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  Anguilla Anguilla - Holiday Rentals in Caribbean Anguilla   

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Anguilla Country: Anguilla (194) | Region: Caribbean (81) |
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79 Caribbean holiday rentals found    page 1 of 3     Subscribe: XML Feed Anguilla, Caribbean, Caribbean holiday rentals
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1 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
2
Sleeps
1
Bedrooms
4
Baths
pets
pool
Villa-House
€11,446, £10,018
From

$ 12,950 /week
or $1,850/night
Min Stay 4 nights
Select

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1 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 12,950 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
The Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an enclave and the top tier services and amenities of a first class resort. Perched above a perfect crescent beach, Bird of Paradise looks across the Caribbean to the mountains of St. Barths and St. Martin. Bird of Paradise boasts not one, but three swimming pool areas, the most extensive bathing system of any villa on Anguilla. The lagoon-style pools are heated and range in depth from three to nine feet. The property manager works exclusively for the villa and will meet and greet you upon arrival at the airport or dock. Your reservation includes a twenty-four hour concierge, daily housekeeping and a grounds person to assist with beach chairs and other requests. With its executive c...

Availability Calendar     booked Booked     Available Available           highlight_off
3 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
6
Sleeps
3
Bedrooms
4
Baths
pets
pool
Villa-House
€12,374, £10,830
From

$ 14,000 /week
or $2,000/night
Min Stay 4 nights
Select

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3 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 14,000 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
The Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an enclave and the top tier services and amenities of a first class resort. Perched above a perfect crescent beach, Bird of Paradise looks across the Caribbean to the mountains of St. Barths and St. Martin. Bird of Paradise boasts not one, but three swimming pool areas, the most extensive bathing system of any villa on Anguilla. The lagoon-style pools are heated and range in depth from three to nine feet. The property manager works exclusively for the villa and will meet and greet you upon arrival at the airport or dock. Your reservation includes a twenty-four hour concierge, daily housekeeping and a grounds person to assist with beach chairs and other requests. With its executive c...

Availability Calendar     booked Booked     Available Available           highlight_off
5 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
8
Sleeps
5
Bedrooms
4
Baths
pets
pool
Villa-House
€12,993, £11,371
From

$ 14,700 /week
or $2,100/night
Min Stay 4 nights
Select

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5 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 14,700 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
The Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an enclave and the top tier services and amenities of a first class resort. Perched above a perfect crescent beach, Bird of Paradise looks across the Caribbean to the mountains of St. Barths and St. Martin. Bird of Paradise boasts not one, but three swimming pool areas, the most extensive bathing system of any villa on Anguilla. The lagoon-style pools are heated and range in depth from three to nine feet. The property manager works exclusively for the villa and will meet and greet you upon arrival at the airport or dock. Your reservation includes a twenty-four hour concierge, daily housekeeping and a grounds person to assist with beach chairs and other requests. With its executive c...

Availability Calendar     booked Booked     Available Available           highlight_off
4 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
8
Sleeps
4
Bedrooms
9
Baths
pets
pool
Villa-House
€17,942, £15,703
From

$ 20,300 /week
or $2,900/night
Min Stay 4 nights
Select

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4 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 20,300 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
Located in Maundays Bay in Anguilla, Infinity at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. With postcard perfect views of neighboring St. Martin and the Caribbean Sea, this chic villa redefines the art of luxury escape. All three main level rooms have direct access to the expansive terrace which leads to the infinity swimming pool with a built-in hot tub. You will find a second swimming pool on the lower deck. Step out of the water into an alfresco shower. The elegant shared spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and en...

