Philipsburg vacation rentals

We found 3,234 vacation rentals — enter your dates for availability

Discover a selection of 74 apartments, 36 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

Showing deals for:Dec 19 - Dec 26

Image gallery for Luxury 5 Bedroom Villa

Pool Deck
10 out of 10 rating
Exceptional
(5 reviews)

Luxury 5 Bedroom Villa

Les Terres Basses, Collectivité de Saint-Martin

9% off
Price is $2,972
$20,807 for 7 nights
All fees included
Luxury 5 Bedroom Villa

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Find out more about Philipsburg

Find out more about Philipsburg

Why visit Philipsburg

  • Stunning Beaches: Enjoy the beautiful, pristine beaches perfect for relaxation and water activities.
  • Historic Forts: Explore the historic forts that offer a glimpse into the island's rich history and breathtaking views.
  • Cultural Experiences: Visit the Philipsburg Courthouse for a taste of local architecture and culture.
  • Outdoor Activities: Engage in various outdoor adventures, from snorkeling to hiking, suitable for all ages.
  • Diverse Accommodation: Choose from a range of vacation rentals, from cozy condos to luxurious villas.

Popular types of accommodation in Philipsburg

When planning your getaway in Philipsburg, Vrbo offers a fantastic selection of vacation rentals to suit your needs. From cozy condos and luxurious villas to spacious apartments, there's something for everyone. Whether you're looking for a relaxing retreat or an adventure-filled trip, our vacation homes and house rentals come with essential amenities to ensure a comfortable stay. Explore your options and find the perfect base for your Philipsburg adventure.

  • Condos: The top choice for vacationers in Philipsburg, offering modern amenities and stunning views, perfect for a comfortable stay.
  • Villas: A luxurious option for those seeking spacious accommodations and private outdoor spaces to relax and enjoy the scenery.
  • Apartments: A popular option for travelers looking for a home-like atmosphere, providing convenience and essential amenities.
  • Houses: Ideal for families or groups, these homes offer privacy and a unique local experience.
  • Guest Houses: A cozy and affordable choice, often providing a more personal touch for your stay in Philipsburg.**

Top attractions in Philipsburg

Philipsburg, Sint Maarten offers a perfect blend of beach, outdoor activities, and stunning scenery for vacationers. Explore popular attractions like the historic Fort and modern college campuses, or relax on the beautiful beaches. For a cultural experience, don't miss the Philipsburg Courthouse. Whether you're traveling solo or with family, there's something for everyone in this vibrant city, making it an ideal destination for a memorable getaway.

  • Great Bay Beach: Enjoy the soft white sands and vibrant beach vibes at Great Bay Beach, perfect for swimming, sunbathing, and soaking in the Caribbean sun.
  • University of St. Martin: Experience the modern atmosphere of the University of St. Martin, where you can appreciate its contemporary architecture and urban feel while learning about local education.
  • Fort Amsterdam: Explore the rich cultural history at Fort Amsterdam, a historic fort offering stunning views and insights into the island's past.

Things to do recommended for couples

For a romantic getaway in Philipsburg, stroll along the scenic Boardwalk, where you can enjoy the beautiful beach vibes and stunning ocean views. It's the perfect place for couples to unwind, savor local cuisine, 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, along with thrilling activities for kids. It's a perfect spot for creating lasting memories together in a beautiful tropical setting.

Things to do recommended for groups

Experience the thrill of golfing at Mullet Bay Golf, just 5 miles from Philipsburg, or explore vibrant shops in the Front Street District and Harbour Point Village, where family-friendly vibes meet local business. Enjoy a perfect blend of outdoor fun and cultural shopping with your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to apply the right filters to meet your needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Philipsburg with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Philipsburg with young kids: Traveling with little ones can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be 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 this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortable and at ease.
  • Planning for a long term stay visiting Philipsburg: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using 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 outdoor activities. Explore the picturesque coastline, discover cozy neighborhoods perfect for a peaceful getaway, and indulge in romantic excursions. Whether you're lounging on excellent beaches or soaking in the beautiful scenery, Philipsburg is an ideal destination for families and couples alike, providing a unique vibe that captures the essence of island life.

  • Upper Prince's Quarter: Nestled close to Philipsburg, Upper Prince's Quarter offers a serene escape for travelers seeking beach, outdoor, and scenic experiences. This charming village is surrounded by beautiful beaches and picturesque bays, providing ample opportunities for relaxation and adventure. Visitors can enjoy various activities, including resort stays and educational experiences, all while soaking in the stunning coastal views. The nearby nudist beach adds a unique aspect to your beach day, ensuring a memorable visit.
  • Little Bay: Just a stone's throw from Philipsburg, Little Bay is a delightful village known for its inviting beaches and scenic landscapes. Travelers flock here to enjoy the vibrant boardwalk, where you can stroll along the shore, savor local cuisine, and take in the breathtaking ocean views. Little Bay is also home to various resorts and educational activities, making it an ideal destination for both relaxation and exploration. The nudist beach nearby offers an adventurous twist for those looking to embrace a liberating beach experience.
  • Indigo Bay: Located near Philipsburg, Indigo Bay is a picturesque neighborhood that captivates visitors with its beautiful beaches and outdoor scenery. This area invites travelers to unwind at luxurious resorts or engage in exciting adventure activities. Indigo Bay's proximity to stunning bays and a nudist beach makes it a perfect spot for sun-seekers and thrill-seekers alike. With its tranquil atmosphere and scenic views, Indigo Bay is an ideal destination for anyone looking to 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January76.6°F (24.8°C)No Rain (Dry)Mostly SunnyAverageSlightly High
February76.1°F (24.5°C)No Rain (Dry)Mostly SunnySlightly LowAverage
March76.3°F (24.6°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
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 SunnyAverageAverage
July80.4°F (26.9°C)Light RainMostly SunnySlightly HighAverage
August81.0°F (27.2°C)Light RainMostly CloudyAverageAverage
September81.3°F (27.4°C)Light RainMostly SunnyAverageSlightly Low
October80.8°F (27.1°C)Light RainMostly CloudySlightly LowSlightly Low
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 a breeze

Are you hoping to save money on your next adventure? Being flexible with your travel dates can make a big difference, as prices can fluctuate. Additionally, consider booking a longer stay to take advantage of substantial discounts. To discover a Vrbo property that aligns with your budget, simply utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer truly has its benefits. Become a part of our One Key rewards program to unlock exclusive member discounts and accumulate OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, and manage your travel arrangements with ease. You can easily access the properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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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