Discover a selection of 252 vacation rentals in Island Harbour, AI that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $500 per night, and condos and villas are popular options for a stay in Island Harbour. Either way, you'll find a rental for everyone's needs.
Destination guide

Laidback luxury in Island Harbour

Studded with sandy coves and colorful fishing boats, Island Harbor is a breath of fresh air. The town sits on the eastern coast of Anguilla and is a favorite with travelers in search of island vibes. Fishing trumps tourism in this slice of the Caribbean, which gives Island Harbour a laidback local flavor. Accommodation comes in the form of luxury Island Harbour vacation rentals, complete with sparkling pools and stunning ocean views. Needless to say, these willl elevate your morning coffee to the next level.

Things to do

Discover Island Harbour's ancient Arawak past

From seawater to salt shaker, the Anguilla Sea Salt Company offers a fascinating look at the island's flourishing salt industry. For a glimpse at Anguilla's Arawak roots, head to Fountain Cavern National Park. Boat tours offer a unique opportunity to view petroglyph rock art inscribed on the limestone sea stacks. While you could easily spend your days visiting Anguilla's pretty churches and historic plantations, lazy afternoons on the terrace of your Island Harbour vacation rental villa are hard to resist.


Beach hopping in Island Harbour

For most visitors, Anguilla is a daydream of sandy beaches, swaying coconut palms and turquoise water. Island Harbour vacation rentals offer easy access to Anguilla's best stretches of sand, including Shoal Bay East. Wind up a day in the sun with fruity rum punch and live reggae tunes at a beachfront bar. Or, retreat to your private deck for sunset cocktails and good company. One of Island Harbour's best kept secrets is its treasure trove of eateries, from authentic Neapolitan pizza to Caribbean fusion.


Winter sunshine in Island Harbour

Peak season picks up in mid-December and runs right through to April. Expect clear skies, calm water and tropical highs that hover around the 80s. From family reunions to romantic escapes, Island Harbour vacation rentals provide a dreamy setting for winter getaways. For a more affordable taste of paradise, consider visiting in shoulder season, which spans May to August. You'll enjoy lower prices, thinner crowds and plenty of sunshine. There's also hurricane season to consider, with high winds recently causing extensive damage on the Caribbean island. For this reason, it's best to avoid June to November.

Natural features

Island Harbour to the cays

At just 16 miles long and 3 miles wide, Anguilla is a pocket-sized slice of paradise. It sits in the Caribbean Sea and is surrounded by a string of cays. The mainland is dotted with towns and villages, including Island Harbour. You can stick to local beaches or daytrip to cays, such as Sandy Island. Just offshore, you'll discover a utopia of colorful coral reefs where you can swim with sea turtles and nurse sharks. Anguilla also boasts some of the Caribbean's best diving, with sites such as Prickly Pear Cays featuring coral-strewn shipwrecks and underwater caverns.

How to get there

Transportation options to and around Island Harbour

Fly into The Valley (AXA-Clayton J. Lloyd Intl.), the closest airport, located 5 mi (8.1 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Grand Case (SFG-L'Esperance), which is 11.2 mi (18.1 km) away.

How many vacation rentals are available around Island Harbour, AI?

Our 2020 property listings offer a large selection of 252 vacation rentals around Island Harbour. From 49 condo and apartment rentals to 134 villa rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Island Harbour?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Island Harbour:

  • Sea Rocks: 24 vacation rentals
  • West End Village: 46 vacation rentals
  • Pelican Key: 178 vacation rentals
  • Les Terres Basses: 426 vacation rentals
  • The Valley: 106 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Island Harbour?

Vrbo offers a large selection of vacation rentals near lovely places in Island Harbour. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Captain's Bay Beach: 285 vacation rentals
  • Scilly Cay: 285 vacation rentals
  • Island Harbor Beach: 285 vacation rentals
  • University of St. Martin: 932 vacation rentals
  • Maho Beach: 970 vacation rentals

But there are many other points of interest around Island Harbour listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Island Harbour?

Yes, of course. Vrbo has 49 Condos/Apartments in Island Harbour. Our other popular types of vacation rentals in Island Harbour include:

  • Villas: 134 rentals available
  • Houses: 51 rentals available
  • Studios: 24 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Island Harbour?

Yes, you can select your preferred vacation rental with pool among our 194 vacation rentals with pool available in Island Harbour. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Island Harbour

    Sea Rocks
    24 vacation rentals
    West End Village
    46 vacation rentals
    Pelican Key
    178 vacation rentals
    Les Terres Basses
    426 vacation rentals
    The Valley
    106 vacation rentals
    Blowing Point
    50 vacation rentals
    Indigo Bay
    45 vacation rentals
    415 vacation rentals
    East End Village
    46 vacation rentals
    Shoal Bay Village
    68 vacation rentals
    Oyster Pond
    29 vacation rentals
    Almond Grove
    20 vacation rentals
    Oyster Pond
    183 vacation rentals
    Mont Vergna
    155 vacation rentals
    426 vacation rentals
    Dawn Beach Estates
    179 vacation rentals
    La Savane
    82 vacation rentals
    Red Pond Estates
    136 vacation rentals
    Lower Prince's Quarter
    21 vacation rentals
    Tamarind Hill Estates
    168 vacation rentals