A turquoise beach with a cruise ship, palm trees, and a mountainous backdrop.

Philipsburg Vacation Rentals

Q: 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 .

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Dates

November 2026

December 2026

Check prices for these dates

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Our top choices for Philipsburg vacation rentals

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

1. MIDTOWN MOTEL SXM

Downtown Philipsburg

brenton

$74 nightly

Nov 20 - Nov 21

Total with taxes and fees

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

Madame's Estate

JoyAnn Carolyn

$114 nightly

Dec 12 - Dec 13

Total with taxes and fees

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

Downtown Philipsburg

$132 nightly

Nov 12 - Nov 13

Total with taxes and fees

A bedroom with a bed, bedside table, chair, and artwork on the walls.

4. The Castle ᴶ

Downtown Philipsburg

Neil C.

$132 nightly

Nov 12 - Nov 13

Total with taxes and fees

A living room with a brown sofa, two red pillows, a small white table, and a floor lamp.

5. The Castle ᴳ

Downtown Philipsburg

$132 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

6. The Castle L - Twin Studio

Downtown Philipsburg

$132 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Downtown Philipsburg

Pat R.

$132 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Downtown Philipsburg

Denise W.

$147 nightly

Nov 12 - Nov 13

Total with taxes and fees

A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

9. Philips Scott House Calinago

Downtown Philipsburg

$206 nightly

Nov 12 - Nov 13

Total with taxes and fees

A beach with rows of umbrellas and lounge chairs, a marina with boats, and a cruise ship docked in the background.

10. Cozy flat on the boardwalk!

Downtown Philipsburg

Robert H.

$187 nightly

Nov 12 - Nov 13

Total with taxes and fees

A hallway with a decorative gate, potted plants, and a fire extinguisher.

11. The Castle ᴵ

Downtown Philipsburg

$147 nightly

Nov 22 - Nov 23

Total with taxes and fees

A beach with rows of sun loungers and umbrellas, a pier with a large ship, and a sailboat in the water.

12. Panoramic Ocean View Flat: St Maarten

Downtown Philipsburg

$333 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Indigo Bay

"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...

Ms Light T.

$1,353 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern room with a dining area, large windows, and a view of the sea.

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

Indigo Bay

Olivia G.

$987 nightly

Nov 27 - Nov 28

Total with taxes and fees

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

Simpson Bay

Prem

$227 nightly

Dec 2 - Dec 3

Total with taxes and fees

A high-rise hotel with a view of the sunset over a marina.

16. Simpson Bay Suites

Simpson Bay

Manishkumar

$144 nightly

Nov 13 - Nov 14

Total with taxes and fees

A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.

17. condostmaarten by the sea -Adults Only-

Indigo Bay

Elouise

$527 nightly

Nov 13 - Nov 14

Total with taxes and fees

A beachfront property with multiple buildings, a beach, and a red arrow pointing to a specific building.

18. Beach Front Studio C3

Simpson Bay

Benjamin

$151 nightly

Nov 14 - Nov 15

Total with taxes and fees

A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

19. Mullet Bay Suites: Your Luxury Stay Awaits

Maho

Susan

$315 nightly

Nov 23 - Nov 24

Total with taxes and fees

A pool area with lounge chairs and a stone wall.

20. Modern apartment with shared pool and generator (2-2B)

Simpson Bay

$210 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Find vacation rentals that suit your style

Top Philipsburg Hotel Reviews

A swimming pool with lounge chairs and a table on a wooden deck, surrounded by greenery and a mountain view.

Villa Jwi Lavi Boutique Hotel

Cul de Sac

10/10 Excellent

My wife and I loved this place. It was smaller and quieter than your typical hotel or resort. The hosts provide a nice little breakfast each morning (croissants and baguettes with local jams, plus fresh fruit and juice). The pool is nice, as are the views. The property is a good location on the island, in my opinion. Easy drive to Anse Marcel on the northern tip (phenomenal beach up there). Also easy drive to Grand Case (best food ever) and Orient Beach (great scene in general). The hosts were...

Cameron

A glass table with a white mug and a loaf of bread, a decorative vase, and a poolside lounge area with a view of purple flowers and palm trees.

