50 Best Caribbean Villas on Holiday Lettings - Vacation rentals

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23,731 Vacation rentals

31

Vacation villa in Jamaica

Saint James Parish / Montego Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Private garden
Pleasant View is a unique and immaculate air conditioned 3 bedroom villa luxuriously furnished with modern furnishings. Including outdoor bar, barbecue, large pool & other amenities. Seven miles west of Sangsters International Airport is Pleasant View, rapturo …see more

from $325 / night

$2210 / week

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from $325 / 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
Villa Vista is available for rent on a weekly or monthly basis. We offer discounts of 10% on stays of 1 month. 15% on 2 months and 20% on 3 months. Check in time is 4 pm on same day turn around of guests. and 3 pm when there is no same day turn around of guests. Chec …see more

from $135 / night

$945 / week

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from $135 / night

(26) Excellent 

24

Vacation villa with swimming pool in Antigua and Barbuda

Willikies / The Peninsula

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
This villa is for those who enjoy peace and tranquillity. The stunning waterfront location at the Peninsula along with the contemporary style is what sets this holiday home apart from others. The villa looks out from the Peninsula, towards Pelican Island and the reef …see more

from $223 / night

$1560 - $3380 / week

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from $223 / night

8

Vacation apartment with shared pool in Caribbean

Saint-Martin / Marigot

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Ouvrez le portillon de votre terrasse et vous êtes sur une plage privée ! ' En solo, en famille, en amoureux, entre amis, professionnel..' un merveilleux séjour vous attend dans ce magnifique studio REZ DE PLAGE, Standing, entièrement rénové-équipé Accès direct sur une …see more

from $101 / night

$628 - $953 / week

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from $101 / night

(2) Excellent 

19

Villa rental in Caribbean with swimming pool, golf nearby

Grande-Terre Island / Saint Francois

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
In a garden 800 m2 with swimming pool landscaped and overlooking clear grapes in Saint François, Guadeloupe spacious villa Beach offers accommodation of quality and comfort. 3 air-conditioned rooms with a Queen size bed (160 cm) sleeping on quality bedding can accomm …see more

from $177 / night

$1233 - $1558 / week

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from $177 / night

(19) Very Good 

Certificate of Excellence

18

Vacation bungalow with shared pool in Caribbean

Grande-Terre Island / Sainte-Anne

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Property situated on a hill ventilated and quiet 1.5 km from the town, from the beach, tourist activities, shops and restaurants. Our two air-conditioned bungalows, wood in the purest creole style, are based in a beautiful tropical garden with private pool in an intimat …see more

Certificate of Excellence

from $45 / night

$314 - $510 / week

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from $45 / night

19

Bungalow rental in Guadeloupe with shared pool

Basse-Terre Island / Pointe-Noire

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Bungalow coconut making advantage of all 3 housing deposits. Coconut is entirely made of wood, consisting of two air-conditioned rooms, with 1 double bed and one with 1 bed double bunk bed single (the beds are fitted with mosquito nets), bathroom with shower and toilet, …see more

from $90 / night

$589 - $667 / week

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from $90 / 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 mi
  • Swimming pool
Palm Villa is the perfect holiday home in Barbados. Its elevated position at Maynards allows the easterly tropical breeze to gently cool you down on the hottest of days. The house has been fully refurbished in 2011 with modern furniture and all the modern conveniences y …see more

from $163 / night

$1138 - $3322 / week

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from $163 / night

6

Dominica Vacation private room rental

Saint George Parish / Roseau

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
A 5 minutes à pied du front de mer où arrive le Ferry de l'Express des Iles, venant de Martinique ou de Guadeloupe, notre Guest House vous attend pour votre séjour dans l'île Nature de la Dominique. Au total, 5 chambres sont au 1er étage, toutes climatisées avec WIFI et …see more

from $50 / night

$346 / week

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from $50 / night

(2) Good 

4

Guadeloupe Vacation bungalow rental

Basse-Terre Island / Trois Rivieres

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
Located in Trois-Rivières, a small town South Basse-Terre, the Checheti farms are for families, large groups of friends (or sports) but also to couples in search of tranquility. From our location in the heart of the "greenest" part of Guadeloupe, lovers of hiking, divin …see more

