Lesser Antilles Holidays from NZ$1,877

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The Latest Lesser Antilles Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
per person
16 Sept - 21 Sept
found 13 hours ago
Return direct flight included
Atlanta (ATL) to Philipsburg (SXM)
8.6/10 Excellent! (906 reviews)
Needs more food options, and updates to the property.

Reviewed on 3 Aug. 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
16 Sept - 21 Sept
found 13 hours ago
Return direct flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (946 reviews)
Wonderful customer service

Reviewed on 3 Aug. 2025

Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Oyster Pond
Save 100% on your flight
per person
16 Sept - 21 Sept
found 13 hours ago
Return direct flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (109 reviews)
Quiet and private - large room

Reviewed on 30 Mar. 2025

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
per person
16 Sept - 21 Sept
found 13 hours ago
Return direct flight included
Atlanta (ATL) to Philipsburg (SXM)
8.4/10 Very Good! (1,013 reviews)
We booked a BEACH FRONT room as we always do when traveling to the Caribbean, but when we got there they told us they were under renovation. They said they UPGRADED us to their Oceans, which was not an upgrade. The room may have been newer, but it was FAR away from the beach and up on the 3rd floor. Our room view was not ideal either as we looked down at the resort roofs. Very unhappy with how this was handled. They should have never allowed us to book beach front if they scheduled renovation. Or they should have notified us prior to our trip.

Reviewed on 5 Aug. 2025

Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
per person
16 Sept - 21 Sept
found 13 hours ago
Return direct flight included
Atlanta (ATL) to Philipsburg (SXM)
8.4/10 Very Good! (243 reviews)
Seabreeze restaurant is great!

Reviewed on 7 Aug. 2025

Our guide on where to stay in Lesser Antilles

Find the best Lesser Antilles areas and neighborhoods for the activities you enjoy most. Learn more about Lesser Antilles
Esperanza

Esperanza

Stroll along the coastal boulevard and visit the collection of shops and restaurants on the main strip in the charming town.

Find hotels in Esperanza

Lesser Antilles Holiday

Our pick of the best Lesser Antilles Hotel Deals

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
5 Estate Bakkeroe, Po Box 7100, St. Thomas, St. Thomas
The price is NZ$678 per night from 7 Sept to 8 Sept
NZ$678
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very Good! (1,023 reviews)
"Stunning property with excellent views of the water and St Thomas island"

Reviewed on 4 Aug. 2025

The Westin St. Thomas Beach Resort & Spa
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay, St. Thomas
The price is NZ$493 per night from 11 Aug to 12 Aug
NZ$493
11 Aug - 12 Aug
includes taxes & fees
8/10 Very Good! (2,162 reviews)
"Property was great! The beach was closed because of a Sargassum seaweed outbreak, this happened after booking and they were not cleaning up so very bad smell when outside around the lobby, main pool and restaurant. Also no tv service was working while there the entire week. Understand things happen ..."

Reviewed on 5 Aug. 2025

Margaritaville Vacation Club - St. Thomas
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road, Maho Bay, Lowlands
The price is NZ$477 per night from 2 Sept to 3 Sept
NZ$477
2 Sept - 3 Sept
includes taxes & fees
7.8/10 Good! (2,458 reviews)
"Just beautiful"

Reviewed on 3 Aug. 2025

Sonesta Maho Beach All Inclusive Resort Casino & Spa
See all 14,596 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.

Discover the most popular places to visit in Lesser Antilles

Sapphire Beach which includes a sandy beach and tropical scenes

Sapphire Beach

Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.

Sapphire Beach
Magens Bay showing a beach

Magens Bay Beach

Appreciate the excellent views of hilly forests as you meander along a scenic trail on your way to this haven of white sand and inviting water.

Magens Bay Beach
Maho Beach

Maho Beach

Why not spend a care-free afternoon at Maho Beach during your travels in Maho Reef? Visit the top-notch restaurants or lively bars in this romantic area.

Maho Beach

Frequently asked questions

How much does a Lesser Antilles holiday package cost?
Explore the best of Lesser Antilles from as low as NZ$1,877. We offer a great selection of hotels, flights and rental cars to suit every budget. Land even better deals when you add some sightseeing tours to your package.
How do I get a cheap travel package to Lesser Antilles?
Search for flights that suit your schedule, add a hotel to your booking and watch the savings stack up with a Lesser Antilles holiday package. It's as simple as that! From flights and hotels to tours and rental cars, Expedia makes travelling cheap and easy. And with more than 550 partner airlines and 1 000 000 hotel options around the globe to choose from, you won't be short of choice.
Where should I stay in Lesser Antilles?
St. Thomas is a terrific place to visit. This is where you'll find impressive sights including Magens Bay Beach and Coki Point Beach. Charlotte Amalie also draws in many travellers eager to check out some of the best attractions in Lesser Antilles. Some of the best are Blackbeards Castle and Fort Christian.
What are the top hotels in Lesser Antilles?
When it comes to hotels in St. Barthelemy, Christopher Hotel and Le Sereno are two excellent options. If you're visiting St. Thomas, Hilltop Villas At Bluebeard's Castle By Capital Holidays and Bunker Hill Hotel are waiting to welcome you.
How far in advance should I book my Lesser Antilles holiday?
Savvy travellers always book early. Airlines usually advertise flight tickets up to 12 months in advance, and this is a great opportunity to land some rock-bottom prices. Boss just told you to take your holiday time next week? No need to worry. Expedia are never short of fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Lesser Antilles travel package include?
Car rentals, flights and hotels — we connect you to the best deals. All you'll have to do is pick your ideal combination. Once you've made your booking, you can add on the exciting stuff like sightseeing activities. Our travel packages make it simple to put together an awesome Lesser Antilles holiday.
What should I know before booking a Lesser Antilles travel package?
Whether it's relaxation or adventure you're craving, a Lesser Antilles holiday package lets you plan your escape your way. Plus, you'll score great discounts just for combining your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Lesser Antilles Expedia holiday package?
Yes, you can. We have more than 550 airline partners worldwide, so pick the carrier that's a good fit for your travel preferences.
If I'm not able to travel, can I cancel my Lesser Antilles holiday package?
We understand — life doesn't always go according to plan. If you've locked in a Lesser Antilles holiday package and have to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to cancel and rebook at no cost. If it's been longer than 24 hours, your hotel, airline or car rental company may impose a fee.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.