Lesser Antilles Luxury Vacations
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Top Luxury vacation packages in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.
Belle Mont Sanctuary Resort
Price was $1,230, price is now $1,020 per person
$1,020
per person
May 10 - May 13
found 1 day ago
Roundtrip flight included
New York (JFK) to Basseterre (SKB)
9.2/10 Wonderful! (125 reviews)
The room/villa was beautiful + beautifully kept. The staff were warm, friendly + helpful.
Reviewed on Feb 19, 2026
Carlisle Bay
Save 100% on your flight
Price was $2,660, price is now $1,860 per person
$1,860
per person
May 10 - May 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. John's (ANU)
9.2/10 Wonderful! (300 reviews)
The staff are terrific, the rooms spacious and everything just feels very luxurious. Lots of attention to detail. Beautiful clean beach. Lots of amenities. Good restaurants and a great little shop.
Reviewed on Dec 2, 2025
Aurora Anguilla Resort & Golf Club
Save 100% on your flight
Price was $3,293, price is now $2,312 per person
$2,312
per person
May 10 - May 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to The Valley (AXA)
9.6/10 Exceptional! (193 reviews)
Every staff member was amazing and went above and beyond to ensure a wonderful stay. Everything was spotless, and the amenities were excellent.
Our only recommendation is regarding the spraying on the plants—we would prefer a more natural approach, as we noticed insects dying on the sidewalks afterward.
Overall, this is a five-star resort, and we will definitely be back.
Reviewed on Feb 8, 2026
Malliouhana Resort Anguilla
Save 100% on your flight
Price was $3,173, price is now $2,440 per person
$2,440
per person
May 10 - May 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to The Valley (AXA)
9.4/10 Exceptional! (93 reviews)
Beaches are unmatched but disappointed in the property given how expensive it is.
Reviewed on Feb 16, 2026
Christopher Hotel
Price was $3,483, price is now $2,896 per person
$2,896
per person
May 10 - May 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Gustavia (SBH)
9.6/10 Exceptional! (231 reviews)
The entire staff was absolutely wonderful along with the view from the pool and room. The overall property needs to be updated and refreshed. Pool area, restaurants or lack of and room were tired. It does not look like the photos.The rug in the bedroom was so dirty with stains, we wore our shoes in the room. Also, it’s a far drive from everything and requires cabs back and forth. We stayed at Eden Rock last trip which was sold out and advised from friends for Christopher. If you are going to spend the money going to St Barths choose another resort for the total experience.
Reviewed on Feb 26, 2026
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View all trips5* Luxury vacations in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.
Carlisle Bay
Save 100% on your flight
Price was $2,660, price is now $1,860 per person
$1,860
per person
May 10 - May 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. John's (ANU)
9.2/10 Wonderful! (300 reviews)
The staff are terrific, the rooms spacious and everything just feels very luxurious. Lots of attention to detail. Beautiful clean beach. Lots of amenities. Good restaurants and a great little shop.
Reviewed on Dec 2, 2025
Aurora Anguilla Resort & Golf Club
Save 100% on your flight
Price was $3,293, price is now $2,312 per person
$2,312
per person
May 10 - May 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to The Valley (AXA)
9.6/10 Exceptional! (193 reviews)
Every staff member was amazing and went above and beyond to ensure a wonderful stay. Everything was spotless, and the amenities were excellent.
Our only recommendation is regarding the spraying on the plants—we would prefer a more natural approach, as we noticed insects dying on the sidewalks afterward.
Overall, this is a five-star resort, and we will definitely be back.
Reviewed on Feb 8, 2026
Malliouhana Resort Anguilla
Save 100% on your flight
Price was $3,173, price is now $2,440 per person
$2,440
per person
May 10 - May 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to The Valley (AXA)
9.4/10 Exceptional! (93 reviews)
Beaches are unmatched but disappointed in the property given how expensive it is.
Reviewed on Feb 16, 2026
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See all available trips from Columbus to Lesser Antilles
View all trips3 Night Luxury vacations in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.
