A coastal town with a beach, rocky shoreline, and a mountain in the background.

Philipsburg Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Philipsburg holiday rentals

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

1. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (253 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is HK$727
HK$764 total
includes taxes & fees
29 Sept - 30 Sept
July Apartments
A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

2. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (73 reviews)
"It was a wonderful stay and experience"
United States
Yollanda
The price is HK$572
HK$686 total
includes taxes & fees
1 Oct - 2 Oct
MIDTOWN MOTEL SXM
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

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is HK$941
HK$1,173 total
includes taxes & fees
29 Sept - 30 Sept
The Castle ᴷ
A beach with rows of umbrellas and lounge chairs, a marina with boats, and a cruise ship docked in the background.

4. Cozy flat on the boardwalk!

Cozy flat on the boardwalk!
Downtown Philipsburg
10.0 out of 10, Exceptional, (2 reviews)
"Host was very accommodating and helpful. Amenities were abundant."
United States
Robert H.
The price is HK$1,177
HK$1,702 total
includes taxes & fees
29 Sept - 30 Sept
Cozy flat on the boardwalk!
A hallway with a decorative gate, potted plants, and a fire extinguisher.

5. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,059
HK$1,301 total
includes taxes & fees
29 Sept - 30 Sept
The Castle ᴵ
A bedroom with a bed, bedside table, chair, and artwork on the walls.

6. The Castle ᴶ

The Castle ᴶ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
"Host was welcoming and the apartment was very clean and inviting. We will Definitely stay here again when we come back. "
United States
Neil C.
The price is HK$941
HK$1,173 total
includes taxes & fees
29 Sept - 30 Sept
The Castle ᴶ
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

7. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is HK$1,200
HK$1,832 total
includes taxes & fees
29 Sept - 30 Sept
Philips Scott House Calinago
A dining area with a table, chairs, a small potted plant, a framed picture on the wall, and a mounted TV.

8. The Castle f

The Castle f
Downtown Philipsburg
8.0 out of 10, Very good, (1 review)
"After a bit of confusion about checking in, we arrived and after that everything was great. It was a surprise to find the window was onto a corridor, but the air con was good so no need to open a window, and also helped to make the room quiet."
United Kingdom
Pat R.
The price is HK$941
HK$1,173 total
includes taxes & fees
29 Sept - 30 Sept
The Castle f
A compact living space with a bed, a dining area, and a kitchenette.

9. The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
The price is HK$941
HK$1,173 total
includes taxes & fees
29 Sept - 30 Sept
The Castle L - Twin Studio
A living room with a brown sofa, two red pillows, a small white table, and a floor lamp.

10. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is HK$941
HK$1,173 total
includes taxes & fees
29 Sept - 30 Sept
The Castle ᴳ
A compact, white front-loading washer and dryer unit in a corner of a room with a tiled floor and a small potted plant.

11. The Castle ᴴ

The Castle ᴴ
Downtown Philipsburg
8.0 out of 10, Very good, (2 reviews)
"Absolutely great place to stay. Only downside is there is a bird that treats her 2 AM and then a rooster from about 5 AM to 9 AM so make sure you bring your earplugs."
United States
Denise W.
The price is HK$1,059
HK$1,301 total
includes taxes & fees
1 Oct - 2 Oct
The Castle ᴴ
A covered outdoor area with a pool, chairs, and a table.

12. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is HK$684
HK$1,281 total
includes taxes & fees
29 Sept - 30 Sept
1-Bedroom Loft Apartment in Point Blanche
A beach with rows of sun loungers and umbrellas, a pier with a large ship, and a sailboat in the water.

13. Panoramic Ocean View Flat: St Maarten

Panoramic Ocean View Flat: St Maarten
Downtown Philipsburg
The price is HK$1,569
HK$2,000 total
includes taxes & fees
29 Sept - 30 Sept
Panoramic Ocean View Flat: St Maarten
An infinity pool with a clear view of the sea, a wooden table with food and drinks, and a lounge area with a view.

14. Luxury 4BR Villa w/ Private Pool & Ocean Views

Luxury 4BR Villa w/ Private Pool & Ocean Views
Indigo Bay
10.0 out of 10, Exceptional, (1 review)
"This property has a breathtaking view and is in the perfect location—close to stores and just minutes from the beaches.Fritz, the host, was amazing! The island had just gone through a major storm the day before we arrived, and despite the circumstances, Fritz was always available and ready to help with anything we needed. He even offered us an extra day to make up for any inconvenience, which was so thoughtful and appreciated.I would absolutely stay here again and would highly recommend this...
United States
Ms Light T.
The price is HK$3,720
HK$8,675 total
includes taxes & fees
29 Sept - 30 Sept
Luxury 4BR Villa w/ Private Pool & Ocean Views
A modern room with a dining area, large windows, and a view of the sea.

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

Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Indigo Bay
10.0 out of 10, Exceptional, (1 review)
"Our stay at Villa Solandra was nothing short of amazing. The check in process was seamless, the communication with the host was always smooth and timely, the villa itself was beautiful. It was clean, great location, and the view is insane. This place was part of the reason we had such a memorable time in St. Maarten. "
United States
Olivia G.
The price is HK$3,263
HK$6,562 total
includes taxes & fees
29 Sept - 30 Sept
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
A rooftop terrace with a pool, lounge chairs, and a view of the sea.

16. Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay

Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Sint Maarten
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$29,485
HK$31,540 total
includes taxes & fees
29 Sept - 30 Sept
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

17. Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1,308 reviews)
"The property was very conveniently located. The rooms were exactly like the pictures and the staff were very lovely."
United States
Erika
The price is HK$860
HK$1,109 total
includes taxes & fees
11 Oct - 12 Oct
Hilton Vacation Club Royal Palm St. Maarten
A high-rise hotel with a view of the sunset over a marina.

18. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (165 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is HK$953
HK$1,067 total
includes taxes & fees
29 Sept - 30 Sept
Simpson Bay Suites
A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

19. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (170 reviews)
"Very good"
United States
Alyssia
The price is HK$1,329
HK$2,232 total
includes taxes & fees
4 Oct - 5 Oct
The Hills Residence
A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.

20. condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.2 out of 10, Wonderful, (43 reviews)
"Love love the property was amazing. Will definitely return."
United States
Muneca
The price is HK$2,371
HK$3,504 total
includes taxes & fees
14 Oct - 15 Oct
condostmaarten by the sea -Adults Only-
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.
View all properties
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

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

10/10 Excellent
"The establishment was nice. Was a little sad they advertise an additional restaurant that they dont currently have. Other than that everything was good."
Tiffany 6-night trip
Posted 4 hours ago
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Find out more about Philipsburg

Search for holiday rentals in Philipsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Philipsburg using one of the methods below:

  • View our selection of featured holiday rentals in Philipsburg
  • Use the map to find apartments and other holiday homes in the Philipsburg neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Philipsburg while they last

Look no further and take a look at our great range of rental properties in Philipsburg!

Frequently asked questions

Can I find holiday rentals in Philipsburg?

Yes, there are holiday rentals close to the most popular sights in Philipsburg, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Philipsburg has to offer?

Philips Scott House Calinago: This highly rated holiday home rental in Philipsburg is in a shopping district, and equipped with air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities such as a microwave and free parking are also available for your convenience. Some other homes for rent in Philipsburg include Villa Flagrantia, Paradise at your pleasure and LUXURY VILLA! KILLER VIEWS! HIGHEST GUEST RATINGS ON ISLAND!.

How many holiday rentals are there in Philipsburg?

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

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 holiday rentals like in Philipsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Philipsburg. Holiday rentals offer extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.