Availability Calendar     booked Booked     Available Available           highlight_off
6 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
12
Sleeps
6
Bedrooms
9
Baths
pets
pool
Villa-House
€24,748, £21,660
From

$ 28,000 /week
or $4,000/night
Min Stay 4 nights
Select

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6 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 28,000 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
Located in Maundays Bay in Anguilla, Infinity at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. With postcard perfect views of neighboring St. Martin and the Caribbean Sea, this chic villa redefines the art of luxury escape. All three main level rooms have direct access to the expansive terrace which leads to the infinity swimming pool with a built-in hot tub. You will find a second swimming pool on the lower deck. Step out of the water into an alfresco shower. The elegant shared spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and en...

Availability Calendar     booked Booked     Available Available           highlight_off
2 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
4
Sleeps
2
Bedrooms
4
Baths
pets
pool
Villa-House
€11,910, £10,424
From

$ 13,475 /week
or $1,925/night
Min Stay 4 nights
Select

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2 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 13,475 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
The Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an enclave and the top tier services and amenities of a first class resort. Perched above a perfect crescent beach, Bird of Paradise looks across the Caribbean to the mountains of St. Barths and St. Martin. Bird of Paradise boasts not one, but three swimming pool areas, the most extensive bathing system of any villa on Anguilla. The lagoon-style pools are heated and range in depth from three to nine feet. The property manager works exclusively for the villa and will meet and greet you upon arrival at the airport or dock. Your reservation includes a twenty-four hour concierge, daily housekeeping and a grounds person to assist with beach chairs and other requests. With its executive c...

Availability Calendar     booked Booked     Available Available           highlight_off
4 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
8
Sleeps
4
Bedrooms
4
Baths
pets
pool
Villa-House
€12,838, £11,236
From

$ 14,525 /week
or $2,075/night
Min Stay 4 nights
Select

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4 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 14,525 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
The Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an enclave and the top tier services and amenities of a first class resort. Perched above a perfect crescent beach, Bird of Paradise looks across the Caribbean to the mountains of St. Barths and St. Martin. Bird of Paradise boasts not one, but three swimming pool areas, the most extensive bathing system of any villa on Anguilla. The lagoon-style pools are heated and range in depth from three to nine feet. The property manager works exclusively for the villa and will meet and greet you upon arrival at the airport or dock. Your reservation includes a twenty-four hour concierge, daily housekeeping and a grounds person to assist with beach chairs and other requests. With its executive c...

Availability Calendar     booked Booked     Available Available           highlight_off
8 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
16
Sleeps
8
Bedrooms
9
Baths
pets
pool
Villa-House
€30,935, £27,074
From

$ 35,000 /week
or $5,000/night
Min Stay 4 nights
Select

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8 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 35,000 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
Located in Maundays Bay in Anguilla, Infinity at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. With postcard perfect views of neighboring St. Martin and the Caribbean Sea, this chic villa redefines the art of luxury escape. All three main level rooms have direct access to the expansive terrace which leads to the infinity swimming pool with a built-in hot tub. You will find a second swimming pool on the lower deck. Step out of the water into an alfresco shower. The elegant shared spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and en...

Availability Calendar     booked Booked     Available Available           highlight_off
4 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
8
Sleeps
4
Bedrooms
9
Baths
pets
pool
Villa-House
€17,942, £15,703
From

$ 20,300 /week
or $2,900/night
Min Stay 4 nights
Select

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4 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 20,300 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
Located in Maundays Bay in Anguilla, Harmony at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. With postcard perfect views of neighboring St. Martin and the Caribbean Sea, this chic villa redefines the art of luxury escape. All three main level rooms have direct access to the expansive terrace which leads to the infinity swimming pool with a built-in hot tub. You will find a second swimming pool on the lower deck. Step out of the water into an alfresco shower. The elegant shared spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and enj...

Availability Calendar     booked Booked     Available Available           highlight_off
7 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
14
Sleeps
7
Bedrooms
9
Baths
pets
pool
Villa-House
€26,604, £23,284
From

$ 30,100 /week
or $4,300/night
Min Stay 4 nights
Select

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7 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 30,100 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
Located in Maundays Bay in Anguilla, Infinity at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. With postcard perfect views of neighboring St. Martin and the Caribbean Sea, this chic villa redefines the art of luxury escape. All three main level rooms have direct access to the expansive terrace which leads to the infinity swimming pool with a built-in hot tub. You will find a second swimming pool on the lower deck. Step out of the water into an alfresco shower. The elegant shared spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and en...

