Discover a selection of 173 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 private pools. Prices start at $135 per night, and villas and houses 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 2021 property listings offer a large selection of 173 vacation rentals around Island Harbour. From 95 villa rentals to 114 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Villas in Island Harbour?

Yes, of course. Vrbo has 95 Villas in Island Harbour. Our other popular types of vacation rentals in Island Harbour include:

  • Houses: 114 rentals available
  • Condos/Apartments: 46 rentals available
  • Studios: 23 rentals available

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

Yes, you can select your preferred vacation rental with pool among our 134 vacation rentals with pool available in Island Harbour. Please use our search bar to access the selection of vacation rentals available.