Oyster Pond Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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.
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 CA $3,867, price is now CA $2,070 per person
CA $2,070
per person
Dec 11 - Dec 18
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
My cousin and I had a great overnight stay @ your hotel. The staff was very helpful. Paul was great !!!

Reviewed on Oct 24, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $6,687, price is now CA $3,069 per person
CA $3,069
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,584 reviews)

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $4,476, price is now CA $2,251 per person
CA $2,251
per person
Jan 14 - Jan 20
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (2,129 reviews)
Great location, close to the strip and the beach

Reviewed on Oct 26, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Save 100% on your flight
Price was CA $4,293, price is now CA $2,565 per person
CA $2,565
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.6/10 Exceptional! (104 reviews)
Super clean, beautiful location. Friendly staff. Safe place. Will book again

Reviewed on Oct 24, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was CA $3,701, price is now CA $2,240 per person
CA $2,240
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,427 reviews)
The staff was very accommodating , resort was clean, Salt restaurant was better than I expected. I would definitely stay here again.

Reviewed on Oct 26, 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 $203 per night from Nov 7 to Nov 8
CA $203
CA $249 total
Nov 7 - Nov 8
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"This Hotel was extremely amazing. Excellent staff. very friendly. They also have all amenities that you can think about and activities. We had an excellent Taxi driver named Alex who was very friendly and informative. I will always stay at this resort . You will not be disappointed."

Reviewed on Oct 27, 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 $404 per night from Oct 29 to Oct 30
CA $404
CA $534 total
Oct 29 - Oct 30
includes taxes & fees
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 $129 per night from Oct 30 to Oct 31
CA $129
CA $154 total
Oct 30 - Oct 31
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"My cousin and I had a great overnight stay @ your hotel. The staff was very helpful. Paul was great !!!"

Reviewed on Oct 24, 2026

Princess Heights Luxury Boutique Condo Hotel
See all 7,791 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
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Frequently asked questions

How much does an Oyster Pond vacation package cost?
Starting from as low as CA $2,070, 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.

Stay near popular Oyster Pond attractions

A coastal landscape with clear turquoise waters, a sandy beach, and a cluster of houses on a hillside.

Dawn Beach

8.4/10 (222 reviews)
Why not spend a carefree afternoon at Dawn Beach during your travels in Oyster Pond? Stroll along the seaside in this relaxing area, or check out its top-notch restaurants.
See properties

Things to do

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $115
per adult
78% of travellers recommend
High-Speed Ferry to St. Barths
St Maarten Beach hopping tour

St Maarten Beach hopping tour (Orient beach and Maho beach combo)

CA $85
per adult
St Maarten Beach hopping tour (Orient beach and Maho beach combo)
Exploring beautiful St.Martin

Adventure Island Tour

CA $92
per adult
Adventure Island Tour
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.