Title: Lesser Antilles Vacation Packages & Trips 2026 from CA $1,062 | Expedia.ca

[Lesser Antilles Travel Guide](https://expedia.ca/Lesser-Antilles.dx3000655870)[Hotels in Lesser Antilles](https://expedia.ca/Lesser-Antilles-Hotels.d3000655870.Travel-Guide-Hotels)[Vacation Rentals in Lesser Antilles](https://expedia.ca/Lesser-Antilles-Vacation-Rentals.d3000655870.Travel-Guide-VacationRentals)[Flights to Lesser Antilles](https://expedia.ca/Cheap-Flights-To-Lesser-Antilles.d3000655870.Travel-Guide-Flights)[Lesser Antilles Car Rentals](https://expedia.ca/Car-Rentals-In-Lesser-Antilles.d3000655870.Car-Rental-Guide)

![](https://images.trvl-media.com/place/3000655870/4e44b64c-f868-42db-a6b5-d230f6850ee4.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Lesser Antilles Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
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Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
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Plan, book, and manage your trip all in one place

### 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](https://www.expedia.ca/Charlotte-Amalie.d3289.Destination-Travel-Guides) at Bolongo Bay and Magens Bay Beach — two popular attractions here. Another great city to add to your itinerary is [Philipsburg](https://www.expedia.ca/Philipsburg.d3331.Destination-Travel-Guides). 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.

## Top Lesser Antilles Vacation Deals

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

![Oyster Bay Beach Resort](https://images.trvl-media.com/lodging/2000000/1100000/1095400/1095348/00eb22aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oyster Bay Beach Resort

Oyster Pond

CA $1,062

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Philipsburg (SXM)

8.6/10 Excellent! (952 reviews)

Everything to me was excellent

Reviewed on Jan 18, 2026

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,428

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

We never did the breakfast, but we did order a room service pizza couple times which was more affordable than eating at the restaurants nearby. It would be nice if there was music around the pool room service was great. Our rooms were clean zero complaints on that. The roads around the property definitely need work, but overall, we definitely enjoyed our stay.

Reviewed on Jan 19, 2026

![Princess Heights Luxury Boutique Condo Hotel](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/3eb207bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,134

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Philipsburg (SXM)

9.2/10 Wonderful! (973 reviews)

Tucked away in a very quiet a gated place this is the perfect place for folks that don't want to be around parties. Pool was nice and the staff was always helpful!

Reviewed on Jan 16, 2026

![Oceans at Divi Little Bay](https://images.trvl-media.com/lodging/75000000/74270000/74267800/74267774/fee04e6c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oceans at Divi Little Bay

CA $1,896

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Philipsburg (SXM)

8.4/10 Very Good! (266 reviews)

A lovely visit! The resort is very well kept and our room was nice and clean - no frills but beautiful view. The pools are fantastic and the beach is amazing. Staff is very nice and friendly. We absolutely loved Caron at the breakfast buffet. The hospitality overall was good.

Reviewed on Jan 18, 2026

![Divi Little Bay Beach Resort](https://images.trvl-media.com/lodging/1000000/480000/470900/470827/e8112429_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Divi Little Bay Beach Resort

CA $1,790

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Philipsburg (SXM)

8.4/10 Very Good! (1,002 reviews)

Clean and always had a beach chair.

Reviewed on Jan 18, 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](https://expedia.ca/Lesser-Antilles.dx3000655870)

![Esperanza](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/243000/243374-Vieques-Island.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Esperanza

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

[Find hotel + flight trips in Esperanza](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Esperanza&DestID=6084481&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/523000/523252-mullet-beach.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Maho

4.5/5(2 area reviews)

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

[Find hotel + flight trips in Maho](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Maho&DestID=553248635976398598&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Cinnamon Bay showing forest scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/117000/117023-St-Thomas-And-St-John.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 hotel + flight trips in Maho Bay Quarter](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Maho%20Bay%20Quarter&DestID=553248635975749486&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/540000/540317-pelican-key.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Pelican Key

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

[Find hotel + flight trips in Pelican Key](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Pelican%20Key&DestID=553248635976196664&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Contant Farms

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

[Find hotel + flight trips in Contant Farms](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Contant%20Farms&DestID=553248635976399752&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Ready to book your vacation to Lesser Antilles?

