Lesser Antilles Vacation Packages 2026 from $995

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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.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

$995

per person

Jan 5 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,001 reviews)

The Villas at Simpson Bay Resort

Pelican Key

$1,477

per person

Jan 5 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Simpson Bay Resort, Marina & Spa

Pelican Key

$1,231

per person

Jan 11 - Jan 15

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

The energy that comes from the staff is extremely rude. You don’t feel very welcomed the parking and the buildings are very confusing. There’s no labeling. The map is really confusing to read. Also there’s no labeling for elevators so I had to carry my luggage up the stairs to the sixth floor and again there’s no one to help to guide you to the elevator either there’s no valet the guy that store is a scam artist.

Reviewed on Oct 21, 2026

The Morgan Resort Spa Village

Save 100% on your flight

$1,077

per person

Jan 5 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (2,412 reviews)

Room was very clean, staff was friendly , room was very cold , you can control to your liking .balcony ocean view was phenomenal. We celebrated our 25th wedding anniversary and staff went above and beyond with our room and a celebratory bottle of champagne with balloons and a beautiful personalized message! Thanks Morgan see you very soon

Reviewed on Oct 21, 2026

Oceans at Divi Little Bay

Save 100% on your flight

$1,394

per person

Jan 5 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Philipsburg (SXM)

8.4/10 Very Good! (586 reviews)

Went on a birthday trip in October and stayed here. The rooms were clean, staff was amazing. I was hesitant about staying because of the reviews but I’m happy I didn’t listen because we had a great time. We will definitely be back again

Reviewed on Oct 21, 2026

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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 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 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 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, Hollywood Casino and Flamingo Beach are top sights worth seeing.

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.

See properties

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.

See properties

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.

See properties

A coastal landscape with turquoise waters, a small island with buildings, and a clear sky.

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.

See properties

A beach with blue lounge chairs and a palm tree.

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.

See properties

A rusted shipwreck with graffiti on its side, partially submerged in the ocean waves.

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.

See properties

A tropical beach with clear turquoise waters, lush greenery, and distant mountains.

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.

See properties

A beach with two palm trees, a red umbrella, and two beach chairs.

Jolly Beach

9.0/10 (789 reviews)

Why not spend a carefree afternoon at Jolly Beach during your travels in Jolly Harbour? While in this relaxing area, you can savor the top-notch restaurants.

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Lesser Antilles Hotel Deals

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

Fully refundableReserve now, pay when you stay

$200 nightly

$209 total

Oct 26 - Oct 27

Total with taxes and fees

9/10 Wonderful! (2,134 reviews)

"The energy that comes from the staff is extremely rude. You don’t feel very welcomed the parking and the buildings are very confusing. There’s no labeling. The map is really confusing to read. Also there’s no labeling for elevators so I had to carry my luggage up the stairs to the sixth floor and ..."

Reviewed on Oct 21, 2026

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay

Fully refundableReserve now, pay when you stay

$503 nightly

$528 total

Nov 21 - Nov 22

Total with taxes and fees

9/10 Wonderful! (2,422 reviews)

"Room was very clean, staff was friendly , room was very cold , you can control to your liking .balcony ocean view was phenomenal. We celebrated our 25th wedding anniversary and staff went above and beyond with our room and a celebratory bottle of champagne with balloons and a beautiful personalized ..."

Reviewed on Oct 21, 2026

Bluebeard's Castle Resort

1331 Estate Taarneberg Charlotte Amalie Saint Thomas

$210 nightly

$236 total

Nov 3 - Nov 4

Total with taxes and fees

9/10 Wonderful! (912 reviews)

"Facilidades nuevas y comodas"

Reviewed on Oct 20, 2026

See all 15,373 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.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

More vacations you might like

Frequently asked questions

How do vacation package prices compare across popular destinations in the Lesser Antilles?

Simpson Bay and Christiansted offer some of the lowest typical prices for a week-long Lesser Antilles vacation package, while St. John's tends to be higher. A week-long trip typically costs around $1,400 per adult in Simpson Bay and Christiansted, around $1,650 in St. Thomas, around $1,750 in Lowlands, and around $1,900 in St. John's.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

How can I save money on a Lesser Antilles vacation package?

When you bundle, you can save up to 30%*. To save money on a Lesser Antilles package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's included in a Lesser Antilles vacation package?