Availability Calendar     booked Booked     Available Available           highlight_off
5 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
10
Sleeps
5
Bedrooms
9
Baths
pets
pool
Villa-House
€21,655, £18,952
From

$ 24,500 /week
or $3,500/night
Min Stay 4 nights
Select

highlight_off

5 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 24,500 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
Located in Maundays Bay in Anguilla, Infinity at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. With postcard perfect views of neighboring St. Martin and the Caribbean Sea, this chic villa redefines the art of luxury escape. All three main level rooms have direct access to the expansive terrace which leads to the infinity swimming pool with a built-in hot tub. You will find a second swimming pool on the lower deck. Step out of the water into an alfresco shower. The elegant shared spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and en...

Availability Calendar     booked Booked     Available Available           highlight_off
3 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
6
Sleeps
3
Bedrooms
6
Baths
pets
Villa-House
€15,468, £13,537
From

$ 17,500 /week
or $2,500/night
Min Stay 4 nights
Select

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3 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 17,500 /week (minimum stay 4 nights)
Pets Allowed |
Overlooking Cove Lagoon and just two minutes away from the pristine two half mile white sand beaches of Maundays and Cove Bay, Mystique at Sheriva is one of Anguilla’s top luxury boutique villas. Located in the chic West End, the villa is situated on a lush 10-acre alcove with stunning views of the Caribbean Sea and St. Martin. The property offers ultimate privacy, yet swift access to the island’s finest beaches, boutiques and restaurants. This expansive villa offers three swimming pools, a hot tub and an alfresco shower. The elegant spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and enjoy some outdoor dining as you overlook the tropical landscape. A complimentary golf cart helps you zip around the grounds. You can also stay on top of yo...

Availability Calendar     booked Booked     Available Available           highlight_off
4 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
8
Sleeps
4
Bedrooms
6
Baths
pets
Villa-House
€20,417, £17,869
From

$ 23,100 /week
or $3,300/night
Min Stay 4 nights
Select

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4 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 23,100 /week (minimum stay 4 nights)
Pets Allowed |
Overlooking Cove Lagoon and just two minutes away from the pristine two half mile white sand beaches of Maundays and Cove Bay, Mystique at Sheriva is one of Anguilla’s top luxury boutique villas. Located in the chic West End, the villa is situated on a lush 10-acre alcove with stunning views of the Caribbean Sea and St. Martin. The property offers ultimate privacy, yet swift access to the island’s finest beaches, boutiques and restaurants. This expansive villa offers three swimming pools, a hot tub and an alfresco shower. The elegant spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and enjoy some outdoor dining as you overlook the tropical landscape. A complimentary golf cart helps you zip around the grounds. You can also stay on top of yo...

Availability Calendar     booked Booked     Available Available           highlight_off
7 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
14
Sleeps
7
Bedrooms
9
Baths
pets
pool
Villa-House
€26,604, £23,284
From

$ 30,100 /week
or $4,300/night
Min Stay 4 nights
Select

highlight_off

7 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 30,100 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
Located in Maundays Bay in Anguilla, Harmony at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. With postcard perfect views of neighboring St. Martin and the Caribbean Sea, this chic villa redefines the art of luxury escape. All three main level rooms have direct access to the expansive terrace which leads to the infinity swimming pool with a built-in hot tub. You will find a second swimming pool on the lower deck. Step out of the water into an alfresco shower. The elegant shared spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and enj...

