15 Best Vacation Rentals in Island Harbour - Holiday Lettings - Cabins

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1,552 Vacation rentals

(13) Very Good 

24

Vacation apartment in Island Harbour

Anguilla / Island Harbour

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
Perfect for 2 Vacation Rental Near Island Harbor and Shoal Bay Beaches James Place Apartments are located in a quiet secure and well maintained community. It is a perfect base from which guests can enjoy the sun, beaches, and relax. The rooms are spacious, modern a …see more

from $80 / night

$590 / week

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from $80 / night

(8) Very Good 

31

Vacation apartment in Island Harbour

Anguilla / Island Harbour

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 3 mi
  • Air conditioning
  • Private garden
Quiet neighborhood. Fully furnished, spacious air conditioned private apartment on Captains Ridge, Island Harbour with a panoramic view of the Atlantic Ocean. Very spacious apartment (over 2,000 square ft). Enjoy the ocean view from the master bedroom, master bathroom, …see more

from $120 / night

$840 / week

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from $120 / night

(3) Excellent 

32

Vacation villa rental

Anguilla / Island Harbour

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior d …see more

from $2,500 / night

$17,500 / week

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from $2,500 / night

10

Home rental in Island Harbour with swimming pool

Anguilla / Island Harbour

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
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. …see more

from $5,000 / night

$35,000 / week

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from $5,000 / night

10

Home rental in Island Harbour with swimming pool

Anguilla / Island Harbour

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Quixotic Villas, Harbour Ridge, Island Harbour, Anguilla Quixotic Villas are a collection of private retreats that nestle amongst Harbour Ridge offering stunning ocean views and relaxing, comfortable Caribbean accommodations. There are four definitive vil …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

25

Vacation villa with swimming pool in Island Harbour

Anguilla / Island Harbour

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Villa Soleil at Captains Bay is a fully air conditioned villa with luxury appointments throughout. . From every vantage point, the villa has the most spectacular views of any villa on the island. Breathtaking views of the ocean from the front and rear of the villa; vi …see more

from $950 / night

$6,650 / week

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avg. 3 hours 40 minutes

from $950 / night

10

Island Harbour Vacation home rental

Anguilla / Island Harbour

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Kiki Villa Shoal Bay Anguilla 10 minute stroll from Shoal Bay Beach This stunning property built in the mediterranean villa style has a pristine white exterior, a pool, terraces and sun deck overlooking Shoal Bay in the distance. Shoal Bay Beach is just …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

(1) Excellent 

10

Home rental in Island Harbour with swimming pool

Anguilla / Island Harbour

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
Wesley House Near Captain's Bay, Anguilla Beautiful location Located 150 feet above sea level, Anguilla's Wesley House is a private, luxury p …see more

from $1,170 / night

$8,190 / week

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from $1,170 / night

13

Island Harbour Vacation villa rental

Anguilla / Island Harbour

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
With impressive views of the Atlantic, the Villa Ultimacy is located in Anguilla and rests between Shoal Bay East and Island Harbor. Peaceful and secluded, it is an eight-room masterpiece of luxury and world-class amenities. It is a fabulous place for the ultimate famil …see more

from $4,000 / night

$7,000 - $70,000 / week

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from $4,000 / night

32

Island Harbour Vacation villa rental

Anguilla / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior d …see more

from $2,300 / night

$16,100 / week

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avg. 2 minutes

from $2,300 / night

32

Island Harbour Vacation villa rental

Anguilla / Island Harbour

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior d …see more

from $2,100 / night

$14,700 / week

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avg. 2 minutes

from $2,100 / night

21

Villa rental in Island Harbour

Anguilla / Island Harbour

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets
Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area …see more

from $1,650 / night

$11,550 / week

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avg. 2 minutes

from $1,650 / night

21

Villa rental in Island Harbour

Anguilla / Island Harbour

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Ask about pets
Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area …see more

from $2,075 / night

$14,525 / week

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avg. 2 minutes

from $2,075 / night

21

Villa rental in Island Harbour

Anguilla / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area …see more

from $1,400 / night

$9,800 / week

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avg. 2 minutes

from $1,400 / night

21

Villa rental in Island Harbour

Anguilla / Island Harbour

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Ask about pets
Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area …see more

from $1,875 / night

$13,125 / week

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avg. 2 minutes

from $1,875 / night

21

Villa rental in Island Harbour

Anguilla / Island Harbour

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area …see more

from $1,100 / night

$7,700 / week

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Responds fast!
avg. 2 minutes

from $1,100 / night

39

Vacation villa in Island Harbour

Anguilla / Island Harbour

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Villa Amarilla on Anguilla sets the standard of excellence on a tropical island known for upscale accommodations. Enter through a welcoming lanai with a profusion of colorful bougainvillea flowers surrounding the intricately designed wrought iron doorway. Step into the …see more

from $2,100 / night

$14,700 - $35,000 / week

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from $2,100 / night