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, Sint Maarten Park and Guana Bay Beach 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.
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,048 reviews)
Centrally located and we 've been staying here for couple years..

Reviewed on Jul. 20, 2025

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,733 reviews)
BEAUTIFUL RESORT CLOSE TO EVERYTHING.

Reviewed on Jul. 25, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,192 reviews)
Great spot, very clean, nice restaurants on property. You don't even notice that you? I don't have all inclusive. The drink rates are not that bad. It is a century located resort and you can walk out into town. And there is casinos, restaurants, nightlife, or at your fingertips

Reviewed on Jul. 25, 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (938 reviews)
This was a great stay and the staff was very friendly. Highly recommend

Reviewed on Jul. 22, 2025

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.6/10 Excellent! (891 reviews)
Great quiet location and still close to everything else. I will be back

Reviewed on Jul. 25, 2025

Ready to book your vacation to Little Bay?

 

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Little Bay Hotel Deals

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Little Bay Road, Philipsburg
Fully refundableReserve now, pay when you stay
The price is CA $315 per night from Aug 1 to Aug 2
CA $315
CA $394 total
Aug 1 - Aug 2
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"The beach was the highlight especially with most of the other side of the island having sargassum. This side was clean and calm. The food at all of the restaurants definitely could have been better, as well as the drinks, but there was a little market that made it easy to cook and prepare some meals ..."

Reviewed on Jul. 21, 2025

Divi Little Bay Beach Resort
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Little Bay Road, Philipsburg, St. Maarten
Fully refundableReserve now, pay when you stay
The price is CA $339 per night from Aug 2 to Aug 3
CA $339
CA $423 total
Aug 2 - Aug 3
includes taxes & fees
8.2/10 Very Good! (243 reviews)
"The property was absolutely amazing!!! The staff was accommodating to your needs & it was so peaceful, calm, & relaxing. (Low season) I WILL BE BACK!"

Reviewed on Jul. 22, 2025

Oceans at Divi Little Bay
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Little Bay, Philipsburg
The price is CA $259 per night from Jul 27 to Jul 28
CA $259
CA $313 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (110 reviews)
"I had an amazing time at this hotel! I’d definitely stay again. It was super clean and quiet, and everyone was so friendly and welcoming."

Reviewed on Jul. 12, 2025

Belair Beach Hotel
See all 3,584 properties in Little Bay
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Little Bay

Great Bay Beach

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.

Great Bay Beach
Fort Amsterdam which includes château or palace, a ruin and military items

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.

Fort Amsterdam
Guana Bay Beach featuring cuddly or friendly animals, landscape views and a sandy beach

Guana Bay Beach

The picturesque shores of this tranquil bay provide a great opportunity to escape the crowds and jump in the crystal clear water for surfing or swimming.

Guana Bay Beach

What to do in Little Bay

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $102
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

CA $203
per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
At the border!

4-Hour Guided ATV/QUAD Tour of Sint Maarten/St. Martin

CA $137
per traveller
100% of travellers recommend
4-Hour Guided ATV/QUAD Tour of Sint Maarten/St. Martin
See all activities in Little Bay

Frequently asked questions

How much does a Little Bay vacation package cost?
Offering great value package deals from CA $940 on Expedia, you'll be surprised at how little a vacation to Little Bay costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Little Bay?
You can typically find lower prices and greater availability in September, October and November. Take a look at our cheap Little Bay vacation packages and you could score some great off-season deals.
How many days is enough for Little Bay?
With around 5 days, you'll have plenty of time to enjoy popular neighbourhoods such as Upper Prince's Quarter and Madame's Estate during your Little Bay vacation. Be sure to also add Sint Maarten Park and Guana Bay Beach to your must-see list. Searching for more adventures? Consider venturing outside of Little Bay on day trips and tours.
How to find the best Little Bay package deals?
Use Expedia's filters to help you find some of the best Little Bay package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Little Bay package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Little Bay vacation as a package?
You can enjoy significant savings on your next Little Bay break by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Little Bay?
If you've got your Little Bay travel dates locked in, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Little Bay?

  1. Choose your dates: What you plan to do in Little Bay and your preferred season will help you decide when to get away.
  2. Budget wisely: On top of the price of your stay, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Little Bay.
  3. Decide your trip length: Consider how long you'd like to spend discovering Little Bay. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the right Little Bay vacation package for you.

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