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
Price was CA $2,638, price is now CA $1,250 per person
CA $1,250
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,810 reviews)

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $4,620, price is now CA $2,332 per person
CA $2,332
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,429 reviews)
Our stay at Simpson Bay Villa was beautiful. The property was beautiful, well maintained. Right on the water and everything was very close by. Restaurants were in walking distance, supermarkets were close by. There was really no reason to leave the resort. Even if you wanted to do tours or visit other islands it was very convenient from this villa. We had a one bedroom apartment, full kitchen, living room just like being at home. There was absolutely nothing to complain about on vacation. Staff was very friendly and helpful with anything we asked. Trust me this is vacation spot you’ll not regret

Reviewed on Jun 30, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,438, price is now CA $1,590 per person
CA $1,590
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
Quiet, peaceful, serene stay. Everything is 5 out of 5!

Reviewed on Jun 25, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was CA $2,305, price is now CA $1,519 per person
CA $1,519
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.6/10 Exceptional! (62 reviews)
Exceptional view from the room

Reviewed on Jul 1, 2026

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was CA $3,072, price is now CA $2,120 per person
CA $2,120
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.4/10 Exceptional! (736 reviews)
Such a great stay here! Everyone is friendly and willing to give you all the great recommendations. I loved my time here and can’t wait to come back!

Reviewed on Jun 27, 2026

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
A nighttime swimming pool surrounded by palm trees and lounge chairs, with buildings in the background.

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 Oyster Bay Marina or Dawn Beach 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

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 $234 per night from Jul 3 to Jul 4
CA $234
CA $280 total
Jul 3 - Jul 4
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Good was good , very relaxing area beautiful breeze all day on the island. I loved every moment of our short trip will be back . I was a bit surprised to see it was not in walking distance of things but now I know. The workers on the property are respectful and beautiful people"

Reviewed on Jul 1, 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 $433 per night from Jul 15 to Jul 16
CA $433
CA $569 total
Jul 15 - Jul 16
includes taxes & fees
8.8/10 Excellent! (313 reviews)
"So the hotel standards other JW Marriotts I have stayed at. The staff are great. The Sargassum was terrible which made outside pool area unbearable. Of course they cannot help this but since the sargassum is not being hauled away the smell is awful! The property is very far from everything, since ..."

Reviewed on Jun 30, 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 $176 per night from Aug 1 to Aug 2
CA $176
CA $211 total
Aug 1 - Aug 2
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Quiet, peaceful, serene stay. Everything is 5 out of 5!"

Reviewed on Jun 25, 2026

Princess Heights Luxury Boutique Condo Hotel
See all 3,589 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.
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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

What to do in Oyster Pond

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $90
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $118
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $103
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
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 $1,250 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.

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