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Island Harbour Vacation Rentals

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50 rentals in Island Harbour.
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Clearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!, vacation rental in Island Harbour

Clearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families, vacation rental in Island Harbour

Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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James Place Apartments, Anguilla , British West Indies, vacation rental in Island Harbour

James Place Apartments, Anguilla , British West Indies

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ocean View Apartment at Captain's Ridge (view from every room), vacation rental in Island Harbour

Ocean View Apartment at Captain's Ridge (view from every room)

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Exclusive Beachfront Villa, vacation rental in Island Harbour

Exclusive Beachfront Villa

5 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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The Hidden Cottage, vacation rental in Island Harbour

The Hidden Cottage

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Wesley House, vacation rental in Island Harbour

Wesley House

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Kiki Villa, vacation rental in Island Harbour

Kiki Villa

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Amarilla Villa, vacation rental in Island Harbour

Amarilla Villa

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Quixotic Villas, vacation rental in Island Harbour

Quixotic Villas

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Very Private Villa Hibernia,  Ocean Front, Pool & sea Gazebo, vacation rental in Island Harbour

Very Private Villa Hibernia, Ocean Front, Pool & sea Gazebo

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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25% Off Posted Winter Rates!! Beautiful 2 BR/2 BA Condo - Spectacular Water View, vacation rental in Island Harbour

25% Off Posted Winter Rates!! Beautiful 2 BR/2 BA Condo - Spectacular Water View

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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LUXURY VILLA 'B ON THE SEA' IN ANGUILLA, 5 ENSUITE BEDROOMS, 2 DECKS, 2 POOLS, vacation rental in Island Harbour

LUXURY VILLA 'B ON THE SEA' IN ANGUILLA, 5 ENSUITE BEDROOMS, 2 DECKS, 2 POOLS

5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Ocean Terrace Luxury 2BR Condos, Spectacular Views, vacation rental in Island Harbour

Ocean Terrace Luxury 2BR Condos, Spectacular Views

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stunning Sea Feathers Villa, vacation rental in Island Harbour

Stunning Sea Feathers Villa

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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BestValue1300/5bd/night. Rent 1 bdr or more,  rates adjusted on a sliding scale, vacation rental in Island Harbour

BestValue1300/5bd/night. Rent 1 bdr or more, rates adjusted on a sliding scale

5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
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Location, Location, Location! Stunning Villa Azure, vacation rental in Island Harbour

Location, Location, Location! Stunning Villa Azure

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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2 Br/2 Bath Oceanfront Condo Steps To Sandy Hill Bay., vacation rental in Island Harbour

2 Br/2 Bath Oceanfront Condo Steps To Sandy Hill Bay.

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Tequila Sunrise Villa in Anguilla, vacation rental in Island Harbour

Tequila Sunrise Villa in Anguilla

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Villa Dulcinea - Ocean views, near beach, outdoor space, great for groups!, vacation rental in Island Harbour

Villa Dulcinea - Ocean views, near beach, outdoor space, great for groups!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful villa with ocean view and terrace, vacation rental in Island Harbour

Beautiful villa with ocean view and terrace

2 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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* Rudy's Guest House  *, vacation rental in Island Harbour

* Rudy's Guest House *

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sandcastle Villa - 10,000 sf Luxury Beachfront Villa + Chevy Tahoe (by owner), vacation rental in Island Harbour

Sandcastle Villa - 10,000 sf Luxury Beachfront Villa + Chevy Tahoe (by owner)

4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Villa Kai, vacation rental in Island Harbour

Villa Kai

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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James Place Apartments, vacation rental in Island Harbour

James Place Apartments

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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7 Palms Villa  - Anguilla - Caribbean, vacation rental in Island Harbour

7 Palms Villa - Anguilla - Caribbean

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Ani North Villa, vacation rental in Island Harbour

Ani North Villa

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Villa SandCastle | Beach Front - Located in Fabulous Limestone Bay with Privat, vacation rental in Island Harbour