Availability Calendar     booked Booked     Available Available           highlight_off
5 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
10
Sleeps
5
Bedrooms
6
Baths
pets
Villa-House
€25,367, £22,201
From

$ 28,700 /week
or $4,100/night
Min Stay 4 nights
Select

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5 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 28,700 /week (minimum stay 4 nights)
Pets Allowed |
Overlooking Cove Lagoon and just two minutes away from the pristine two half mile white sand beaches of Maundays and Cove Bay, Mystique at Sheriva is one of Anguilla’s top luxury boutique villas. Located in the chic West End, the villa is situated on a lush 10-acre alcove with stunning views of the Caribbean Sea and St. Martin. The property offers ultimate privacy, yet swift access to the island’s finest beaches, boutiques and restaurants. This expansive villa offers three swimming pools, a hot tub and an alfresco shower. The elegant spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and enjoy some outdoor dining as you overlook the tropical landscape. A complimentary golf cart helps you zip around the grounds. You can also stay on top of yo...

Availability Calendar     booked Booked     Available Available           highlight_off
6 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
12
Sleeps
6
Bedrooms
9
Baths
pets
pool
Villa-House
€24,748, £21,660
From

$ 28,000 /week
or $4,000/night
Min Stay 4 nights
Select

highlight_off

6 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 28,000 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
Located in Maundays Bay in Anguilla, Harmony at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. With postcard perfect views of neighboring St. Martin and the Caribbean Sea, this chic villa redefines the art of luxury escape. All three main level rooms have direct access to the expansive terrace which leads to the infinity swimming pool with a built-in hot tub. You will find a second swimming pool on the lower deck. Step out of the water into an alfresco shower. The elegant shared spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and enj...

Availability Calendar     booked Booked     Available Available           highlight_off
5 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
10
Sleeps
5
Bedrooms
9
Baths
pets
pool
Villa-House
€21,655, £18,952
From

$ 24,500 /week
or $3,500/night
Min Stay 4 nights
Select

highlight_off

5 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 24,500 /week (minimum stay 4 nights)
Swimming Pool
Pets Allowed |
Located in Maundays Bay in Anguilla, Harmony at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve. With postcard perfect views of neighboring St. Martin and the Caribbean Sea, this chic villa redefines the art of luxury escape. All three main level rooms have direct access to the expansive terrace which leads to the infinity swimming pool with a built-in hot tub. You will find a second swimming pool on the lower deck. Step out of the water into an alfresco shower. The elegant shared spaces offer tech-savvy comforts such as plasma televisions, DVD players, poolside Bose surround sound and Wi-Fi so that your stay can be as relaxing or as festive as you desire. Fire up the barbeque and enj...

Availability Calendar     booked Booked     Available Available           highlight_off
3 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
6
Sleeps
3
Bedrooms
4
Baths
pets
pool
Villa-House
€9,899, £8,664
From

$ 11,200 /week
or $1,600/night
Min Stay 5 nights
Select

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3 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 11,200 /week (minimum stay 5 nights)
Swimming Pool
Pets Allowed |
Please note that this property is next to a construction project, please inquire with one of our Villa Specialists for details. Like an ivory showpiece glinting in the sun, Sandcastle is your private palace right by the sands of the Caribbean Sea. Welcome to sunny Anguilla, a magical island known for its watersports, nightlife and friendly local vibration. Take in the magnificent views of the ever changing hues of the Atlantic Ocean and tropical horizon right at your doorstep. An idyllic boutique villa awaits! The outdoor oasis at Sandcastle includes an expansive second story infinity swimming pool with plenty of deck seating, beach chairs and umbrellas. The consummate entertainer won’t be able to resist whipping up some fabulous cocktails at the poolside bar with a stellar ocean view. Lovely alfresco dining can be a daily event with a barbeque and outdoor dining set under the shaded la...

