Philipsburg Vacation Rentals from CA $113: Short-Term Rentals for 2026

Q: What's the top vacation rental in Philipsburg?

Philips Scott House Calinago : Visitors like this Philipsburg vacation home rental. It 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. Some other homes for rent in Philipsburg include LUXURY VILLA! KILLER VIEWS! HIGHEST GUEST RATINGS ON ISLAND! and Villa Flagrantia, Paradise at your pleasure .

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Philipsburg vacation rentals

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

1. MIDTOWN MOTEL SXM

Downtown Philipsburg

brenton

CA $113 total

includes taxes & fees

Nov 26 - Nov 27

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

2. July Apartments

Madame's Estate

JoyAnn Carolyn

CA $168 total

includes taxes & fees

Dec 3 - Dec 4

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.

3. The Castle ᴷ

Downtown Philipsburg

CA $198 total

includes taxes & fees

Nov 5 - Nov 6

A compact, white front-loading washer and dryer unit in a corner of a room with a tiled floor and a small potted plant.

4. The Castle ᴴ

Downtown Philipsburg

Denise W.

CA $221 total

includes taxes & fees

Nov 7 - Nov 8

A compact living space with a bed, a dining area, and a kitchenette.

5. The Castle L - Twin Studio

Downtown Philipsburg

CA $198 total

includes taxes & fees

Nov 5 - Nov 6

A compact living space with a kitchenette, a dining area with a table and chairs, a bed with a blue cover, and a potted plant.

6. The Castle f

Downtown Philipsburg

Pat R.

CA $198 total

includes taxes & fees

Nov 5 - Nov 6

A living room with a brown sofa, two red pillows, a small white table, and a floor lamp.

7. The Castle ᴳ

Downtown Philipsburg

CA $188 total

includes taxes & fees

Nov 13 - Nov 14

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

8. The Castle ᴶ

Downtown Philipsburg

Neil C.

CA $198 total

includes taxes & fees

Nov 5 - Nov 6

A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

9. Philips Scott House Calinago

Downtown Philipsburg

CA $301 total

includes taxes & fees

Nov 5 - Nov 6

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

10. The Castle ᴵ

Downtown Philipsburg

CA $221 total

includes taxes & fees

Nov 29 - Nov 30

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

11. Cozy flat on the boardwalk!

Downtown Philipsburg

Robert H.

CA $274 total

includes taxes & fees

Nov 4 - Nov 5

A beach with rows of sun loungers and umbrellas, a pier with a large ship, and a sailboat in the water.

12. Panoramic Ocean View Flat: St Maarten

Downtown Philipsburg

CA $498 total

includes taxes & fees

Nov 4 - Nov 5

A modern room with a dining area, large windows, and a view of the sea.

13. Villa Solandra – 3BR Oceanfront Sunset w/ Pool

Indigo Bay

Olivia G.

CA $1,297 total

includes taxes & fees

Nov 16 - Nov 17

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

14. Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay

Carmelle,

CA $333 total

includes taxes & fees

Dec 2 - Dec 3

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

15. A View of Airplanes, the Beach, and Lolos in Grand-Case

Grand-Case

CA $206 total

includes taxes & fees

Nov 5 - Nov 6

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

16. The Hills Residence

Simpson Bay

Harold

CA $484 total

includes taxes & fees

Nov 16 - Nov 17

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

17. Mullet Bay Suites: Your Luxury Stay Awaits

Maho

Kenneth

CA $441 total

includes taxes & fees

Nov 8 - Nov 9

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

18. Simpson Bay Suites

Simpson Bay

Manishkumar

CA $211 total

includes taxes & fees

Nov 6 - Nov 7

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

19. condostmaarten by the sea -Adults Only-

Indigo Bay

Elouise

CA $769 total

includes taxes & fees

Nov 4 - Nov 5

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

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

South Reward

Trevayne

CA $320 total

includes taxes & fees

Nov 5 - Nov 6

View all properties

Find vacation rentals that suit your style

Apartments

Villas

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Philipsburg Hotel Reviews

Holland House Beach Hotel

8/10 Good

"Staff was lovely, it was located in an ideal spot to allow us explore. But the mosquitos in the elevators were scary."

