Title: Little Bay Vacation Packages & Trips 2026 from CA $1,153 | Expedia.ca

[Hotels in Little Bay](https://expedia.ca/Little-Bay-Hotels.d553248635976383999.Travel-Guide-Hotels)[Vacation Rentals in Little Bay](https://expedia.ca/Little-Bay-Vacation-Rentals.d553248635976383999.Travel-Guide-VacationRentals)[Little Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Little-Bay.d553248635976383999.Car-Rental-Guide)

![](https://images.trvl-media.com/place/3331/35560c7a-b205-48a5-83f7-cf31c431e5f6.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Little Bay Vacation Packages

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#### Your Little Bay Vacation

The stress-free way to experience this exciting city is with a customized Little Bay vacation package. Stay in the neighborhood of Upper Princes Quarter, which is good for shopping, coastal beaches and nature or choose someplace else — our package deals are all about you. Make your trip to Little Bay even more exciting by including some sightseeing. [Little Bay Beach](https://www.expedia.ca/Little-Bay-Beach-Philipsburg.d553248621532873750.Vacation-Attraction), [Sint Maarten Park](https://www.expedia.ca/Sint-Maarten-Park-Philipsburg.d553248621533158276.Vacation-Attraction) and [Guana Bay Beach](https://www.expedia.ca/Guana-Bay-Beach-Philipsburg.d506436.Vacation-Attraction) are some of the major attractions you'll want to explore. Your ideal Little Bay vacation is just clicks away. Search hotels, airfares and more on Expedia for an adventure that's tailored to suit your style.

## Top Little Bay Vacation Deals

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

![Princess Heights Luxury Boutique Condo Hotel](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/2af67816_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,153

per person

Jun 4 - Jun 11

found 4 hours ago

Roundtrip non-stop flight included

Montreal Metropolitan Airport (YHU) to Philipsburg (SXM)

9.2/10 Wonderful! (1,007 reviews)

We loved this hotel for our family of 4\. Lovely staff, unbeatable views/balcony, amazing fully stocked kitchen, delicious breakfast every morning, and wonderful pool too! This place had it all. We loved the location too - ideal to get to beaches on both sides with a rental car. Thank you for a very memorable stay!

Reviewed on Mar 21, 2026

![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/00ffc84a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Villas at Simpson Bay Resort

Pelican Key

CA $1,624

per person

Jun 4 - Jun 11

found 4 hours ago

Roundtrip non-stop flight included

Montreal Metropolitan Airport (YHU) to Philipsburg (SXM)

9.2/10 Wonderful! (1,387 reviews)

Friendly staff, good amenities and relaxed atmosphere. This is the only place in the Caribbean that I have not experienced harassment and aggressive behaviours, such as tip coercion, forcing services, etc. The citizens of St. Maarten are friendly and kind. The island also feels extremely safe. The staff at Simpson Bay are nice, professional and responsive.

Reviewed on Mar 22, 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 $1,375

per person

Jun 4 - Jun 11

found 4 hours ago

Roundtrip non-stop flight included

Montreal Metropolitan Airport (YHU) to Philipsburg (SXM)

9/10 Wonderful! (1,629 reviews)

Omg! Sint Marteen was AMAZING the resort, PERFECT! Staff were so nice & friendly! They kept me laughing. The stay was so comfortable. I would stay here EVERY TIME! I absolutely loved it! 10/10 HIGHLY RECOMMEND!

Reviewed on Mar 19, 2026

![La Playa Orient Bay](https://images.trvl-media.com/lodging/1000000/910000/908100/908054/1f35d541_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Playa Orient Bay

CA $1,454

per person

Jun 4 - Jun 11

found 4 hours ago

Roundtrip non-stop flight included

Montreal Metropolitan Airport (YHU) to Philipsburg (SXM)

9.4/10 Exceptional! (668 reviews)

The hotel location is excellent to walk everywhere - beach, restaurants, shops. The staff is friendly, professional and knowledgeable, especially Elena. The room was spacious, clean and had everything you need for a relaxing beach vacation. The breakfast is improved from last year and has more options to choose from. The restaurant staff could improve in greeting clients and restaurant cleanness.