from $71 / night

$449 - $505 / week

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from $71 / night

(5) Very Good 

20

Barbados Vacation 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
SPECIAL OFFER FOR JULY & AUGUST 2016 - BOOK ONE WEEK AND RECEIVE THE SECOND WEEK HALF PRICE- EMAIL FOR QUOTE. This development is situated in Jamestown Park, Holetown, in the heart of Barbados' west coast. The apartments are only a 4 minute walk to Settlers beach; also …see more

from $98 / night

$683 - $1047 / week

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from $98 / night

(19) Excellent 

16

Studio rental in Martinique with shared pool

Arrondissement of Le Marin / Sainte-Luce

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
In a quiet and secure residence with private parking, charming luxury studio fully equipped for you to enjoy a pleasant stay (kitchen, bathroom with walk-in shower, flat screen TV, DVD player, internet WIFI). You can dine in peace on the terrace overlooking the pool and …see more

from $68 / night

$393 - $449 / week

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from $68 / night

(3) Good 

4

Caribbean Vacation gite rental

Basse-Terre Island / Trois Rivieres

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Located in Trois-Rivières, a small town South Basse-Terre, the Checheti farms are for families, large groups of friends (or sports) but also to couples in search of tranquility. From our location in the heart of the "greenest" part of Guadeloupe, lovers of hiking, divin …see more

from $61 / night

$382 - $426 / week

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from $61 / night

(3) Excellent 

33

Vacation apartment with shared pool in Caribbean

Saint-Martin / Anse Marcel

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Quiet, romantic, this Deluxe Suite is 5 minutes walk from the beach. It is the ideal place for a memorable Honeymoon !!!! Located on a hill overlooking the beach of L'ANSE MARCEL, the Hibiscus Suite Royal Privilege is located on the French side of St. Martin near Orient …see more

from $113 / night

$785 / week

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from $113 / night

(24) Excellent 

17

Vacation townhouse with swimming pool in Caribbean

Saint James Parish / Holetown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
With interior spaces inspired by New York lofts,12 ft high ceilings, huge rooms, and plenty of natural light, Hillside Villas at Limegrove is a unique Caribbean environment. With over 3,400 sq feet of internal space, over three floors, with three double bedrooms and bat …see more

from $364 / night

$2548 - $5187 / week

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from $364 / night

(4) Excellent 

16

Vacation apartment in Martinique

Arrondissement of Le Marin / Riviere-Salee

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
HOUSING BLUE MADRAS OR OCEANE Your apartment F2 BLUE MADRAS located on the ground floor includes a private terrace to relax or options outdoors (table, chairs, parasol) A living room furnished with a seating area A fitted kitchen for your stay an air-conditioned room de …see more

from $45 / night

$314 / week

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from $45 / night

(4) Excellent 

21

Bungalow rental in Caribbean with shared pool

Grande-Terre Island / Sainte-Anne

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
'coconut flower' in Sainte - Anne, located 5 minutes by car from the beach of the caravelle and 15 minute walk... The bungalow offers you all the amenities: - terrace with equipped kitchenette - very nice with a sofa lounge in bed very comfortable for 2 extra persons, …see more

from $85 / night

$561 / week

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from $85 / night

(11) Excellent 

21

Antigua and Barbuda Vacation villa rental

Saint Phillip Parish / Long Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
The villa itself provides luxury accommodation including a magnificent large master bedroom with 4 poster bed and ensuite bathroom with its own large balcony offering lovely sea views over the bay. There are 2 twin bedrooms each with ensuite bathrooms and one additiona …see more

from $571 / night

$4000 - $6300 / week

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from $571 / night

(4) Excellent 

29

Vacation condo with shared pool in Caribbean

Grand Cayman / Seven Mile Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Our beach-front vacation home offers guests a luxury standard of vacation accommodation, with incredible views across the bay and over the pristine sands of Seven Mile Beach. Large luxury condos like those at Sea Breeze are hard to find on Grand Cayman, sleeping up to …see more

from $860 / night

$10200 - $15500 / week

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from $860 / night

36

Caribbean Vacation villa rental

Grande-Terre Island / Sainte-Anne

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Sainte-Anne, Villa 4 bedrooms, sleeps 7, 2 bathrooms, Pool & SPA. Ideal for a stay with family or friends. Villa independent on one level F5, contemporary style and Creole architecture, near the town and beaches with private pool and spa for a relaxing and enjoyable sta …see more

