Oyster Pond Vacations from $765

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Your Oyster Pond Vacation

When a city getaway is calling, answer it with a vacation package to Oyster Pond. The neighborhood of Upper Princes Quarter, which is great for shopping, coastal beaches and nature, makes a terrific base for your adventures. A trip to Oyster Pond is a wonderful opportunity to do some sightseeing. Make sure you visit big-name attractions such as Pinel Island, Marigot Market and Fort St. Louis. Stop daydreaming and start doing. Check out the multitude of options on Expedia today and finally put your Oyster Pond vacation plans into gear!

The Latest Oyster Pond vacation packages

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
Price was $1,361, price is now $765 per person
$765
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,345 reviews)
Met every need we had.

Reviewed on Sep 30, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,743, price is now $867 per person
$867
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,241 reviews)
The staff was friendly and accommodating. The room was beautiful and spacious. The view from the room was amazing ( over looks the ocean and pool). Lots of options for food onsite. Package included free breakfast.

Reviewed on Sep 29, 2025

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 $1,504, price is now $875 per person
$875
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,116 reviews)
Loved this resort so much. Gorgeous suite and steps away from the beach and nightlife.

Reviewed on Sep 30, 2025

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,467, price is now $880 per person
$880
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.4/10 Exceptional! (592 reviews)
It was okay, could be better

Reviewed on Sep 15, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
Price was $1,340, price is now $820 per person
$820
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,004 reviews)
The hotel is keep up they clean the lobby ever day breakfast area facing the water also very clean the servers are really good take care of all your needs and the rest of the staff are all very nice and easy to get things taken care of

Reviewed on Sep 28, 2025

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Discover the most popular places to visit in Oyster Pond

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

Dawn Beach

3/5(2 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.

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

Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

$149
per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
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
5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

$139
per adult
100% of travellers recommend
5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix
See all activities in Oyster Pond

Oyster Pond Hotel Deals

Les Balcons d'Oyster Pond

Les Balcons d'Oyster Pond

15 Avenue du Lagon, Oyster Pond
9.4/10 Exceptional! (80 reviews)
"Claude was very nice and helpful. She informed us of local restaurants and services. Great view!"

Reviewed on Aug 25, 2025

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Les Balcons d'Oyster Pond
Avenue du lagon

Avenue du lagon

Av. du lagon, Oyster Pond, Collectivité de Saint-Martin
$1,883 nightly
The price is $1,958 total per night from Oct 2 to Oct 3
$1,958 total
Oct 2 - Oct 3
Total with taxes and fees
Avenue du lagon
Colombus Résidence

Colombus Résidence

29, Rue de l'Escale, Oyster Pond
9.4/10 Exceptional! (105 reviews)
"Super quiet and friendly area"

Reviewed on May 23, 2025

Get rates
Colombus Résidence
See all 3,557 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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Frequently asked questions

How much does an Oyster Pond vacation package cost?
You can snap up a vacation package to this top destination from $765 on Expedia. But how much your vacation to Oyster Pond costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Oyster Pond?
If you'd like to snag a cheap Oyster Pond vacation package, consider traveling in February, July and December. You'll generally find lower prices on flights and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Oyster Pond?
When planning your Oyster Pond vacation, a handful of days will be enough to see the best spots. Make sure to visit Oyster Bay Marina — it's one of the major attractions in this destination. If you're looking for more activities, consider basing yourself here and heading off on some day tours from Oyster Pond.
Is it worth booking a vacation package to Oyster Pond?
Oyster Pond offers everything you need for a wonderful escape. Begin your Oyster Pond vacation on a high note by exploring popular attractions like Dawn Beach.
How to find the best Oyster Pond package deals?
Finding a cheap Oyster Pond package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add some filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Oyster Pond package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Oyster Pond vacation as a package?
You can enjoy significant savings on your next Oyster Pond getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Oyster Pond?
Secure incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Oyster Pond escape.
How to plan a trip to Oyster Pond?

  1. Pick your travel dates: What you plan to do in Oyster Pond and your preferred season will help you decide when to get away.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Oyster Pond.
  3. Use our trip planning tool to discover Oyster Pond: Research every part of your trip to Oyster Pond with this handy planner. Invite friends or family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go away for: Now that you know more about Oyster Pond, you can work out the perfect length of your vacation. Pull together a draft plan and allocate enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Oyster Pond vacation package.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some exciting things to do in Oyster Pond. Book tickets or make reservations as soon as you can to save time and skip the hassle of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Oyster Pond vacation packages?
If you're anything like us, you love traveling the world but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Oyster Pond trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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.