Oyster Pond Vacation Packages

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Your Oyster Pond Vacation

When a fun city getaway is calling, answer it with a vacation package to Oyster Pond. The neighborhood of Upper Princes Quarter, which is good for shopping, coastal beaches and nature, makes a great base for your adventures. Make your trip to Oyster Pond even more fun and exciting by including some sightseeing. Pinel Island, Marigot Market and Fort St. Louis are among the popular attractions you'll want to explore. Expedia will help you escape your daily routine. Tailor your vacation to Oyster Pond to suit your travel style, whatever that may be.

Top Oyster Pond Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,192 reviews)
Great location, beautiful beach and friendly staff.

Reviewed on Jul. 18, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,192 reviews)
This is our second time staying here. We love the views. The service and staff are amazing! Can’t wait to go back!

Reviewed on Jul. 18, 2025

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Save 100% on your flight
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
8.6/10 Excellent! (891 reviews)
Over all will stay again

Reviewed on Jul. 15, 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
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (938 reviews)
It was a very romantic intimate stay. Paul the driver is very professional and made sure all our transportation was taken care of. Go to Maho beach and Nowhere special for live music and drinks. The room was fully equipped with a kitchen the housekeeping came every day. The only complaint was the smell from the sea moss from dawn beach but apparently it’s normal this time of year.

Reviewed on Jul. 13, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
We had a group of 7 couples that went on a power boat excursion, ATV ride and schooner excursion. They were all fantastic, great food and fun.

Reviewed on Jul. 17, 2025

Where to stay in Oyster Pond

Find the best Oyster Pond areas and neighborhoods for the activities you enjoy most. Learn more about Oyster Pond
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Oyster Pond

2 out of top 10 points of interest in this area
4/5(13 area reviews)

Oyster Pond is a destination visitors seek out for is beaches, abundant dining options, and seaside views. You might want to check out attractions like Dawn Beach or Oyster Bay Marina while you're exploring the neighborhood.

Find hotels in Oyster Pond

Oyster Pond Beach Vacation

Forget the stresses of daily life and completely relax during your Oyster Pond vacation. There's nothing more invigorating than a cool ocean breeze and the soothing rhythm of waves crashing onto the shore. Organize your trip to Oyster Pond the quick and easy way by locking in one of our Oyster Pond vacation packages. Many travelers opt to spend their nights close to Dawn Beach, a must-see only 0.48 kilometres from the city center.

Things You Should Know About Oyster Pond

Ready to book your vacation to Oyster Pond?

 

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Oyster Pond Hotel Deals

JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa

5 out of 5
144 Oyster Pond Resort, Building A, Oyster Pond, Sint Maarten
The price is CA $460 per night from Aug 1 to Aug 2
CA $460
CA $597 total
Aug 1 - Aug 2
includes taxes & fees
8.8/10 Excellent! (189 reviews)
"Property was lovely, excellent service however it was that time of year in the North that the seaweed took over the beach. The hotel tried to contain it but the smell was overwhelming."

Reviewed on Jul. 12, 2025

JW Marriott St. Maarten Beach Resort & Spa
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 $226 per night from Jul 28 to Jul 29
CA $226
CA $271 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very Good! (893 reviews)
"Over all will stay again"

Reviewed on Jul. 15, 2025

Oyster Bay Beach Resort
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond Road No 156, Dawn Beach, Oyster Pond
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jul 20 to Jul 21
CA $179
CA $214 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (939 reviews)
"It was a very romantic intimate stay. Paul the driver is very professional and made sure all our transportation was taken care of. Go to Maho beach and Nowhere special for live music and drinks. The room was fully equipped with a kitchen the housekeeping came every day. The only complaint was the ..."

Reviewed on Jul. 13, 2025

Princess Heights Luxury Boutique Condo Hotel
See all 3,628 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

What to do in Oyster Pond

Captain Alan's Three Island Snorkelling & Beach Adventure

CAPTAIN ALAN'S 4hr -3 Islands-snorkeling-turtles-beach ADVENTURE

CA $122
per adult
CAPTAIN ALAN'S 4hr -3 Islands-snorkeling-turtles-beach ADVENTURE
St.Martin/St.Maarten Magical Tour

St.Martin/St.Maarten Magical Tour

CA $96
per adult
100% of travellers recommend
St.Martin/St.Maarten Magical Tour
St. Maarten 4 Hour Sightseeing Tour

St. Maarten 4 Hour Sightseeing Tour

CA $84
per adult
St. Maarten 4 Hour Sightseeing Tour
See all activities in Oyster Pond

Frequently asked questions

How much does an Oyster Pond vacation package cost?
You can snap up a vacation package to this top destination from CA $726 on Expedia. But how much your vacation to Oyster Pond costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Oyster Pond?
The off-season is the best time to head to Oyster Pond if you're on a budget. Another tip for scoring cheap Oyster Pond vacation packages? Try to avoid visiting during public holidays and any major festivals or events.
How many days is enough for Oyster Pond?
We recommend booking an Oyster Pond vacation for at least 5 days. This will give you plenty of time to check off top attractions including Grand Case Beach and Orient Bay, as well as explore neighbourhoods like Pelican Key and Upper Prince's Quarter. You might even be able to make time for a day trip (or two) beyond Oyster Pond.
Is it worth booking a vacation package to Oyster Pond?
It's no wonder an Oyster Pond vacation is on the to-do list of many travellers. Top attractions like Dawn Beach are just the beginning of things to see and do here.
How to find the best Oyster Pond package deals?
Bagging a cheap Oyster Pond package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most affordable Oyster Pond package deals. Want a simple trick to get 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 an Oyster Pond vacation as a package?
You can enjoy significant savings on your next Oyster Pond break by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Oyster Pond?
If you have your Oyster Pond travel dates finalized, book as early as you can to snap up some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Oyster Pond?

  1. Pick your dates: What you'd like to do in Oyster Pond and your favourite season can help you decide when to go.
  2. Plan your budget wisely: In addition to the price of your accommodations, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that could arise during your trip to Oyster Pond.
  3. Decide how long to go for: Now that you know more about Oyster Pond, you can figure out the right length of your break. Put together a draft plan and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Oyster Pond vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.