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

Philipsburg Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Philipsburg vacation rentals

Deluxe Double Room | Down comforters, WiFi (free), bed sheets

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
$93 nightly
The price is $97
Sep 24 - Sep 25
Total with taxes and fees
July Apartments
Room, 1 King Bed, Non Smoking, Ocean View | Iron/ironing board, WiFi

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
$82 nightly
The price is $86
Oct 21 - Oct 22
Total with taxes and fees
MIDTOWN MOTEL SXM
Private kitchen

3. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
$140 nightly
The price is $150
Sep 22 - Sep 23
Total with taxes and fees
The Castle ᴷ
Interior

4. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
$155 nightly
The price is $166
Sep 22 - Sep 23
Total with taxes and fees
The Castle ᴵ
On the beach

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.
$211 nightly
The price is $223
Sep 22 - Sep 23
Total with taxes and fees
Cozy flat on the boardwalk!
Deluxe Apartment, Courtyard View | Blackout drapes, WiFi (free)

6. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
$207 nightly
The price is $217
Sep 28 - Sep 29
Total with taxes and fees
Philips Scott House Calinago
Interior

7. 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.
$140 nightly
The price is $150
Sep 26 - Sep 27
Total with taxes and fees
The Castle ᴶ
Interior

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.
$140 nightly
The price is $150
Sep 22 - Sep 23
Total with taxes and fees
The Castle f
Private kitchen

9. The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
$140 nightly
The price is $150
Sep 26 - Sep 27
Total with taxes and fees
The Castle L - Twin Studio
Interior

10. 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.
$155 nightly
The price is $166
Oct 1 - Oct 2
Total with taxes and fees
The Castle ᴴ
Living area

11. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
$140 nightly
The price is $150
Sep 22 - Sep 23
Total with taxes and fees
The Castle ᴳ
Outdoor dining

12. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
$153 nightly
The price is $158
Sep 26 - Sep 27
Total with taxes and fees
1-Bedroom Loft Apartment in Point Blanche
Beach towels

13. Panoramic Ocean View Flat: St Maarten

Panoramic Ocean View Flat: St Maarten
Downtown Philipsburg
$268 nightly
The price is $268
Sep 23 - Sep 24
Total with taxes and fees
Panoramic Ocean View Flat: St Maarten
Pool

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.
$1,207 nightly
The price is $1,259
Sep 22 - Sep 23
Total with taxes and fees
Luxury 4BR Villa w/ Private Pool & Ocean Views
Dining

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.
$854 nightly
The price is $891
Sep 28 - Sep 29
Total with taxes and fees
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Terrace/patio

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)
$4,299 nightly
The price is $4,299
Sep 22 - Sep 23
Total with taxes and fees
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
On the beach, sun loungers, beach umbrellas, beach towels

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, (1,303 reviews)
"Perfect location."
United States
Andre
$169 nightly
The price is $177
Oct 4 - Oct 5
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
Terrace/patio

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
$130 nightly
The price is $136
Sep 22 - Sep 23
Total with taxes and fees
Simpson Bay Suites
Amazing Top Floor Apartment | Balcony

19. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (169 reviews)
"Very good"
United States
Alyssia
$251 nightly
The price is $263
Oct 7 - Oct 8
Total with taxes and fees
The Hills Residence
Outdoor pool

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
$428 nightly
The price is $447
Oct 14 - Oct 15
Total with taxes and fees
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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"We love this Simpsons bay resort. We are repeat visitors. We are very comfortable here and love the location:)"
kimberly 7-night trip
Posted less than an hour ago
Simpson Bay Resort, Marina & Spa

Price trends for vacation rentals in Philipsburg

Less expensive
More expensive
Next month
June
January
$521
Month
Price
January
$608
February
$391
March
$401
April
$405
May
$373
June
$284
July
$319
August
$286
September
$317
October
$521
November
$437
December
$415
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Philipsburg. Select dates and complete search for nightly totals inclusive of taxes and fees.

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Philipsburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $86 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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 Front Street District.

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.