Divi Little Bay Beach Resort

8/10 Good

"Overall, I thought this was a great property to stay at. It offers a beautiful private beach, several dining options, and a variety of included water activities for guests to enjoy. Most of the staff members were kind and courteous, although a few seemed less than enthusiastic when assisting guests. One thing I noticed was a difference in how some staff members treated guests with all-inclusive bracelets versus those without them. In some instances, guests without the all-inclusive bracelet seemed to receive more attentive service, which I found a bit unusual. Another area that needs improvement is housekeeping. We stayed for four nights and five days, and our room was not serviced daily. We had to request housekeeping on one occasion, and on another day, our room was not cleaned at all. Consistent housekeeping should be a standard, regardless of how long a guest stays. Overall, I would stay here again and would recommend this all-inclusive resort. However, I believe there is room for improvement when it comes to providing consistent, attentive service to all guests, regardless of their booking package, and ensuring housekeeping stays on schedule. After a long day enjoying the beach and pool, there is nothing better than returning to a clean, refreshed room. As far as the beach view... Incredible."

Belair Beach Hotel

10/10 Excellent

"This hotel was absolutely perfect for staying in St. Masrten. While the cost was much lower than other options on the island, it didn't feel like I missed out on anything at all. The hotel sits right on the beach, with rooms offering a beautiful view of the ocean. The room I stayed in felt more like an apartment than a hotel, which was quite lovely. It had a full kitchen, dining area, living room, large patio with furniture, and 2 bedrooms each with their own private bathrooms. I also couldn't hear a single sound from any other rooms near me, although the early morning sweeping can be heard through the window. You can also hear the birds singing right around 5am, which in my opinion is the most beautiful sound mixed with the crashing ocean waves. The hotel itself has a perfect convenience store with everything you could need (including alcohol and water) and incredibly helpful and friendly staff. There's a cafe with a bar that serves delicious food, and they have a nice schedule of activities you can participate in if you haven't booked yourself full like I did. The beach itself is astonishingly beautiful. The hotel provides chairs and umbrellas labeled with your room number so nobody steals your spot. They give you cards to trade for a towel when needed, and the towels smell so fresh and clean every time. I even met some partial owners of the hotel who were incredibly kind and offered AMAZING recommendations for food. I will definitely stay here next time I visit."

Find out more about Philipsburg

Everything you need to know about Philipsburg 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 Philipsburg 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 Philipsburg vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Philipsburg vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Philipsburg. 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 Philipsburg 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 Philipsburg vacation rentals we have selected for you start as low as CA $113 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Philipsburg rentals

At Expedia, we put the best Philipsburg 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 Philipsburg 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 Philipsburg 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 Philipsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Philipsburg?

Yes, we give you a choice of vacation rentals close to well known local attractions in Philipsburg, or you can select a secluded option if you'd like a relaxing place to stay. Visitors like the array of shops and scenic seaside in Philipsburg. While you're in the area, you can also enjoy the top-notch restaurants and entertainment venues.

What's the top vacation rental in Philipsburg?

Philips Scott House Calinago: Visitors like this Philipsburg vacation home rental. It 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. Some other homes for rent in Philipsburg include LUXURY VILLA! KILLER VIEWS! HIGHEST GUEST RATINGS ON ISLAND! and Villa Flagrantia, Paradise at your pleasure.

How many vacation rentals are there in Philipsburg?

Choose from 23 Expedia vacation rentals in Philipsburg for a memorable vacation.

What can I see and do in Philipsburg?

Great Bay Beach and Little Bay Beach are a couple of scenic spots to enjoy the outdoors, whereas Museum of Sint Maarten is one of the cultural attractions. Other places in town to visit include Port of St. Maarten and Rainforest Adventures St. Maarten.

What are vacation rentals like in Philipsburg?

Vacation rentals are privately owned properties you can reserve for several days or longer in Philipsburg. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.

Philipsburg Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Philipsburg vacation rentals

1. MIDTOWN MOTEL SXM

2. July Apartments

3. The Castle ᴷ

4. The Castle ᴴ

5. The Castle L - Twin Studio

6. The Castle f

7. The Castle ᴳ

8. The Castle ᴶ

9. Philips Scott House Calinago

10. The Castle ᴵ

11. Cozy flat on the boardwalk!

12. Panoramic Ocean View Flat: St Maarten

13. Villa Solandra – 3BR Oceanfront Sunset w/ Pool

14. Hilton Vacation Club Royal Palm St. Maarten

15. A View of Airplanes, the Beach, and Lolos in Grand-Case

16. The Hills Residence

17. Mullet Bay Suites: Your Luxury Stay Awaits

18. Simpson Bay Suites

19. condostmaarten by the sea -Adults Only-

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

Find vacation rentals that suit your style

Top Philipsburg Hotel Reviews

Holland House Beach Hotel

Find out more about Philipsburg

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app