Availability Calendar     booked Booked     Available Available           highlight_off
4 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
8
Sleeps
4
Bedrooms
4
Baths
pets
pool
Villa-House
€11,755, £10,288
From

$ 13,300 /week
or $1,900/night
Min Stay 5 nights
Select

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4 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 13,300 /week (minimum stay 5 nights)
Swimming Pool
Pets Allowed |
Please note that this property is next to a construction project, please inquire with one of our Villa Specialists for details. Like an ivory showpiece glinting in the sun, Sandcastle is your private palace right by the sands of the Caribbean Sea. Welcome to sunny Anguilla, a magical island known for its watersports, nightlife and friendly local vibration. Take in the magnificent views of the ever changing hues of the Atlantic Ocean and tropical horizon right at your doorstep. An idyllic boutique villa awaits! The outdoor oasis at Sandcastle includes an expansive second story infinity swimming pool with plenty of deck seating, beach chairs and umbrellas. The consummate entertainer won’t be able to resist whipping up some fabulous cocktails at the poolside bar with a stellar ocean view. Lovely alfresco dining can be a daily event with a barbeque and outdoor dining set under the shaded la...

Availability Calendar     booked Booked     Available Available           highlight_off
10 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
20
Sleeps
10
Bedrooms
12
Baths
pool
Villa-House
€53,208, £46,568
From

$ 60,200 /week
or $8,600/night
Min Stay 3 nights
Select

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10 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 60,200 /week (minimum stay 3 nights)
Swimming Pool

Perched on the breathtaking cliffs overlooking Anguilla's Little Bay, Ani Estate is 2 luxury villas (Ani North and Ani South) aimed at delivering a remarkable holiday experience. Designed with the highest level of detail in contemporary style, Ani Estate is a one-of-a-kind Caribbean island escape. This 10 bedroom estate, with 2 fully outfitted villas, is perfect for larger groups and family gatherings. The property includes facilities and amenities expected within a world-class resort but secluded within your own private enclave. Ani's full service team is here to anticipate your every need. Your personal concierge works with you prior to your arrival to plan a range of services, activities, dining experiences, and excursions - be it a week of action and adventure or complete relaxation. A full staff strives to exceed your expectations for escape and deliver a package of meals, service...

Availability Calendar     booked Booked     Available Available           highlight_off
4 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
8
Sleeps
4
Bedrooms
4
Baths
pets
pool
Villa-House
€12,343, £10,803
From

$ 13,965 /week
or $1,995/night
Min Stay 7 nights
Select

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4 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 13,965 /week (minimum stay 7 nights)
Swimming Pool
Pets Allowed |
7 Palms Villa design is Caribbean Casual with Breathtaking views that juts out for an incredibly living experience. The Caribbean Island interiors and living spaces are perfect for a tropical holiday. With spacious indoor and outdoor living and dining areas, 7 Palms Anguilla offers ample room for a large group to gather or a variety of havens for an individual to find solitude and relaxation on a number of living levels. Located on Anguilla's Leeward north side near Shoal Bay Beach overlooking some of Anguilla's most beautiful reefs, you will never tire of the mesmerizing breathtaking views. You can see parrot fish, sea turtles, whales and lobsterman. In addition to the beauty of the surf breaking on the reefs, the panoramic views include Shoal Bay Beach to the west and Scrub Island to the east. The sound of the waves breaking on the nearby rocks will further soothe and relax the sense...

Availability Calendar     booked Booked     Available Available           highlight_off
5 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
10
Sleeps
5
Bedrooms
6
Baths
pets
pool
Villa-House
€30,935, £27,074
From

$ 35,000 /week
or $5,000/night
Min Stay 1 night
Select

highlight_off

5 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 35,000 /week (minimum stay 1 night)
Swimming Pool
Pets Allowed |
Villa Modena Cove Bay Anguilla Comfortably Sleeps 10 Guests Villa Modena is private and palatial and set upon one acre of land near the Cap Juluca Hotel on Cove Bay. A combination of a two storey main house and a one storey clubhouse provides 5 stunning bedrooms with private bathrooms sleeping 10 guests. Gold & Onyx Doors Surroundind the air conditioned living spaces and bedrooms are floor to ceiling glass doors framed with gold and onyx. Simply beautiful and exotic. Outdoor Movies This state of the art villa has surround sound, WiFi internet, plasma TV's in each room and the technology for guests to sit under the beautiful Anguillan stars and enjoy a movie, or two. Private Tennis Court The clubhouse, with its 2 bedrooms and bathrooms also has a sitting area, bar and is close to the private full size tennis court. Adult Infinity Pool & 2 Childrens' Pools The main swimming area, an infini...

