Philipsburg vacation rentals

We found 3,268 vacation rentals — enter your dates for availability

Discover a selection of 69 apartments, 37 condos, and other vacation rentals in Philipsburg that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll find the amenities you need and want, which might include parking and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Philipsburg

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Find out more about Philipsburg

Find out more about Philipsburg

Why visit Philipsburg

  1. Beautiful Beaches: Relax on stunning beaches with soft sands and crystal-clear waters.
  2. Cultural Experiences: Immerse yourself in the local culture through vibrant events and historical sites.
  3. Charming Downtown: Explore the lively downtown area filled with shops, restaurants, and local art.
  4. Outdoor Activities: Enjoy a variety of excursions and outdoor adventures in breathtaking surroundings.
  5. Diverse Accommodations: Choose from a range of vacation rentals, from cozy apartments to luxurious villas.

Popular types of accommodation in Philipsburg

Planning a getaway to Philipsburg? The excitement begins with finding the perfect place to stay! From charming apartments and cozy condos to luxurious villas and cabin rentals, Philipsburg offers a variety of accommodations to suit every traveler's needs. Discover the best vacation rentals in Philipsburg that provide comfort and convenience, ensuring a memorable experience in this beautiful destination.

  • Apartments: The top choice for vacation rentals in Philipsburg, offering convenient amenities and close proximity to attractions.
  • Condos: A popular option for travelers seeking a blend of comfort and luxury, often featuring stunning views and shared facilities.
  • Villas: Ideal for those desiring spaciousness and privacy, perfect for families or groups wanting a more upscale experience.
  • Houses: A great option for visitors looking for a home-like atmosphere, suitable for families or friends traveling together.**

Top attractions in Philipsburg

Philipsburg, Sint Maarten, is perfect for beach and outdoor vacations, offering stunning scenery and cultural experiences. Popular attractions include beautiful beaches, vibrant bays, and modern educational institutions. Visitors can explore a range of activities such as a photo tour, bookstore trail, and various vacation rentals. Don't miss the chance to relax on the beach and immerse yourself in the local culture while enjoying this tropical paradise.

  1. Great Bay Beach: A stunning stretch of golden sand with crystal-clear waters, Great Bay Beach offers a perfect spot for sunbathing and swimming. Enjoy vibrant beach vibes, local eateries, and water sports for an exhilarating day in the sun.
  2. University of St. Martin: This modern university provides a unique blend of academia and urban energy. Explore its beautiful campus and enjoy the lively atmosphere, ideal for those interested in local culture and education.
  3. Fort Amsterdam: A historic fort with rich cultural significance, Fort Amsterdam offers panoramic views of the harbor. Discover its fascinating history and enjoy the serene surroundings that reflect Sint Maarten's heritage.

Things to do recommended for couples

For a romantic getaway in Philipsburg, stroll along the enchanting Philipsburg Boardwalk, where you can soak in the beach vibes and enjoy the beautiful ocean views. It's the perfect spot for couples to relax, dine, and create unforgettable memories together.

Things to do recommended for families

Families visiting Philipsburg can experience the excitement of Rainforest Adventures St. Maarten, a recreation park that offers wellness and relaxation vibes, perfect for creating lasting memories together. It's an excellent destination for kids to enjoy outdoor fun while parents unwind in a beautiful setting.

Things to do recommended for groups

Experience the thrill of gaming at Paradise Plaza or Hollywood Casino, both offering vibrant city vibes just 3 miles from Philipsburg. For a laid-back day, enjoy a round of golf at Mullet Bay Golf, 5 miles away, surrounded by beautiful outdoor scenery.

What do I need to keep in mind when booking a vacation in Philipsburg

When planning your trip—whether you’re with a group, traveling as a family, bringing your pets along, or seeking extended stays—be sure to prioritize your preferences when filtering options. Here are some helpful booking tips for Vrbo.

  • Traveling to Philipsburg with a group: Think about how many bedrooms you require, as well as any additional features like a full kitchen or outdoor area for group activities. The good news is that you can easily filter for all these options and more on Vrbo.
  • Traveling to Philipsburg with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Philipsburg: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Philipsburg: If you're searching for vacation rentals that offer discounts for stays of a month or longer, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Philipsburg

Philipsburg, Sint Maarten, offers an unforgettable vacation experience with its stunning beaches and vibrant atmosphere. Explore the charming downtown area, relax in tropical paradise settings, and enjoy excursions that cater to both romantic getaways and family-friendly adventures. Nearby neighborhoods provide breathtaking scenery and opportunities for outdoor activities, making Philipsburg the perfect destination for a week of relaxation and exploration in this Caribbean gem.