from $201 / night

$1401 - $2231 / week

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from $201 / night

(7) Excellent 

16

Villa rental in Caribbean with swimming pool, golf nearby

Punta Cana / Bavaro Beach

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
This spacious villa is ideal for large families or friends traveling together. With 4 complete bedrooms, each with their complete bathroom, and a maids quarter. This beautiful villa is situated in the gated residential Cocotal Golf & Country Club with a beautiful view o …see more

from $300 / night

$2000 - $3350 / week

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from $300 / night

(7) Very Good 

23

Vacation villa with swimming pool in Caribbean

Saint James Parish / Weston

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to our piece of paradise on the west coast of Barbados, just north of Holetown. Westshore Beach House has been fully renovated in a contemporary style to provide a secluded hideaway, situated on the beach. A beautiful beachfront house with spectacular ocean vie …see more

from $800 / night

$5600 / week

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from $800 / night

(20) Excellent 

27

Caribbean Vacation gite rental

Grande-Terre Island / Port-Louis

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Hello we are happy to welcome you in our small complex made up of apartments type T2 with a capacity of 3 people: a bedroom with 2 air-conditioned spaces, a kitchen room / living fully equipped (micro wave, dishes, juicer , coffee maker, refrigerator, electric plates .. …see more

from $51 / night

$354 / week

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from $51 / night

(15) Excellent 

16

Vacation 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 mi
  • Swimming pool
Cool Runnings is a fully air conditioned spacious 2 bedroom, 2 en suite bathroom apartment, with separate powder room. It boasts its own spacious private terrace, tropical garden, and private pool . It is situated at the rear and quietest part of the small Beac …see more

from $195 / night

$1365 - $2984 / week

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from $195 / night

(10) Excellent 

29

Villa rental in Caribbean with swimming pool

Samana Province / Las Galeras

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Villa Punta Coral is a spa­cious Caribbean dream home located on the Samaná penin­sula in the Domini­can Repub­lic. Splen­didly sit­u­ated within 60 meters of the coral shore, the deep blue ocean is a per­ma­nent part of the expe­ri­ence at the villa. It also lies right …see more

from $150 / night

$756 - $1890 / week

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from $150 / night

(21) Very Good 

23

Vacation 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 mi
  • Swimming pool
Welcome! This is a two bedroom holiday villa situated in Fitts Village on the spectacular West Coast of Barbados. It is one of fourteen homes just two miles away from Sandy Lane on a small gated estate. They are set in tropical gardens with a shared pool. The vi …see more

from $91 / night

$637 - $767 / week

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from $91 / night

(8) Excellent 

19

Vacation apartment with shared pool in Barbados

Saint Peter Parish / Gibbes

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Ashanti is a new apartment in the residential area of Gibbes. It offers a clean and spacious open plan living area with 3 bedrooms all with en-suite bathrooms Ashanti is just a 5-10 minute stroll from the beautiful Gibbes beach, with the more commercial Mullens Beach wi …see more

from $150 / night

$1040 - $1248 / week

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from $150 / night

(8) Very Good 

20

Vacation villa with shared pool, golf nearby in Caribbean

Jolly Harbour / Jolly Harbour Villas

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Villa North Shore is a luxury Villa in Antigua set within lush and well-tended tropical gardens. Villa North Shore is an ideal base from which to explore the island of Antigua or make use of the many varied amenities within Jolly Harbour itself - Antigua's premier marin …see more

from $104 / night

$715 - $910 / week

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from $104 / night

(1) Excellent 

21

Vacation apartment in Caribbean

Saint James Parish / Lower Carlton

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
WE ARE 299 PACES FROM ONE OF THE MOST DESERTED AND BEAUTIFUL BEACHES OF THE WEST COAST...THUNDER BAY... OUR ROOF TERRACE BOASTS STUNNING SEA VIEWS AND A COOL CARIBBEAN BREEZE! WE AIM TO GIVE LAID BACK CARIBBEAN SERVICE...VERY FRIENDLY! Barbados is a safe and very frie …see more