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2 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
16
Sleeps
2
Bedrooms
2
Baths
pets
Villa-House
€3,100, £2,713
From

$ 3,507 /week
or $501/night
Min Stay 1 night
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2 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 3,507 /week (minimum stay 1 night)
Pets Allowed |
Bellaconstantina Villa Little Harbour Anguilla Villa Suites Each Suite has 2 double bedrooms & 2 bathrooms Close to Anguillas Southern Coastline 4 Villa Suites overlooking the Ocean This property is a collection of 4 villa suites. Each suite has 2 double bedrooms, 2 bathrooms a living room and kitchen. All 4 suites can be booked together or just one. Each has a separate entrance. WiFi, AC, Catering, Baby Sitting & Flat Screen TVs Each suite has WiFi, the bedrooms are air conditioned and have ceiling fans to help maintain a super cool atmosphere throughout. There are additional services available, at extra charge, such as provisioning, catering and baby sitting. Each suite has a flat screen TV. Simply contact the team to arrange the services that best suit your group. 33 Fabulous Beaches & World Class Restaurants Anguilla is surrounded by 33 beaches, some rocky but the most popular are fi...

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8 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
16
Sleeps
8
Bedrooms
8
Baths
pets
Villa-House
€12,405, £10,857
From

$ 14,035 /week
or $2,005/night
Min Stay 1 night
Select

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8 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 14,035 /week (minimum stay 1 night)
Pets Allowed |
Bellaconstantina Villa Little Harbour Anguilla 4 Villa Suites Each Suite has 2 double bedrooms & 2 bathrooms Close to Anguillas Southern Coastline 4 Villa Suites overlooking the Ocean This property is a collection of 4 villa suites. Each suite has 2 double bedrooms, 2 bathrooms a living room and kitchen. All 4 suites can be booked together or just one. Each has a separate entrance. WiFi, AC, Catering, Baby Sitting & Flat Screen TVs Each suite has WiFi, the bedrooms are air conditioned and have ceiling fans to help maintain a super cool atmosphere throughout. There are additional services available, at extra charge, such as provisioning, catering and baby sitting. Each suite has a flat screen TV. Simply contact the team to arrange the services that best suit your group. 33 Fabulous Beaches & World Class Restaurants Anguilla is surrounded by 33 beaches, some rocky but the most popular are ...

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4 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
16
Sleeps
4
Bedrooms
4
Baths
pets
Villa-House
€6,199, £5,426
From

$ 7,014 /week
or $1,002/night
Min Stay 1 night
Select

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4 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 7,014 /week (minimum stay 1 night)
Pets Allowed |
Bellaconstantina Villa Little Harbour Anguilla 4 Villa Suites Each Suite has 2 double bedrooms & 2 bathrooms Close to Anguillas Southern Coastline 4 Villa Suites overlooking the Ocean This property is a collection of 4 villa suites. Each suite has 2 double bedrooms, 2 bathrooms a living room and kitchen. All 4 suites can be booked together or just one. Each has a separate entrance. WiFi, AC, Catering, Baby Sitting & Flat Screen TVs Each suite has WiFi, the bedrooms are air conditioned and have ceiling fans to help maintain a super cool atmosphere throughout. There are additional services available, at extra charge, such as provisioning, catering and baby sitting. Each suite has a flat screen TV. Simply contact the team to arrange the services that best suit your group. 33 Fabulous Beaches & World Class Restaurants Anguilla is surrounded by 33 beaches, some rocky but the most popular are ...

