Anguilla Luxury Vacations

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Photo by Anguilla Tourist Board

Top Luxury vacation packages in Anguilla

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

Malliouhana Resort Anguilla

$3,067
per person
Oct 21 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
9.6/10 Exceptional! (107 reviews)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

Save 100% on your flight
$9,718
per person
Nov 10 - Nov 14
just found
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
9.6/10 Exceptional! (205 reviews)
Ceblue Luxury Villas

Ceblue Luxury Villas

$3,512
per person
Nov 10 - Nov 14
just found
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
10/10 Exceptional! (11 reviews)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

$5,077
per person
Nov 10 - Nov 14
just found
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
9.6/10 Exceptional! (263 reviews)
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

$6,267
per person
Oct 11 - Oct 17
found 6 hours ago
Roundtrip flight included
Hartford (BDL) to The Valley (AXA)
9.6/10 Exceptional! (161 reviews)
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See all available trips from Columbus to Anguilla
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5* Luxury vacations in Anguilla

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

Malliouhana Resort Anguilla

$3,067
per person
Oct 21 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
9.6/10 Exceptional! (107 reviews)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

Save 100% on your flight
$9,718
per person
Nov 10 - Nov 14
just found
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
9.6/10 Exceptional! (205 reviews)
Ceblue Luxury Villas

Ceblue Luxury Villas

$3,512
per person
Nov 10 - Nov 14
just found
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
10/10 Exceptional! (11 reviews)
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

Ceblue Luxury Villas

$2,409
per person
Nov 12 - Nov 15
found 17 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to The Valley (AXA)
10/10 Exceptional! (11 reviews)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

Save 100% on your flight
$3,357
per person
Nov 13 - Nov 16
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to The Valley (AXA)
9.6/10 Exceptional! (205 reviews)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

$2,565
per person
Oct 23 - Oct 26
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to The Valley (AXA)
9.6/10 Exceptional! (107 reviews)
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

Aurora Anguilla Resort & Golf Club

$2,992
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to The Valley (AXA)
9.6/10 Exceptional! (205 reviews)
Ceblue Luxury Villas

Ceblue Luxury Villas

$3,512
per person
Nov 10 - Nov 14
just found
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
10/10 Exceptional! (11 reviews)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

$3,067
per person
Oct 21 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
9.6/10 Exceptional! (107 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Anguilla
View all trips

All you need to know about luxury vacations in Anguilla

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 $2,409. 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

Zemi Beach House, LXR Hotels & Resorts

Shoal Bay East Shoal Bay
  • 18 min drive from Meads Bay
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! (289 reviews)
"Zemi Beach Anguilla is just awesome!"

Reviewed on Sep 8, 2026

Get rates
Zemi Beach House, LXR Hotels & Resorts
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

Barnes Bay West End Village
  • 5 min walk from Meads Bay
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 ...
Four Seasons Resort and Residences Anguilla
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

Maundays Bay Maunday's Bay
  • 25 min walk from Meads Bay
$1,568 nightly
$1,753 total
Oct 11 - Oct 12
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 ...
Cap Juluca, A Belmond Hotel, Anguilla
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.

Things to do

Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

$77
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

$159
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
Exploring beautiful St.Martin

Adventure Island Tour

$65
per adult
Adventure Island Tour
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.