Anguilla Romantic Vacations 2026

Photo by Anguilla Tourist Board

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Romantic vacation packages in Anguilla

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

Four Seasons Resort and Residences Anguilla

$2,443

per person

Oct 31 - Nov 3

found 9 hours ago

Roundtrip flight included

Providence (PVD) to The Valley (AXA)

9.6/10 Exceptional! (263 reviews)

Aurora Anguilla Resort & Golf Club

Save 100% on your flight

$2,740

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to The Valley (AXA)

9.6/10 Exceptional! (205 reviews)

Malliouhana Resort Anguilla

Save 100% on your flight

$3,385

per person

Nov 27 - Dec 1

found 12 hours ago

Roundtrip non-stop flight included

New York (JFK) to The Valley (AXA)

9.6/10 Exceptional! (107 reviews)

Cap Juluca, A Belmond Hotel, Anguilla

$5,637

per person

Nov 27 - Dec 1

found 12 hours ago

Roundtrip non-stop flight included

New York (JFK) to The Valley (AXA)

9.6/10 Exceptional! (161 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Anguilla

View all trips

5* Romantic vacations in Anguilla

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

Aurora Anguilla Resort & Golf Club

Save 100% on your flight

$2,740

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to The Valley (AXA)

9.6/10 Exceptional! (205 reviews)

Malliouhana Resort Anguilla

Save 100% on your flight

$3,385

per person

Nov 27 - Dec 1

found 12 hours ago

Roundtrip non-stop flight included

New York (JFK) to The Valley (AXA)

9.6/10 Exceptional! (107 reviews)

Cap Juluca, A Belmond Hotel, Anguilla

$5,637

per person

Nov 27 - Dec 1

found 12 hours ago

Roundtrip non-stop flight included

New York (JFK) to The Valley (AXA)

9.6/10 Exceptional! (161 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Anguilla

View all trips

3 Night Romantic vacations in Anguilla

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

Malliouhana Resort Anguilla

Save 100% on your flight

$2,549

per person

Nov 28 - Dec 1

found 13 hours ago

Roundtrip flight included

Miami (MIA) to The Valley (AXA)

9.6/10 Exceptional! (107 reviews)

Aurora Anguilla Resort & Golf Club

$2,581

per person

Nov 28 - Dec 1

found 13 hours ago

Roundtrip flight included

Miami (MIA) to The Valley (AXA)

9.6/10 Exceptional! (205 reviews)

Cap Juluca, A Belmond Hotel, Anguilla

$4,231

per person

Nov 28 - Dec 1

found 13 hours ago

Roundtrip flight included

Miami (MIA) to The Valley (AXA)

9.6/10 Exceptional! (161 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Anguilla

View all trips

4 Night Romantic vacations in Anguilla

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

Aurora Anguilla Resort & Golf Club

Save 100% on your flight

$2,740

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to The Valley (AXA)

9.6/10 Exceptional! (205 reviews)

Malliouhana Resort Anguilla

Save 100% on your flight

$3,385

per person

Nov 27 - Dec 1

found 12 hours ago

Roundtrip non-stop flight included

New York (JFK) to The Valley (AXA)

9.6/10 Exceptional! (107 reviews)

Four Seasons Resort and Residences Anguilla

$3,240

per person

Oct 31 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

New Orleans (MSY) to The Valley (AXA)

9.6/10 Exceptional! (263 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Anguilla

View all trips

How can I find the best Anguilla vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Anguilla romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Anguilla?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Anguilla?

Put a price on love with stunning deals for duos starting at just $2,443. Prices and availability are subject to change. Additional terms may apply.

Can I book Anguilla spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Anguilla?

To book a loved-up break in Anguilla, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Anguilla with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Anguilla romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

Top Romantic Anguilla Hotels

Aurora Anguilla Resort & Golf Club

Rendezvous Bay Rendezvous Bay

25 min walk from Meads Bay

$895 nightly

$999 total

Oct 28 - Oct 29

Total with taxes and fees

A spa, in-room massages, and ocean-view dining await couples looking for a romantic getaway at this upscale resort. The property also offers a garden, soaking ...

Four Seasons Resort and Residences Anguilla

Barnes Bay West End Village

5 min walk from Meads Bay

$1,023 nightly

$1,139 total

Oct 15 - Oct 16

Total with taxes and fees

Fall in love again at this upscale resort. You and your special someone are sure to love the soaking tubs, hot tub, and spa. You'll also appreciate the in-room ...

Malliouhana Resort Anguilla

Malliouhana West End Village

8 min walk from Meads Bay

$1,074 nightly

$1,199 total

Oct 21 - Oct 22

Total with taxes and fees

Fall in love again at this upscale resort. You and your special someone are sure to love the hot tub, spa, and in-room massages. You'll also appreciate the ocean-view ...

See all 341 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.