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

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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

$81 nightly

Dec 10 - Dec 11

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 11 - Dec 12

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

$129 nightly

Nov 11 - Nov 12

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.

$129 nightly

Nov 11 - Nov 12

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

$129 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

$129 nightly

Nov 11 - Nov 12

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.

7. The Castle ᴴ

Downtown Philipsburg

Denise W.

$143 nightly

Nov 11 - Nov 12

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.

8. The Castle f

Downtown Philipsburg

Pat R.

$129 nightly

Nov 11 - Nov 12

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 11 - Nov 12

Total with taxes and fees

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

10. The Castle ᴵ

Downtown Philipsburg

$143 nightly

Nov 22 - Nov 23

Total with taxes and fees

A balcony with a view of the sea, a table, and two chairs.

11. Cozy flat on the boardwalk!

Downtown Philipsburg

Robert H.

$198 nightly

Nov 11 - Nov 12

Total with taxes and fees

A terrace with wicker furniture, a hanging chair, and a view of boats at a marina.

12. Panoramic Ocean View Flat: St Maarten

Downtown Philipsburg

$327 nightly

Nov 11 - Nov 12

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.

$1,272 nightly

Nov 11 - Nov 12

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.

$999 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

$167 nightly

Nov 22 - Nov 23

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 11 - Nov 12

Total with taxes and fees

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

17. Mullet Bay Suites: Your Luxury Stay Awaits

Maho

Kenneth

$348 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern kitchen with a dining area, a grey sofa, and a TV.

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

Grand-Case

$144 nightly

Dec 10 - Dec 11

Total with taxes and fees

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-

Indigo Bay

Elouise

$527 nightly

Nov 11 - Nov 12

Total with taxes and fees

A poolside area with a wooden table, lounge chairs, and a view of the ocean.

20. Blue Sail Apartments - Two-Bedroom Apartments

Pelican Key

Heidi

$130 nightly

Nov 11 - Nov 12

Total with taxes and fees

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Find vacation rentals that suit your style

Top Philipsburg Hotel Reviews

A balcony with a view of a beach and ocean.

Holland House Beach Hotel

Downtown Philipsburg

10/10 Excellent

Ellen Wyszynski

July Apartments

Madame's Estate

10/10 Excellent

Dulcie

A neatly made bed with a red bedspread, two matching lamps on either side, and a colorful pillow on the headboard.

Alicia's Inn

Downtown Philipsburg

10/10 Excellent

Jeanina the manager and Renicia were fantastic hosts. They went out of their way to ensure you had a great stay. Customer service here at times even exceeded 3 & 4 star properties. Complimentary wifi that consistently worked hassle free. Stayed several days. A clean, bright, well maintained 2 1/2 Star+ property for value minded travelers. Would stay here again. Would recommend this boutique property to a friend.

Leeward Islands

A pool area with a waterfall feature, surrounded by wooden deck chairs and covered seating areas.

Belair Beach Hotel

Belair

10/10 Excellent

Have been going to Sint Maarten for 7 years now. Stayed at a few places, next door at Divi twice. Last year, Divi changed exchange rules.Would not let us exchange.(3-5 yr rule?) We loved that area/the employees at Divi.Knew Belair was next door. I was very tentative about how our unit at Belair was going to compare. I can now tell you-I have already booked my exchange for this year back at Belair!! The fact that all unit are RIGHT ON THE BEACH is great. Even if you don't like being in the water,...

luvsintmaaten

A pool area with lounge chairs, palm trees, and a view of the ocean.

Oceans at Divi Little Bay

Philipsburg

10/10 Excellent

All the staff members were amazing, like Ms. Sandrine at the reception desk. Everybody was very helpful and patient with us. The hotel is new and clean, the beach is nice although it was rarely cleaned. We had an All-Inclusive package. The food was good, there were no lines, just some waiting time, as usual. The only part that we did not like was the entertainment. The music by the Gizmo's bar was very loud, it was not pleasant to eat there. The only outdated schedule for the entertainment was...

Sofiya

A bedroom with a bed, bedside tables, a chair, a desk, and a mirror.

Calinago Friendly Family Sxm Home

Downtown Philipsburg

10/10 Excellent

charity

A covered outdoor seating area with wicker furniture and potted plants.

L'Esperance Hotel

Philipsburg

10/10 Excellent

juana

A room with a sofa, a glass table with a bottle, curtains, a TV, and a view of the ocean.

Horizon View Beach Hotel

Downtown Philipsburg

10/10 Excellent

The hotel is in a very nice location, 10 steps and you are on the beach! The hotel is cooperating with a nice little bar , good drinks and nice service, right outside called The Pink Flamingo, ask for Stephan.... so you can get free deck chairs and sun umbrella, fantastic! A local Supermarket in a walking distance otherwise take the local bus for € 1.50 and in few minutes it will take to a bigger one. Buses are leaving right behind the hotel from the Backstreet taking you allover this...

Monica

A circular window view of a beach with a swimming pool, palm trees, and a sandy area with umbrellas.

Seaview Beach Hotel

Downtown Philipsburg

10/10 Excellent

Seaview is in the middle of Philipsburg and walking distance to restaurants, stores and beach rentals. Three tours where they picked me up within walking distance of Seaview are listed below. I was by myself so they combined me with a group. 1)Bernard's island tour with beach $45 US. 2)Tiki Hut snorkeling park $51. 3)Coconut Reef surfing school, $69. 95% of the town closes as soon as the cruise ship leaves. No night life. No ship= empty town. The only thing open is McDonald's (10am-11pm...

Anonymous traveler

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 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 person sitting at a table with a book, a croissant, and a cup.

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

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

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 $84 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

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Upfront pricing

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 ᴴ

8. The Castle f

9. Philips Scott House Calinago

10. The Castle ᴵ

11. Cozy flat on the boardwalk!

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. Mullet Bay Suites: Your Luxury Stay Awaits

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

19. condostmaarten by the sea -Adults Only-

20. Blue Sail Apartments - Two-Bedroom Apartments

Find vacation rentals that suit your style

Top Philipsburg Hotel Reviews

Holland House Beach 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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