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

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16 Vacation rentals

14

Vacation villa in Island Harbour

Anguilla / Island Harbour

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Location: Anguilla 7 Bedrooms, 6.5 Baths , Washer, TV, Preferred Lifestyle, Pool, Microwave, Maid Service, Internet, Hair Dryer, Dryer, Dish Washer, Coffee Maker, Ceiling Fans, Cable, Blender, Beach Chairs, BBQ, Air Conditioning Bedrooms Only Villa Description Neares …see more

from $1550 / night

$10850 / week

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from $1550 / night

11

Vacation villa with shared pool in Island Harbour

Anguilla / Island Harbour

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
CATALINA VILLA- Shoal Bay Village, Anguilla; PERFECT FOR ONE OR TWO COUPLES OR A FAMILY WITH 1-3 CHILDREN!! This cute Caribbean Style newly built (2012-14) home has two beautiful Bedrooms and each has its own En Suite Bathroom with Shower and double vanities. Perfe …see more

from $119 / night

$1743 / week

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from $119 / night

(3) Very Good 

28

Vacation apartment in Island Harbour

Anguilla / Island Harbour

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night 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 $107 / night

$743 / week

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from $107 / 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 villas, Villa Amor …see more

from $575 / night

$4025 - $7000 / week

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from $575 / night

(12) 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 $110 / night

$750 / week

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from $110 / 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 a 10 minute stro …see more

from $800 / night

$5600 - $7000 / week

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from $800 / 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 $2500 / night

$17500 / week

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Responds fast!
avg. 2 minutes

from $2500 / night

36

Vacation villa in Island Harbour

Anguilla / Island Harbour

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Tamarind villa overlooks the Atlantic on the north eastern end of the island. This villa is just a five minute drive from Shoal Bay East, one of the most beautiful beaches in the Caribbean. With its large principle rooms and comfortable settings, its the perfect place f …see more

from $792 / night

$5544 - $9800 / week

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avg. 2 hours 8 minutes

from $792 / night

25

Vacation villa with swimming pool in Island Harbour

Anguilla / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

$6650 / week

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from $950 / night

20

Vacation villa in Island Harbour

Anguilla / Island Harbour

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Nestled in an amazing ocean front location, this exclusive 3 bedroom, 3 bathroom villa is open-air living in contemporary design. Verdant gardens, natural stone swimming pool, Jacuzzi and seaside gazebo in expansive private grounds. You will enjoy your own private hidea …see more

from $918 / night

$6419 - $11900 / week

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Responds fast!
avg. 2 hours 8 minutes

from $918 / 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 $2100 / night

$14700 / week

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Responds fast!
avg. 2 minutes

from $2100 / 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 $2300 / night

$16100 / week

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Responds fast!
avg. 2 minutes

from $2300 / 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 $2100 / night

$14700 - $35000 / week

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from $2100 / night

29

Villa rental in Island Harbour

Anguilla / Island Harbour

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Villa Amarilla's design is Caribbean with an Italian influence in its yellow stucco walls, turquoise shutters and red tile roof. The cool island interiors by the owners in collaboration with award-winning Dallas interior designer David Salem & Associates have hints of M …see more

from $2100 / night

$14700 - $35000 / week

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from $2100 / night

18

Vacation villa in Island Harbour

Anguilla / Island Harbour

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This is a private and tranquil villa located in the Sea Rocks area of the island between Shoal Bay and Island Harbour, 4 minute drive to Shoal Bay beach and situated on the rocky cliff overlooking the sea. Jems Villa offers the discriminating traveler two bedrooms and t …see more

from $538 / night

$3767 - $6286 / week

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Responds fast!
avg. 2 hours 8 minutes

from $538 / 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 $1000 / night

$7000 - $70000 / week

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from $1000 / night