Oyster Pond Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Ardilla Mexicano

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

Top Holiday Package Deals in Oyster Pond

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $1,709, price is now CA $1,056 per person
CA $1,056
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.6/10 Excellent! (1,006 reviews)
Staff was some of the most friendly people on the island. Biggest downfall was the insane amount of seaweed, cannot swim in beach and seaweed left a horrible smell even in our room we could smell it. They try to bulldoze it away so it’s not their fault it’s just the unfortunate beach condition.

Reviewed on Apr 18, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $3,544, price is now CA $1,378 per person
CA $1,378
per person
Jun 19 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,382 reviews)
The staff was great and very accommodating

Reviewed on Apr 18, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,979, price is now CA $1,608 per person
CA $1,608
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.8/10 Excellent! (1,635 reviews)
I think this resort is in a great location. Love the beach, seating, drinks and the daily 2 for 1 specials. On arrival though, we got little to no direction on where our room was, or even a general overview - that would have been helpful.

Reviewed on Apr 17, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,200, price is now CA $1,196 per person
CA $1,196
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,002 reviews)
Staff were really great and helpful!

Reviewed on Apr 16, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $3,111, price is now CA $1,924 per person
CA $1,924
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9/10 Wonderful! (2,052 reviews)
Great view to the beach

Reviewed on Apr 18, 2026

Oyster Pond Hotel Deals

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
10 Emerald Merit Rd Oyster Pond
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Apr 27 to Apr 28
CA $225
CA $270 total
Apr 27 - Apr 28
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Staff was some of the most friendly people on the island. Biggest downfall was the insane amount of seaweed, cannot swim in beach and seaweed left a horrible smell even in our room we could smell it. They try to bulldoze it away so it’s not their fault it’s just the unfortunate beach condition.

Reviewed on Apr 18, 2026

Oyster Bay Beach Resort
JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa

5 out of 5
144 Oyster Pond Resort Oyster Pond Sint Maarten
The price is CA $683 per night from May 3 to May 4
CA $683
CA $854 total
May 3 - May 4
includes taxes & fees
8.8/10 Excellent! (286 reviews)
Beyond amazing stay at the Marriott in St. Maarten — truly the best customer service I’ve experienced at any hotel. From the moment we arrived, everything exceeded expectations. The rooms are gorgeous, modern, spacious, and impeccably clean, with stunning ocean views and great amenities. The gym ...

Reviewed on Apr 11, 2026

JW Marriott St. Maarten Beach Resort & Spa
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond Road No 156 Oyster Pond
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from May 1 to May 2
CA $246
CA $295 total
May 1 - May 2
includes taxes & fees
Princess Heights Luxury Boutique Condo Hotel
See all 7,773 properties in Oyster Pond
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Oyster Pond vacation package cost?
Starting from as low as CA $1,056, you can tailor make your Oyster Pond package the way you want. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Oyster Pond?
Bundle your hotels and flights with Expedia to save big on your next big adventure. With more than 550 air carriers and 1,000,000 properties across the globe, your Oyster Pond vacation package can be tailored exactly to suit your budget. With all those extra dollars, why not include a few interesting activities and tours? It's an easy way to unlock even more bargains. Your dream getaway to Oyster Pond is closer than you thought!
Where should I stay in Oyster Pond?
With so much to explore in Oyster Pond, it makes sense to lock in a hotel near its attractions. Dawn Beach, Oyster Bay Marina and Coralita Beach are some fascinating ones to put on your to-do list.
What are the top hotels in Oyster Pond?
Get your escape off to a great start by booking a stay at Literally Oceanfront Villa Alabaster. It's one of most popular properties in Oyster Pond. Another comfortable option is Les Balcons d'Oyster Pond.
How far in advance should I book my Oyster Pond vacation?
While not all air carriers advertise ticket prices early, you can usually look up international flights on Expedia up to a year in advance. This is the time you can nab some fantastic deals. If you're booking late, there's a chance you could get lucky. Low prices occasionally become available only weeks before departure.
What does an Expedia Oyster Pond travel package include?
It comes down to what sort of trip you're planning. Oyster Pond vacation deals can include car rentals, flights and hotels. You can mix and match to create the travel package that suits you. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking an Oyster Pond travel package?
A travel package can be easier on the hip pocket than individually booking all you need for your escape. For example, combine your flights, hotels and rental cars and save a packet. No matter your vacation goals, there's bound to be a package that best suits your budget.
Can I choose my airline with an Oyster Pond Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you're looking to fly to Oyster Pond in economy or business class, simply choose from the available airline options. Expedia has access to more than 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Oyster Pond vacation package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Oyster Pond vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.

Things to do

Underwater Sculpture Park Snorkel Adventure

Underwater Sculpture Park Snorkel Adventure

CA $62
per adult
Underwater Sculpture Park Snorkel Adventure
The Original Eco Tour Full-Day Around the Island of Sint Maarten

The Original Eco Tour Full-Day Around the Island of Sint Maarten

CA $205
per adult
100% of travellers recommend
The Original Eco Tour Full-Day Around the Island of Sint Maarten
St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

Sightseeing Tour of the French and Dutch Sides of Island

CA $77
per adult
90% of travellers recommend
Sightseeing Tour of the French and Dutch Sides of Island
See all activities in Oyster Pond
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.