Title: Lesser Antilles Vacation Packages & Trips 2026 from CA $1,261 | 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  
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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 $1,261

per person

Apr 17 - Apr 23

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

8.6/10 Excellent! (952 reviews)

Great stay. Good property and good restaurants choices.

Reviewed on Feb 5, 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 $1,400

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

Room was spacious and spotless. Staff was friendly and helpful. The pools were perfect!

Reviewed on Feb 6, 2026

![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Villas at Simpson Bay Resort

Pelican Key

CA $2,252

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

It was our 2nd time there. It was great. We love being able to walk to restaurants and live music. Staff is always friendly and funny!

Reviewed on Feb 6, 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 $1,372

per person

Apr 17 - Apr 23

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

9.2/10 Wonderful! (973 reviews)

Room was very clean and staff was friendly. The room was spacious and elegant and had a great view.

Reviewed on Feb 5, 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 $2,041

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

8.4/10 Very Good! (266 reviews)

Location was great, room spacious and comfortable. Majority of staff were very pleasant but a few were less than enthusiastic about service. Food was very average and there were no fine dining experiences. Great if you want Burgers, pizza and mediocre entrees. All inclusive drink options were limited and it was tiresome having to sign for everything despite having the all inclusive bracelet. Entertainment was fairly minimal unless you wanted to play bingo.

Reviewed on Feb 6, 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)

![Mullet Bay Beach which includes a beach, tropical scenes and general coastal views](https://images.trvl-media.com/place/506439/f4f081a5-a810-40ee-9ada-b4aa3354d106.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=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=Maho&DestID=553248635976398598&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Esperanza](https://images.trvl-media.com/place/6084481/e696555f-59a8-4507-8d40-e227be7ae6c0.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=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=Esperanza&DestID=6084481&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Cinnamon Bay featuring tropical scenes and a sandy beach](https://images.trvl-media.com/place/6068171/2dcfaa55-6fa6-46f5-a195-440beabd041d.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=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=Maho%20Bay%20Quarter&DestID=553248635975749486&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Pelican Key showing a sandy beach, general coastal views and a coastal town](https://images.trvl-media.com/place/553248635976196664/3a98ed37-7f56-481f-968d-fd4224533886.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=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=Pelican%20Key&DestID=553248635976196664&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Cruz Bay, St John, United States Virgin Islands](https://images.trvl-media.com/place/553248635976399752/d5f46338-b1f8-4162-8c73-a41a854fb932.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=Des%20Moines,%20Iowa,%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

![Bluebeard's Castle Resort](https://images.trvl-media.com/lodging/123000000/122150000/122147400/122147352/w1173h784x0y1-4df40712_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Bluebeard's Castle Resort

1331 Estate Taarneberg Charlotte Amalie Saint Thomas

CA $286

CA $385 total

Feb 10 - Feb 11

includes taxes & fees

8.6/10 Excellent! (62 reviews)

Room was clean but had strong scent of cleaning chemicals. Location is best with a car. We did not have a car and could walk to town and cruise ship area, but coming back at night it’s best to use a taxi as the immediate area at the bottom of the hill is not well lit. Nice pool and bar area overlooking ...

Reviewed on Feb 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=122147352&PinnedHotelID=122147352&HadPinnedHotel=true&regionId=3000655870)

![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 $557

CA $685 total

Feb 15 - Feb 16

includes taxes & fees

8.8/10 Excellent! (1,991 reviews)

I love the view from the room, although it could have been cleaner in the bathroom. The staff was friendly. Much smaller resort than what I'm used to staying at but it is nice. THERE IS NO DIRECT BEACH ACCESS. For the price I did not expect that. You must walk around to Maho beach to touch sand. ...

Reviewed on Feb 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%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 $688

CA $774 total

Feb 9 - Feb 10

includes taxes & fees

7.8/10 Good! (2,357 reviews)

Rooms were nice & spacious. Helpful staff

Reviewed on Feb 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=11796106&PinnedHotelID=11796106&HadPinnedHotel=true&regionId=3000655870)

[See all 14,577 properties in Lesser Antilles](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%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://images.trvl-media.com/place/6068151/b8253a08-7234-4ab9-8c70-7ffa4ae3b3f6.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 featuring a sandy beach, tropical scenes and general coastal views](https://images.trvl-media.com/place/6005110/6e8f0de8-ac78-4dad-9594-26fe7dd05386.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)

![Maho beach](https://images.trvl-media.com/place/8941/b6338664-4cf8-4430-88c6-3eddef02d441.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Maho Beach

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. 

[](https://expedia.ca/Maho-Beach-Lowlands.d6079649.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.

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