Island Harbour Vacations from $931

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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.
West End Bay Condos

West End Bay Condos

3.5 out of 5
Price was $1,362, price is now $931 per person
$931
per person
Feb 9 - Feb 15
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
Save 100% on your flight
Price was $6,172, price is now $4,370 per person
$4,370
per person
Feb 9 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
19.2/10 Exceptional! (181 reviews)
My wife and I arrived at Aurora Anguilla Resort & Golf Club on November 15, and our stay has been nothing short of exceptional. From the warm welcome by bellman Kevin, who greeted us by name, to Zenobia’s smooth check-in with rum punches and cool towels, the service was impeccable. Our ocean-view suite on the 6th floor overlooking Rendezvous Bay was spotless and beautifully maintained. Resort ambassador Justin made our 7th anniversary truly special, surprising us with a chilled bottle of Fearless rosé from Sonoma County and chocolate-covered strawberries. The staff across the resort elevated our experience—Sweet Z at the beach, Elbert with snorkeling gear, and Marlon, who took me fishing twice where we caught blue runners, white backs, lizard fish, and snooks. We also enjoyed wonderful service from Maureen, Joyce, Javed, Khiry, and Toni at D. Richards Steakhouse, where vocalist Jeanette added to the atmosphere. Dinner at Sharky’s was another highlight. The activities kept us busy: a challenging bike ride between the Merrywing and Rendezvous sides, gym workouts, and relaxing beach time. Nightly turndown service was always appreciated. Dining at Breezes, Olivia’s, C-Level, the café, and the Thursday Lobster BBQ never disappointed—we ate enough lobster and crayfish to last the year. Anguilla may now be our favorite Caribbean island. At checkout, we were even sent off with parting rum punches. Visiting the week before T-giving made the resort feel quiet, intimate & unforgettable.

Reviewed on Nov 21, 2025

Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $6,734, price is now $4,865 per person
$4,865
per person
Feb 9 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
18.8/10 Exceptional! (89 reviews)
A beautiful property on Meads bay. Great service. Restaurant is a wellness comparing to Four Seasons nearby

Reviewed on Aug 2, 2025

Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $23,871, price is now $17,414 per person
$17,414
per person
Feb 9 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
No reviews
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,614, price is now $2,089 per person
$2,089
per person
Feb 9 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
18.4/10 Exceptional! (25 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

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

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

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

Private Beach Hike Sunrise Serenity

Private Beach Hike Sunrise Serenity

$75
per adult
Private Beach Hike Sunrise Serenity
Bay Petites Cayes

St. Martin or St. Maarten: Nature Hike Secret Beach Tour

$89
per adult
St. Martin or St. Maarten: Nature Hike Secret Beach Tour
All-Inclusive Local Guided Pinel Island Tour

All-Inclusive Local Guided Pinel Island Tour

$159
per adult
100% of travellers recommend
All-Inclusive Local Guided Pinel Island Tour
See all activities in Island Harbour

Island Harbour Hotel Deals

Lovely 6-bedroom Villa with Pool

Lovely 6-bedroom Villa with Pool

Island Harbor Anguilla
$3,683 nightly
The price is $3,983 total per night from Nov 26 to Nov 27
$3,983 total
Nov 26 - Nov 27
Total with taxes and fees
Lovely 6-bedroom Villa with Pool
Sienna is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!

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

Shoal Bay
Get rates
Sienna is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!
Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families

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

Island Harbour Anguilla
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
See all 339 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.

Find the Best Island Harbour Vacation Packages

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.

Island Harbour Essential Information

Language
English
Currency
East Caribbean dollars
Closest Airport
Clayton J. Lloyd Intl. Airport (AXA)
Max Temp Winter
80ºF
Max Temp Summer
80ºF
Top Sights
Shoal Bay Beach, Maundays Bay and Crocus Bay Beach

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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 $931 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.

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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.