Little Bay Vacations from $592

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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.
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 $990, price is now $592 per person
$592
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,116 reviews)
Restaurants are nearby. Hotel is very nice and the room was very nice and comfortable. Upon arrival and departure, the receptionists were very cordial and helpful. I will definitely stay at this place again. Thank you for your hospitality.

Reviewed on Oct 5, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,685, price is now $1,241 per person
$1,241
per person
Jan 4 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,241 reviews)
This property is excellent for the money that you spend. It’s a budget hotel with budget people. The pool bar will get crowded during happy hour and that’s ok. They Don’t over decorate the property and that’s ok. The grass and garden is gorgeous. The view of the ocean is gorgeous. Everything is walking distance. The restaurants are FANTASTIC! The red piano bar is amazing! We loved it. The staff was great! The internet was slow.

Reviewed on Oct 11, 2025

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $1,662, price is now $787 per person
$787
per person
Jan 4 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,345 reviews)
Great stay at the Simpsonbay Resort. Resort is nearby to the best entertainment spots and dinner as well.

Reviewed on Oct 13, 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 $2,492, price is now $1,328 per person
$1,328
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (964 reviews)
Keep up your awesome work Team Princess Heghts! Your friends Anvar & Svetlana

Reviewed on Sep 25, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
Price was $1,775, price is now $1,040 per person
$1,040
per person
Jan 4 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,004 reviews)
The breakfast options were amazing, dinner was amazing .. the view amazing.. definitely consider booking at this resort Check in process was easy

Reviewed on Oct 2, 2025

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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

4.5/5(88 reviews)

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

2/5(2 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.

Fort Amsterdam

What to do in Little Bay

Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

$100
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

$65
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
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
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
$229 nightly
The price is $240 total per night from Oct 15 to Oct 16
$240 total
Oct 15 - Oct 16
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"We have stayed here before. Beautiful ocean view and well cared for property. Excellent beach. Great parking available and the entire staff was friendly."

Reviewed on Sep 28, 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
$233 nightly
The price is $244 total per night from Oct 15 to Oct 16
$244 total
Oct 15 - Oct 16
Total with taxes and fees
8.2/10 Very Good! (262 reviews)
"It was nice"

Reviewed on Sep 20, 2025

Oceans at Divi Little Bay
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Little Bay, Philipsburg
$212 nightly
The price is $221 total per night from Oct 26 to Oct 27
$221 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (114 reviews)
"The Belair is a quiet hotel with great service and nice Cafe available for dinner. The mini market on site was a huge convenience. You won’t find a nicer beach on the island. Snorkeling off the beach was fun and convenient. Love the Belair Beach Hotel. Don’t change a thing ❤️"

Reviewed on Aug 10, 2025

Belair Beach Hotel
See all 3,574 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.

Little Bay Essential Information

Language
Dutch
Currency
Netherlands Antillean guilders
Local Welcome
Hallo
Local Goodbye
Dag
Closest Airport
Princess Juliana Intl. Airport (SXM)
Top Sights
Sint Maarten Park, Little Bay Beach and Guana Bay Beach

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Frequently asked questions

How much does a Little Bay vacation package cost?
You'll find cheap prices from $592 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.