A coastal town with a beach, a mountain, and a clear blue sky.

Little Bay Vacations from $770

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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

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    Discover the most popular places to visit in Little Bay

    Fort Amsterdam

    Rating: 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.

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    What to do in Little Bay

    Sand Dollar Snorkeling Adventure

    Half Day Snorkeling Adventure

    $65

    per adult

    100% of travelers recommend

    Tango Sunset Dinner Cruise

    Tango Sunset Cruise with Caribbean Dinner & Open Bar

    $77

    per adult

    94% of travelers recommend

    Guided UTV/ Side by Side Tour of Sint Maarten/ St. Martin

    ATV/UTV Guided Tour to Maho Beach – Cruise Passengers

    $800

    per traveler

    0% of travelers recommend

    See all activities in Little Bay

    Little Bay Hotel Deals

    Oceans at Divi Little Bay

    A pool area with lounge chairs, palm trees, and a view of the ocean.
    • Address: Little Bay Road, Philipsburg, St. Maarten, 961, SX
    • Location: 0.5 mi from Little Bay
    • Star rating: 4/5
    • Guest rating: 8.4/10 (Very good, 616 reviews)
    • Price: $328 nightly, $344 total, Dec 3 - Dec 4, Total with taxes and fees

    Belair Beach Hotel

    An aerial view of a beach resort with rows of sun loungers and umbrellas, a pool, and a building with a blue facade.
    • Address: Little Bay, Philipsburg, SX
    • Location: Belair, 0.5 mi from Little Bay
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 226 reviews)
    • Price: $190 nightly, $198 total, Nov 30 - Dec 1, Total with taxes and fees
    • Review: Best thing about this vacation was Ms Brenda, the lady in the restaurant!! She was very catering and was extremely helpful with sending us to other staff workers to help us get around the island!! We used all the benefits of Bel-Air Beach Resort 🫶🏻 I’d go back over and over again!! Thanks Ms Brenda

    L'Esperance Hotel

    A covered outdoor seating area with wicker furniture and potted plants.
    • Address: 4 Tiger Road, Philipsburg, SX
    • Location: 0.3 mi from Little Bay
    • Star rating: 2.5/5
    • Guest rating: 8.4/10 (Very good, 154 reviews)
    • Price: $149 nightly, $155 total, Nov 15 - Nov 16, Total with taxes and fees

    Divi Little Bay Beach Resort

    A resort pool with lounge chairs, palm trees, and a view of the ocean.
    • Address: Little Bay Road, Philipsburg, SX
    • Location: 0.7 mi from Little Bay
    • Star rating: 4/5
    • Guest rating: 8.2/10 (Very good, 1002 reviews)
    • Price: $296 nightly, $311 total, Nov 23 - Nov 24, Total with taxes and fees
    • Review: "The beach is stunning! The beds suck, you feel every coil in the king beds. We had multiple rooms booked in our party and everyone had the same complaints. Bar staff was not friendly upon learning we had the all inclusive option with staff often telling us they were going on break or serving us last. Food was fresh and delicious but the buffet for dinner never opened and was Italian every single night despite the sign representing every night was a different theme. Plenty of beach and pool...

    The Paradise Inn

    A swimming pool with clear blue water, steps leading into the pool, and a few lounge chairs by the poolside.
    • Address: Senna road # 7, Philipsburg, SX
    • Location: 0.6 mi from Little Bay
    • Star rating: 3/5
    • Guest rating: 8/10 (Very good, 518 reviews)
    • Price: $101 nightly, $106 total, Nov 15 - Nov 16, Total with taxes and fees
    • Review: The bed was extremely uncomfortable. My back hurts. Staff was polite and helpful except for this one front desk agent who gave attitude when I asked a question. They charge $100 as a deposit in case of damages and gave it back at the end of my stay. The room is not the best but the location is very convenient and it’s gated with security at night.

    condostmaarten by the sea -Adults Only-

    A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.
    • Address: 38 Marina Terrace, Cole Bay, SX
    • Location: Indigo Bay, 0.7 mi from Little Bay
    • Star rating: 4/5
    • Guest rating: 9.2/10 (Wonderful, 44 reviews)
    • Price: $527 nightly, $550 total, Nov 15 - Nov 16, Total with taxes and fees
    • Review: Every thing was perfect, clean , quiet,beautiful views, definitely on my list to revisit.The host was very informative about the whole process he was very polite guy

    MIDTOWN MOTEL SXM

    A view from inside a building looking out to a beach with clear turquoise water and a distant ship.
    • Address: Kruythoffsteeg#10, Philipsburg, SX
    • Location: Downtown Philipsburg, 0.8 mi from Little Bay
    • Star rating: 2.5/5
    • Guest rating: 7.6/10 (Good, 76 reviews)
    • Price: $74 nightly, $78 total, Nov 25 - Nov 26, Total with taxes and fees
    • Review: The place was amazing

    The Villas at Simpson Bay Resort

    A resort with multiple hotel buildings, a marina, and a clear blue ocean.
    • Address: Billy Folly Road No. 37A, Simpson Bay, SX
    • Location: 1.9 mi from Little Bay
    • Star rating: 4/5
    • Guest rating: 9.2/10 (Wonderful, 1615 reviews)
    • Price: $285 nightly, $297 total, Dec 11 - Dec 12, Total with taxes and fees
    • Review: Everything good except the check in. We booked and paid 11 months in advance but when we got to check in they didn’t have a room for us. It took them 90 mins to find a room and then made us change rooms half way through our stay. We had to re-pack and wait 2 hours for the next room to be ready.

    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 $770 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.