Oyster Pond Vacation Packages

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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!

Top Oyster Pond Vacation Deals

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
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

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

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)
We loved our stay at La Playa! From the moment we arrived the staff was so friendly and helpful with anything we needed. The property itself and the rooms were extremely clean and well kept. The small villa style apartments gave the place a really cool and quaint feel. The beach bar and beach area were also incredible. Tristan at the beach was also very helpful with chairs and service throughout the day. There was some sargassum during our stay but the staff cleaned the beach each morning and kept everything as nice as they possibly could have. 10/10 recommend staying here- we already can’t wait to go back!

Reviewed on Jul 2, 2026

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $2,416, price is now CA $1,699 per person
CA $1,699
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
8.8/10 Excellent! (1,000 reviews)
Loved my stay here, I will say customer service here is a bit different as the culture is very relaxed, but the staff took great care of me and had great advice about excursions! If you are planning to come just know that you will be a bit farther from most activities as the resort is a bit tucked away so your cab fare will be higher, and some cab companies do not service to the resort. Other than that great views, amazing food and drinks!

Reviewed on Jul 1, 2026

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was CA $2,932, price is now CA $2,069 per person
CA $2,069
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)
Amazing

Reviewed on Jun 27, 2026

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Oyster Pond Hotel Deals

Les Balcons d'Oyster Pond

Les Balcons d'Oyster Pond

15 Avenue du Lagon Oyster Pond
9.6/10 Exceptional! (141 reviews)
"I would recommend this place to anyone, Coco is great for anything related to the island. She got us a rental car for a really good price on a very short notice. The pool in the cottage is very nice as well. Room is well clean with good amenities."

Reviewed on Jun 18, 2026

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Les Balcons d'Oyster Pond
Colombus Résidence

Colombus Résidence

29, Rue de l'Escale Oyster Pond
9.6/10 Exceptional! (133 reviews)
"A beach house located in very secluded area on the top of the hill on the French side of the island. We came on a Thursday in our room to find small but bothering mosquitoes and ants. It came from outside every day we needed to get rid of them did the mosquito killer device. Our bathroom and toilet ..."

Reviewed on May 22, 2026

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Colombus Résidence
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $403 per night from Aug 2 to Aug 3
CA $403
CA $515 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,248 reviews)
"This place was amazing"

Reviewed on Jul 1, 2026

The Morgan Resort Spa Village
See all 3,599 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

The All Ages Tarzan Swing

The Best Catamaran Day Sail in St Maarten

CA $201
per adult
98% of travellers recommend
The Best Catamaran Day Sail in St Maarten
Underwater Sculpture Park Snorkel Adventure

Underwater Sculpture Park Snorkel Adventure

CA $62
per adult
Underwater Sculpture Park Snorkel Adventure
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'll find cheap prices from CA $1,590 on Expedia for your Oyster Pond getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Oyster Pond costs.
What are the cheapest months to go to Oyster Pond?
To pick up cheap Oyster Pond vacation packages, plan your trip outside of busy periods like public holidays and major festivals. You'll typically find lower prices and better availability for hotels and flights.
How many days is enough for Oyster Pond?
We'd suggest booking an Oyster Pond vacation for around 9 days. This gives you time to tick off top sights such as Grand Case Beach and Orient Bay, as well as check out neighbourhoods like Pelican Key and Upper Prince's Quarter. You might even be able to slot in a day trip (or two) beyond Oyster Pond.
Is it worth booking a vacation package to Oyster Pond?
Oyster Pond is a good vacation destination with attractions like Dawn Beach among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, an Oyster Pond vacation promises a good time for everyone.
How to find the best Oyster Pond package deals?
Use Expedia's filters to help you find some unbeatable Oyster Pond package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Oyster Pond package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book an Oyster Pond vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations and flights individually. Better still, you can customize your Oyster Pond getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Oyster Pond?
Score incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Oyster Pond adventure.
How to plan a trip to Oyster Pond?

  1. Choose when to go: Check your schedule and get packing. Your preferred time of year and the activities available will also help you decide when to visit Oyster Pond.
  2. Budget wisely: Besides the price of your stay, you should factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Oyster Pond.
  3. Decide how long to go for: Now that you're more familiar with Oyster Pond, you can figure out the perfect length of your vacation. Create a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose an Oyster Pond vacation package that brings all your bookings together.

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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.