A Lesser Antilles vacation package typically lets you combine flights, hotel stays, and rental cars, based in one of the region's top destinations like St. Thomas, Simpson Bay, or Lowlands.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

Which destinations in the Lesser Antilles offer the best-value vacation package deals?

Christiansted, St. Thomas, and Simpson Bay are some of the top destinations for cheap Lesser Antilles vacation package deals. For an affordable weekend getaway, Christiansted is often among the most budget-friendly options, with package prices starting around $310 per adult. For notable bundle savings, St. John's is often among the best options, with flight-and-hotel bundles saving around $305 per adult.Browse cheap vacation packages in the Lesser Antilles on Expedia to compare current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

When is the best time to visit the top destinations in the Lesser Antilles?

The best time for a Lesser Antilles vacation package depends on which destination you choose.St. Barthelemy is busiest from May through July, when highs range from around 81°F to 83°F. For fewer crowds, August and December are quieter, with highs around 80°F to 84°F.St. Thomas sees the most visitors in December, March, and July, with highs around 81°F to 84°F. For a quieter trip, January, and from September to October are less busy, with highs around 83°F to 84°F.St. John is most popular in March, July, and December, when highs are around 78°F to 80°F. For fewer crowds, January, and from September to October are quieter, with highs around 83°F to 84°F.Christiansted is busiest from February to March, and in July, with highs around 79°F to 83°F. For a more relaxed visit, from October to November are quieter, with highs around 82°F to 84°F.

What package types are available across the top destinations in the Lesser Antilles?

Lesser Antilles vacation packages across its popular destinations offer a variety of travel styles:

Budget: In Lowlands, Adonis Cupecoy provides a modern stay with free breakfast and free WiFi, often praised by travelers for its contemporary design.
Couples: Simpson Bay features options like Mary's Boon Beach Resort & Spa, which includes an outdoor pool and spa, with travelers frequently highlighting the great food and beautiful location.
Family: For family trips to St. Thomas, Limetree Beach Resort by Club Wyndham offers family rooms and a lovely pool, with travelers noting the welcoming staff.
Luxury: St. John's has luxury stays such as Hodges Bay Resort & Spa, an HQ Luxury Resort & Residences, which features a hot tub and game room, and travelers often praise its well-maintained rooms and great breakfast.
All-inclusive: In St. Thomas, Bolongo Bay Beach Resort offers an all-inclusive experience with a game room and outdoor pool, and travelers frequently mention the fantastic food and incredible staff.

Which destinations should I consider for a Lesser Antilles vacation?

For a Lesser Antilles vacation, pick your base by the kind of trip you want:

St. Thomas: A popular package base, ideal for travelers seeking extensive beach activities, scenic views, and adventure.
Simpson Bay: A great choice for those who enjoy beaches alongside city and urban attractions, offering a lively mix of outdoor and town experiences.
St. John's: Suited for visitors looking for a blend of beautiful beaches, outdoor activities, and access to city attractions and local culture.
St. Barthelemy: Offers more lodging choices and is known for its upscale beaches, scenic views, and cultural attractions, making it a strong option for a luxury or romantic getaway.

Is Lesser Antilles better suited for a beach vacation or a cultural trip?

The Lesser Antilles is primarily known for its beaches, making it an ideal choice for a beach vacation. Most constituent islands offer stunning coastlines, scenic views, and abundant outdoor activities like swimming and snorkeling.However, the region also provides cultural experiences. Destinations like St. Barthelemy feature cultural attractions around Gustavia Harbor, while St. Thomas offers historical insights at the Caribbean Genealogy Library. St. John's in Antigua is home to heritage sites such as Nelson's Dockyard, allowing travelers to combine relaxation with exploration of local history and charm.

Which airports serve the main destinations in the Lesser Antilles?

For a Lesser Antilles vacation, several key airports serve the main islands. Cyril E. King Airport (STT) is a primary gateway for St. Thomas and St. John. Princess Juliana International Airport (SXM) serves St. Maarten/St. Martin, including areas like Simpson Bay and Lowlands. V.C. Bird International Airport (ANU) is the main entry point for St. John's and the island of Antigua.

What are the top things to do across the destinations in the Lesser Antilles?

A Lesser Antilles vacation spans several distinct destinations, each offering unique attractions:Browse and book things to do in the Lesser Antilles on Expedia.

