Island Harbour Vacations from $1,919

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Your Island Harbour Vacation

When you organize a vacation package to Island Harbour, you can relax and enjoy your getaway knowing that all your travel plans are in order. Uncover the wonders of this vibrant city from your base in a neighborhood like Little Dix, which is good for coastal beaches. Shoal Bay Beach, Crocus Bay Beach and Sandy Hill Beach are just some of the many sights worth checking out during your trip to Island Harbour. Your dream Island Harbour vacation is a few clicks away. Search hotels, airfares and more on Expedia for a getaway that's tailored to suit your style.

The Latest Island Harbour vacation packages

Price found within the past 48 hours. Click for updated prices.
Coralito Bay Suites & Villas

Coralito Bay Suites & Villas

3.5 out of 5
per person
Oct 9 - Oct 15
found 22 hours ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
9.8/10 Exceptional! (9 reviews)
I couldn’t have asked for a better location to celebrate my birthday. The villa and the property were breathtaking. The owner, Ivor, and the staff were so friendly, accommodating, and available! Grocery stores, boutiques, and restaurants were minutes away. The beach was right outside your door. Request the Pelican Villa. The view was amazing.

Reviewed on Jun 25, 2025

Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
9.6/10 Exceptional! (236 reviews)
Our second visit. It was a nice stay!

Reviewed on Jul 8, 2025

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
9.6/10 Exceptional! (226 reviews)
We loved everything about this property!

Reviewed on Jul 30, 2025

Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
per person
Oct 15 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
9.6/10 Exceptional! (132 reviews)
Phenomenal service coupled with a friendly staff.

Reviewed on Jul 25, 2025

6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
per person
Oct 15 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Island Harbour
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Discover the most popular places to visit in Island Harbour

Scilly Cay

Explore the lovely green spaces of Scilly Cay and enjoy the snorkeling spots in Island Harbour. Stroll along the seaside in this quaint area, or check out its top-notch restaurants.

Scilly Cay

Island Harbor Beach

Why not spend a carefree afternoon at Island Harbor Beach during your travels in Island Harbour? Wander the parks and waterfront while you're in the area.

Island Harbor Beach

Captain's Bay Beach

If a restful vacation is part of your travel plans, Captain's Bay Beach might be the perfect place to seek out during your trip to Island Harbour. Wander the parks and waterfront while you're in the area.

Captain's Bay Beach

What to do in Island Harbour

Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch

Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch

$135
per adult
86% of travellers recommend
Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch
Pinel Island!!

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

$139
per adult
100% of travellers recommend
Best Of Full-Day Snorkeling and Beach Excursion with Hot Lunch in Sint Maarten
Private Beach Hike Sunrise Serenity

Private Beach Hike Sunrise Serenity

$75
per adult
Private Beach Hike Sunrise Serenity
See all activities in Island Harbour

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 May 17, 2025

Get rates
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 Jul 7, 2025

Get rates
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!
Lovely 6-bedroom Villa with Pool

Lovely 6-bedroom Villa with Pool

Island Harbor
$3,735 nightly
The price is $4,035 total per night from Aug 4 to Aug 5
$4,035 total
Aug 4 - Aug 5
Total includes taxes and fees
Lovely 6-bedroom Villa with Pool
See all 356 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.

Island Harbour Beach Vacation

Listen to the soothing sound of waves rolling into the shore and gaze out over the sparkling waters during your Island Harbour vacation. 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 Harbor Beach, just 0.5 miles from the downtown area, and live out your vacation fantasies without hurting your budget.

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Frequently asked questions

How much does an Island Harbour vacation package cost?
You can pick up a vacation package to this destination from $1,919 on Expedia. But how much your vacation 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?
If you're looking to score a cheap Island Harbour vacation package, consider traveling in January, August and December. You're likely to find lower prices on flights and accommodations during these months — ideal for a budget-friendly break.
How many days is enough for Island Harbour?
You can easily visit all the leading sights in Island Harbour within a few days, including the popular Scilly Cay. If you want a longer Island Harbour vacation, check out what kind of excursions and activities are available nearby.
Is it worth booking a vacation package to Island Harbour?
Well known for its walking trails, fishing and underwater activities, an Island Harbour vacation is a hit with all types of travelers. Be sure to check out main sights like Island Harbor Beach and Scilly Cay, and consider renting a car for day trips to discover even more.
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 vacation package as early as possible.
Is it cheaper to book an Island Harbour vacation as a package?
You can enjoy significant savings on your next Island Harbour break by booking a personalized vacation 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 vacation package to Island Harbour?
If you have your Island Harbour vacation 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 when to get away: Check your diary and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to vacation in Island Harbour.
  2. Set your budget: Factor in costs like transportation, flights and meals when working out how much to put aside for your trip to Island Harbour. Then, pick a hotel that works with your budget, whether that's an affordable stay or a deluxe getaway.
  3. Explore Island Harbour using our trip planning tool: Gain insights into the most popular attractions and best properties for your trip to Island Harbour. You can also save your must-visit places, collaborate with family and friends and manage all your plans in one place.
  4. Decide how long to go for: Now that you're more familiar with Island Harbour, you can work out the perfect length of your break. Put together a rough plan and give yourself enough time for all the things you want to do.
  5. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, lock in the right Island Harbour vacation package for you.
  6. Book any day trips or activities: Here's the fun part — organizing everything you want to do and see. Explore some of the best things to do in Island Harbour in Island Harbour and book your tickets early to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Island Harbour vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Island Harbour vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.