from $60 / night

$400 / week

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from $60 / night

(10) Excellent 

20

Vacation 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 mi
  • Swimming pool
La Villa ZEN est une villa très exceptionnelle où l'harmonie règne. Dès que vous passerez le portail, vous sentirez une véritable sérénité. Là, tout est luxe, calme et volupté… Un magnifique Bouddha en marbre blanc, un GAZEBO indonésien, un jardin luxuriant… l'am …see more

from $353 / night

$2466 - $6624 / week

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from $353 / night

(13) Excellent 

36

Vacation 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
Cactus House is a 'World Class' property sitting majestically in a peaceful location on the hillside overlooking Jolly Harbour. It offers absolute privacy and tranquility for your total relaxation, yet is only a minute across the road from two of the best beaches on …see more

from $325 / night

$2275 - $3614 / week

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from $325 / night

13

Vacation 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 mi
  • Swimming pool
  • Child friendly
Island Vibz is located in close proximity to Ocho Rios Center, Dunn's River Falls, Dolphin Cove, Chukka Cove, Blue Hole, Konoko Falls, Marguaritaville, Duty Free Shops and many more local attractions....... This is the ideal vacation home for couples, solo adventurers, …see more

from $120 / night

$800 / week

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from $120 / night

(9) Excellent 

24

Caribbean Vacation villa rental

Antigua / Dickenson Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Imagine yourself in the early evening, sundowner in hand as you relax and watch the fireball sun kissing the horizon between the islands of Redonda and Nevis. The sky is cloudless. Is this a night for the fabled green flash? Silk Cotton Villa enjoys a fabulous location …see more

from $372 / night

$2600 - $5200 / week

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from $372 / night

5

Apartment rental in Grenada

South Coast / Grand Anse

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Our one bedroom apartments have an air-conditioned bedroom with ceiling fans in the living room and bedrooms. They are fully furnished and have a full kitchen with stove, microwave, refrigerator and kitchenware. Queen sized bed + Pull out Sofa. Grand Anse Shopping Cent …see more

from $93 / night

$622 - $696 / week

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from $93 / night

(7) Very Good 

10

Vacation villa rental

Montserrat / Woodlands

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Fabulous 2 bedroom villa with pool and fantastic sea views located on Montserrat the idyllic and untouched Caribbean Island. The villa is located on a half an acre lot of lush rainforest in the most exclusive Woodlands area of the island. The beach is just a short 7 min …see more

from $175 / night

$950 - $1551 / week

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from $175 / night

(12) Excellent 

24

Caribbean Vacation villa rental

Saint James Parish / Holetown

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
BRUADAIR is located in the parish of St James which is on the exclusive platinum west coast of Barbados! . It has taken a lot of vision and resource to complete this wonderful villa, built within beautiful tropical surroundings on old plantation land (Lascelles) …see more

from $715 / night

$5005 / week

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from $715 / night

(15) Very Good 

18

Vacation 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
As soon as you walk through the front door you are struck by the sheer tranquillity and elegance of your surroundings. Mot Mot Lodge is beautifully appointed with everything you could wish for to make your stay a relaxing and rejuvenating experience. A short walk throug …see more

from $299 / night

$2093 / week

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from $299 / night

(12) Excellent 

29

Caribbean Vacation 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 mi
  • Swimming pool
Coco House standing in its own quiet grounds, is the largest of the 3 Villas on Hamilton Estate, which is situated by Jolly Harbour & the 5* Sugar Ridge Hotel. Jolly Harbour offers shopping, a large supermarket & many restaurants plus the Hotel's pools, gym and spa are …see more

from $221 / night

$1547 / week

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from $221 / night

5

Vacation apartment rental

All Saints / Buckleys Heights

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
The Buckleys Country Club has its own distinctive flavour that will exceed your expectations and transform your moments on the island into everlasting memories. Land, water, wind and sun in perfect harmony as nature intended will greet you daily. Indulge yourself and d …see more

from $91 / night

$637 / week

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from $91 / night

11

Vacation apartment in Caribbean

Arrondissement of Le Marin / Trois-Ilets

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
Housing located on the 1st floor (one floor building) Studio for 2 people, with kitchen and full bathroom, balcony View of the Fort de France and Lamentin airport Close to shops, beach 200m, restaurants, shuttle boats, house games (Casino), spa, bakery, museums, golf, h …see more

from $44 / night

$303 - $337 / week

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from $44 / night

1