Which destinations in the Lesser Antilles have all-inclusive resorts?

You'll find all-inclusive resorts in the Lesser Antilles across several destinations, which can be part of your Lesser Antilles vacation package:Christiansted offers some of the cheaper all-inclusive resorts in the Lesser Antilles. Browse all-inclusive resorts in the Lesser Antilles on Expedia.

Are there family vacation packages in the Lesser Antilles with kid-friendly amenities?

Family vacation packages in the Lesser Antilles can feature resorts with a range of kid-friendly amenities across several islands:

The Ritz-Carlton, St. Thomas: In St. Thomas, this 5-star resort, rated 7.5 out of 10 by travelers, offers a kids club and game room, with travelers often praising the amazing staff.
Simpson Bay Resort, Marina & Spa: In Simpson Bay, this 4-star property, rated 8.1 out of 10 by travelers, includes a playground and family rooms, and guests frequently highlight the absolutely delicious breakfast.
Royal Islander Resort La Terrasse: Lowlands offers this 4-star resort with spacious family rooms and a fitness center, noted by travelers for its overall spaciousness.
Blue Waters Resort & Spa: In St. John's, this 5-star resort, rated 8.7 out of 10 by travelers, provides a game room and kids club, with guests often mentioning the beautiful ocean view rooms.

What luxury vacation packages are available in the Lesser Antilles?

Luxury Lesser Antilles vacation packages can be found across several of its stunning islands, offering high-end resort experiences:Most Lesser Antilles vacation packages pair the hotel with flights. Browse luxury vacation packages in the Lesser Antilles on Expedia to compare options.

Which destinations in the Lesser Antilles have adults-only resorts?

Several destinations in the Lesser Antilles offer adults-only resorts that can be booked as part of a Lesser Antilles vacation package:Browse adults-only resorts in the Lesser Antilles on Expedia to compare.

When should I book vacation packages for the top destinations in the Lesser Antilles?

Booking times for a Lesser Antilles vacation package vary by destination, with most travelers booking around 5 to 8 weeks before departure.Travelers tend to book Lesser Antilles trips most often from February to August. If you're planning a spontaneous getaway, Expedia also offers last-minute Lesser Antilles vacation packages.

How many days do you need for a Lesser Antilles vacation?

Most Lesser Antilles vacation packages last around 4 to 5 days, but the ideal trip length depends on where you're going and what you'd like to experience.A destination primarily known for its beaches and outdoor activities, St. Thomas is well suited to a trip of around 4 days. Week-long trips are most popular, allowing time to enjoy iconic spots like Sapphire Beach.Known for its beaches and scenic views, Simpson Bay rewards a stay of around 5 days. Week-long trips are most popular, giving travelers ample time to experience famous Maho Beach.With its beautiful beaches and scenic views, Lowlands is ideal for a trip of around 4 days. Week-long trips are most popular, providing enough time to relax on Mullet Bay Beach.

Can I change or cancel my Lesser Antilles vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Lesser Antilles vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Lesser Antilles vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Lesser Antilles vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Lesser Antilles?

To find last-minute vacation packages to Lesser Antilles, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Lesser Antilles vacation packages?

Free cancellation on a Lesser Antilles vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Lesser Antilles vacation as a package or separately?

An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Lesser Antilles getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Lesser Antilles vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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

Lesser Antilles Vacations from $995

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Lesser Antilles Vacation

The Latest Lesser Antilles vacation packages

Princess Heights Luxury Boutique Condo Hotel

The Villas at Simpson Bay Resort

Simpson Bay Resort, Marina & Spa

The Morgan Resort Spa Village

Oceans at Divi Little Bay

Where to stay in Lesser Antilles

Esperanza

Maho

Maho Bay Quarter

Contant Farms

Pelican Key

Stay near popular Lesser Antilles attractions

Sapphire Beach

Maho Beach

Virgin Islands National Park

Magens Bay Beach

Bolongo Bay

Flamenco Beach

Trunk Bay

Jolly Beach

Lesser Antilles Hotel Deals

Simpson Bay Resort, Marina & Spa

The Morgan Resort Spa Village

Bluebeard's Castle Resort

Find the Best Lesser Antilles Vacation Packages

Things to do in Lesser Antilles

Best time to go to Lesser Antilles

Tips to save on your trip to Lesser Antilles

More vacations you might like

Frequently asked questions

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