Oyster Pond Vacation Rentals

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Our top choices for Oyster Pond vacation rentals

8.0 out of 10, Very Good, (1)
"The feature of the unit is the view! For the price it’s a great deal - especially if you have a car. The unit is clean - but the shower only runs really hot. "
United States
Jennifer
$126 nightly
The price is $130
Jan 5 - Jan 6, 2026
Total with taxes and fees
Lovely Studio Apartment with Pool & Nature Views!

Condo resort in Oyster Pond

Dawn Beach Club Resort Sint Maarten
4.0 star property
8.8 out of 10, Excellent, (21)
"Wonderful vacation spot in st maarten"
United States
Debasis
$723 nightly
The price is $755
Jan 12 - Jan 13, 2026
Total with taxes and fees
Dawn Beach Club Resort Sint Maarten
3.0 star property
$527 nightly
The price is $550
Dec 30 - Dec 31
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.1

Villa in Tamarind Hill Estates

Villa Sophia: Oceanfront w/ Generator & Pool
$2,318 nightly
The price is $2,420
Jan 8 - Jan 9, 2026
Total with taxes and fees
Villa Sophia: Oceanfront w/ Generator & Pool
3.5 star property
$527 nightly
The price is $550
Dec 30 - Dec 31
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.2
3.0 star property
2.0 out of 10, (1)
$914 nightly
The price is $956
Dec 30 - Dec 31
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.3
10.0 out of 10, Exceptional, (2)
"Wow. We can’t say enough about this amazing experience. The hosts are wonderful. We were just on their fantastic boat for one night - the last night of our trip, but it was perfect. We had a sail out to Tintamarre, a pristine and beautiful little deserted (amd conservation protected) island. We snorkeled, had apps and Karim’s signature cocktail as the sun went down. Then Sophie served us a great dinner out on the deck of the boat, including her delicious homemade bread! We stargazed and slept...
United States
Sheri W.
$2,575 nightly
The price is $2,575
Jan 2 - Jan 3, 2026
Total with taxes and fees
Tintamarre exclusive dinner and night at anchor
$1,183 nightly
The price is $1,224
Jan 2 - Jan 3, 2026
Total with taxes and fees
UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED

Houseboat in Collectivité de Saint-Martin

Your half-day cruise with scenic Zephyr and water activities
$1,692 nightly
The price is $1,692
Jan 2 - Jan 3, 2026
Total with taxes and fees
Your half-day cruise with scenic Zephyr and water activities

Aparthotel in Downtown Philipsburg

MIDTOWN MOTEL SXM
2.5 star property
8.0 out of 10, Very Good, (1)
"The staff was extremely helpful "
United States
Joycelyn
$81 nightly
The price is $85
Jan 9 - Jan 10, 2026
Total with taxes and fees
MIDTOWN MOTEL SXM

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.8 out of 10, Excellent, (61)
"Enjoyed my stay "
United States
Shakia
$298 nightly
The price is $312
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Hills Residence

Aparthotel in Madame's Estate

July Apartments
3.0 star property
9.2 out of 10, Wonderful, (157)
"Amazing place. "
United States
Cristina
$77 nightly
The price is $80
Jan 2 - Jan 3, 2026
Total with taxes and fees
July Apartments

Aparthotel in Pelican Key

FLAMINGO BEACH
3.5 star property
FLAMINGO BEACH
4.0 star property
9.8 out of 10, Exceptional, (116)
"Great apartment and great location!"
United States
Miljan
$314 nightly
The price is $329
Jan 7 - Jan 8, 2026
Total with taxes and fees
Mullet Bay Suites: Your Luxury Stay Awaits
$164 nightly
The price is $170
Jan 9 - Jan 10, 2026
Total with taxes and fees
Charming studio with splendid Caribbean Sea view & pool/beach access
9.0 out of 10, Wonderful, (9)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
$98 nightly
The price is $98
Dec 31 - Jan 1, 2026
Total with taxes and fees
Lovely room in a nice villa with a big garden, close to Friars bay beach
4.0 star property
9.0 out of 10, Wonderful, (1166)
"Room was great, resort was great, staff was great"
Canada
Gisele
$408 nightly
The price is $428
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

Vacation Home in Weymouth Hill, Sint Maarten

Quiet cozy flat in the centre of the island.
8.0 out of 10, Very Good, (1)
$217 nightly
The price is $217
Jan 11 - Jan 12, 2026
Total with taxes and fees
Quiet cozy flat in the centre of the island.

Aparthotel in Downtown Philipsburg

Sea Palace
3.0 star property
8.6 out of 10, Excellent, (113)
"Great staff. Excellent room. Awesome views. The young lady with the glasses at the front desk is the best ever. Didn't get her name unfortunately. "
United States
Elizabeth
$215 nightly
The price is $226
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sea Palace

Apartment in Collectivité de Saint-Martin

Happy Residence - Orient Beach 09
9.6 out of 10, Exceptional, (5)
"The property was very nice. A few improvements like more bath towel's and beach towels would be nice."
United States
Joseph
$261 nightly
The price is $261
Jan 5 - Jan 6, 2026
Total with taxes and fees
Happy Residence - Orient Beach 09
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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Top Oyster Pond Hotel Reviews

Price trends for vacation rentals in Oyster Pond

Less expensive
More expensive
Next month
June
January
$763
Month
Price
January
$763
February
$720
March
$532
April
$484
May
$530
June
$412
July
$530
August
$506
September
$503
October
$510
November
$412
December
$562
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Oyster Pond. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Oyster Pond

Everything you need to know about Oyster Pond vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oyster Pond vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oyster Pond vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oyster Pond vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oyster Pond. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oyster Pond in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $80 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oyster Pond rentals

At Expedia, we put the best Oyster Pond vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oyster Pond rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oyster Pond vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oyster Pond. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Oyster Pond?

Yes, we give you a choice of vacation rentals close to popular sights in Oyster Pond, or you can go with a secluded option if you're looking for relaxation. Visitors to Oyster Pond speak positively about the scenic seaside and top-notch restaurants in this destination. Make sure you have time to check out the cafes while you're in the area.

What are some of the best vacation rentals that Oyster Pond has to offer?

DawnBeach Club 4 Bed/4Bath Villa With Swimming Pool, Beach and Resorts Access. : This Oyster Pond vacation home rental offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the terrace in this rental home to help you unwind. Our travelers also rate Tropical Oasis in St. Martin 5 min to beach! Huge private pool+panoramic views!! as a favorite home for rent in Oyster Pond.

How many vacation rentals are there in Oyster Pond?

Choose from 19 Expedia vacation rentals in Oyster Pond for a memorable vacation.

What’s there to see and do in Oyster Pond?

Dawn Beach and Guana Bay are a couple of lovely local spots to get outside and enjoy nature. While here, Oyster Bay Marina and Gibb's Bay Beach are other places worth a visit.

What’s a vacation rental in Oyster Pond like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Oyster Pond. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.