  • Simpson Bay: Located only 3 miles from Philipsburg, Simpson Bay is a vibrant coastal city that beckons travelers with its stunning beaches and picturesque scenery. Known for its laid-back atmosphere, visitors can enjoy a variety of outdoor activities, from sunbathing on the beautiful sandy shores to exploring the vibrant boardwalk lined with shops and restaurants. Notable attractions include the famous nudist beach and the serene bay, perfect for water sports enthusiasts. With a range of resorts that cater to all types of travelers, Simpson Bay is an ideal destination for relaxation and adventure alike.
  • Lowlands: Just 5 miles from Philipsburg, Lowlands is a captivating area that offers an inviting mix of stunning natural beauty and recreational opportunities. This scenic locale is renowned for its beautiful beaches and outdoor experiences, making it a favorite among sun-seekers and nature lovers. Visitors can explore the area’s upscale resorts and enjoy leisurely strolls along the boardwalk. The nearby nudist beach and tranquil bay add to the allure, providing a perfect setting for water activities and sunbathing. Lowlands is a must-visit for those looking to unwind and soak up the sun.
  • Oyster Pond: Situated just 2 miles from Philipsburg, Oyster Pond is a serene and scenic destination that captivates travelers with its picturesque landscape and tranquil waters. This charming area is ideal for beach lovers and outdoor enthusiasts alike, offering opportunities for relaxation and exploration. Visitors can stroll along the scenic boardwalk, enjoy the local resorts, and take in the stunning views of the bay. With access to beautiful beaches, including a nudist beach, Oyster Pond promises a delightful escape for those looking to bask in the sun and enjoy the natural beauty of Sint Maarten.

Best time to go to Philipsburg

If you're planning a trip to Philipsburg, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs in March to April and July, while off-peak times, like February, May and October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January76.6°F (24.8°C)No Rain (Dry)Mostly SunnyAverageAverage
February76.1°F (24.5°C)No Rain (Dry)Mostly SunnySlightly LowAverage
March76.3°F (24.6°C)No Rain (Dry)Mostly SunnySlightly HighAverage
April77.0°F (25.0°C)No Rain (Dry)Mostly SunnySlightly HighAverage
May78.4°F (25.8°C)Light RainMostly SunnySlightly LowAverage
June79.9°F (26.6°C)Light RainMostly SunnyAverageSlightly Low
July80.4°F (26.9°C)Light RainMostly SunnySlightly HighSlightly High
August81.0°F (27.2°C)Light RainMostly CloudyAverageSlightly High
September81.3°F (27.4°C)Light RainMostly SunnyAverageSlightly Low
October80.8°F (27.1°C)Light RainMostly CloudySlightly LowAverage
November79.5°F (26.4°C)Light RainMostly CloudyAverageSlightly Low
December78.1°F (25.6°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash™ on your whole booking. Being the organizer has its perks! Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash™ on qualifying stays. Sign up today and start enjoying the benefits!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your existing travel arrangements, or review your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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 things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Philipsburg a one-of-a-kind vacation spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

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

Exploring the beaches and other natural features in Philipsburg

Travelers enjoy Philipsburg for its island views and seaside. Whether you're looking for adventure or just want to take in the scenery, Philipsburg is a great place to get outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Orient Bay Beach (4.6 mi / 7.4 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)
  • Flamingo Beach (3.2 mi / 5.2 km)
  • Coconut Grove Beach (3.3 mi / 5.3 km)

Seasonal weather in Philipsburg

Travelers enjoy Philipsburg for its boating. If you're planning a vacation around warm-weather activities, September, August, October and July are the hottest months to visit, when temperatures average 81°F.

Transportation options to and around Philipsburg

The nearest airport is in Princess Juliana Intl. Airport (SXM), located 4.4 mi (7 km) from the city center. 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 vacation rental?
When looking for the best area to stay in Philipsburg, Sint Maarten for your vacation rental, consider the Great Bay area. This vibrant neighborhood is popular for its stunning beachfront views and easy access to various amenities. Here, you'll find an abundance of vacation properties ranging from charming condos to luxurious beachfront villas, making it a favored choice among visitors.

