Philipsburg holiday lettings

We found 3,239 holiday rentals — enter your dates for availability

Discover a selection of 73 apartments, 29 flats and other holiday rentals in Philipsburg that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Philipsburg

Showing deals for:15 May - 22 May

Image gallery for Luxury 5 Bedroom Villa

Pool Deck
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Luxury 5 Bedroom Villa

Collectivité de Saint-Martin

9% off
Price is £6,756
for 7 nights, 1 villa
£965 per night
includes taxes & fees
Luxury 5 Bedroom Villa

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

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    More space, more privacy, more amenities — more value

Head to the captivating city of Philipsburg

Enjoy the entertainment and other features of Philipsburg. Well known for its beaches, shopping and island views, this romantic city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Philipsburg

Are you searching for attractions to visit while you're in town? Venture out of your holiday home and check out everything that Philipsburg has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Mullet Bay Golf (4.9 mi / 7.9 km)
  • Aurora International Golf Club (11.4 mi / 18.3 km)

Exploring the beaches and other natural features in Philipsburg

Travellers enjoy Philipsburg for its island views and seaside. Whether you're an adventurous traveller or just want to appreciate the scenery, Philipsburg is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Maho Beach (4.9 mi / 7.8 km)
  • Great Bay Beach (0.7 mi / 1.1 km)
  • Little Bay Beach (1.2 mi / 1.9 km)
  • Dawn Beach (2.4 mi / 3.9 km)
  • Kim Sha Beach (3.1 mi / 4.9 km)
  • Flamingo Beach (3.2 mi / 5.2 km)

Seasonal weather in Philipsburg

Travellers enjoy Philipsburg for its boating. If you're planning a holiday around warm-weather activities, September, August, October and July are the hottest months to visit, when temperatures average 27°C.

Transport options to and around Philipsburg

The nearest airport is in Philipsburg (SXM-Princess Juliana Intl.), located 4.4 mi (7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Grand Case (SFG-L'Esperance), which is 5 mi (8.1 km) away.

Frequently asked questions

What is the best area to stay in Philipsburg when booking a holiday rental?
When considering a holiday rental in Philipsburg, Sint Maarten, a popular area to stay in is the beachfront neighbourhood of Great Bay. This location offers stunning views and easy access to the beautiful sandy beach that lines the waterfront. Here, you'll find a vibrant atmosphere with a variety of beachfront bars and restaurants, making it superb for those who enjoy a lively social scene. Not far from Great Bay is Fort Amsterdam, a historic site that provides insight into the island's historic past, along with breathtaking panoramas of the coastline.

Another appealing area is the lively Front Street, known for its duty-free shopping and a range of dining options. This bustling street is at the heart of Philipsburg and is superb for those who enjoy immersing themselves in local culture. Along Front Street, visitors can explore the Sint Maarten Museum, which showcases the island's rich history and heritage.
How much does it cost to rent a holiday home in Philipsburg?
Prices for holiday rentals in Philipsburg vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Philipsburg to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Philipsburg holiday house rentals?
You can find great discounts on house rentals in Philipsburg on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Philipsburg?
For renting a beach house in Philipsburg, Sint Maarten, the area along Great Bay Beach is particularly appealing. This vibrant stretch of coastline offers a variety of holiday rentals, including charming beachfront villas and modern apartments. Many properties in this area come with amenities such as outdoor terraces, private pools, and direct access to the sandy beach, making them great for families or groups looking to enjoy the sun and sea.

The neighbourhood of Simpson Bay, just a short drive from Philipsburg, is another excellent choice for beach house rentals. Here, you'll find a mix of waterfront properties featuring spacious living areas, well-equipped kitchens, and often stunning views of the lagoon. Some rentals also offer amenities like private docks, which are ideal for those wishing to explore the nearby islands by boat.

Additionally, the nearby Maho Beach area is known for its lively atmosphere and proximity to the famous Sunset Beach Bar, where visitors can enjoy the great experience of watching planes land just overhead. Beach houses in this region often come with outdoor dining spaces, BBQ facilities, and proximity to local shops and restaurants.
Are there any houseboat rentals in Philipsburg?
In Philipsburg, houseboat rentals are indeed available, offering a unique and charming way to experience this beautiful destination. Visitors can expect several houseboats moored in picturesque settings, often with stunning views of the Caribbean Sea and easy access to the beach. These rentals typically come with amenities such as fully equipped kitchens, comfortable living areas, and outdoor decks for sunbathing or enjoying the sunset. Staying on a houseboat allows travellers to immerse themselves in the vibrant local culture while being close to attractions like the historic Front Street and the lively Great Bay Beach.
What is the most popular type of holiday rental accomodation in Philipsburg?
In Philipsburg, villas are the most popular type of holiday rental, with around 82 available throughout the area. These spacious properties often come with luxurious amenities such as private pools, outdoor terraces, and stunning views of the Caribbean Sea, making them ideal for families or groups seeking a lavish getaway.

