A turquoise beach with a cruise ship, palm trees, and a mountainous backdrop.

Philipsburg Vacation Rentals

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 .

Dates

November 2026

December 2026

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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 $123 total

includes taxes & fees

Nov 7 - Nov 8

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 $172 total

includes taxes & fees

Dec 7 - Dec 8

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 13 - Nov 14

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 13 - Nov 14

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 13 - Nov 14

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

6. The Castle f

Downtown Philipsburg

Pat R.

CA $198 total

includes taxes & fees

Nov 13 - Nov 14

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 $198 total

includes taxes & fees

Dec 2 - Dec 3

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 13 - Nov 14

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 9 - Nov 10

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

10. The Castle ᴵ

Downtown Philipsburg

CA $221 total

includes taxes & fees

Dec 2 - Dec 3

A balcony with a view of the sea, a table, and two chairs.

11. Cozy flat on the boardwalk!

Downtown Philipsburg

Robert H.

CA $266 total

includes taxes & fees

Nov 7 - Nov 8

A terrace with wicker furniture, a hanging chair, and a view of boats at a marina.

12. Panoramic Ocean View Flat: St Maarten

Downtown Philipsburg

CA $477 total

includes taxes & fees

Nov 7 - Nov 8

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 $1,477 total

includes taxes & fees

Nov 27 - Nov 28

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 $302 total

includes taxes & fees

Nov 11 - Nov 12

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 $208 total

includes taxes & fees

Nov 7 - Nov 8

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 $609 total

includes taxes & fees

Dec 7 - Dec 8

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 $445 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 25 - Nov 26

A swimming pool with clear water, a grassy area, and a view of a coastal landscape with buildings.

19. condostmaarten by the sea -Adults Only-

Indigo Bay

Elouise

CA $771 total

includes taxes & fees

Nov 7 - Nov 8

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

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Find vacation rentals that suit your style

Top Philipsburg Hotel Reviews

A balcony with a view of a beach and ocean.

Holland House Beach Hotel

Downtown Philipsburg

10/10 Excellent

Debra

July Apartments

Madame's Estate

10/10 Excellent

Robin

A neatly made bed with a red bedspread, two matching lamps on either side, and a colorful pillow on the headboard.

Alicia's Inn

Downtown Philipsburg

10/10 Excellent

Excellent place to stay. Very clean and air-conditioned and staff are very friendly and ready to help you out at any point in time. I had a great experience. I like the fact that it is away from the strip as it is much quieter than the beachfront hotels (and much more cost-friendly too), but still only a 2 minute walk away. Very close to the ferry docks and you can catch a minibus to anywhere on the island right from the front door. I would definitely stay here again.

Kenneth J

A pool area with a waterfall feature, surrounded by wooden deck chairs and covered seating areas.

Belair Beach Hotel

Belair

10/10 Excellent

The Belair Beach Hotel resort is fairly small, with a smaller but nice beach. The resort assigns beach chairs to your room when you check in and they are reserved for you until check out. The 2 bedroom 2 bathroom kitchenett suite was excellent, all of the sutes have full front ocean views with A full double balcony with all glass walls . The view is indeed spectacular You are literally 30 feet from the beach. The furniture was dated but still comfortable and functional, the beds and bedding were...

Cliff

A bedroom with a bed, bedside tables, a chair, a desk, and a mirror.

Calinago Friendly Family Sxm Home

Downtown Philipsburg

10/10 Excellent

Chetan

A room with a sofa, a glass table with a bottle, curtains, a TV, and a view of the ocean.

Horizon View Beach Hotel

Downtown Philipsburg

10/10 Excellent

Stacey

A resort pool with lounge chairs, palm trees, and a view of the ocean.

Divi Little Bay Beach Resort

Philipsburg

10/10 Excellent

Peter Victor

MIDTOWN MOTEL SXM

Downtown Philipsburg

10/10 Excellent

The Drive from the airport wasn't long. The Hostess was friendly, helpful and checked us in quick all I had to give was my name. The room was nice clean and spacious we had a queen size bed, the washroom had its linens and toiletries. Having a view of the beach and Cruise ships was nice. The location was perfect because it was literally close to everything. Convenience stores, shopping, restaurant and the beach. There were activities in walking distance as well. It was a lovely stay and we...

Reshanna

A circular window view of a beach with a swimming pool, palm trees, and a sandy area with umbrellas.

Seaview Beach Hotel

Downtown Philipsburg

10/10 Excellent

Jessica

A glass table with a white mug and a loaf of bread, a decorative vase, and a poolside lounge area with a view of purple flowers and palm trees.

Pomme Cannelle Luxury Suites & Spa

Orient Bay

10/10 Excellent

Wilf

A person sitting at a table with a book, a croissant, and a cup.

Le Martin Boutique Hôtel

Cul de Sac

10/10 Excellent

10/10 experience at Le Martin Hotel. From the hospitality, to the beautiful decor, to the daily breakfast, to the pool oasis - everything was perfect. Marion and her staff go above and beyond to make your stay just perfect. It was peaceful, quiet and the perfect place to relax and recharge. Only note is that it was a bit difficult to find as maps and waze direct you to the wrong spot. I loved the proximity to Pinel Island as well as both Grand Case and Orient Bay beaches

Michelle

A swimming pool with lounge chairs and a table on a wooden deck, surrounded by greenery and a mountain view.

Villa Jwi Lavi Boutique Hotel

Cul de Sac

10/10 Excellent

Dawn

A beach resort with palm trees, a pathway, and a view of the ocean.

Orient Beach Hotel

Orient Bay

10/10 Excellent

We had an incredible week at Orient Beach Hotel. Our immediate first impression was the genuinely warm welcome from the front desk team member, Junior. This positive energy remained through the week and was complemented by the incredible hotel manager, Myriam, and the attentive housekeeping staff. Room and views were exactly as pictured. We couldn’t have planned it any better. Thank you!! We hope to be back.

Luigi

A balcony with a view of the ocean, a bottle of champagne, two wine glasses, and a book titled "Linda Van Rijn Zoutelande".

La Vista Hotel

Pelican Key

10/10 Excellent

I stayed at the property from August 22-29. Great location, very clean, wonderful property and friendly staff. Rooms were cleaned daily, kitchen did not lack any appliances or dishes, plenty of towels daily, super comfortable bed and pillows, wifi worked wonderfully as well as the air conditioners and the pressure in the shower with hot water was amazing. Check in was quick and easy, late check out available as well as a great shower area near the pool with toiletries and towels to get ready...

Marta

A balcony with a view of the sea, a bed with towels, and two white wicker chairs.

Le Temps des Cerises Hotel Beach

Grand Case

10/10 Excellent

Heather

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 $102 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.

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

10/10 Excellent

Find out more about Philipsburg

Philipsburg vacation rentals: An excellent choice for every season

How to find incredible deals on Philipsburg rentals

Frequently Asked Questions

Can I find vacation rentals in Philipsburg?

What's the top vacation rental in Philipsburg?

How many vacation rentals are there in Philipsburg?

What can I see and do in Philipsburg?

What are vacation rentals like in Philipsburg?

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