Pomme Cannelle Luxury Suites & Spa

Orient Bay

10/10 Excellent

Pauline & Jeremy!!! Fantastic warm welcome! You can tell that these owners absolutely love their guests. Too many details to mention from the private jacuzzi to concierge services provided by Pauline. Beautiful interiors, comfortable beds. Gated neighborhood 5 minutes on foot to Orient Bay beaches and restaurants. Good old fashioned bed and breakfast atmosphere. Oh!! The amazing, not-to-miss breakfast! Highly recommended.

Lara Abigail

A pool area with lounge chairs, umbrellas, and inflatable rings.

Le Martin Boutique Hôtel

Cul de Sac

10/10 Excellent

Elizabeth

A beach resort with palm trees, a pathway, and a view of the ocean.

Orient Beach Hotel

Orient Bay

10/10 Excellent

This is the perfect place to have an ocean view room that is beautifully done. The hotel doesn’t offer a ton of amenities, but it’s in a great location on a beautiful beach. Come here to enjoy time with a partner, have access to beach restaurants and activities and rent a car to explore the island. Our concierge, Junior, was amazing and saved us by getting our passports to us after we had already arrived to the airport!

Anonymous traveler

A balcony with a view of the sea, a bed with towels, and two white wicker chairs.

Le Temps des Cerises Hotel Beach

Grand Case

10/10 Excellent

The hotel, which is only a few weeks old, and which is owned by the same people who own Sol E Luna nearby, is a classy, first rate property, right on the beach in Grand Case, with a staff that couldn't have been more friendly and helpful. All nine rooms have balconies with full ocean views. The design and styling are very contemporary and absolutely perfect. And, oh, the dining scene in Grand Case can't be beat!

Len

Mullet Bay Suites: Your Luxury Stay Awaits

Maho

10/10 Excellent

I highly recommend Mullet Bay Suites for its cleanliness, modern amenities, and comfort. The suites offer stunning views, especially in the morning, and feature convenient parking and robust security. The property is just a short walk to the beach, adding to its appeal. The management is excellent, and we received a warm welcome from the property manager, Emmanuel, who greeted us with cold towels and local banana rum—a delightful touch! Emmanuel is attentive, kind, and responsive, providing...

Juanita

A coastal resort with a swimming pool, beach access, and lush greenery.

Grand Case Beach Club

Grand Case

10/10 Excellent

First time to the island. This resort was absolutely beautiful. Two areas for sun and beach. Beach chairs and umbrellas, water sports… we never had to wake up super early to get a chair which was awesome! We snorkeled around the resort, saw lots of fish, star fish, and found about 10 whole sand dollars! Food was very reasonably priced and delicious. Drinks were good - not watered down. Staff was very helpful and kind, check in was easy and our room was ready when we arrived. Rooms had all the...

Karrie

A covered outdoor seating area with wicker furniture and a view of the sea.

La Villa Hibiscus

Orient Bay

10/10 Excellent

We spent 4 nights at La Hibiscus. Really enjoyed everything about it. Florian gave us a free upgrade to the Jasmine suite. Large, comfortable bed, great shower and bathroom. Great terrace for sunning and looking at the mountains. We had the pool to ourselves which we loved. Very hands off approach by management which meant great privacy which we like. Only 5 minutes to Orient Beach….great choice of restaurants including a couple of breakfast places. Will definitely come back. FYI….renting a car...

Sid

A poolside bar with a view of a pool and lounge chairs.

Hotel L'Esplanade

Grand Case

10/10 Excellent

My wife and I stayed at the Hotel L'Esplanade for a week! And it was out first time here on the French side and we enjoyed it a lot. Very comfortable and spacious accommodations with large bedroom, bathroom and Living/dining room with the full kitchen if you decide to ignore all of the restaurants nearby and decide to make a meal yourself. Big, beautiful terrace to enjoy breakfast or sip wine while watching the sunset. The pool is peaceful, and the food is freshly grilled right before you, while...

Mikhail

A large, white-roofed villa with a pool, surrounded by lush greenery and a view of the ocean.

