Anguilla Luxury Vacations 2026

Photo by Anguilla Tourist Board

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Top Luxury vacation packages in Anguilla

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

Ceblue Luxury Villas

$1,825

per person

Oct 31 - Nov 1

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to The Valley (AXA)

10/10 Exceptional! (8 reviews)

Malliouhana Resort Anguilla

$2,709

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to The Valley (AXA)

9.6/10 Exceptional! (103 reviews)

Cap Juluca, A Belmond Hotel, Anguilla

$4,505

per person

Oct 14 - Oct 18

found 24 hours ago

Roundtrip non-stop flight included

New York (NYC) to The Valley (AXA)

9.6/10 Exceptional! (158 reviews)

Perfection situated on stunning Mandauys Bay. Everything was top notch! Grounds were beautiful, room clean and nicely appointed. We were upgraded to a Premium Beachfront room on the 2nd floor of our Villa with a gorgeous view of the crystal clear water and white sandy beach. Daily breakfast with menu items and buffet was delicious. LOVED the Cap Shack! Fish tacos and rum punch a must! We would definitely return to this lovely spot.

Reviewed on Aug 5, 2026

Aurora Anguilla Resort & Golf Club

$9,152

per person

Oct 17 - Oct 18

found 1 day ago

Roundtrip flight included

Detroit (DTT) to The Valley (AXA)

9.6/10 Exceptional! (202 reviews)

Asian restaurant hostess was rude.

Reviewed on Jul 16, 2026

Four Seasons Resort and Residences Anguilla

$9,240

per person

Oct 17 - Oct 18

found 1 day ago

Roundtrip flight included

Detroit (DTT) to The Valley (AXA)

9.8/10 Exceptional! (259 reviews)

I love the four seasons in Anguilla!! This is my 3rd time going to the island and I wouldn't stay anywhere else!’Nothing but top notch service!! Amazing time!!

Reviewed on Jul 28, 2026

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5* Luxury vacations in Anguilla

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

Ceblue Luxury Villas

$1,825

per person

Oct 31 - Nov 1

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to The Valley (AXA)

10/10 Exceptional! (8 reviews)

Malliouhana Resort Anguilla

$2,709

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to The Valley (AXA)

9.6/10 Exceptional! (103 reviews)

Cap Juluca, A Belmond Hotel, Anguilla

$4,505

per person

Oct 14 - Oct 18

found 24 hours ago

Roundtrip non-stop flight included

New York (NYC) to The Valley (AXA)

9.6/10 Exceptional! (158 reviews)

Reviewed on Aug 5, 2026

Don't see what you're looking for?

See all available trips from Columbus to Anguilla

View all trips

3 Night Luxury vacations in Anguilla

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

Ceblue Luxury Villas

$1,825

per person

Oct 31 - Nov 1

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to The Valley (AXA)

10/10 Exceptional! (8 reviews)

Malliouhana Resort Anguilla

$2,709

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to The Valley (AXA)

9.6/10 Exceptional! (103 reviews)

Aurora Anguilla Resort & Golf Club

$9,152

per person

Oct 17 - Oct 18

found 1 day ago

Roundtrip flight included

Detroit (DTT) to The Valley (AXA)

9.6/10 Exceptional! (202 reviews)

Asian restaurant hostess was rude.

Reviewed on Jul 16, 2026

Don't see what you're looking for?

See all available trips from Columbus to Anguilla

View all trips

4 Night Luxury vacations in Anguilla

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

Aurora Anguilla Resort & Golf Club

$2,863

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to The Valley (AXA)

9.6/10 Exceptional! (202 reviews)

Asian restaurant hostess was rude.

Reviewed on Jul 16, 2026

Malliouhana Resort Anguilla

$3,144

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Greenville (GSP) to The Valley (AXA)

9.6/10 Exceptional! (103 reviews)

Four Seasons Resort and Residences Anguilla

$3,369

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to The Valley (AXA)

9.8/10 Exceptional! (259 reviews)

I love the four seasons in Anguilla!! This is my 3rd time going to the island and I wouldn't stay anywhere else!’Nothing but top notch service!! Amazing time!!

Reviewed on Jul 28, 2026

Don't see what you're looking for?

See all available trips from Columbus to Anguilla

View all trips

What can I expect from a luxury Anguilla vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Anguilla vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Anguilla?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Anguilla luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $1,825. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Anguilla?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Anguilla with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Anguilla?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Anguilla with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Anguilla with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Anguilla Hotels

Zemi Beach House, LXR Hotels & Resorts

Shoal Bay East Shoal Bay

9 min walk from Shoal Bay Beach

$669 nightly

$745 total

Aug 15 - Aug 16

Total with taxes and fees

Pamper yourself with a luxury stay at Zemi Beach House, LXR Hotels & Resorts, where you can enjoy amenities like Champagne service, Frette Italian sheets, and ...

9.8/10 Exceptional! (283 reviews)

"From the warm welcome from Vernesha to the beautiful music played by the saxophonist and keyboard player, the personalized note and cookie at turndown, Zemi was a moment. We loved every bit of it and will return."

Reviewed on Aug 13, 2026

Four Seasons Resort and Residences Anguilla

Barnes Bay West End Village

19 min drive from Shoal Bay Beach

$1,068 nightly

$1,190 total

Aug 15 - Aug 16

Total with taxes and fees

Four Seasons Resort and Residences Anguilla is a sumptuous 5-star beach property where you can be treated to deep soaking bathtubs and premium bedding. The 3 ...

9.6/10 Exceptional! (260 reviews)

"I love the four seasons in Anguilla!! This is my 3rd time going to the island and I wouldn't stay anywhere else!’Nothing but top notch service!! Amazing time!!"

Reviewed on Jul 28, 2026

Cap Juluca, A Belmond Hotel, Anguilla

Maundays Bay Maunday's Bay

21 min drive from Shoal Bay Beach

$1,727 nightly

$1,931 total

Aug 15 - Aug 16

Total with taxes and fees

Cap Juluca, A Belmond Hotel, Anguilla is one of the Maunday's Bay lavish 5-star beach properties where you can treat yourself to deep soaking bathtubs and Champagne ...

9.6/10 Exceptional! (160 reviews)

"Perfection situated on stunning Mandauys Bay. Everything was top notch! Grounds were beautiful, room clean and nicely appointed. We were upgraded to a Premium Beachfront room on the 2nd floor of our Villa with a gorgeous view of the crystal clear water and white sandy beach. Daily breakfast with ..."

Reviewed on Aug 5, 2026

See all 365 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.