Lesser Antilles Luxury Vacations 2026

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Top Luxury vacation packages in Lesser Antilles

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

Aurora Anguilla Resort & Golf Club

$1,689

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to The Valley (AXA)

9.6/10 Exceptional! (205 reviews)

Scrub Island Resort, Spa & Marina

Save 100% on your flight

$2,162

per person

Nov 20 - Nov 27

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Tortola (EIS)

9/10 Wonderful! (200 reviews)

First impression is everything to me and when you look at this resort online that is

Reviewed on Aug 25, 2026

Carlisle Bay

$2,147

per person

Nov 20 - Nov 22

found 9 hours ago

Roundtrip flight included

New York (JFK) to St. John's (ANU)

9.2/10 Wonderful! (319 reviews)

Hermitage Bay – Antigua and Barbuda

Save 100% on your flight

$6,498

per person

Oct 20 - Oct 23

found 15 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to St. John's (ANU)

10/10 Exceptional! (34 reviews)

Ceblue Luxury Villas

$2,686

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip 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 Lesser Antilles

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5* Luxury vacations in Lesser Antilles

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

Aurora Anguilla Resort & Golf Club

$1,689

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to The Valley (AXA)

9.6/10 Exceptional! (205 reviews)

Scrub Island Resort, Spa & Marina

Save 100% on your flight

$2,162

per person

Nov 20 - Nov 27

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Tortola (EIS)

9/10 Wonderful! (200 reviews)

First impression is everything to me and when you look at this resort online that is

Reviewed on Aug 25, 2026

Carlisle Bay

$2,147

per person

Nov 20 - Nov 22

found 9 hours ago

Roundtrip flight included

New York (JFK) to St. John's (ANU)

9.2/10 Wonderful! (319 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Lesser Antilles

View all trips

3 Night Luxury vacations in Lesser Antilles

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

Scrub Island Resort, Spa & Marina

$1,410

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Tortola (EIS)

9/10 Wonderful! (200 reviews)

First impression is everything to me and when you look at this resort online that is

Reviewed on Aug 25, 2026

Carlisle Bay

$2,161

per person

Nov 21 - Nov 24

found 8 hours ago

Roundtrip flight included

Atlanta (ATL) to St. John's (ANU)

9.2/10 Wonderful! (319 reviews)

Sonesta Ocean Point All Inclusive, Adults Only Resort

$2,088

per person

Nov 20 - Nov 23

found 3 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Philipsburg (SXM)

8.8/10 Excellent! (1,005 reviews)

Despite other reviews I have seen, I was very impressed with the service we received. All the staff were great and personable. The rooms were cleaned daily and the view from the room was amazing. The food was delicious. Azul was our favorite. The sunset was spectacular. I definitely recommend the Ocean Point.

Reviewed on Sep 19, 2026

Don't see what you're looking for?

See all available trips from Columbus to Lesser Antilles

View all trips

4 Night Luxury vacations in Lesser Antilles

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

Aurora Anguilla Resort & Golf Club

$1,689

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to The Valley (AXA)

9.6/10 Exceptional! (205 reviews)

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight

$2,173

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

8.8/10 Excellent! (1,005 reviews)

Reviewed on Sep 19, 2026

Carlisle Bay

Save 100% on your flight

$2,559

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to St. John's (ANU)

9.2/10 Wonderful! (319 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Lesser Antilles

View all trips

What can I expect from a luxury Lesser Antilles vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Lesser Antilles 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 Lesser Antilles?

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 Lesser Antilles 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 $1,410. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Lesser Antilles?

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 Lesser Antilles 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 Lesser Antilles?

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 Lesser Antilles 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 Lesser Antilles 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 Lesser Antilles Hotels

Zemi Beach House, LXR Hotels & Resorts

Shoal Bay East Shoal Bay

33 min drive from Oyster Bay Marina

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 ...

Sonesta Ocean Point All Inclusive, Adults Only Resort

1A Rhine Rd. Lowlands

13 min drive from Oyster Bay Marina

Sonesta Ocean Point All Inclusive, Adults Only Resort is a Lowlands luxury 5-star beach property where you can pamper yourself with Champagne service, massage ...

8.8/10 Excellent! (1,005 reviews)

"Despite other reviews I have seen, I was very impressed with the service we received. All the staff were great and personable. The rooms were cleaned daily and the view from the room was amazing. The food was delicious. Azul was our favorite. The sunset was spectacular. I definitely recommend the ..."

Reviewed on Sep 19, 2026

Four Seasons Resort and Residences Anguilla

Barnes Bay West End Village

26 min drive from Oyster Bay Marina

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 ...

See all 15,310 properties in Lesser Antilles

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.