Villa Destinations » Caribbean

Luxury Villas in the Caribbean

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Things happen at a different pace at a luxury villa in the Caribbean. Stresses seem to ebb away like the tide. Each island has a unique style and atmosphere, and whichever you choose for your luxury villa holiday, you can be sure to do one thing – relax.

Read our caribbean holiday guide

Caribbean Island Holidays

Luxury Villa Holiday Rentals in Anguilla Caribbean

Anguilla

Luxury Villa Holiday Rentals in Barbados Caribbean

Barbados

Luxury Villa Holiday Rentals in St Barths Caribbean

St Barths

Luxury Villa Holiday Rentals in British Virgin Islands Caribbean

The British Virgin Islands (BVI’s)

Turks and Caicos. Perfect Beach

Turks and Caicos

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Browse Luxury Villas in the Caribbean

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Sunset 5

Villa Kasari East, Anguilla

Caribbean

Catered or Self-Catered

Bedrooms: 6

Guests: 12

  • Beachfront location

  • Heated swimming pool

  • Outdoor Jacuzzi

  • Rooftop garden

$48,216 (low season) to $150,675 (high season) per week

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Villa Niamh, Anguilla

Caribbean

Catered or Self-Catered

Bedrooms: 9

Guests: 10 - 20

  • Beachfront location

  • Infinity pool & Jacuzzi

  • Tennis & basketball court

  • Use of golf carts

$52,090 (low season) to $241,080 (high season) per week

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Villa Rockstar, St. Barths

Caribbean

Catered

Bedrooms: 6

Guests: 12

  • Beachfront location

  • Hot tub & swimming pool

  • Recording studio

  • Spa cabins

$155,400 (low season) to $252,000 (high season) per week

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Le Bleu, Little Harbour, Anguilla
Villa Le Bleu pool deck, Little Harbour Estates
Villa Le Bleu and Villa Indigo

Villa Bianchi, Anguilla

Caribbean

Catered

Bedrooms: 11

Guests: 20

  • Cinema room

  • Floodlit tennis court

  • Private beach

  • Swimming pools & hot tub

$70,840 (low season) to $183,120 (high season) per week

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Villa Caelum, Anguilla

Caribbean

Catered

Bedrooms: 9

Guests: 18 - 22

  • Beachfront location

  • Bicycles & water sports

  • Infinity pool & beach Jacuzzi

  • Tennis court

$184,513 (low season) to $307,503 (high season) per week

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The Villa at Sandy Lane Luxury Villa Holidays Barbados Caribbean 2
The Villa at Sandy Lane Luxury Villa Holidays Barbados Caribbean 1
The Villa at Sandy Lane Luxury Villa Holidays Barbados Caribbean 3

The Villa at Sandy Lane, Barbados

Caribbean

Catered

Bedrooms: 5

Guests: 10

  • Access to hotel facilities

  • Dining gazebo

  • Near the beach

  • Outdoor hot tub

$100,519 (low season) to $215,618 (high season) per week

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Pool View 6
Pool view 2
Sunset 5

Villa Kasari West, Anguilla

Caribbean

Bedrooms: 5

Guests: 10

  • Beachfront location

  • Infinity pool

  • Outdoor Jacuzzi

  • Rooftop gardens

$42,189 (low season) to $116,235 (high season) per week

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necker island beach pool jacuzzi
necker island beach pool

Necker Island, British Virgin Islands

Caribbean

Catered

Bedrooms: 18

Guests: 34 - 40

  • Beach Jacuzzi for 30 people

  • Private island

  • Swim up bar at infinity pool

  • Zip line to beach

$735,000 (low season) to $735,000 (high season) per week

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Villa Serene, Anguilla

Caribbean

Catered

Bedrooms: 8

Guests: 14 - 20

  • Beachfront location

  • Grotto on the beach

  • Swimming pool & Jacuzzi

  • Tennis courts & gym

$36,162 (low season) to $236,775 (high season) per week

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The Beach House Villa, Anguilla
The Beach House, Meads Bay
The Beach House Villa

Villa Ocean, Anguilla

Caribbean

Catered

Bedrooms: 8

Guests: 16

  • Beachfront location

  • Cinema room

  • Infinity pool & Jacuzzi

  • Tennis court

$88,550 (low season) to $229,320 (high season) per week

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Moskito Island beach house infinity pool
beach villa pool and view
beach house terrace chess

Moskito Island, BVIs

Caribbean

Catered

Bedrooms: 11

Guests: 22 - 24

  • Private island

  • Swim up bar

  • Tennis court

  • Watersports

$175,000 (low season) to $254,100 (high season) per week

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ANI Anguilla Resort from afar 3
ANI Anguilla Resort North Villa Sitting Room
ANI Anguilla Resort North Villa Pool