One of the top attractions nearby is the beautiful Great Bay Beach, where you can relax on soft sands or engage in water sports. Additionally, the area is home to the historic Fort Amsterdam, offering a glimpse into the island's rich history and breathtaking panoramic views of the coastline. Staying in the Great Bay area allows you to immerse yourself in local culture while enjoying convenient access to shopping and dining options along the lively boardwalk.

Another great option is the Philipsburg area itself, which offers a bustling atmosphere with a variety of vacation rentals available, including stylish apartments and cozy guesthouses. This area is superb for those who want to be in the heart of the action. You'll be close to the famous Front Street, known for its duty-free shops and lively marketplaces, as well as the scenic Sint Maarten Museum, which showcases the island's history and culture.
How much does it cost to rent a vacation home in Philipsburg?
Prices for vacation 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 vacation 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 an excellent choice. This picturesque beach offers a variety of vacation rentals that provide stunning ocean views and direct access to the sandy shores. Many properties in this area feature amenities such as private balconies, outdoor dining spaces, and fully equipped kitchens, superb for enjoying the coastal lifestyle.

Additionally, the vicinity of Front Street is ideal for travelers looking for a vibrant atmosphere. Here, you'll find beachfront condos and villas that often include pools, fitness centers, and proximity to local shops and restaurants, making it convenient to experience the local culture and cuisine.

Just a short distance from Philipsburg, the Simpson Bay area presents even more options, with waterfront properties that may include features like private docks, outdoor lounges, and access to water sports activities. This region is known for its lively nightlife and beachfront bars, adding to the allure for those seeking both relaxation and entertainment.
Are there any houseboat rentals in Philipsburg?
Yes, you can find houseboat rentals in Philipsburg, Sint Maarten. These unique accommodations offer a charming way to experience the beauty of the Caribbean. Travelers can expect amenities such as comfortable sleeping areas, kitchenette facilities for preparing meals, and outdoor decks to enjoy the stunning views of the harbor and surrounding waters. Staying on a houseboat allows guests to be close to points of interest like Great Bay Beach and the vibrant local markets, providing a distinctive blend of relaxation and adventure.
What is the most popular type of vacation rental accomodation in Philipsburg?
In Philipsburg, villas are the most popular type of vacation rental, with about 86 available throughout the area. These luxurious properties often feature multiple bedrooms, private pools, and stunning ocean views, providing an ideal setting for relaxation and entertainment. Many villas include amenities such as fully equipped kitchens, outdoor dining areas, and spacious living rooms, making them superb for families or groups looking to enjoy the beautiful Caribbean surroundings.

Apartments are also quite common, with around 48 options available. These accommodations generally offer a more home-like atmosphere, often including kitchens, cozy living spaces, and balconies to enjoy the tropical climate. For those seeking a more compact option, there are about 29 condos that provide similar amenities, typically with access to shared facilities like pools and fitness areas.

In addition to these, there are about 19 vacation houses which cater to travelers wanting a bit more space, featuring private yards and outdoor spaces. Lastly, there are several houseboats available, offering a great experience for those looking to stay on the water.
Are there any family house rentals in Philipsburg?
In Philipsburg, Sint Maarten, there are numerous family-friendly house rentals available, with around 92 options to choose from. The area features a variety of neighborhoods that cater to families, offering comfortable accommodations close to stunning beaches and local attractions. Many properties include spacious living areas, fully equipped kitchens for family meals, and outdoor spaces great for children to play.

Visitors can enjoy the vibrant atmosphere of Great Bay Beach, just a short distance away, where families can enjoy water sports or relax under the sun. Additionally, the nearby Philipsburg Boardwalk offers shops, restaurants, and opportunities for leisurely strolls along the waterfront. Outdoor activities, such as snorkeling and exploring the island's natural beauty, are easily accessible from these rentals, ensuring a memorable stay for everyone.
Can I rent a vacation home with a pool or hot tub in Philipsburg?
In Philipsburg, Sint Maarten, travelers can find a variety of vacation homes available for rent that feature pools and hot tubs, with around 130 options to choose from. This stunning Caribbean destination offers several neighborhoods where these properties are located, including the beachfront areas close to Great Bay Beach, known for its beautiful views and proximity to local attractions.

