Little Bay Vacations from $935

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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.

The Latest Little Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Maho
Save 100% on your flight
Price was $1,548, price is now $935 per person
$935
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
7/10 Good! (670 reviews)
Pool and access to beach was great. But hotel especially rooms were very unkept, some things were rusty, none of the jacuzzis worked.

Reviewed on Aug 11, 2025

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $2,053, price is now $999 per person
$999
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,291 reviews)
It was kids friendly and very accommodating

Reviewed on Aug 28, 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $2,324, price is now $1,176 per person
$1,176
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (960 reviews)
No restaurants, nothing nearby. Don't even waste time on breakfast, just go get your own. It's quiet and quaint. Not many amenities. Coming back but won't stay there.

Reviewed on Aug 28, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $2,671, price is now $1,421 per person
$1,421
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
Family friendly and amazing staff

Reviewed on Aug 29, 2025

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Save 100% on your flight
Price was $2,278, price is now $1,215 per person
$1,215
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,084 reviews)
The property was good.

Reviewed on Aug 29, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Little Bay

Great Bay Beach showing general coastal views, a sandy beach and a coastal town

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
Philipsburg Boardwalk

Philipsburg Boardwalk

Philipsburg Boardwalk is just one of the places to see in Philipsburg, so why not enjoy the other things to explore during your travels? Stroll along the area's beaches or simply enjoy its restaurants.

Philipsburg Boardwalk
Fort Amsterdam showing building ruins, military items and a castle

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

What to do in Little Bay

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

$75
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

$149
per adult
84% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
Sightseeing Tour of the French and Dutch Sides of the Island

St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

$56
per adult
80% of travellers recommend
St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island
See all activities in Little Bay

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
$292 nightly
The price is $307 total per night from Aug 30 to Aug 31
$307 total
Aug 30 - Aug 31
Total with taxes and fees
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
$272 nightly
The price is $285 total per night from Aug 30 to Aug 31
$285 total
Aug 30 - Aug 31
Total with taxes and fees
Oceans at Divi Little Bay
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Little Bay, Philipsburg
$195 nightly
The price is $203 total per night from Sep 1 to Sep 2
$203 total
Sep 1 - Sep 2
Total with taxes and fees
Belair Beach Hotel
See all 3,589 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.

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Frequently asked questions

How much does a Little Bay vacation package cost?
You'll find cheap prices from $935 on Expedia for your Little Bay break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Little Bay costs.
What are the cheapest months to go to Little Bay?
July, October and December are the best times to look for cheap Little Bay vacation packages. Choosing to travel in less busy months means you'll typically find better prices on flights and accommodations.
How many days is enough for Little Bay?
Generally, a handful of days is enough to check out the major sights during your Little Bay vacation. However, if you prefer to have more time to unwind or go on day trips, think about extending your itinerary.
How to find the best Little Bay package deals?
Landing a cheap Little Bay package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Little Bay package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Little Bay vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still have the flexibility to create a customized Little Bay vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Little Bay?
If you're planning a spur-of-the-moment Little Bay adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Little Bay?

  1. Choose when to go: Check your diary and pack your bags. Your preferred season and the available activities will also help you decide when to escape to Little Bay.
  2. Set your budget: Factor in costs like flights, food and transportation when calculating how much to save for your trip to Little Bay. Then, choose a hotel that matches your budget, whether that's a wallet-friendly option or a more upscale retreat.
  3. Organize your Little Bay getaway with our trip planning tool: Look for and book accommodations and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Little Bay together.
  4. Decide how long to go away for: Now that you're up to speed on Little Bay, you can figure out the perfect length of your break. Create a rough itinerary and give yourself enough time to cover everything you want to do.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Little Bay vacation package.
  6. Book any activities or excursions: Now to the fun part — organizing everything you want to see and do. Browse some of the incredible things to do in Little Bay and book your tickets early to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Little Bay vacation packages?
Secure your dream getaway to Little Bay with our Book Now, Pay Later vacations. No need to save up or wait until your next paycheck — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.