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
7.6 out of 10, Good, (76 reviews)
"The place was amazing"
United States
brenton
The price is NZ$150
includes taxes & fees
9 Nov - 10 Nov
MIDTOWN MOTEL SXM

2. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (254 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is NZ$224
includes taxes & fees
8 Dec - 9 Dec
July Apartments

3. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is NZ$255
includes taxes & fees
9 Nov - 10 Nov
The Castle ᴷ

4. 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$255
includes taxes & fees
11 Nov - 12 Nov
The Castle ᴶ

5. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is NZ$255
includes taxes & fees
13 Nov - 14 Nov
The Castle ᴳ

6. The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
The price is NZ$255
includes taxes & fees
11 Nov - 12 Nov
The Castle L - Twin Studio

7. 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$285
includes taxes & fees
9 Nov - 10 Nov
The Castle ᴴ

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 NZ$255
includes taxes & fees
9 Nov - 10 Nov
The Castle f

9. 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$388
includes taxes & fees
9 Nov - 10 Nov
Philips Scott House Calinago

10. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The Castle ᴵ

11. 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$353
includes taxes & fees
9 Nov - 10 Nov
Cozy flat on the boardwalk!

12. Panoramic Ocean View Flat: St Maarten

Panoramic Ocean View Flat: St Maarten
Downtown Philipsburg
The price is NZ$635
includes taxes & fees
11 Nov - 12 Nov
Panoramic Ocean View Flat: St Maarten

13. 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$2,524
includes taxes & fees
10 Nov - 11 Nov
Luxury 4BR Villa w/ Private Pool & Ocean Views

14. 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$1,827
includes taxes & fees
27 Nov - 28 Nov
Villa Solandra – 3BR Oceanfront Sunset w/ Pool

15. 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, (1,332 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is NZ$389
includes taxes & fees
11 Nov - 12 Nov
Hilton Vacation Club Royal Palm St. Maarten

16. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (169 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is NZ$273
includes taxes & fees
9 Nov - 10 Nov
Simpson Bay Suites

17. Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.6 out of 10, Exceptional, (185 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
The price is NZ$586
includes taxes & fees
10 Nov - 11 Nov
Mullet Bay Suites: Your Luxury Stay Awaits

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

A View of Airplanes, the Beach, and Lolos in Grand-Case
Grand-Case
The price is NZ$265
includes taxes & fees
9 Nov - 10 Nov
A View of Airplanes, the Beach, and Lolos in Grand-Case

19. condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.2 out of 10, Wonderful, (44 reviews)
"Every thing was perfect, clean , quiet,beautiful views, definitely on my list to revisit.The host was very informative about the whole process he was very polite guy"
United States
Elouise
The price is NZ$993
includes taxes & fees
9 Nov - 10 Nov
condostmaarten by the sea -Adults Only-

20. Blue Sail Apartments - Two-Bedroom Apartments

Blue Sail Apartments - Two-Bedroom Apartments
Pelican Key
6.0 out of 10, (3 reviews)
"Check in was seamless accommodations were exactly as expected and the staff were very friendly. We noticed many things were brand new and we were informed that there was a new owner- appears that they are working hard!"
United States
Heidi
The price is NZ$239
includes taxes & fees
9 Nov - 10 Nov
Blue Sail Apartments - Two-Bedroom Apartments
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 LUXURY VILLA! KILLER VIEWS! HIGHEST GUEST RATINGS ON ISLAND! and Villa Flagrantia, Paradise at your pleasure.

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.