Title: Simpson Bay Vacation Packages & Trips 2026 from CA $1,381 | Expedia.ca

[Simpson Bay Travel Guide](https://expedia.ca/Simpson-Bay.dx8941)[Hotels in Simpson Bay](https://expedia.ca/Simpson-Bay-Hotels.d8941.Travel-Guide-Hotels)[Vacation Rentals in Simpson Bay](https://expedia.ca/Simpson-Bay-Vacation-Rentals.d8941.Travel-Guide-VacationRentals)[Flights to Simpson Bay](https://expedia.ca/Cheap-Flights-To-Simpson-Bay.d8941.Travel-Guide-Flights)[Things to do in Simpson Bay](https://expedia.ca/Things-To-Do-In-Simpson-Bay.d8941.Travel-Guide-Activities)[Simpson Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Simpson-Bay.d8941.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6079645/6ddfb4b7-17de-437b-b316-7183fc85675f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Simpson Bay Vacation Packages

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

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

#### Your Simpson Bay Vacation

With a vacation package to Simpson Bay, all the organizing is done beforehand. This gives you a lot more time to discover some of the features that define this beachfront city, such as its lively atmosphere, beaches and cosmopolitan vibe. If sightseeing is on the to-do list during your trip to Simpson Bay, check out leading attractions like [Maho Beach](https://www.expedia.ca/Maho-Beach-Lowlands.d6079649.Vacation-Attraction), [Marigot Market](https://www.expedia.ca/Marigot-Market-Marigot.d6073145.Vacation-Attraction) and [Fort St. Louis](https://www.expedia.ca/Fort-St-Louis-Marigot.d502880.Vacation-Attraction). Don't delay visiting this destination any longer. Your dream Simpson Bay vacation is a couple of clicks away with Expedia.

## Top Simpson Bay Vacation Deals

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

![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 $1,381

per person

Mar 18 - Mar 23

found 6 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

Shuttle should be available as long as the casino is open. Better food - Juliette's was the only good restaurant but its a limited menu. We only received housekeeping services 2 out of 6 days we were there. Spotty wi-fi Beach is small \*\*On a positive note, the shuttle and front desk are very responsive and were appreciated

Reviewed on Jan 5, 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

CA $1,921

per person

Apr 1 - Apr 6

found 4 hours ago

Roundtrip flight included

Montreal (YMQ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

Overall great experience and amenities

Reviewed on Dec 31, 2025

![Panorama Residences at Monte Vista](https://images.trvl-media.com/lodging/121000000/120450000/120440200/120440175/89140f9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Panorama Residences at Monte Vista

Point Blanche

CA $1,705

per person

Mar 20 - Mar 27

just found

Roundtrip flight included

Toronto (YTO) to Philipsburg (SXM)

10/10 Exceptional! (1 review)

This is a 4.5 star. Would have been a 5 except for a couple of mechanical issues. Suite itself was fantastic. Panoramic view of the water and island was exceptional. Very secure and quiet. We would definitely come back.

Reviewed on Jan 4, 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 $2,193

per person

Apr 1 - Apr 6

found 4 hours ago

Roundtrip flight included

Montreal (YMQ) to Philipsburg (SXM)

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

Tout était très bien!!

Reviewed on Jan 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 $2,186

per person

Apr 1 - Apr 6

found 4 hours ago

Roundtrip flight included

Montreal (YMQ) to Philipsburg (SXM)

8.4/10 Very Good! (266 reviews)

Not crowded. Amazing beach

Reviewed on Jan 1, 2026

## Simpson Bay Beach Vacation

There's nothing like a Simpson Bay vacation to put a spring in your step. The soothing sound of rolling surf and the smell of salty sea air are sure to rejuvenate your mind and body. To be close to the city centre on your trip to Simpson Bay, find a hotel around Simpson Bay Beach (just 2 kilometres away). If you're planning to stay for a while, take a peek at our Simpson Bay vacation deals. Not only will you be able to save cash, you'll also have other amazing beaches near you to explore, like Kim Sha Beach and Lay Bay Beach.

