Island Harbour Holidays

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Island Harbour Holiday

Island Harbour Beach Holiday

Listen to the soothing sound of waves rolling into the shore and gaze out over the sparkling waters during your Island Harbour holiday. If you're craving some time out, a trip to Island Harbour is your ticket to rest and relaxation. We have plenty of Island Harbour packages to select from. Book one near Island Harbour Beach, just 0.80 kilometres from the downtown area, and live out your holiday fantasies without hurting your budget.

Our pick of the best Island Harbour Hotel Deals

Beautiful 2000 sq. ft Sunrise & Sunset Penthouse near Shoal Bay Beach, Anguilla

Beautiful 2000 sq. ft Sunrise & Sunset Penthouse near Shoal Bay Beach, Anguilla

Canifest
9.6/10 Exceptional! (10 reviews)
Anguilla and surrounding Islands
"It was the relaxing stay on an island with beautiful beaches that we needed to get away, from the New York City Life style."

Reviewed on 17 May 2025

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Beautiful 2000 sq. ft Sunrise & Sunset Penthouse near Shoal Bay Beach, Anguilla
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Island Harbour
10/10 Exceptional! (4 reviews)
Family Vacay
"The property has gorgeous views and great snorkeling. Plenty of room for our party of 12. We had a wonderful time here!"

Reviewed on 7 Jul. 2025

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Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!
Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families

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

Island Harbour
Perfect vacation!
"Gorgeous, clean with beautiful views. Amazing staff. We had the best time!"

Reviewed on 4 Jan. 2024

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Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families
See all 355 properties in Island Harbour
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

What to do in Island Harbour

Pinel Island!!

Best Of Full-Day Snorkeling and Beach Excursion with Hot Lunch in Sint Maarten

NZ$231
per adult
100% of travellers recommend
Best Of Full-Day Snorkeling and Beach Excursion with Hot Lunch in Sint Maarten
Anguilla In Style

Anguilla In Style

NZ$217
per adult
Anguilla In Style
Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch

Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch

NZ$224
per adult
86% of travellers recommend
Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch
See all activities in Island Harbour

Frequently asked questions

How much does an Island Harbour holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday to Island Harbour costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Island Harbour?
The off-season is the best time to travel to Island Harbour if you're hoping to keep costs down. Another tip for getting cheap Island Harbour holiday packages? Avoid visiting during public holidays and any major events or festivals.
How many days is enough for Island Harbour?
Allow at least 4 days for your Island Harbour holiday if you want to take in everything that makes this place unique. Explore key areas, including Sea Rocks and Sandy Hill. Then head to the top sights like Scilly Cay and Scilly Cay. With a good itinerary, you'll be kept busy with room for some me-time too. Want to venture beyond Island Harbour? Consider fitting in an excursion or two.
Is it worth booking a holiday package to Island Harbour?
Island Harbour has all the ingredients you need for an amazing trip — underwater activities, walking trails and festivals are just the start. Whether you want to visit sights such as Island Harbour Beach and Scilly Cay, or venture off the beaten track, you'll find plenty to see and do on your Island Harbour holiday.
How to find the best Island Harbour package deals?
Use Expedia's filter tool to help you find some fabulous Island Harbour package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Island Harbour package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book an Island Harbour holiday as a package?
You can enjoy significant savings on your next Island Harbour break by booking a personalised holiday package. Click on the "Package" heading, then enter your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Island Harbour?
If you have your Island Harbour holiday dates confirmed, book as early as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Island Harbour?

  1. Choose your dates: What you plan to do in Island Harbour and your favourite season will help you decide when to get away.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and food to flights and activities. Your hotel will probably be the largest expense during your trip to Island Harbour.
  3. Decide how many days away: Start by compiling a list of the attractions you'd like to get to in Island Harbour. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick an Island Harbour holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.