Choose your dates

## Lesser Antilles Hotel Deals

![The Morgan Resort Spa Village](https://images.trvl-media.com/lodging/18000000/17530000/17525000/17524915/bf19cc27_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay 

Fully refundableReserve now, pay when you stay

CA $534

CA $661 total

Feb 17 - Feb 18

includes taxes & fees

8.8/10 Excellent! (1,942 reviews)

Amazing views! The Morgan Resort made it a great stay for my group of 20\. Food was amazing as well.

Reviewed on Jan 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=17524915&PinnedHotelID=17524915&HadPinnedHotel=true&regionId=3000655870)

![Margaritaville Vacation Club - St. Thomas](https://images.trvl-media.com/lodging/12000000/11800000/11796200/11796106/29cf8be8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay St. Thomas 

CA $650

CA $731 total

Jan 20 - Jan 21

includes taxes & fees

7.8/10 Good! (2,342 reviews)

Nice partial view of ocean. Clean facility! Near attractions. Staff was very friendly/accommodating. No seaweed smells/issues in January.

Reviewed on Jan 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=20%2F01%2F2026&endDate=21%2F01%2F2026&selected=11796106&PinnedHotelID=11796106&HadPinnedHotel=true&regionId=3000655870)

![Sonesta Maho Beach All Inclusive Resort Casino & Spa](https://images.trvl-media.com/lodging/1000000/570000/565700/565666/45414036_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands 

CA $713

CA $862 total

Jan 20 - Jan 21

includes taxes & fees

7.8/10 Good! (2,840 reviews)

Beautifly all inclusive resort.

Reviewed on Jan 18, 2026

[](https://expedia.ca/Hotel-Search?startDate=20%2F01%2F2026&endDate=21%2F01%2F2026&selected=565666&PinnedHotelID=565666&HadPinnedHotel=true&regionId=3000655870)

[See all 14,519 properties in Lesser Antilles](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F01%2F2026&endDate=21%2F01%2F2026&regionId=3000655870)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Lesser Antilles

![Sapphire Beach which includes a sandy beach and tropical scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/117000/117319-Sapphire-Beach.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sapphire Beach

Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.

[](https://expedia.ca/Sapphire-Beach-St-Thomas.d6068151.Vacation-Attraction)

![Orient Bay Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/540000/540271-orient-bay.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Orient Bay Beach

Nothing says vacation like spending a lazy day at Orient Bay Beach, a popular beach in Orient Bay. Check out the top-notch restaurants or lively bars in this romantic area. 

[](https://expedia.ca/Orient-Bay-Beach-Orient-Bay.d6005110.Vacation-Attraction)

![Trunk Bay which includes island views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/117000/117236-Trunk-Bay.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Trunk Bay

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

[](https://expedia.ca/Trunk-Bay-St-John.d6068195.Vacation-Attraction)

## Frequently asked questions

### Can I cancel my flight booking to Lesser Antilles due to COVID-19?

### What's the best way to find cheap flights to Lesser Antilles that have flexible change policies?

### What are some of the general tips for travelers to Lesser Antilles during the COVID-19 outbreak?

> - Investigate if any travel restrictions apply to your origin and destination before booking. Also check if there are any requirements you'll need to follow on arrival, such as health testing.
> - Wear a face mask during airport screening. A TSA employee will require you to temporarily lower your mask to verify your identity.
> - Instead of handing a TSA employee your boarding pass, position it straight on the reader yourself. Then, hold it up for inspection.
> - You're allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on bag. This will need to be removed for screening.
> - Remove items from your pocket, such as your keys, phone and wallet, and place them in your carry-on instead of the bins. This will minimize handling during screening.
> - Separate any food you're carrying for X-ray screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA officer to touch and inspect your belongings.

### Which airlines fly to Lesser Antilles?

### How can I find cheap tickets to Lesser Antilles?

### How much is a flight to Lesser Antilles?

### What are the most popular airports to fly into in Lesser Antilles?

### When is the cheapest time to fly to Lesser Antilles?

### How much is a plane ticket to Lesser Antilles?

### Which airlines with flights to Lesser Antilles employ COVID-19 cleanliness policies?

> - JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
> - Cape Air - this airline is known for providing passenger masks and cleaning with disinfectant.
> - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

## Explore a world of travel with Expedia

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

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