Anguilla Beach Vacations

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Photo by Anguilla Tourist Board
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    Save up to CA $4,200 when you book a flight and hotel together*
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Flight and Beach hotel deals in Anguilla

Price found within the past 48 hours. Click for updated prices.
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

CA $3,771
per person
Nov 17 - Nov 22
found 12 hours ago
Roundtrip flight included
Montreal (YMQ) to The Valley (AXA)
9.6/10 Exceptional! (205 reviews)
Ceblue Luxury Villas

Ceblue Luxury Villas

CA $5,899
per person
Nov 15 - Nov 22
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
10/10 Exceptional! (11 reviews)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

CA $7,338
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (263 reviews)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

CA $6,121
per person
Nov 15 - Nov 22
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.8/10 Exceptional! (287 reviews)
Zemi Beach Anguilla is just awesome!

Reviewed on Sep 8, 2026

Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

CA $6,431
per person
Nov 17 - Nov 22
found 12 hours ago
Roundtrip flight included
Montreal (YMQ) to The Valley (AXA)
9.6/10 Exceptional! (107 reviews)
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5* Beach holidays in Anguilla

Price found within the past 48 hours. Click for updated prices.
Ceblue Luxury Villas

Ceblue Luxury Villas

CA $5,899
per person
Nov 15 - Nov 22
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
10/10 Exceptional! (11 reviews)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

CA $7,338
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (263 reviews)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

CA $6,121
per person
Nov 15 - Nov 22
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.8/10 Exceptional! (287 reviews)
Zemi Beach Anguilla is just awesome!

Reviewed on Sep 8, 2026

Don't see what you're looking for?
See all available trips from DeKalb to Anguilla
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3 Night Beach holidays in Anguilla

Price found within the past 48 hours. Click for updated prices.
Ceblue Luxury Villas

Ceblue Luxury Villas

CA $2,908
per person
Nov 19 - Nov 22
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to The Valley (AXA)
10/10 Exceptional! (11 reviews)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

CA $3,189
per person
Nov 19 - Nov 22
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to The Valley (AXA)
9.8/10 Exceptional! (287 reviews)
Zemi Beach Anguilla is just awesome!

Reviewed on Sep 8, 2026

Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

CA $5,731
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
9.6/10 Exceptional! (161 reviews)
Don't see what you're looking for?
See all available trips from DeKalb to Anguilla
View all trips

4 Night Beach holidays in Anguilla

Price found within the past 48 hours. Click for updated prices.
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

CA $2,349
per person
Oct 29 - Nov 2
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
9.6/10 Exceptional! (205 reviews)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

CA $3,072
per person
Nov 7 - Nov 11
just found
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (107 reviews)
Ceblue Luxury Villas

Ceblue Luxury Villas

CA $3,736
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to The Valley (AXA)
10/10 Exceptional! (11 reviews)
Don't see what you're looking for?
See all available trips from DeKalb to Anguilla
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Find the best beach vacations in Anguilla

What are some benefits when booking beach vacations in Anguilla?

When you travel to the beach in Anguilla, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

How can I book the best beach vacations in Anguilla?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Anguilla trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Anguilla?

There are quite a few things you can do to get cheap beach vacations in Anguilla. Prices range from CA $2,349, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Anguilla. These package deals let you save by booking your accommodation and your flight together with savings of up to 33.

Why should I book family beach vacations?

When you're travelling with the family to Anguilla, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Anguilla?

It's easy to find a beachfront vacation accommodation in Anguilla using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Anguilla as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Anguilla is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Caribbean. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in Anguilla

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

Rendezvous Bay Rendezvous Bay
  • 17 min drive from Shoal Bay Beach
CA $1,156
CA $1,451 total
Oct 16 - Oct 17
includes taxes & fees
Book a stay at this luxury resort in Rendezvous Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...
Aurora Anguilla Resort & Golf Club
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

Rendezvous Bay Rendezvous Bay
  • 17 min drive from Shoal Bay Beach
CA $222
CA $278 total
Sep 25 - Sep 26
includes taxes & fees
Book a stay at this beach hotel in Rendezvous Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very good! (345 reviews)
"Its a great place to unwind and relax"

Reviewed on Sep 10, 2026

Anguilla Great House Beach Resort
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

Shoal Bay East Shoal Bay
  • 9 min walk from Shoal Bay Beach
CA $923
CA $1,172 total
Oct 16 - Oct 17
includes taxes & fees
Book a stay at this luxury resort in Shoal Bay. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (289 reviews)
"Zemi Beach Anguilla is just awesome!"

Reviewed on Sep 8, 2026

Zemi Beach House, LXR Hotels & Resorts
See all 355 properties in Anguilla
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.

Things to do

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $112
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
St Maarten Beach hopping tour

St Maarten Beach hopping tour (Oreint beach and Maho beach combo)

CA $83
per adult
St Maarten Beach hopping tour (Oreint beach and Maho beach combo)
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $220
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
See all activities in Anguilla

More vacations you might like

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