Rentals in Philipsburg typically come with amenities such as private pools, relaxing hot tubs, and outdoor spaces great for enjoying the tropical climate. Many properties also include fully equipped kitchens, spacious living areas, and terraces or balconies that offer stunning ocean or sunset views.
Can I find long-stay vacation rentals in Philipsburg?
A long-stay vacation rental in Philipsburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Philipsburg?
In Philipsburg, Sint Maarten, there are several pet-friendly house rentals available, with options that cater to various group sizes and preferences. Many of these vacation homes come equipped with modern amenities, including fully equipped kitchens, spacious living areas, and outdoor spaces such as patios or balconies, superb for enjoying the Caribbean breeze. Some properties may even offer private pools or easy access to nearby beaches, making them ideal for families or groups traveling with pets.

The area boasts beautiful beaches like Great Bay Beach, which is just a short distance from many rentals, providing ample opportunities for walks and relaxation by the sea. Additionally, the vibrant downtown area offers pet-friendly cafes and shops, allowing travelers to enjoy the local culture while including their furry companions.
Are there any remote work vacation rentals in Philipsburg?
In Philipsburg, Sint Maarten, there are plenty of remote work vacation rentals available, with around 150 options to choose from. This vibrant area, known for its stunning beaches and lively atmosphere, provides travelers with the superb backdrop for both work and leisure. Many of these properties are equipped with essential amenities for remote work, such as high-speed Wi-Fi, dedicated office spaces, and comfortable desk chairs, ensuring a productive environment.

Travelers can expect a variety of accommodations, ranging from condos with ocean views to spacious villas, often featuring modern kitchens and outdoor areas for relaxation. The proximity to local attractions, including the famous Great Bay Beach and Fort Amsterdam, offers opportunities to unwind after a day of work. Philipsburg's lively promenade also provides a delightful selection of restaurants and shops, making it an ideal destination for those balancing work and vacation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Philipsburg vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Philipsburg with parking available—perfect for families or travelers 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 WiFi, kitchens, and both private and shared pools. Many vacation rentals offer guests a comfortable experience with modern conveniences, allowing for self-catering and socializing. Travelers can often find properties equipped with blenders for preparing smoothies or cocktails, enhancing their stay in this vibrant Caribbean destination.
When is the best time to visit Philipsburg for a vacation rental?
The best time to visit Philipsburg for a vacation rental is during the peak season from July to September. This lively period draws travelers eager to soak up the sun and enjoy the vibrant atmosphere of this beautiful Caribbean destination. With warm temperatures averaging in the mid-80s to low 90s Fahrenheit, it's superb for beach activities, water sports, and exploring the charming streets of Philipsburg.

July, in particular, is a highlight as it features festive events and an influx of visitors drawn to the island's stunning beaches and lively nightlife. Travelers can indulge in various outdoor adventures, from snorkeling in crystal-clear waters to enjoying delicious local cuisine at beachfront restaurants. The lively summer vibe makes it an ideal time for families and groups looking for a memorable getaway.

For those seeking a more budget-friendly experience, consider planning your trip in February. This month often offers excellent deals on vacation rentals while still providing pleasant weather, with temperatures ranging from the low 70s to mid-80s Fahrenheit.
How early should I book a Philipsburg vacation rental?
Book your Philipsburg vacation 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 vacation 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 engage in a variety of attractions that showcase the island's rich culture and natural beauty. The Great Bay Beach is a major draw, offering pristine sands and crystal-clear waters, with numerous vacation rentals nearby providing easy beach access. The boardwalk along the beach is lined with shops, restaurants, and bars, making it a lively spot for both relaxation and entertainment.

For those interested in history, Fort Amsterdam, located at the entrance of the bay, provides a glimpse into the island's historic past and offers stunning views of the surrounding area. The vibrant Front Street is another highlight, known for its duty-free shopping and charming boutiques, where travelers can find unique local goods.

Additionally, the nearby Sint Maarten Museum gives insight into the island's heritage and culture, making it a worthwhile visit for history enthusiasts.
Can I change or cancel my Philipsburg home rental booking on Vrbo?
To find Philipsburg vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Philipsburg vacation 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.

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