Oyster Pond Vacation Rentals from CA $115: Short-Term Rentals for 2026

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

Philips Scott House Calinago : You might want to consider this vacation home rental near Oyster Pond, which is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Oyster Pond vacation rentals

A view through a window with a pool and a mountainous landscape.

1. Lovely Studio Apartment with Pool & Nature Views!

Oyster Pond

Jennifer

CA $184 total

includes taxes & fees

Oct 9 - Oct 10

A large swimming pool surrounded by palm trees and lounge chairs, with a hotel building in the background.

2. Dawn Beach Club Resort Sint Maarten

Oyster Pond

Gavin

CA $1,070 total

includes taxes & fees

Oct 3 - Oct 4

A multi-story building with a pool, surrounded by hilly terrain.

3. Singh Luxury Apartments With sea View, Apt.2

Oyster Pond

CA $587 total

includes taxes & fees

Oct 9 - Oct 10

A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the ocean.

4. Singh Luxury Apartments With sea View, Apt.3

Oyster Pond

CA $1,164 total

includes taxes & fees

Oct 9 - Oct 10

A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the sea.

5. Singh Luxury Apartments With sea View, Apt.1

Oyster Pond

CA $587 total

includes taxes & fees

Oct 9 - Oct 10

A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.

6. July Apartments

Madame's Estate

JoyAnn Carolyn

CA $138 total

includes taxes & fees

Oct 1 - Oct 2

A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

7. MIDTOWN MOTEL SXM

Downtown Philipsburg

Yollanda

CA $115 total

includes taxes & fees

Oct 15 - Oct 16

A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

8. Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay

Carmelle,

CA $200 total

includes taxes & fees

Oct 11 - Oct 12

A bedroom with a red bedspread, white headboard, and two red pillows. There are two paintings on the wall, a closet with a sliding door, and a bathroom visible in the background.

9. The Castle ᴷ

Downtown Philipsburg

CA $212 total

includes taxes & fees

Oct 16 - Oct 17

A covered patio with a table and chairs, surrounded by potted plants and overlooking a scenic view of hills and houses.

10. Lovely room in a nice villa , close to Friars bay and happy bay

Saint-martin

Kurt

CA $174 total

includes taxes & fees

Oct 1 - Oct 2

A high-rise hotel with a view of the sunset over a marina.

11. Simpson Bay Suites

Simpson Bay

Manishkumar

CA $214 total

includes taxes & fees

Oct 8 - Oct 9

A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.

12. condostmaarten by the sea -Adults Only-

Indigo Bay

Muneca

CA $634 total

includes taxes & fees

Oct 14 - Oct 15

A bedroom with a bed, bedside table, chair, and artwork on the walls.

13. The Castle ᴶ

Downtown Philipsburg

Neil C.

CA $212 total

includes taxes & fees

Oct 16 - Oct 17

A balcony with white railings, a bench, and two chairs.

14. Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

South Reward

Trevayne

CA $326 total

includes taxes & fees

Oct 1 - Oct 2

A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

15. The Hills Residence

Simpson Bay

Alyssia

CA $403 total

includes taxes & fees

Oct 4 - Oct 5

A hallway with a decorative gate, potted plants, and a fire extinguisher.

16. The Castle ᴵ

Downtown Philipsburg

CA $235 total

includes taxes & fees

Oct 1 - Oct 2

A beach with rows of umbrellas and lounge chairs, a marina with boats, and a cruise ship docked in the background.

17. Cozy flat on the boardwalk!

Downtown Philipsburg

Robert H.

CA $286 total

includes taxes & fees

Oct 1 - Oct 2

A modern kitchen with a dining area, a grey sofa, and a TV.

18. View planes, beach & lolos in Grand-Case

Grand-Case

CA $224 total

includes taxes & fees

Oct 1 - Oct 2

A dining area with a table, chairs, a small potted plant, a framed picture on the wall, and a mounted TV.

19. The Castle f

Downtown Philipsburg

Pat R.