Belle Mont Sanctuary Resort
Price was $1,230, price is now $1,020 per person
$1,020
per person
May 10 - May 13
found 1 day ago
Roundtrip flight included
New York (JFK) to Basseterre (SKB)
9.2/10 Wonderful! (125 reviews)
The room/villa was beautiful + beautifully kept. The staff were warm, friendly + helpful.
Reviewed on Feb 19, 2026
Malliouhana Resort Anguilla
Price was $2,559, price is now $1,983 per person
$1,983
per person
May 12 - May 15
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to The Valley (AXA)
9.4/10 Exceptional! (93 reviews)
Beaches are unmatched but disappointed in the property given how expensive it is.
Reviewed on Feb 16, 2026
Aurora Anguilla Resort & Golf Club
Save 100% on your flight
Price was $2,918, price is now $2,379 per person
$2,379
per person
Apr 9 - Apr 12
found 18 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to The Valley (AXA)
9.6/10 Exceptional! (193 reviews)
Every staff member was amazing and went above and beyond to ensure a wonderful stay. Everything was spotless, and the amenities were excellent.
Our only recommendation is regarding the spraying on the plants—we would prefer a more natural approach, as we noticed insects dying on the sidewalks afterward.
Overall, this is a five-star resort, and we will definitely be back.
Reviewed on Feb 8, 2026
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See all available trips from Columbus to Lesser Antilles
View all trips4 Night Luxury vacations in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.
Tamarind Hills Resort & Villas
Price was $4,042, price is now $1,947 per person
$1,947
per person
May 11 - May 15
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to St. John's (ANU)
9.4/10 Exceptional! (201 reviews)
Service needs attention. We had multiple issues during our stay in terms of service. Hotel is understaffed. There is no urgency in addressing requests. We have stayed is 5 star hotels around the world and this hotel is severely lacking in service. The price we paid does not match the experience we had. The beach is beautiful and we loved our beach attendant Daniel who went above and beyond. Chef at wild tamarind is great and food was flavorful. They ran out of towels on the beach, no trash can placed in our room (had to ask multiple times to get a trash can), asked for a streamer and they didn’t have one, room was filled with mosquitoes, no porter available to take us up the hill at night…the list of short comings is long. Please train your staff and hire more staff so this is not the norm.
Reviewed on Feb 22, 2026
Carlisle Bay
Price was $7,080, price is now $4,147 per person
$4,147
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Detroit (DTT) to St. John's (ANU)
9.2/10 Wonderful! (300 reviews)
The staff are terrific, the rooms spacious and everything just feels very luxurious. Lots of attention to detail. Beautiful clean beach. Lots of amenities. Good restaurants and a great little shop.
Reviewed on Dec 2, 2025
Aurora Anguilla Resort & Golf Club
Save 100% on your flight
Price was $3,293, price is now $2,312 per person
$2,312
per person
May 10 - May 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to The Valley (AXA)
9.6/10 Exceptional! (193 reviews)
Every staff member was amazing and went above and beyond to ensure a wonderful stay. Everything was spotless, and the amenities were excellent.
Our only recommendation is regarding the spraying on the plants—we would prefer a more natural approach, as we noticed insects dying on the sidewalks afterward.
Overall, this is a five-star resort, and we will definitely be back.
Reviewed on Feb 8, 2026
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See all available trips from Columbus to Lesser Antilles
View all tripsAll you need to know about luxury vacations in Lesser Antilles
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 $1,020. 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
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 ...
9.6/10 Exceptional! (254 reviews)
Wonderful, friendly staff, delicious food choices, clean rooms
Reviewed on Feb 24, 2026
Sonesta Ocean Point All Inclusive, Adults Only Resort
1A Rhine Rd. Lowlands
Sonesta Ocean Point All Inclusive, Adults Only Resort is a Lowlands luxury 5-star all-inclusive property where you can pamper yourself with Champagne service, ...
8.6/10 Excellent! (1,006 reviews)
Clean room and the view looks out to the beach and the pool. staff are nice.
Reviewed on Mar 10, 2026
Four Seasons Resort and Residences Anguilla
Barnes Bay West End Village
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! (247 reviews)
Great Service!!!
Reviewed on Feb 4, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.