Lesser Antilles Luxury Vacations

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Flight and Luxury hotel deals in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.
Belle Mont Sanctuary Resort

Belle Mont Sanctuary Resort

CA $1,813
per person
Oct 25 - Oct 30
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Basseterre (SKB)
9.2/10 Wonderful! (135 reviews)
The location, the craftsmanship, the staff.

Reviewed on Sep 3, 2026

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

Save 100% on your flight
CA $3,202
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to The Valley (AXA)
9.6/10 Exceptional! (205 reviews)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight
CA $2,438
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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

The Cove Suites at Blue Waters Resort and Spa

The Cove Suites at Blue Waters Resort and Spa

CA $3,671
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. John's (ANU)
9/10 Wonderful! (20 reviews)
Scrub Island Resort, Spa & Marina

Scrub Island Resort, Spa & Marina

CA $3,806
per person
Nov 29 - Dec 5
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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

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5* Luxury holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight
CA $2,438
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

Save 100% on your flight
CA $3,202
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to The Valley (AXA)
9.6/10 Exceptional! (205 reviews)
The Cove Suites at Blue Waters Resort and Spa

The Cove Suites at Blue Waters Resort and Spa

CA $3,671
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. John's (ANU)
9/10 Wonderful! (20 reviews)
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3 Night Luxury holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight
CA $2,056
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

Carlisle Bay

Carlisle Bay

CA $2,488
per person
Nov 8 - Nov 11
found 20 hours ago
Roundtrip flight included
Kingston (KIN) to St. John's (ANU)
9.2/10 Wonderful! (319 reviews)
Ceblue Luxury Villas

Ceblue Luxury Villas

Save 100% on your flight
CA $3,523
per person
Nov 12 - Nov 15
just found
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
10/10 Exceptional! (11 reviews)
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4 Night Luxury holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight
CA $2,438
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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

Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

Save 100% on your flight
CA $5,793
per person
Nov 23 - Nov 27
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.8/10 Exceptional! (287 reviews)
Carlisle Bay

Carlisle Bay

Save 100% on your flight
CA $2,964
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Calgary (YYC) to St. John's (ANU)
9.2/10 Wonderful! (319 reviews)
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Plan the perfect luxury Lesser Antilles vacation with Expedia

What are some benefits when booking luxury Lesser Antilles vacations?

When you book a luxury Lesser Antilles vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Lesser Antilles?

If you're looking for something luxurious in Lesser Antilles, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,813, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 14. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Lesser Antilles. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Lesser Antilles?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Lesser Antilles.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Lesser Antilles. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Lesser Antilles?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Lesser Antilles or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Lesser Antilles. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Lesser Antilles

Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

Shoal Bay East Shoal Bay
  • 33 min drive from Oyster Bay Marina
Book a stay at this luxury resort in Shoal Bay. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
Zemi Beach House, LXR Hotels & Resorts
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

1A Rhine Rd. Lowlands
  • 13 min drive from Oyster Bay Marina
Book a stay at this luxury property in Lowlands. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
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

Sonesta Ocean Point All Inclusive, Adults Only Resort
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

Barnes Bay West End Village
  • 26 min drive from Oyster Bay Marina
Book a stay at this luxury resort in West End Village. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. ...
Four Seasons Resort and Residences Anguilla
See all 15,321 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.

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.