Lesser Antilles Holidays from £1,241

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Your Lesser Antilles Holiday

With your travel plans organised before you leave home, our holiday packages to Lesser Antilles let you focus on more important things, like having fun! One of the best places to do that is Basseterre, which is known for its views, history and culture. Begin your trip to Lesser Antilles with a couple of nights in St. Thomas visiting popular sights like Virgin Islands National Park and Bolongo Bay. Charlotte Amalie is another top city that draws crowds from near and far. Bolongo Bay and Magens Bay Beach are two of the top places to see here. Quit dreaming and get packing, because your Lesser Antilles holiday is just clicks away with Expedia.

Top Lesser Antilles Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
Save 100% on your flight
£1,241
per person
10 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
The on-site restaurant options were great. Pelican Grill and Cocoa Beach Bar had great food and drinks. Enjoyed the family movie night at the villa pool. Enjoyed the welcome party at the marina pool. Direct access to the beach was another great perk. Don’t normally order room service, but enjoyed the great prices and prompt delivery service.

Reviewed on 5 Sept 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
£1,501
per person
21 Nov - 28 Nov
found 24 hours ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
£1,322
per person
10 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
The property was beautiful, clean and the staff was impeccable! They put a bottle of wine in my room on my birthday. The front desk was amazing and also the housekeepers.

Reviewed on 13 Aug 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

£1,887
per person
10 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9/10 Wonderful! (2,390 reviews)
Outdoor pool

Reviewed on 5 Sept 2026

Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
£1,542
per person
21 Nov - 28 Nov
found 24 hours ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The View🏖️

Reviewed on 1 Sept 2026

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
A beach with turquoise water, people swimming, and a mountain in the background.

Maho Bay Quarter

If you're spending some time in Maho Bay Quarter, Maho Beach and Cinnamon Bay Beach are top sights worth seeing.

Find hotels in Maho Bay Quarter
A beach with blue and white striped umbrellas, clear turquoise water, and a sailboat in the distance.

Maho

While visiting Maho, you might make a stop by sights like Mullet Bay Beach and Mullet Bay.

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A sunset over a calm sea with several boats, a sandy beach, and a distant mountain range.

Esperanza

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

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A beach with thatched umbrellas, a pier, and boats in the background.

Pelican Key

While visiting Pelican Key, you might make a stop by sights like Flamingo Beach and Lay Bay Beach.

Find hotels in Pelican Key
A coastal town with a marina, lush greenery, and a sunset over the ocean.

Contant Farms

If you're spending some time in Contant Farms, Great Cruz Bay and Turner Bay are top sights worth seeing.

Find hotels in Contant Farms

Things to do in Lesser Antilles

The Lesser Antilles offers a picturesque getaway with stunning beaches and scenic landscapes, perfect for outdoor adventures. Visitors can enjoy a range of activities, including island tours, boating, and cinema experiences. Exploring St Lucia is a must, while various inclusive holiday packages cater to those seeking convenience. Be sure to discover the best trips around the region for an unforgettable experience in this beautiful Caribbean paradise.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Best time to go to Lesser Antilles

The best time to visit Lesser Antilles depends on your weather preferences. The hottest average temperature around Lesser Antilles is in September, when weather is mostly sunny and rainfall is light rain. The coolest average temperature around Lesser Antilles is in February and March. March is mostly sunny.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudiness
January78.3°F (25.700000000000003°C)No RainMostly Sunny
February77.7°F (25.4°C)No RainMostly Sunny
March77.7°F (25.4°C)No RainMostly Sunny
April78.8°F (26.0°C)No RainMostly Sunny
May80.4°F (26.9°C)Light RainMostly Sunny
June81.7°F (27.6°C)Light RainMostly Sunny
July82.2°F (27.9°C)Light RainMostly Sunny
August82.8°F (28.200000000000003°C)Light RainMostly Sunny
September82.9°F (28.3°C)Light RainMostly Sunny
October82.6°F (28.1°C)Light RainMostly Sunny
November81.1°F (27.3°C)Light RainMostly Cloudy
December79.5°F (26.4°C)No RainMostly Sunny

Tips to save on your trip to Lesser Antilles

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Lesser Antilles.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Lesser Antilles

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
£141
13 Sept - 14 Sept
includes taxes & fees
9/10 Wonderful! (1,995 reviews)
"The on-site restaurant options were great. Pelican Grill and Cocoa Beach Bar had great food and drinks. Enjoyed the family movie night at the villa pool. Enjoyed the welcome party at the marina pool. Direct access to the beach was another great perk. Don’t normally order room service, but enjoyed ..."

Reviewed on 5 Sept 2026

Simpson Bay Resort, Marina & Spa
The Morgan Resort Spa Village

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
£348
4 Oct - 5 Oct
includes taxes & fees
9/10 Wonderful! (2,394 reviews)
"Outdoor pool"

Reviewed on 5 Sept 2026

The Morgan Resort Spa Village
The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

5 Estate Bakkeroe St. Thomas St. Thomas
£279
1 Oct - 2 Oct
includes taxes & fees
8.4/10 Very good! (1,457 reviews)
"Hidden fees were supper problematic!!"

Reviewed on 5 Sept 2026

The Westin St. Thomas Beach Resort & Spa
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Stay near popular Lesser Antilles attractions

A beach with clear turquoise water, a large tree, and a distant hill with buildings.

Sapphire Beach

9.0/10 (1,479 reviews)
Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.
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A beach with clear turquoise waters, a large airplane flying overhead, and a row of hotels in the background.

