Lesser Antilles Vacations from $1,081

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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

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $2,330, price is now $1,081 per person
$1,081
per person
Jan 17 - Jan 21
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (2,129 reviews)

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,786, price is now $1,364 per person
$1,364
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,584 reviews)
Good trip

Reviewed on Nov 10, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $2,419, price is now $1,195 per person
$1,195
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
A perfect place to get away from everyone. Clean. Spacious. Loved the kitchen with utensils. AC worked great. Was a bit warm though in the bedroom. Stayed in a one bedroom oceanview facing the Marriott. Stayed on 1st floor. Elevation is like on 10th floor. Definitely will return. Balcony is not single and can walk across the rooms on Balcony. The view of St. Barths is charming.

Reviewed on Nov 10, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,905, price is now $1,160 per person
$1,160
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (2,427 reviews)

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was $2,482, price is now $1,584 per person
$1,584
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.6/10 Exceptional! (104 reviews)
Super clean, beautiful location. Friendly staff. Safe place. Will book again

Reviewed on Oct 24, 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

The pristine beaches and ample dining options are top of the list for many visitors to Esperanza. A stop by Esperanza Malecon or Black Sand Beach might round out your trip.

Find hotels in Esperanza

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

Lesser Antilles Hotel Deals

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
$223 nightly
The price is $233 total per night from Dec 11 to Dec 12
$233 total
Dec 11 - Dec 12
Total with taxes and fees
Simpson Bay Resort, Marina & Spa
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
$558 nightly
The price is $582 total per night from Nov 12 to Nov 13
$582 total
Nov 12 - Nov 13
Total with taxes and fees
The Morgan Resort Spa Village
Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
$159 nightly
The price is $179 total per night from Nov 18 to Nov 19
$179 total
Nov 18 - Nov 19
Total with taxes and fees
9/10 Wonderful! (965 reviews)
"Kitchenette, Comfortable room."

Reviewed on Nov 11, 2026

Bluebeard's Castle Resort
See all 15,324 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.

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.

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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.