Lesser Antilles Vacation Packages 2026 from $691

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Your Lesser Antilles Vacation

See and do more with a vacation package to Lesser Antilles. Whether you're going for the views, history, culture, or something else, our package deals make travel planning easy. With so many things to explore on a trip to Lesser Antilles, it can be difficult to know where to start. Kick off your journey in Charlotte Amalie at Bolongo Bay and Magens Bay Beach — two popular attractions here. Another great city to add to your itinerary is Philipsburg. Be sure not to miss Maho Beach and Great Bay Beach. Start packing your suitcase, because your Lesser Antilles vacation is just a few clicks away with Expedia.

The Latest Lesser Antilles vacation packages

Price found within the past 48 hours. Click for updated prices.

Simpson Bay Resort, Marina & Spa

Pelican Key

$691

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9/10 Wonderful! (1,922 reviews)

The staff were amazing, food was great, beach was clean and very easy to access. Our only small issues were that it was not really handicapped friendly, and parking was tight. We had a big van that we rented to hold my dad motorized wheel chair and we had to take up 2 spots each time we parked or we wouldn’t be able to get in the car if someone parked next to us. The curbs did not have handicapped access to get on and off with the motorized wheelchair. It was amazing other wise and we would return in the future.

Reviewed on Aug 16, 2026

The Villas at Simpson Bay Resort

Pelican Key

$775

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,484 reviews)

We loved the Beach Bar put back. Super friendly. Great food and drinks! The location of the hotel is in a great place. It's close enough to walk to several restaurants and also the supermarket.

Reviewed on Aug 16, 2026

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

$762

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,003 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 Aug 13, 2026

La Playa Orient Bay

$801

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.4/10 Exceptional! (773 reviews)

Close to the beach, friendly staff , good restaurants.

Reviewed on Aug 15, 2026

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight

$1,743

per person

Sep 23 - Sep 28

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

8.8/10 Excellent! (1,003 reviews)

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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.

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.

A beach with blue and white striped umbrellas, clear turquoise water, and a sailboat in the distance.

Maho

Along with restaurants, resorts and shops just steps from soft, white sand, this beachfront neighborhood offers the thrilling experience of plane spotting.

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.

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

Pelican Key

If you're spending some time in Pelican Key, Flamingo Beach and Lay Bay Beach are top sights worth seeing.

Stay near popular Lesser Antilles attractions

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 vacation like spending a lazy day at Maho Beach, a popular beach in Maho Reef. Check out the top-notch restaurants or lively bars in this romantic area.

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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 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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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 vacation is part of your travel plans, Flamenco Beach might be the perfect place to seek out during your trip to Culebra. Stroll along the seaside or seek out the snorkeling spots.

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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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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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Lesser Antilles Hotel Deals

The Westin St. Thomas Beach Resort & Spa

5 Estate Bakkeroe St. Thomas St. Thomas

$335 nightly

$377 total

Sep 7 - Sep 8

Total with taxes and fees

8.4/10 Very Good! (1,395 reviews)

"Great resort to stay at!!"

Reviewed on Aug 17, 2026

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay

Fully refundableReserve now, pay when you stay

$503 nightly

$526 total

Sep 15 - Sep 16

Total with taxes and fees

9/10 Wonderful! (2,352 reviews)

"The views are amazing the front desk is so helpful with accommodations. The property is super clean ! i would definitely stay here over and over again !"

Reviewed on Aug 16, 2026

Bluebeard's Castle Resort

1331 Estate Taarneberg Charlotte Amalie Saint Thomas

$220 nightly

$249 total

Sep 15 - Sep 16

Total with taxes and fees

See all 15,161 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.

Find the Best Lesser Antilles Vacation Packages

Things to do in Lesser Antilles

The Lesser Antilles offers a perfect blend of beach vacations, scenic views, and outdoor activities. Enjoy thrilling experiences like birdwatching holidays, island tours, and exciting package tours. Whether you're exploring the vibrant local culture through cinema or sailing the turquoise waters, there's something for every traveler. Don't miss the chance to discover the unique charm of these beautiful islands on your next vacation.

*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.

Calendar Month	Temperature	Precipitation	Cloudiness
January	78.3°F (25.700000000000003°C)	No Rain	Mostly Sunny
February	77.7°F (25.4°C)	No Rain	Mostly Sunny
March	77.7°F (25.4°C)	No Rain	Mostly Sunny
April	78.8°F (26.0°C)	No Rain	Mostly Sunny
May	80.4°F (26.9°C)	Light Rain	Mostly Sunny
June	81.7°F (27.6°C)	Light Rain	Mostly Sunny
July	82.2°F (27.9°C)	Light Rain	Mostly Sunny
August	82.8°F (28.200000000000003°C)	Light Rain	Mostly Sunny
September	82.9°F (28.3°C)	Light Rain	Mostly Sunny
October	82.6°F (28.1°C)	Light Rain	Mostly Sunny
November	81.1°F (27.3°C)	Light Rain	Mostly Cloudy
December	79.5°F (26.4°C)	No Rain	Mostly 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.
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