Maho Beach

8.8/10 (2,865 reviews)
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.
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A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Virgin Islands National Park

9.6/10 (899 reviews)
Hike on scenic trails, explore sugar plantation ruins and snorkel along an underwater trail in this pristine nature park, which covers much of St. John.
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A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Trunk Bay

9.6/10 (1,107 reviews)
Backed by palms, this stretch of sparkling white sand is regularly ranked as one of the most beautiful beaches in the world.
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A beach with white sand, turquoise water, and a green hill in the background.

Flamenco Beach

9.2/10 (225 reviews)
If a restful holiday is part of your travel plans, Flamenco Beach might be the perfect place to visit during your trip to Culebra. Stroll along the seaside or seek out the snorkelling spots.
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A sandy beach with clear turquoise water, a large tree, and a hill with greenery in the background.

Magens Bay Beach

9.4/10 (1,559 reviews)
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.
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A beach with blue lounge chairs and a palm tree.
Photo by Waterlogged Travels

Bolongo Bay

8.2/10 (352 reviews)
Commune with nature and explore the great outdoors at Bolongo Bay during your travels in St. Thomas. Wander the beautiful beaches in this relaxing area.
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A turquoise beach with clear water, two boats, and people swimming.

Mullet Bay Beach

9.2/10 (1,536 reviews)
Shady palm trees, warm and clear water, white sand and good surfing waves make this hamlet a favorite with locals, particularly on the weekends.
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Frequently asked questions

Why should I book my Lesser Antilles holiday with Expedia?
Expedia has you covered for every detail of your upcoming Lesser Antilles getaway. You'll always land the best deal possible, but when you bundle your flights, hotel and/or car hire into a holiday package, you'll score even bigger savings. Want to really make the most of your stay? Add a few fun tours and activities to your package. We offer flexible cancellation policies on almost all bookings, so you won't need to worry if you have to change your plans. Visit our Customer Service Portal link to discover more.
When is the best time of year to holiday in Lesser Antilles?
To enjoy the energy of peak season, pack your bags for February, March and May. September, October and December are typically quieter and a smart idea if you'd rather escape the crowds. Arrange your trip to Lesser Antilles based on what type of holiday you're looking for. January is the coolest month, when daytime temperatures average 25ºC. In August, the warmest period, you'll experience temperatures of around 28ºC during the day.
What are the top hotels for my holiday in Lesser Antilles?
For properties in St. Barthelemy with friendly service and comfortable beds, look up Christopher Hotel and Tropical Hotel St Barth. If you plan to visit St. Thomas as well, you'll get a great night's sleep at The Westin Beach Resort & Spa at Frenchmans Reef or Castle Villas at Bluebeards by Capital Holidays.
How do I get a cheap holiday to Lesser Antilles?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, hire cars and activities — we've got them all. Select the combination that best suits you and watch your savings grow. Of course, holidays are never a one-size-fits-all. That's why we offer more than 400 airlines and 321,000 properties throughout the world, so you can customise your Lesser Antilles holiday your way. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Lesser Antilles holiday?
Organise your holiday in Lesser Antilles around major attractions such as Dickenson Bay Beach and The Baths. Many tourists also highly recommend Maho Beach and Magens Bay Beach.
What are the best cities to stay in when on holiday in Lesser Antilles?
There are lots of fantastic places to stay in Lesser Antilles, such as Marigot. This city is home to iconic sights including Marigot Market and Fort St. Louis. Another option is to head to St. John, where you'll find Trunk Bay and Annaberg Plantation. If you have the time, explore both vibrant cities!
Do I need a visa for my Lesser Antilles holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any necessary documentation. Your nationality and the purpose of your visit, whether it be for holidays or work, will determine if you need a visa for Lesser Antilles. Also be sure that your passport is up to date and has at least six months validity remaining beyond your intended date of return. Do all your travel planning well ahead of time to avoid any last-minute surprises.
What should I wear on my Lesser Antilles holiday?
Although everyone's style varies, it can be useful to have some guidelines for what to bring during your holiday in Lesser Antilles. Consider looking up social media before leaving for inspiration on local dress codes or fashion trends. It's also a good idea to check the local weather forecast so you can pack the right clothes. August is the warmest month in Lesser Antilles, with average temperatures of 28ºC. January is when much of this destination is at its coolest, so pack to suit daytime temperatures of around 25ºC.
What does an Expedia Lesser Antilles holiday include?
Flights, hire cars and hotels — we have them covered. With Expedia, you can create your Lesser Antilles travel package the way you like it. All you have to do is determine what you need. Once you've made your booking, why not add extras like activities and experiences? The more you bundle, the bigger the savings! Expedia has a wide array of properties in Lesser Antilles, providing you with the freedom to customise your holiday. Villas and private holiday homes are two of the most sought-after stays for our guests here.
Does Expedia offer Book Now, Pay Later Lesser Antilles holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fabulous getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Check out these flexible payment options:
  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's convenient instalment plans. If paying in multiple instalments sounds right for you, choose this option at checkout.
  • No-deposit holidays: If not paying upfront for your getaway makes pressing that "book now" button more stress-free, go for a no-deposit holiday plan with Klarna so that you can Book Now, Pay Later!
Can I choose my airline with a Lesser Antilles Expedia holiday?
You can, and with over 400 airlines to pick from globally, you've got lots of choice. Have a look through the available options and see which airline best suits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.