The Paradise Peak - Adults Only

Marigot

10/10 Excellent

Everything about this Inn was excellent! The owners greet you with a smile. My stay started with happy hour in the veranda overlooking the pool. During my three night stay, happy hour was the place to connect, meet the other guests staying at this unique B&B, and make new friends. The breakfasts were simple, but filling with lots of choices for varied tastes, including delicious island marmalades. In fact, I went to the supermarket to bring home the guava one — so delicious. This is a place...

Vincent

A beachside lounge with lounge chairs and umbrellas, overlooking the sea.

Holland House Beach Hotel

Downtown Philipsburg

10/10 Excellent

Ellen Wyszynski

A beachfront hotel with a pool, palm trees, and a clear blue sky.

Azure Hotel and Art Studio

Simpson Bay

10/10 Excellent

Mitchell

A swimming pool with clear blue water, a building with balconies, and palm trees.

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

10/10 Excellent

We rented a two bedroom unit (really two one bedroom units connected by a short hallway) with our 21 year-old triplets. It was a perfect setup for us. My wife and I took one unit, and our kids took the other. The resort is in a very convenient location- also very well-maintained. There are a number of restaurants and bars within walking distance, which our kids really liked because they could go out without waiting for us to drive them somewhere. There is a small grocery store about 100...

John

A wooden deck with a view of a beach and ocean.

Baker's Suites

Simpson Bay

10/10 Excellent

Kathy

A pool with lounge chairs and umbrellas, surrounded by palm trees and a clear sky.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

10/10 Excellent

Third stay in St Maarten/Martin since 1993. By far the nicest hotel of my 3 stays. While not directly on a beach, a short drive to Orient, or across the street to Dawn Beach at the Westin. We were on the upper level, building B and had a great view of the ocean across the street. Actually you can drove about anywhere on the island in 30 to 45 minutes depending on traffic. We stayed the first week of November 2015 and full season had not kicked in. The traffic is slow and you have to be...

Island visitor

A resort with multiple hotel buildings, a marina, and a clear blue ocean.

The Villas at Simpson Bay Resort

Pelican Key

10/10 Excellent

Angelice

A beach with clear turquoise waters, a sandy shore, and several beach umbrellas.

Palm Court Residence & Hotel at Orient Beach

Orient Bay

10/10 Excellent

Great staff! Had trouble with our rental car company and staff arranged to have different company drop car at hotel for us, such a breeze! Awesome morning breakfast, chocolate croissants were very tasty! Great proximity to the beach and a variety of restaurants in Orient Village. You MUST dine at La Table d'Antoine; best onion soup and duck breast w/5 vinegars, to die for!! Hotel has arrangement with Kakoa Beach Bar, so it as easy to get lounge chairs and umbrella each morning. If you're...

Pam

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 $78 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.

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 Rainforest Adventures St. Maarten.

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.

Philipsburg Vacation Rentals

Check prices for these dates

Our top choices for Philipsburg vacation rentals

1. MIDTOWN MOTEL SXM

2. July Apartments

3. The Castle ᴷ

4. The Castle ᴶ

5. The Castle ᴳ

6. The Castle L - Twin Studio

7. The Castle f

8. The Castle ᴴ

9. Philips Scott House Calinago

10. Cozy flat on the boardwalk!

11. The Castle ᴵ

12. Panoramic Ocean View Flat: St Maarten

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

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

15. Hilton Vacation Club Royal Palm St. Maarten

16. Simpson Bay Suites

17. condostmaarten by the sea -Adults Only-

18. Beach Front Studio C3

19. Mullet Bay Suites: Your Luxury Stay Awaits

20. Modern apartment with shared pool and generator (2-2B)

Find vacation rentals that suit your style

Top Philipsburg Hotel Reviews

Villa Jwi Lavi Boutique Hotel

10/10 Excellent

Find out more about Philipsburg

Everything you need to know about Philipsburg vacation rentals

Philipsburg vacation rentals: An excellent choice for every season

How to find incredible deals on Philipsburg rentals

Frequently Asked Questions

Can I find vacation rentals in Philipsburg?

What's the top vacation rental in Philipsburg?

How many vacation rentals are there in Philipsburg?

What can I see and do in Philipsburg?

What are vacation rentals like in Philipsburg?

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