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

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19 Vacation rentals

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

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

$4026 - $7000 / week

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from $575 / night

(11) 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) 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 overlooking Island Harbour village, miles of ocean, and Scilly Cay. Enjoy the ocean view from the master bedroom, master bathroom, living/dining area, kitchen and laundry area. Second bedr …see more

from $75 / night

$525 / week

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from $75 / night

24

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 $1250 / night

$8750 - $18550 / week

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from $1250 / night

(2) 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. 4 minutes

from $2500 / night

16

Island Harbour Vacation villa rental

Anguilla / Island Harbour

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Relaxed and comfortably designed, this cozy 4 bedroom new build is perfect for a large family or a group of friends. Situated on the hillside of Shoal Bay East. Kiki Villa offers a 180 degree view of the beautiful, turquoise blue sea. Just a 10 minute walk from the vill …see more

from $1200 / night

$8400 - $17500 / week

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from $1200 / night

27

Island Harbour Vacation villa rental

Anguilla / Island Harbour

8 16 4 nights min

  • 8 bedrooms
  • Sleeps 16
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Picturesquely situated on Anguilla's southeast shoreline, Ultimacy Villa is an eight bedroom super villa located in the upscale neighborhood of Sea Rocks, nestled between the villages of Shoal Bay and Island Harbour. This three story home is considered one of Anguilla's …see more

from $3375 / night

$23625 / week

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from $3375 / 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

25

Vacation home in Island Harbour

Anguilla / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Soleil Villa at Captain's Bay is a new 5,500 square foot vacation villa and features four air conditioned bedroom suites. From every vantage point, the villa has the most spectacular views of Scrub Island, Scilly Cay, Captains Bay and Savannah Bay. Luxury awaits you in …see more

from $950 / night

$6650 / week

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from $950 / night

43

Vacation villa in Island Harbour

Anguilla / Island Harbour

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Child friendly
Living up to its name, the Villa Beachcourt in Anguilla really does hold court over its own private beach in the sparsely populated Shoal Bay. It is considered one of the finest properties on the island and is large enough to house up to 16 guests comfortably in style a …see more

from $1100 / night

$7700 - $32585 / week

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from $1100 / 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. 4 minutes

from $2300 / 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. 4 minutes

from $2100 / 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

30

Vacation home with shared pool in Island Harbour

Anguilla / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fountain Beach Villa is located on Shoal Bay East on the tropical island of Anguilla and is a short walk to Shoal Bay Beach. The villa features four bedroom suites each with a private bathroom, an outdoor shower garden, air conditioning and a flat screen TV. Indoor spac …see more

from $1800 / night

$12600 / week

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from $1800 / night

8

Island Harbour Vacation villa rental

Anguilla / Island Harbour

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Praised in Architectural Digest twice, this ultra modern villa is the ideal vacation spot for the well traveled who appreciate architectural beauty, unspoiled nature, tranquility, privacy, simple elegance and personalized service. Two four bedroom grand villas, four …see more

from $6395 / night

$44765 / week

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from $6395 / night

24

Vacation villa with swimming pool in Island Harbour

Anguilla / Island Harbour

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Mahal Oceanfront  is located in Black Garden Bay with access to its own secluded beach on the tropical island of Anguilla. Sprawled out over 4,500 square feet of lavishing living space, this contemporary and family-friendly villa accommodates up to 12 guests and …see more

from $895 / night

$6265 / week

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from $895 / 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