Apartments are also quite common, with about 51 options found in convenient locations near the beach and local attractions like the Great Bay Beach and the historic Fort Amsterdam. Most apartments feature fully equipped kitchens, comfortable living areas, and some even provide balconies for enjoying the warm sea breezes.
Are there any family house rentals in Philipsburg?
In Philipsburg, Sint Maarten, there is a wealth of family-friendly rental options available, with around 96 properties to choose from. This vibrant area is known for its stunning beaches and lively atmosphere, making it an excellent choice for family gatherings. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor terraces or balconies where guests can enjoy the tropical scenery.
Can I rent a holiday home with a pool or hot tub in Philipsburg?
In Philipsburg, Sint Maarten, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 129 options to choose from. The city, known for its stunning beaches and vibrant atmosphere, offers various neighbourhoods where travellers can find these amenities, including the popular Great Bay area and the more tranquil Simpson Bay.
Can I find long-stay holiday rentals in Philipsburg?
A long-stay holiday rental in Philipsburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Philipsburg?
In Philipsburg, there are numerous pet-friendly house rentals available, with around 31 options for travellers to consider. Many of these properties are located close to the beautiful beaches, providing easy access to sun-soaked shores and inviting waters. Expect to find holiday rentals equipped with amenities such as private pools, outdoor terraces, and fully furnished kitchens, making them comfortable for families and groups travelling with pets.

The beachfront area near Great Bay is particularly appealing, where you'll discover a range of charming villas and apartments with stunning ocean views. These accommodations often feature spacious living areas and pet-friendly policies, ensuring that your furry companions can enjoy the holiday as well. Additionally, the proximity to local shops, restaurants, and vibrant nightlife adds to the convenience and enjoyment of your stay.
Are there any remote work holiday rentals in Philipsburg?
In Philipsburg, Sint Maarten, there are numerous remote work holiday rentals available, with around 162 options to choose from. Travellers can expect a variety of properties that cater to remote working needs, often featuring dedicated office spaces, desks, and fast Wi-Fi to ensure productivity during their stay. Many accommodations also include amenities such as ergonomic desk chairs and laptop workspaces, allowing for a comfortable working environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Philipsburg holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Philipsburg with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Philipsburg?
In Philipsburg, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many rentals also feature a pool, providing a refreshing spot for relaxation after a day of exploring the nearby beaches or shopping areas.
When is the best time to visit Philipsburg for a holiday rental?
The best time to visit Philipsburg for a holiday rental is during the peak season from July to September. This period attracts sun-seeking travellers eager to bask in the tropical climate and enjoy vibrant beach life. With temperatures typically hovering around 30°C, it's great for indulging in outdoor activities like swimming, snorkelling, and exploring the stunning coastline.

July, in particular, stands out as the most popular month, as visitors flock to partake in the lively atmosphere and numerous festivities, including the renowned Carnival celebrations. The warm, sunny days create an inviting environment for both relaxation and adventure, making it an excellent choice for those seeking a lively holiday experience.

For those looking to save a bit while still enjoying the beauty of Philipsburg, February presents a wonderful alternative. This month, often regarded as the low season, offers visitors a more tranquil experience with fewer crowds. It's a great time to take leisurely strolls along the beach or explore local shops and restaurants without the hustle and bustle of peak tourism.
How early should I book a Philipsburg holiday rental?
Book your Philipsburg holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Philipsburg?
In Philipsburg, visitors can explore a range of attractions that showcase the island's vibrant culture and natural beauty. The historic Front Street is lined with colourful shops and offers a lively atmosphere, great for those looking to indulge in some retail therapy or sample local cuisine. Nearby, Fort Amsterdam provides a glimpse into the island's historic past, with stunning views of the waterfront.

The Great Bay Beach is another highlight, where holiday rentals offer easy access to the sandy shores and crystal-clear waters, ideal for sunbathing and water sports. For a taste of local history and art, the Sint Maarten Museum is located not far from the centre and provides insights into the island's rich heritage.
Can I change or cancel my Philipsburg home rental booking on Vrbo?
To find Philipsburg holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Philipsburg holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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