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6 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
16
Sleeps
6
Bedrooms
6
Baths
pets
Villa-House
€9,305, £8,144
From

$ 10,528 /week
or $1,504/night
Min Stay 1 night
Select

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6 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 10,528 /week (minimum stay 1 night)
Pets Allowed |
Bellaconstantina Villa Little Harbour Anguilla 4 Villa Suites Each Suite has 2 double bedrooms & 2 bathrooms Close to Anguillas Southern Coastline 4 Villa Suites overlooking the Ocean This property is a collection of 4 villa suites. Each suite has 2 double bedrooms, 2 bathrooms a living room and kitchen. All 4 suites can be booked together or just one. Each has a separate entrance. WiFi, AC, Catering, Baby Sitting & Flat Screen TVs Each suite has WiFi, the bedrooms are air conditioned and have ceiling fans to help maintain a super cool atmosphere throughout. There are additional services available, at extra charge, such as provisioning, catering and baby sitting. Each suite has a flat screen TV. Simply contact the team to arrange the services that best suit your group. 33 Fabulous Beaches & World Class Restaurants Anguilla is surrounded by 33 beaches, some rocky but the most popular are ...

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8 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
16
Sleeps
8
Bedrooms
10
Baths
pool
Villa-House
€66,288, £58,015
From

$ 74,998 /week
or $10,714/night
Min Stay 7 nights
Select

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8 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 74,998 /week (minimum stay 7 nights)
Swimming Pool

The Beach House has an unparalleled beachfront location and is the ultimate in the Caribbean. It sits on the soft white sands of Meads Bay, one of the most beautiful beaches on Anguilla and possibly the world. Set within beautifully landscaped gardens and offering 8 spacious master bedrooms, 10 master baths and two powder rooms, the architecture of this inspired home is designed to capture the natural beautify of Anguilla, with its spectacular sunsets and ocean views. With more than a dozen dedicated outdoor deck and lounge areas, there is no shortage of spaces for entertaining or quiet solitude. The setting for this incredible home is as stunning as the design. Built on one acre of prime beachfront land on the powdery white sand of Meads Bay in the island's west end, with just under 17,000 square feet of total living space, the Beach House is a modern masterpiece. Inspired by the nat...

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3 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
rate 5/5 Reviews (1)
6
Sleeps
3
Bedrooms
3
Baths
pets
pool
Villa-House
€5,964, £5,220
From

$ 6,748 /week
or $964/night
Min Stay 1 night
Select

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3 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 6,748 /week (minimum stay 1 night)
Swimming Pool
Pets Allowed |
Wesley House Near Captain's Bay, Anguilla Beautiful location Located 150 feet above sea level, Anguilla's Wesley House is a private, luxury property. It has amazing panoramic views over 5 islands, and from this rental guests are sure to fall in love with the Caribbean. The nearest beach is a 5 minute drive, and many other beautiful beaches are a 10 to 15 minute drive away. One of the best things about Anguilla is it's miles of coast line, and you can appreciate this even whilst looking out at the white sand from the infinity pool. Wesley House comes with snorkelling equipment, so why not kick off your holiday by heading down to the beach and doing some exploring. Anguilla also arguably has some of the best restaurants in the world, and there are beach bars that cannot be missed, as well as a long list of activities to get involved in including scuba diving, fishing, and horse riding. Op...