## Things You Should Know About Simpson Bay

- Why not think about [Simpson Bay beach hotels](https://www.expedia.ca/d8941-tBeachHotel.Travel-Guide-Filter-Hotels?lang=en&rfrr=ATG.LP.BodyContent) for your next vacation? See what's available — there's nothing like staying at just minutes from the water.
- If your idea of an amazing beach vacation involves staying in one of our villas, [Cocovaa](https://www.expedia.ca/Simpson-Bay-Hotels-Cocovaa.h93830243.Hotel-Information) or [The Morgan Resort & Spa](https://www.expedia.ca/Lowlands-Hotels-Alegria-An-Ascend-Hotel-Collection-Member.h66544170.Hotel-Information) will suit you perfectly.

## Ready to book your vacation to Simpson Bay?

Choose your dates

## Simpson Bay 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 

CA $448

CA $564 total

Jan 15 - Jan 16

includes taxes & fees

8.8/10 Excellent! (1,921 reviews)

Great place great staff.

Reviewed on Dec 28, 2025

[](https://expedia.ca/Hotel-Search?startDate=15%2F01%2F2026&endDate=16%2F01%2F2026&selected=17524915&PinnedHotelID=17524915&HadPinnedHotel=true&regionId=8941)

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay 

CA $306

CA $368 total

Jan 7 - Jan 8

includes taxes & fees

8.8/10 Excellent! (1,554 reviews)

Fantastic property. Absolutely not one complaint.

Reviewed on Dec 31, 2025

[](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=1256868&PinnedHotelID=1256868&HadPinnedHotel=true&regionId=8941)

![Hilton Vacation Club Flamingo Beach St. Maarten](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/67b50717_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay 

CA $460

CA $519 total

Feb 1 - Feb 2

includes taxes & fees

9/10 Wonderful! (1,391 reviews)

Staff amazing the room amazing the view amazing this was a 10/10

Reviewed on Dec 31, 2025

[](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=796441&PinnedHotelID=796441&HadPinnedHotel=true&regionId=8941)

[See all 460 properties in Simpson Bay](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&regionId=8941)

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 Simpson Bay

![Kim Sha Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/523000/523265-kim-sha-beach.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Kim Sha Beach

4/5(17 reviews)

Why not spend a carefree afternoon at Kim Sha Beach during your travels in Simpson Bay? Check out the shops and top-notch restaurants in this romantic area. 

[](https://expedia.ca/Kim-Sha-Beach-Simpson-Bay.d6079645.Vacation-Attraction)

![Hollywood Casino which includes a casino and interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/48000/48457-Hollywood-Casino.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Hollywood Casino

Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.

[](https://expedia.ca/Hollywood-Casino-Pelican-Key.d6079643.Vacation-Attraction)

### What to do in Simpson Bay

![High-Speed Ferry to St. Barths](https://mediaim.expedia.com/localexpert/176989/803f204c-e59b-47d1-9a40-1a59056c3ffb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### High-Speed Ferry to St. Barths

CA $103

per adult

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/high-speed-ferry-to-st-barths.a176989.activity-details)

![Panoramic view of vibrant St. Martin ](https://mediaim.expedia.com/localexpert/413439/1889a377-cdfa-4a6e-bdf7-cb7a36cef979.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Edge Ferry Tickets to St. Barts

CA $137

per adult

**84%** of travellers recommend

[](https://expedia.ca/things-to-do/edge-ferry-tickets-to-st-barts.a413439.activity-details)

![Sand Dollar Snorkeling Adventure](https://mediaim.expedia.com/localexpert/253868/cee07738-52cd-498c-b693-2512d348c7bb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Half Day Snorkeling Adventure 

CA $89

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/half-day-snorkeling-adventure.a253868.activity-details)

[See all activities in Simpson Bay](https://expedia.ca/things-to-do/search?rid=8941)

## Explore a world of travel with Expedia

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