CA $212 total

includes taxes & fees

Oct 9 - Oct 10

A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

20. Mullet Bay Suites: Your Luxury Stay Awaits

Maho

Kenneth

CA $487 total

includes taxes & fees

Oct 11 - Oct 12

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Top Oyster Pond Hotel Reviews

Simpson Bay Resort, Marina & Spa

10/10 Excellent

"The only problem was American visitors who were not following the rules at the pool. They were aggressive, rude and used very foul language with me when I politely asked them to turn off their boom box, stop throwing things around and respect other people at the pool. I got absolutely no support from the bartender when Americans wouldn’t stop what they were doing. She was condescending and joined the Americans in shouting abuse at me. When I called security I got a very annoyed guard who was impatient and obviously sided with the Americans. I have complained to the resort requesting a response but have heard absolutely nothing. For the rest of my time there I kept running into the Americans which kind of ruined my holiday."

Villa Angelina with Amazing Panoramic Views. Enjoy the quiet at Oyster Pond

8/10 Good

"The view was definitely the showstopper. You could not beat the views of the Oyster Bay, the Atlantic Ocean, St. Barth to the east and Anguilla to the north.The inside of the house was clean but needed to be updated. Beds were comfortable and they had all the essentials for the house.The location was great. It was in a quiet neighborhood.And let's face it, Saint Maarten is not that big so you could drive from one point of the island to the other in about 20 to 30 minutes, depending on traffic.We were disappointed upon arrival, how the outside of the property looked. It looked like no one had clean the patio, area where the grill was or the pool area in anticipation of our arrival. There were broken chairs from the patio set laying out.I got up the next morning and washed off those areas myself so that we could use them without feeling like we was stepping in dirty areas. I say all of this the say, the view made up for all of this. I think the property was recently bought, so I just think it needs a little work and they would have a gem on their hands.If you ask, what I stay there again? I would.The view!!"

LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site

10/10 Excellent

"This was an excellent property and was exactly as advertised. Beautiful villa, very roomy and comfortable. We did not rent a car and used a taxi for the week. The expense was about the same and this way we didn’t have to drive. Communication with everyone was so easy and pleasant. We didn’t get to access the ocean because the sargassum was very heavy but they removed as much as they could every morning and there was never an unpleasant smell. By the end of the week, the winds had changed and kept the seaweed to a minimum. My family really enjoyed the quiet area of Oyster Bay/Dawn Beach and the space of the villa for a family of six. Overall, we had an excellent time and enjoyed our stay!!"

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oyster Pond vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oyster Pond vacation rentals we have selected for you start as low as CA $115 per night. Entering your travel dates in the search wizard 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.

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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 popular beaches 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?

Philips Scott House Calinago: You might want to consider this vacation home rental near Oyster Pond, which is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience.

How many vacation rentals are there in Oyster Pond?

Choose from 20 Expedia vacation rentals in Oyster Pond for a memorable vacation.

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

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

Oyster Pond Vacation Rentals

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Check prices for these dates

Our top choices for Oyster Pond vacation rentals

1. Lovely Studio Apartment with Pool & Nature Views!

2. Dawn Beach Club Resort Sint Maarten

3. Singh Luxury Apartments With sea View, Apt.2

4. Singh Luxury Apartments With sea View, Apt.3

5. Singh Luxury Apartments With sea View, Apt.1

6. July Apartments

7. MIDTOWN MOTEL SXM

8. Hilton Vacation Club Royal Palm St. Maarten

9. The Castle ᴷ

10. Lovely room in a nice villa , close to Friars bay and happy bay

11. Simpson Bay Suites

12. condostmaarten by the sea -Adults Only-

13. The Castle ᴶ

14. Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

15. The Hills Residence

16. The Castle ᴵ

17. Cozy flat on the boardwalk!

18. View planes, beach & lolos in Grand-Case

19. The Castle f

20. Mullet Bay Suites: Your Luxury Stay Awaits

Find vacation rentals that suit your style

Top Oyster Pond Hotel Reviews

Simpson Bay Resort, Marina & Spa

Find out more about Oyster Pond

Explore a world of travel with Expedia

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