Island Harbour Vacations from $913

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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.
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,142, price is now $913 per person
$913
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
8/10 Very Good! (236 reviews)
The place is in need of some upkeep and modernization. The showers are old and the grout needs to be redone. Levers and knobs kept falling off of doors and windows. Needs an upgrade. Really disappointed in the food options in the evenings. The menu should be redone and prices reconsidered. Too Americanized and should give a sample of local fare. The beachside bar and grill was appropriate but closed so early it was not an option if you had daytime excursions planned offsite. It should be open later.

Reviewed on Aug 11, 2025

Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $19,942, price is now $13,904 per person
$13,904
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
No reviews
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was $3,154, price is now $2,431 per person
$2,431
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
9.6/10 Exceptional! (164 reviews)
Gorgeous gorgeous resort! water park was fantastic, staff was the most friendliest we've met. Justin Time was most accommodating for us in every way. The valet was great, the rooms smelled amazing and were very clean. Food was also exceptional. There was a cafe in the lobby which we went to quite often. The beach was so beautiful and overall the family had the most wonderful time and we would rank this to be one of our favorite resorts.

Reviewed on Aug 11, 2025

Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Price was $3,425, price is now $2,720 per person
$2,720
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
9.4/10 Exceptional! (88 reviews)
A beautiful property on Meads bay. Great service. Restaurant is a wellness comparing to Four Seasons nearby

Reviewed on Aug 2, 2025

Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $1,969, price is now $1,652 per person
$1,652
per person
Nov 8 - Nov 15
found 11 hours ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
9.2/10 Wonderful! (24 reviews)
Beach here is amazing and the surf is so easy to get in/out of. Rooms are nice and have everything you need. The hotel is relatively isolated and there is nowhere nearby to get dinner, so a rental car is needed or be prepared for an expensive taxi ride. A few beach restaurants for lunch are available. Breakfast is basic, comes to you in your room. Staff is wonderful and they will help you get whatever you need.

Reviewed on May 14, 2025

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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 beautiful beaches in this relaxing area, or check out its lively bars.

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

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
Anguilla In Style

Anguilla In Style

$131
per adult
Anguilla In Style
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
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
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 Jan 4, 2024

Get rates
Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families
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!!
See all 359 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 $913 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.