests and palm trees cover the coasts. It’s like someone has turned up the colour saturation on your television. Head to Antigua’s Stingray City, a marine life petting zoo, for a hands-on experience you’ll never forget.

Top Destination reviews

Fire fly cottage with ocean view
Beautiful peaceful stay

We were looking for a remote cabin in peace and this was the perfect place. Quiet, relaxing and in the countryside. The hosts Geneva and Sean were lovely and helpful and easy to communicate with. We will definitely be back when need a quiet getaway in nature … see more
Sea Break 4BR Villa - Beachfront
Paradise!

We stayed here 3/25-4/1/23. Once you decide you are going to vacation on TCI and once you decide that you are going to stay on Long Bay vs. Grace Bay, because you want room to spread out and a little privacy, then Brise de Mer is the spot for you. Amazing house with all the amenities right on the beach, with its own pool. Breathtaking views. Watch the kite-boarders cruise on by. Perfect for families or couples.see more
Clean 1bedroom with a turquoise view
Unit 58..Marlon

It was a wonderful stay..clean and Marlon was so attentive when needed ! comfortable with beautiful views...I would rent again for sure ! No complaints at all... just what I needed ! … see more
Millennium Park Trincity Vacation Home
Safe, peaceful and quiet!

I booked this house for my parents to stay in April 2023. They had nothing but positive things to say about it. It's a nice quiet community that they felt very safe in. They are looking forward to coming back next year. Thank you Nicholas and Natalie! … see more
TRAVELERS' CHOICE AWARD Villa Sol 2 minute walk to the Caribbean Sea
Amazing house and fabulous owners

Where do I start, Jean and Harry greeted us at our arrival which we got there a bit earlier than expected but they allowed us to check in and gave us the tour of the home which was immaculate, beautiful and so spacious. They provided everything we needed and more. If I could give them stars ✨ I would. They are the most thoughtful, caring and genuine couple who cares for their guests. We can’t wait to return and spend more time at their lovely home see more
Brand New Luxury 4 Bed, Ensuite Villa - Kokomo
Girl’s holiday

I have had several holidays in this beautiful villa, it as everything you could possibly imagine, you can be on the beach or at a beach bar in a 5 minute walk, you can watch the sunset on the beach every night if you wanted to,.The supermarket is also 5 minutes away ,so if you would like to sit outside the villa and enjoy a glass of wine and some lunch it is perfectly okay,see more

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