A wooden pier extending into calm waters with sailboats anchored nearby.

Simpson Bay Vacations from $737

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Simpson Bay Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Aug 28 - Aug 30

    Simpson Bay Resort, Marina & Spa + Flight

    Pelican Key
    2 nights
    4.0 star property
    9.0/10 - Wonderful (1,896 reviews)
    "Simpson Bay Resort is truly wonderful. The staff is warm and friendly. The view is spectacular and to top it off you can walk to many casinos and eateries. Now on the down side, I DO NOT recommend you eat dinner at Ka Patrona. Their breakfast is good but dinner is a bust! The food was tasteless and unappealing. How can you mess up spaghetti with garlic and oil? Other than that, I highly recommend Simpson Bay Resort."
    Reviewed July 19, 2026
    Roundtrip Atlanta (ATL) - Saint Martin (SXM)
    ATL - SXMNonstop SXM - ATL1 stop
    $1,094
    $737
    per traveler
    found 1 day ago
    Simpson Bay Resort, Marina & Spa
  • Oct 13 - Oct 17

    The Villas at Simpson Bay Resort + Flight

    Pelican Key
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,474 reviews)
    Roundtrip Atlanta (ATL) - Saint Martin (SXM)
    ATL - SXM1 stop SXM - ATL1 stop
    $2,569
    $1,054
    per traveler
    found 1 day ago
    The Villas at Simpson Bay Resort
  • Aug 22 - Aug 27

    Divi Little Bay Beach Resort + Flight

    Philipsburg
    5 nights
    4.0 star property
    8.2/10 - Very Good (1,007 reviews)
    "The property is beautiful and convenient to Philipsburg. The amenities on the property are great, with the little Mini Mart having everything you may need at reasonable prices. Divi is in a little secluded bay, so it is peaceful and calm, as opposed to the business of Simpson Bay Area."
    Reviewed July 19, 2026
    Roundtrip Atlanta (ATL) - Saint Martin (SXM)
    ATL - SXMNonstop SXM - ATL1 stop
    Save 100% on your flight
    $2,272
    $1,478
    per traveler
    found 1 day ago
    Divi Little Bay Beach Resort
  • Aug 22 - Aug 27

    Oceans at Divi Little Bay + Flight

    Philipsburg
    5 nights
    4.0 star property
    8.4/10 - Very Good (485 reviews)
    "The room was beautiful. The stuff could be better. No room service. Anybody can charge things to your room."
    Reviewed July 19, 2026
    Roundtrip Atlanta (ATL) - Saint Martin (SXM)
    ATL - SXMNonstop SXM - ATL1 stop
    Save 100% on your flight
    $2,508
    $1,689
    per traveler
    found 1 day ago
    Oceans at Divi Little Bay
  • Oct 12 - Oct 16

    La Playa Orient Bay + Flight

    Orient Bay
    4 nights
    4.0 star property
    9.4/10 - Exceptional (761 reviews)
    "Overall it was a wonderful place, but here are few things we did not like - beach service shut down at 5pm, so even the bathroom/shower to rinse off the sands were turned off after 5pm. Only 2 bath towels for us in the room, so I didn’t have a towel for my hair. There was no hair conditioner, you need to buy one there or BYO. Very strict beach towel rules, they will charge a fee if you lose your towel. Very strict Nespresso capsule allocation - you only get 2 per day, so I had to go buy more..."
    Reviewed July 19, 2026
    Roundtrip Atlanta (ATL) - Saint Martin (SXM)
    ATL - SXMNonstop SXM - ATLNonstop
    $1,308
    $908
    per traveler
    found 1 day ago
    La Playa Orient Bay

Where to stay in Simpson Bay

Find the best Simpson Bay areas and neighborhoods for the activities you enjoy most. Learn more about Simpson Bay
Learn more about Simpson Bay

Pelican Key

If you're spending some time in Pelican Key, Flamingo Beach and Lay Bay Beach are top sights worth seeing.

Discover the most popular places to visit in Simpson Bay

What to do in Simpson Bay

Simpson Bay Hotel Deals

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.

Frequently Asked Questions

How much does a Simpson Bay vacation package cost?

You'll find cheap prices from $737 on Expedia for your Simpson Bay getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Simpson Bay costs.

What are the cheapest months to go to Simpson Bay?

September, November and December are great times to look for cheap Simpson Bay vacation packages. Choosing to travel in less busy months means you can generally find lower prices on accommodations and flights.

How many days is enough for Simpson Bay?

Allow at least 4 days for your Simpson Bay vacation to really immerse yourself in all that makes this place special. Wander around popular neighborhoods, including Cay Bay Hill and Little Bay. Then make a beeline for major sights like Lay Bay Beach and Hollywood Casino. With a good itinerary, you'll be kept busy with room for some rest time too. Want to travel outside of Simpson Bay? Consider squeezing in an excursion or two.

Is it worth booking a vacation package to Simpson Bay?

From leading attractions such as Simpson Bay Beach and Kim Sha Beach to its epic coastal beaches, a Simpson Bay vacation guarantees an unforgettable adventure. With so much to see and do, find out for yourself why Simpson Bay is such a good vacation destination.

How to find the best Simpson Bay package deals?

Start your search for a Simpson Bay package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Simpson Bay package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Simpson Bay adventure off to a flying start.

Is it cheaper to book a Simpson Bay vacation as a package?

An Expedia vacation package could score you significant savings when compared to arranging stays and flights individually. Better still, you can customize your Simpson Bay escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

When to book a vacation package to Simpson Bay?

If you're considering a spontaneous Simpson Bay trip, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking ahead.

How to plan a trip to Simpson Bay?

  1. Choose your travel dates: The things you plan to do in Simpson Bay and your preferred season can help you decide when to go.
  2. Plan your budget wisely: Besides the price of your hotel, you should consider other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Simpson Bay.
  3. Use Expedia's trip planning tool to discover Simpson Bay: Research every part of your trip to Simpson Bay with this handy planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how many days away: Start by making a list of all the activities and attractions you'd like to experience in Simpson Bay. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Simpson Bay vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Read our dedicated travel guide to find some awesome things to do in Simpson Bay. Book tickets or make reservations in advance to save time and avoid the hassle of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Simpson Bay vacation packages?

Your Simpson Bay getaway should be a relaxing escape from your busy life, not a reason for money worries. So to allow you that extra flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.