Lesser Antilles Holidays from NZ$4,852

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The Latest Lesser Antilles Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
21 Jun - 27 Jun
found 10 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9.2/10 Wonderful! (872 reviews)
The walk to the beach, unsafe, the lpathways are to steep

Reviewed on 30 Apr. 2025

Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
per person
21 Jun - 27 Jun
found 10 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
8.4/10 Very Good! (223 reviews)
The staff, Lauren at the Pizza restaurant, Jay at the Bar near the pool

Reviewed on 14 Apr. 2025

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
per person
21 Jun - 27 Jun
found 10 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9.4/10 Exceptional! (482 reviews)
The hotel was the same as the pictures on their website. The room we had on the third floor was excellent with a nice size refrigerator and freezer which we used only to store some wine, water and I made some ice just because there was an ice tray. The hotel had a very convenient large ice machine. The staff were very friendly and helpful for the most part ,we had some miscommunication issues with the staff replenishing the coffee in the room but they made up for it by giving us some extra. It was no big deal. Only other issue was that when we went to lunch the first few days at the very convenient beach side restaurant the staff kept asking us if we had reservations even though the restaurant was never fully occupied. We then said we would like a reservation every day for lunch and the issue ended. The restaurant had many tables available every day so I’m not sure why they made such a requirement. The breakfast was a nice meal with a great view. Very relaxing way to start the day. There are many restaurants (8 or 9) for dinner a short walk from the hotel as well as a two small grocery stores which also sell wine and spirits, a good pizzeria ,ice cream shop, bakery and deli. Everything you would need plus a beautiful beach.

Reviewed on 29 Apr. 2025

Esmeralda Resort

Esmeralda Resort

4 out of 5
per person
21 Jun - 27 Jun
found 10 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
8.6/10 Excellent! (446 reviews)
Location is amazing! Staff is too! Swimming pool right outside the patio door, mini kitchen worked great. L’Astrolabe breakfast was perfect and dinners were too! Fridays and Mondays are a do not miss. A few quick minutes to the beach where your chair awaits, with staff to help you there! The beach restaurant’s food is also amazing! If you do not rent a car, it is easy to get a taxi. I used the same person the whole time. He was great. This property is lovely and I would definitely come back! There’s bird watching, the surf is perfect, food, entertainment for my style, bar, and no clocks. It is lovely.

Reviewed on 26 Apr. 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
per person
21 Jun - 27 Jun
found 10 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9/10 Wonderful! (1,002 reviews)
Beautiful and clean! Staff always about to assist in anything needed. Reuben, Kelly and Kenisha at the beach bar were so great

Reviewed on 30 Apr. 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

The beaches and abundant dining options are top of the list for many visitors to Esperanza. A stop by Esperanza Malecon or Sun Bay might round out your trip.

Find hotels in Esperanza

Lesser Antilles Holiday

Our pick of the best Lesser Antilles Hotel Deals

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$389 per night from 4 May to 5 May
NZ$389
includes taxes & fees
4 May - 5 May
7.8/10 Good! (2,176 reviews)
"The facility was nice."

Reviewed on 27 Apr. 2025

Sonesta Maho Beach All Inclusive Resort Casino & 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$971 per night from 2 May to 3 May
NZ$971
includes taxes & fees
2 May - 3 May
8.2/10 Very Good! (1,939 reviews)
"I loved everything about our stay. Our room was beautiful, quiet, private. I thought the entire staff was very friendly. Drinks were good, food was pretty good. I only wish i had stayed longer to enjoy some of the activities the resort offers."

Reviewed on 28 Apr. 2025

Margaritaville Vacation Club - St. Thomas
Simpson Bay Resort, Marina & Spa
Simpson Bay Resort, Marina & Spa
4 out of 5
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is NZ$241 per night from 17 May to 18 May
NZ$241
includes taxes & fees
17 May - 18 May
8.8/10 Excellent! (1,082 reviews)
"Property was very nice and well maintained. My room was very clean and spacious. There were many dining options nearby."

Reviewed on 30 Apr. 2025

Simpson Bay Resort, Marina & Spa
See all 14,771 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.

Frequently asked questions

How much does a Lesser Antilles holiday package cost?
Explore the best of Lesser Antilles from as low as NZ$4,852. 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.

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
Maho Beach

Maho Beach

Nothing says holiday like spending a lazy day at Maho Beach, a popular beach in Maho Reef. Visit the top-notch restaurants or lively bars in this romantic area.

Maho Beach
Trunk Bay which includes island images

Trunk Bay

Backed by palms, this stretch of sparkling white sand is regularly ranked as one of the most beautiful beaches in the world.

Trunk Bay
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.