Island Harbour Holidays

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Island Harbour Beach Holiday

The smell of salty sea air and gorgeous coastal vistas are just the start of things to look forward to on your Island Harbour holiday. If you want to save on your trip to Island Harbour, here's a tip — opt for one of our Island Harbour holiday deals. Lock in one near Captain's Bay Beach, just 2 kilometres from the centre of town and a must-see while here. Alternatively, pick a package that puts you close to Island Harbour Beach, another stunning stretch of coast. Whichever you choose, you'll be left with extra dollars in your holiday budget to play with.

Things You Should Know About Island Harbour

  • If your idea of holiday bliss includes being just steps from the shoreline, the scent of salty air drifting through your window and crashing waves lulling you to sleep, check out our Island Harbour beach hotels.
  • Villas are one more popular choice for a visit to Island Harbour. Anguilla Breeze and Villa Exclusivity at Captain's Bay have everything you need to make your beach holiday enjoyable.

Top hotels in Island Harbour

The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach
The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach
Canifest
9.6/10 Exceptional! (9 reviews)
3 Days of Sun and Fun
"Our Hosts were lovely and very helpful recommending beaches to go to and restaurants to dine at. The Penthouse has an easy layout, comfy beds and seating areas for easy conversations."

Reviewed on 28 Feb 2025

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The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!
Island Harbour
10/10 Exceptional! (4 reviews)
Amazing Anguilla vacation
"Caribbean Rhapsody was truly a perfect place to stay in Anguilla. The pictures don't do it justice. Amazing ocean views, falling asleep to crashing Waves every night. Absolutely perfect. The villa was also amazing. It is actually set up as 3 separate units with shared spaces, each with their own ..."

Reviewed on 24 Jan 2025

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Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!
Breathtaking Shoal Bay Villa
Breathtaking Shoal Bay Villa
Sea Rocks Retreat
Scam
"I booked this property in Dec of 2024 to arrive in Feb 2025. Upon arriving we had not received any details for the property despite multiple attempts. We had some of our guest go and locate the property to find this property had been abandoned. I finally reached the host and she said that there was ..."

Reviewed on 1 Mar 2025

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Breathtaking Shoal Bay Villa
See all 380 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.

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.

What to do in Island Harbour

Pinel Island!!

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

€128
per adult
100% of travellers recommend
Best Of Full-Day Snorkeling and Beach Excursion with Hot Lunch in Sint Maarten
Genevie

Captain Bob Speed Boat, Snorkeling, Beach Tour & Lunch St Maarten

€128
per adult
88% of travellers recommend
Captain Bob Speed Boat, Snorkeling, Beach Tour & Lunch St Maarten
Come to visit me

The Original Eco Tour Full-Day Around the Island of Sint Maarten

€138
per adult
100% of travellers recommend
The Original Eco Tour Full-Day Around the Island of Sint Maarten
See all activities in Island Harbour
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.