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3 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
6
Sleeps
3
Bedrooms
2
Baths
pets
Villa-House
€2,054, £1,798
From

$ 2,324 /week
or $332/night
Min Stay 1 night
Select

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3 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 2,324 /week (minimum stay 1 night)
Pets Allowed |
Beach Villa Ella Barnes Bay Beach Anguilla Sugary White Sandy Beachfront Barnes Bay Beach situated outside the villa is a crescent bay of impossibly fine sand offering beautiful views over to the nearby islands and the azure blue waters that surround Anguilla. Beach chairs have been set out amongst the shady grape trees on the beach providing a cool relaxing viewpoint over the bay to Prickly Pear and Dog Island. A BBQ is also provided for guests enjoyment. House-Keeping This lovely villa also boasts a maid service every other day, included in the cost of the weekly rental. Colonial Style Terraces The villas facade is an impressive colonial style painted in a tropical blue with white columns and terraces. The terraces offer shaded, cool areas perfect for cocktails, BBQ's and al fresco dining. Open Plan & Well Equipped The simple, uncluttered interior is open plan with a kitchen leading in...

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5 bed Home for rent in Caribbean, Caribbean, Anguilla
Anguilla holiday rentals in Caribbean, Caribbean
Caribbean 
10
Sleeps
5
Bedrooms
5
Baths
pets
pool
Villa-House
€15,468, £13,537
From

$ 17,500 /week
or $2,500/night
Min Stay 1 night
Select

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5 bed Home for rent in Caribbean, Caribbean, Anguilla

From $ 17,500 /week (minimum stay 1 night)
Swimming Pool
Pets Allowed |
Villa Amarilla Island Harbour Anguilla Italian Influenced Design Designed by the Anguillan architect Carl Williams, this villa combines a Caribbean approach with Italian influences such as yellow stucco walls, turquoise shutters and a red tile roof. Award Winning Interior Designer The owners in collaboration with Dallas based award winning designer David Salem & Associates created a Moroccan influenced interior. The main living room is beautifully furnished with a comfortable Ralph Lauren rattan sofa and easy chairs providing masses of space for guests to unwind. Comfortably Accommodating up to 10 Guests The villa comprises of 5 en suite bedrooms, each with a comfortable kingsize bed. 2 of the bedrooms can be arranged with twin beds if required. Sophisticated Kitchen The villa kitchen has a GE Profile five burner gas top cooker, double ovens, microwave, dishwasher, fridge, freezer and se...

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FEATURED ANGUILLA HOLIDAY RENTALS
Anguilla Holiday rentals in Island Harbour, Island Harbour
Anguilla
Holiday Home
Island Harbour
Island Harbour
Sleeps: 10
From € 15,468 /week
Anguilla Holiday rentals in Sandy Hill Bay, Sandy Hill Bay
Anguilla
Holiday Home
Sandy Hill Bay
Sandy Hill Bay
Sleeps: 6
From € 3,644 /week
Anguilla Holiday rentals in Caribbean, Caribbean
Anguilla
Holiday Home
Caribbean
Caribbean
Sleeps: 6
From € 2,054 /week
Anguilla Holiday rentals in Caribbean, Caribbean
Anguilla
Holiday Home
Caribbean
Caribbean
Sleeps: 16
From € 66,288 /week
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Welcome to our Caribbean holiday rentals and Caribbean vacation home rentals page.

Find Caribbean villa rentals using the search facility or use the region links to browse through specific Caribbean holiday region. We advertise holiday home ads listed direct by owners or agents. holiday rentals in Caribbean are all furnished self catering lets in Caribbean that rent on short term bases and all of our listings come with weekly prices and pictures. To search for a specific type of vacation accommodation, select your letting type, Villa, House, Apartment, Condo, Townhouse, Barn, Farm, Chateau, Island, Castle, Flat, Penthouse, Hotel or even beach front mansions, lakeside cabins or winter skiing chalets. You can also search for condo rentals with pools or other suitability using our advanced search facility, Golfing getaways, Fishing Cabins, surfing and beachfront condos. All of our Caribbean vacation rental adverts are updated daily and you are free to contact the owner or agent directly. With a large selection of property adverts, from cheap Caribbean properties to luxury resort homes for rent in Caribbean . Property owners easily advertise your vacation home in Caribbean , see our advertising packages for full details.
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