Villa SandCastle | Beach Front - Located in Fabulous Limestone Bay with Privat

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Zenaida, vacation rental in Island Harbour

Zenaida

7 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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Ani South, vacation rental in Island Harbour

Ani South

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Sandcastle Anguilla, vacation rental in Island Harbour

Sandcastle Anguilla

4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Kishti Black, vacation rental in Island Harbour

Kishti Black

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Dreamcatcher - luxury villa, stunning views over turquoise seas, vacation rental in Island Harbour

Dreamcatcher - luxury villa, stunning views over turquoise seas

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sea Feathers Bay Anguilla BWI, vacation rental in Island Harbour

Sea Feathers Bay Anguilla BWI

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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7 bedroom Villa, vacation rental in Island Harbour

7 bedroom Villa

7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Enchanting, Family Friendly 3bdr, adjustable fee for more or less bedrooms, vacation rental in Island Harbour

Enchanting, Family Friendly 3bdr, adjustable fee for more or less bedrooms

3 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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MODERN VILLA WITH POOL AND STUNING OCEAN VIEWS, vacation rental in Island Harbour

MODERN VILLA WITH POOL AND STUNING OCEAN VIEWS

1 bedroom
3 bathrooms
Sleeps 11
Match: Sleeps
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COZY AND PRIVATE FOR TWO COUPLES TRAVELING TOGETHER, vacation rental in Island Harbour

COZY AND PRIVATE FOR TWO COUPLES TRAVELING TOGETHER

2 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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EXQUISITE FRIENDLY SPECTACULAR VIEWS 4BDRM VILLA, vacation rental in Island Harbour

EXQUISITE FRIENDLY SPECTACULAR VIEWS 4BDRM VILLA

4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Crystal Sunrise Villa, vacation rental in Island Harbour

Crystal Sunrise Villa

7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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NEW SANDCASTLE BEACH HOUSE + Jeep Wrangler + Pool & Jacuzzi, vacation rental in Island Harbour

NEW SANDCASTLE BEACH HOUSE + Jeep Wrangler + Pool & Jacuzzi

3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Villa Tasha, a luxury seafront villa on the Caribbean sea, next to a beach, vacation rental in Island Harbour

Villa Tasha, a luxury seafront villa on the Caribbean sea, next to a beach

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Zenaida Estate | Beach View - Located in Magnificent Sandy Hill with Private Po, vacation rental in Island Harbour

Zenaida Estate | Beach View - Located in Magnificent Sandy Hill with Private Po

1 bedroom
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Zenaida Estate | Beach View - Located in Wonderful Sandy Hill with Private Pool, vacation rental in Island Harbour

Zenaida Estate | Beach View - Located in Wonderful Sandy Hill with Private Pool

1 bedroom
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Villa Tequila Sunrise | Beach Front - Located in Wonderful Dropsey Bay with Pr, vacation rental in Island Harbour

Villa Tequila Sunrise | Beach Front - Located in Wonderful Dropsey Bay with Pr

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Villa Tequila Sunrise | Beach Front - Located in Exquisite Dropsey Bay with Pr, vacation rental in Island Harbour

Villa Tequila Sunrise | Beach Front - Located in Exquisite Dropsey Bay with Pr

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Zenaida Estate | Beach View - Located in Stunning Sandy Hill with Private Pool, vacation rental in Island Harbour

Zenaida Estate | Beach View - Located in Stunning Sandy Hill with Private Pool

1 bedroom
4 bathrooms
Sleeps 8
Match: Sleeps
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Paradise in Tranquility Anguilla, vacation rental in Island Harbour

Paradise in Tranquility Anguilla

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stylish Place in Front of the Caribbean Sea - 3 Guests - Colonia furniture, vacation rental in Island Harbour

Stylish Place in Front of the Caribbean Sea - 3 Guests - Colonia furniture

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach, vacation rental in Island Harbour

The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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