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.
Genesis Residences

Genesis Residences

2.5 out of 5
Price was CA $2,160, price is now CA $1,810 per person
CA $1,810
per person
Jan 1 - Jan 6
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.8/10 Exceptional! (8 reviews)
Our stay at Genesis Residence in Anguilla was absolutely wonderful! The property was beautiful, clean, comfortable, and in an excellent location with easy access to some of the island’s best beaches, restaurants, and attractions. What truly made our experience exceptional was the staff. Geraldine was incredibly friendly, attentive, and genuinely committed to making sure we had everything we needed. The warm hospitality made us feel right at home from the moment we arrived. If you’re looking for a relaxing, well-maintained place to stay with outstanding service and a fantastic location, I highly recommend Genesis Residence. We had an amazing vacation and look forward to staying here again on our next trip to Anguilla!

Reviewed on Jul 24, 2026

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was CA $4,778, price is now CA $3,416 per person
CA $3,416
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to The Valley (AXA)
9.6/10 Exceptional! (207 reviews)

Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was CA $5,043, price is now CA $4,104 per person
CA $4,104
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
9/10 Wonderful! (34 reviews)
stayed there in previous years, the hotel would need some upgrade. not to make it luxury, but not so „run out“. maybe depends on room you stay in, they have different standards/settings… location is quiet and probably most beautiful beach/spot, very private and relaxing.

Reviewed on May 15, 2026

6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Save 100% on your flight
Price was CA $13,291, price is now CA $11,237 per person
CA $11,237
per person
Jan 4 - Jan 8
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
No reviews

Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Save 100% on your flight
Price was CA $38,969, price is now CA $33,028 per person
CA $33,028
per person
Jan 3 - Jan 10
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to The Valley (AXA)
9.8/10 Exceptional! (50 reviews)
Beautiful property and lovely staff. The room was clean and very comfortable. The location on the beach was perfect.

Reviewed on Oct 12, 2026

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?

 

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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! (35 reviews)
"I can’t say enough wonderful things about the property or our stay. The villa was beautiful inside and out with amazing views. Every single thing you could possibly need was provided. We hated to leave and can’t wait to come back. It’s spacious and the floor plan is perfect. We hope to return again ..."

Reviewed on Aug 24, 2026

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

Cozy one bedroom studio

The Valley
The price is CA $196 per night from Nov 3 to Nov 4
CA $196
CA $269 total
Nov 3 - Nov 4
includes taxes & fees
9.8/10 Exceptional! (10 reviews)
"Loved both the property and the Hosts. The location was amazing, very convenient and the place was spotless, spacious, beautiful and fully equipped. Had everything needed for a super comfortable and relaxing stay. Hosts were responsive and caring, treated me as part of their Family. Also very thankful ..."

Reviewed on Aug 11, 2026

Cozy one bedroom studio
See all 353 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

Little Bay

Anguilla Getaway Cruise

CA $211
per adult
92% of travellers recommend
Anguilla Getaway Cruise
Picture & Shopping

Anguilla Explorer Land and Sea Excursion

CA $225
per adult
Anguilla Explorer Land and Sea Excursion
Genevie

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

CA $211
per adult
90% of travellers recommend
Captain Bob Speed Boat, Snorkeling, Beach Tour & Lunch St 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 $1,810 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.

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