ÀNI Anguilla, Anguilla

Caribbean

Catered

Bedrooms: 10

Guests: 6 - 20

  • Clifftop hot tubs

  • Golf buggy service to beach

  • Tennis court

  • Two infinity pools

$172,200 (low season) to $301,350 (high season) per week

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Tranquility Aug 2021 12

Villa Tranquility, Turks and Caicos

Caribbean

Catered

Bedrooms: 11

Guests: 22

  • Beachfront location

  • Paddle boards & kayaks

  • Private dock

  • Tennis & basketball

$154,000 (low season) to $434,500 (high season) per week

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Hawksbill Luxury Summer Villa Turks and Caicos Caribbean 23
Hawksbill Luxury Summer Villa Turks and Caicos Caribbean 29
Hawksbill Luxury Summer Villa Turks and Caicos Caribbean 36

Hawksbill, Turks and Caicos

Caribbean

Catered

Bedrooms: 11

Guests: 22

  • Beachfront location

  • Floodlit tennis court

  • Heated outdoor swimming pool

  • Private dock

$154,000 (low season) to $429,000 (high season) per week

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Coral House Luxury Summer Villa Turks and Caicos Caribbean 2
Coral House Luxury Summer Villa Turks and Caicos Caribbean 21
Coral House Luxury Summer Villa Turks and Caicos Caribbean 15

Coral House, Turks and Caicos

Caribbean

Catered

Bedrooms: 7

Guests: 14

  • Beachfront location

  • Heated outdoor swimming pool

  • Home cinema room

  • Paddle boards & kayaks

$60,830 (low season) to $264,000 (high season) per week

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Long Bay Villas AnguillaDJI 0080 Edit SKY
Long Bay Villas Anguilla Sky 6
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Villa Saffir, Anguilla

Caribbean

Catered or Self-Catered

Bedrooms: 5

Guests: 10

  • Beachfront location

  • Infinity pool

  • Outdoor Jacuzzi

  • Water sports

$38,745 (low season) to $117,096 (high season) per week

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Beach House wide view

The Mill House, Barbados

Caribbean

Catered

Bedrooms: 8

Guests: 8 - 16

  • Beach house at Gibbes Beach

  • Gardens with orchard

  • Jacuzzi & swimming pool

  • Tennis court

$21,070 (low season) to $31,220 (high season) per week

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CRYSTAL SPRINGS JAN 2015 POOL LOOKING WEST TO SEA
CRYSTAL SPRINGS JAN 2015 POOL LOOKING TO EXTERIOR
CRYSTAL SPRINGS JAN 2015 ANNEX TERRACE LUNCH

Villa Camassia, Barbados

Caribbean

Catered

Bedrooms: 10

Guests: 20 - 22

  • Cinema room

  • Infinity pool

  • Secret cove beach

  • Speed boat & watersports

$94,500 (low season) to $126,000 (high season) per week

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ILLUSIONS at SUGAR HILL REAR EXTERIOR TWILIGHT
ILLUSIONS at SUGAR HILL VIEW OVER POOL
ILLUSIONS at SUGAR HILL REAR EXTERIOR

Villa Iresine, Barbados

Caribbean

Catered

Bedrooms: 4

Guests: 8

  • Access to tennis courts

  • BBQ

  • Sea views

  • Swimming pool

$12,600 (low season) to $38,500 (high season) per week

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Villa Jade ∏Pierre Carreau 3
Villa Jade ∏Pierre Carreau 1 1
Villa Jade ∏Pierre Carreau 23

Villa Jasmine, St. Barths

Caribbean

Catered or Self-Catered

Bedrooms: 8

Guests: 14

  • Cinema room

  • Gym

  • Infinity pool & Jacuzzi

  • Steam room

$36,000 (low season) to $174,000 (high season) per week

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Pricing Information

Our guide prices show the range of weekly prices from the low season to the high season. If the property has catering options, the low price is for the lowest level e.g. self-catered, and the high price is for the highest level e.g. catered.

What are the 'Low Season' and 'High Season' rates?

Low and high seasons vary by location and by property, but the general pattern is as follows:

Chalets
Low season is usually early/mid-December, mid-January, plus the summer months.
Mid season is usually early February, March and April.
High season is usually Xmas, New Year and mid/end February.

European Villas
Low season is usually April, May and October.
Mid season is usually June and September.
High season is usually July and August.

Caribbean Villas
Low season is usually June to November.
Mid season is usually November to mid-December and mid-April to June.
High season is usually mid-December to mid-April.