Island Harbour Vacation Packages

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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.

Top Island Harbour Vacation Deals

Price found within the past 48 hours. Click for updated prices.
West End Bay Condos

West End Bay Condos

3 out of 5
Price was CA $3,379, price is now CA $3,256 per person
CA $3,256
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
9.8/10 Exceptional! (6 reviews)
Excelente localización

Reviewed on May 7, 2026

6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Price was CA $13,871, price is now CA $12,658 per person
CA $12,658
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
No reviews

Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was CA $3,565, price is now CA $3,405 per person
CA $3,405
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
8/10 Very good! (47 reviews)
Great staff. Spacious and very clean rooms. Must have a car. In between seasons, yacuzzi nor hot tubs were operational (waiting for parts).

Reviewed on Mar 28, 2026

White Sands Anguilla

White Sands Anguilla

3.5 out of 5
Price was CA $3,556, price is now CA $3,556 per person
CA $3,556
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
10/10 Exceptional! (3 reviews)
Much larger and nicer than the pics show. Perfect for families. Great location near the ferry and Rendezvous Bay.

Reviewed on Apr 5, 2025

6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Price was CA $11,589, price is now CA $9,847 per person
CA $9,847
per person
Aug 22 - Aug 28
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to The Valley (AXA)
No reviews

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 Harbour Beach, just 0.80 kilometres from the downtown area, and live out your vacation fantasies without hurting your budget.

Ready to book your vacation to Island Harbour?

 

Choose your dates

Island Harbour Hotel Deals

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

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

Island Harbour Anguilla
10/10 Exceptional! (32 reviews)
"Amazing stay!! Our 3rd year in a row. Locations is perfect, accommodations impeccable and service is top notch. Thank you Reuben and staff!"

Reviewed on Jul 7, 2026

Get rates
Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families
Cozy one bedroom studio

Cozy one bedroom studio

The Valley
The price is CA $198 per night from Jul 15 to Jul 16
CA $198
CA $273 total
Jul 15 - Jul 16
includes taxes & fees
9.8/10 Exceptional! (9 reviews)
"We had such a wonderful experience at this property! The space was spotless, cozy, beautifully finished, and matched the description perfectly. The location was great, walking distance to a bakery with delicious pastries, and just a few minutes' drive to beaches, shops, and restaurants. Communication ..."

Reviewed on Mar 24, 2026

Cozy one bedroom studio
Zen is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!

Zen is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!

Shoal Bay
Get rates
Zen is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!
See all 370 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Island Harbour attractions

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.
See properties

What to do in Island Harbour

2 Hour Scheduled Group Snorkel Tour to Little Bay Marine Park

Anguilla Based: 2-Hr Group Snorkel at Little Bay Marine Park.

CA $142
per adult
Anguilla Based: 2-Hr Group Snorkel at Little Bay Marine Park.
Anguilla In Style

Anguilla In Style

CA $212
per adult
100% of travellers recommend
Anguilla In Style
The Original Eco Tour Full-Day Around the Island of Sint Maarten

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

CA $212
per adult
100% of travellers recommend
The Original Eco Tour Full-Day Around the Island of Sint Maarten
See all activities in Island Harbour

Frequently asked questions

How much does an Island Harbour vacation package cost?
You'll find cheap prices from CA $3,256 on Expedia for your Island Harbour escape. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Island Harbour costs.
What are the cheapest months to go to Island Harbour?
To pick up cheap Island Harbour vacation packages, organize your trip outside of peak times such as public holidays. You'll typically find lower prices and better availability for flights and hotels.
How many days is enough for Island Harbour?
We suggest planning an Island Harbour vacation for around 4 days. This will allow you time to tick off popular sights including Island Harbour Beach and Little Bay, as well as explore neighbourhoods like Sea Rocks and Sandy Hill. You might even be able to make time for a day trip beyond Island Harbour.
Is it worth booking a vacation package to Island Harbour?
Whether you'd like to explore attractions such as Island Harbour Beach and Scilly Cay on your Island Harbour vacation, or coming for its great underwater activities, walking trails and festivals, there's something for everyone here. With so many things to see and do, you'll soon learn why so many people think Island Harbour is a good vacation destination.
How to find the best Island Harbour package deals?
Use Expedia's filter tool to find some unbeatable Island Harbour package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Island Harbour package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book 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 Island Harbour retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Island Harbour?
Land incredible discounts by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Island Harbour adventure.
How to plan a trip to Island Harbour?

  1. Choose your dates: The things you plan to do in Island Harbour and your preferred season will help you decide when to go.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodations will likely be the largest expense during your trip to Island Harbour.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Island Harbour. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose an Island Harbour vacation package that brings all your bookings together.

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