Reviewed on Mar 18, 2026

![Panorama Residences at Monte Vista](https://images.trvl-media.com/lodging/121000000/120450000/120440200/120440175/27f0cc56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Panorama Residences at Monte Vista

Point Blanche

CA $1,737

per person

Jun 4 - Jun 11

found 4 hours ago

Roundtrip non-stop flight included

Montreal Metropolitan Airport (YHU) to Philipsburg (SXM)

9.6/10 Exceptional! (29 reviews)

The hotel is just built, excellent design, fully equipped, great ocean view, shops are 12 minutes drive. Note that the hotel is located on top of the mountain and the access is very steep road about 1 mile, also the offered concierge service is not satisfactory.

Reviewed on Mar 19, 2026

## Ready to book your vacation to Little Bay?

Choose your dates

## Little Bay Hotel Deals

![Oceans at Divi Little Bay](https://images.trvl-media.com/lodging/75000000/74270000/74267800/74267774/60ff747c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Oceans at Divi Little Bay

Little Bay Road Philipsburg St. Maarten

Fully refundableReserve now, pay when you stay

CA $382

CA $488 total

Apr 18 - Apr 19

includes taxes & fees

8.2/10 Very Good! (350 reviews)

No laundry pool area nice

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=18%2F04%2F2026&endDate=19%2F04%2F2026&selected=74267774&PinnedHotelID=74267774&HadPinnedHotel=true&regionId=553248635976383999)

![Belair Beach Hotel](https://images.trvl-media.com/lodging/1000000/910000/904800/904701/161e604c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Belair Beach Hotel

Little Bay Philipsburg 

CA $282

CA $340 total

Apr 6 - Apr 7

includes taxes & fees

8.6/10 Excellent! (141 reviews)

Maid staff was excellent. they kept the room very clean .l

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=904701&PinnedHotelID=904701&HadPinnedHotel=true&regionId=553248635976383999)

![L'Esperance Hotel](https://images.trvl-media.com/lodging/4000000/3960000/3953100/3953037/521d0e54_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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L'Esperance Hotel

4 Tiger Road Philipsburg 

CA $191

CA $220 total

Mar 23 - Mar 24

includes taxes & fees

8.4/10 Very Good! (143 reviews)

nice facility and amenities, friendly staff crowded location and parking was limited

Reviewed on Mar 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=3953037&PinnedHotelID=3953037&HadPinnedHotel=true&regionId=553248635976383999)

[See all 3,532 properties in Little Bay](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&regionId=553248635976383999)

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 Little Bay

![Great Bay Beach showing general coastal views, a sandy beach and a coastal town](https://images.trvl-media.com/place/6338950/46fc7f61-e6f6-4086-89f2-a96dde0b265c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Great Bay Beach

If a restful vacation is part of your travel plans, Great Bay Beach might be the perfect place to seek out during your trip to Philipsburg. Check out the shops and top-notch restaurants in this romantic area. 

[](https://expedia.ca/Great-Bay-Beach-Philipsburg.d6338950.Vacation-Attraction)

![Fort Amsterdam which includes château or palace, a ruin and military items](https://images.trvl-media.com/place/502879/46df681c-cee4-49e7-9752-6835b75738b4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Fort Amsterdam

The remains of the first Dutch military base in the Caribbean offer stunning views across the ocean and over the town of Philipsburg behind it.

[](https://expedia.ca/Fort-Amsterdam-Philipsburg.d502879.Vacation-Attraction)

![Museum of Sint Maarten which includes art and interior views](https://images.trvl-media.com/place/502882/af4a98aa-fc42-4d6e-8fcd-2f2ca2c3ed45.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Museum of Sint Maarten

Discover where the native population originally came from and learn about major events in the island’s colonial, social and natural past.

[](https://expedia.ca/Museum-Of-Sint-Maarten-Downtown-Philipsburg.d502882.Vacation-Attraction)

### What to do in Little Bay

![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)

![Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line](https://mediaim.expedia.com/localexpert/466226/f1e62739-a072-49a6-976a-ce1a3facd837.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $218

per adult

**90%** of travellers recommend

[](https://expedia.ca/things-to-do/sky-explorer-flying-dutchman-schooner-sentry-hill-line.a466226.activity-details)

[See all activities in Little Bay](https://expedia.ca/things-to-do/search?rid=553248635976383999)

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