Little Bay Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
CA $1,332
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water.
Reviewed on Sep 14, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
CA $1,796
per person
Dec 12 - Dec 19
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
The beach and the views from our room was amazing! The beach has clear calm water. It was a fantastic time!
Reviewed on Sep 23, 2026
Panorama Residences at Monte Vista
Point Blanche
CA $1,986
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Philipsburg (SXM)
9.6/10 Exceptional! (93 reviews)
I a wonderful stay! The place was clean, comfortable, and exactly as described. The location was convenient, and everything we needed was provided. The host was friendly, responsive, and made the whole experience easy and enjoyable. We really appreciated the attention to detail and would definitely stay here again. Highly recommend!
Reviewed on Sep 23, 2026
Ready to book your vacation to Little Bay?
Little Bay Hotel Deals
Divi Little Bay Beach Resort
Little Bay Road Philipsburg
Fully refundableReserve now, pay when you stay
CA $219
CA $286 total
Oct 3 - Oct 4
includes taxes & fees
8.2/10 Very good! (1,008 reviews)
"Good"
Reviewed on Sep 23, 2026
Oceans at Divi Little Bay
Little Bay Road Philipsburg St. Maarten
Fully refundableReserve now, pay when you stay
CA $273
CA $358 total
Oct 25 - Oct 26
includes taxes & fees
Belair Beach Hotel
Little Bay Philipsburg
CA $229
CA $276 total
Oct 1 - Oct 2
includes taxes & fees
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.
Stay near popular Little Bay attractions
Fort Amsterdam
8.8/10 (245 reviews)
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.
What to do in Little Bay
Half Day Snorkeling Adventure
CA $91
per adult
100% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $107
per adult
94% of travellers recommend
Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch
CA $189
per adult
86% of travellers recommend
Frequently asked questions
How much does a Little Bay vacation package cost?
Offering great value package deals from CA $1,332 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?
- Choose your dates: What you plan to do in Little Bay and your preferred season will help you decide when to get away.
- 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.
- 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.
- 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.
