Oyster Pond Vacations from $718

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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.

The Latest Oyster Pond vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Save 100% on your flight
Price was $1,214, price is now $718 per person
$718
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,084 reviews)
Most convenient hotel to stay, due to an array of shopping and dinning options near the property.

Reviewed on Aug 27, 2025

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $2,053, price is now $999 per person
$999
per person
Oct 29 - Nov 4
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,291 reviews)
It was a great stay however the room itself was the problem. I originally booked a room with two beds and upon arrival they said they

Reviewed on Aug 27, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,740, price is now $956 per person
$956
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
Always a great time at Simpson Bay. Which is why continue to come here year after year:)

Reviewed on Aug 27, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
Price was $1,726, price is now $959 per person
$959
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
Perfect hotel. Right in the center of the Main Street on the entire island. I recommend staying here. Everything is walkable. Ferry is a 5 min walk which goes to St Barth. Room was very clean and comfortable. Great shower and AC. Parking is 100 feet away. Staff tells u when u pull up to the hotel where to park.

Reviewed on Aug 26, 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
Price was $1,456, price is now $810 per person
$810
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (960 reviews)
This property was very nice and astonishing. The area was quiet and lovely place to have a vacation at. The beds were so comfortable after a day of activities and excursions. The place is very peaceful and beautiful. The staff were amazing as well. The views were amazing. I would definitely recommend.

Reviewed on Aug 15, 2025

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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
3.5/5(99 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

Discover the most popular places to visit in Oyster Pond

Dawn Beach featuring a coastal town, general coastal views and landscape views

Dawn Beach

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.

Dawn Beach

Coralita Beach

Why not spend a lazy afternoon at Coralita Beach during your trip to Oyster Pond? Wander the beautiful beaches and seaside in this romantic area.

Coralita Beach

What to do in Oyster Pond

St Maarten

Private St Maarten Island Sightseeing Tour

$560
per traveler
Private St Maarten Island Sightseeing Tour
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

$75
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

$149
per adult
84% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
See all activities in Oyster Pond

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
$189 nightly
The price is $197 total per night from Sep 1 to Sep 2
$197 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (922 reviews)
"Everything was very nice. The free breakfast was very limited- contintental breakfast. The hotel shuttle was a local taxi & cost $35. We needed an accommodation for our big anniv. celebration but nobody seemed to help us nor provide for us, which was a bottle of cider instead of alcohol. That was ..."

Reviewed on Aug 25, 2025

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, Building A, Oyster Pond, Sint Maarten
$319 nightly
The price is $336 total per night from Sep 1 to Sep 2
$336 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (204 reviews)
"This is a beautiful property on a quiet part of the Island. The resort pool is world class. The hotel is modern and well cared for. The staff is top notch. We’ve stayed here twice and will again."

Reviewed on Aug 22, 2025

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, Dawn Beach, Oyster Pond
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $156 total per night from Aug 29 to Aug 30
$156 total
Aug 29 - Aug 30
Total with taxes and fees
9.2/10 Wonderful! (952 reviews)
"This property was very nice and astonishing. The area was quiet and lovely place to have a vacation at. The beds were so comfortable after a day of activities and excursions. The place is very peaceful and beautiful. The staff were amazing as well. The views were amazing. I would definitely ..."

Reviewed on Aug 15, 2025

Princess Heights Luxury Boutique Condo Hotel
See all 3,592 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.

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 0.3 miles (0.5 km) from the city center.

Things You Should Know About Oyster Pond

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Frequently asked questions

How much does an Oyster Pond vacation package cost?
You'll find cheap prices from $718 on Expedia for your Oyster Pond getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Oyster Pond costs.
What are the cheapest months to go to Oyster Pond?
July, October and December are great times to search for cheap Oyster Pond vacation packages. Choosing to travel in quieter periods means you'll typically find lower prices on flights and accommodations.
How many days is enough for Oyster Pond?
With a well-planned schedule, you can easily tick off the main Oyster Pond sights in a handful of days. But if you prefer to discover hidden gems or go on day trips, consider booking your Oyster Pond vacation for longer.
Is it worth booking a vacation package to Oyster Pond?
Oyster Pond offers everything you need for an unforgettable escape. Begin your Oyster Pond vacation on a high note by visiting major attractions like Dawn Beach.
How to find the best Oyster Pond package deals?
Start your search for an Oyster Pond package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Oyster Pond package deal right away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oyster Pond adventure off to a flying start.
Is it cheaper to book an Oyster Pond vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can customize your Oyster Pond escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Oyster Pond?
If you're considering a spontaneous Oyster Pond 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 find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Oyster Pond?

  1. Choose when to go: Check your calendar and pack your bags. Your favorite season and the available activities will also help you decide when to visit Oyster Pond.
  2. Calculate your budget: Ensure you have enough money to pay for everything from food and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Oyster Pond.
  3. Discover Oyster Pond using our trip planning tool: Gain insights into the leading attractions and best stays for your trip to Oyster Pond. You can also save your favorite locations, collaborate with your group and organize all your plans in one place.
  4. Determine how many days away: Start by compiling a list of the activities and sights you want to get to in Oyster Pond. Then, estimate how long you'll need for each, along with any travel time.
  5. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the ideal Oyster Pond vacation package for you.
  6. Book any activities or excursions: Here's the fun part — organizing everything you want to do and see. Browse some of the exciting things to do in Oyster Pond and book your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Oyster Pond vacation packages?
Set off on your dream getaway to Oyster Pond with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait for payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to budget for your trip and snap up cheap deals while they last.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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