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

Philipsburg Holiday Rentals

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Our top choices for Philipsburg holiday rentals

1. 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 NZ$146
includes taxes & fees
29 Sept - 30 Sept
MIDTOWN MOTEL SXM

2. 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 NZ$170
includes taxes & fees
25 Sept - 26 Sept
July Apartments

3. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is NZ$261
includes taxes & fees
25 Sept - 26 Sept
The Castle ᴷ

4. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is NZ$289
includes taxes & fees
25 Sept - 26 Sept
The Castle ᴵ

5. 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 NZ$384
includes taxes & fees
29 Sept - 30 Sept
Cozy flat on the boardwalk!

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 NZ$261
includes taxes & fees
26 Sept - 27 Sept
The Castle ᴶ

7. 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 NZ$261
includes taxes & fees
25 Sept - 26 Sept
The Castle f

8. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is NZ$397
includes taxes & fees
25 Sept - 26 Sept
Philips Scott House Calinago

9. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is NZ$261
includes taxes & fees
25 Sept - 26 Sept
The Castle ᴳ

10. The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
The Castle L - Twin Studio

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 NZ$289
includes taxes & fees
1 Oct - 2 Oct
The Castle ᴴ

12. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is NZ$285
includes taxes & fees
26 Sept - 27 Sept
1-Bedroom Loft Apartment in Point Blanche

13. Panoramic Ocean View Flat: St Maarten

Panoramic Ocean View Flat: St Maarten
Downtown Philipsburg
Panoramic Ocean View Flat: St Maarten

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 NZ$2,027
includes taxes & fees
29 Sept - 30 Sept
Luxury 4BR Villa w/ Private Pool & Ocean Views

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 NZ$1,501
includes taxes & fees
29 Sept - 30 Sept
Villa Solandra – 3BR Oceanfront Sunset w/ Pool

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 NZ$7,156
includes taxes & fees
29 Sept - 30 Sept
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay

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, (1,306 reviews)
"Perfect location."
United States
Andre
The price is NZ$309
includes taxes & fees
4 Oct - 5 Oct
Hilton Vacation Club Royal Palm St. Maarten

18. 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 NZ$476
includes taxes & fees
6 Oct - 7 Oct
The Hills Residence

19. 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 NZ$238
includes taxes & fees
28 Sept - 29 Sept
Simpson Bay Suites

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 NZ$780
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.
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Top Philipsburg Hotel Reviews

Find out more about Philipsburg

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Philipsburg holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Philipsburg. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Philipsburg. Seeing all the best attractions is bound to make you fall in love with Philipsburg. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Philipsburg short-term rentals, that won’t be hard to do.

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.