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

Philipsburg Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Philipsburg holiday rentals

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

1. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.6 out of 10, Good, (75 reviews)
"The place was amazing"
United States
brenton
The price is AU$114
includes taxes & fees
27 Oct - 28 Oct
MIDTOWN MOTEL SXM
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

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 AU$160
includes taxes & fees
25 Oct - 26 Oct
July Apartments
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 Castle ᴷ
A bedroom with a bed, bedside table, chair, and artwork on the walls.

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

5. The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
The Castle L - Twin Studio
A living room with a brown sofa, two red pillows, a small white table, and a floor lamp.

6. The Castle ᴳ

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

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

8. 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 AU$239
includes taxes & fees
25 Oct - 26 Oct
The Castle ᴴ
A balcony with a view of the sea, a table, and two chairs.

9. 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 AU$323
includes taxes & fees
4 Nov - 5 Nov
Cozy flat on the boardwalk!
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

10. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is AU$308
includes taxes & fees
24 Nov - 25 Nov
Philips Scott House Calinago
A covered outdoor area with a pool, chairs, and a table.

11. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is AU$343
includes taxes & fees
28 Oct - 29 Oct
1-Bedroom Loft Apartment in Point Blanche
A terrace with wicker furniture, a hanging chair, and a view of boats at a marina.

12. Panoramic Ocean View Flat: St Maarten

Panoramic Ocean View Flat: St Maarten
Downtown Philipsburg
The price is AU$401
includes taxes & fees
27 Oct - 28 Oct
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.

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 AU$1,867
includes taxes & fees
26 Oct - 27 Oct
Luxury 4BR Villa w/ Private Pool & Ocean Views
A modern room with a dining area, large windows, and a view of the sea.

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.
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

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, (1,323 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is AU$276
includes taxes & fees
5 Nov - 6 Nov
Hilton Vacation Club Royal Palm St. Maarten
A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

16. 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 AU$448
includes taxes & fees
1 Nov - 2 Nov
Mullet Bay Suites: Your Luxury Stay Awaits
A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

17. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (172 reviews)
"Very good"
United States
Alyssia
The price is AU$493
includes taxes & fees
6 Nov - 7 Nov
The Hills Residence
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, (168 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is AU$215
includes taxes & fees
25 Oct - 26 Oct
Simpson Bay Suites
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-

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 AU$708
includes taxes & fees
26 Oct - 27 Oct
condostmaarten by the sea -Adults Only-
A balcony with white railings, a bench, and two chairs.

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

Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
South Reward
10.0 out of 10, Exceptional, (3 reviews)
"Home away from home "
United States
Trevayne
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"Awesome staff"
Alanor 3-night trip
Posted 4 hours ago
Simpson Bay Resort, Marina & Spa

Find out more about Philipsburg

Everything you need to know about Philipsburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Philipsburg holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Philipsburg holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Philipsburg holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Philipsburg holiday rentals we have selected for you start as low as AU$114 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Philipsburg rentals

At Expedia, we put the best Philipsburg holiday 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 holiday.

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 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.