Philipsburg vacation rentals

We found 3,219 vacation rentals — enter your dates for availability

Discover a selection of 25 homes, 64 apartments, 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:Aug 22 - Aug 29
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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:

  • 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

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:

  • 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)
  • 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?
Upper Prince’s Quarter is one of the more sought-after neighborhoods to book a vacation property in Philipsburg. Spend your stay here and enjoy the comfort and privacy that comes with having a whole place to yourself.
What is the most popular type of vacation rental accommodation in Philipsburg?
According to our research, villas are the most popular type of property in Philipsburg. But of course, everyone’s idea of an awesome trip will differ. Vrbo has vacation rentals of all shapes and sizes, and we’ll help you find your ideal match.
How much does it cost to rent a vacation rental in Philipsburg?
The average price for a vacation home in Philipsburg is based on several factors, including property type, length of stay and season. Whether you’re searching for a sprawling villa with space for extended family or a quaint cottage for just you and the kids, just enter your dates of travel to discover stays with unbeatable value.
How much does it cost to rent a beach house in Philipsburg?
The average price for a vacation rental by the beach in Philipsburg depends on when you’ll be there and the type and size of property you’re searching for. You can find prices easily and quickly on Vrbo by entering your travel dates and destination. Then use the filter tool to select the number of bedrooms and amenities essential to you, like air conditioning, WiFi and a hot tub.
Are there pet-friendly vacation rentals in Philipsburg?
There certainly are. You can choose from 327 vacation rentals that allow pets in Philipsburg on Vrbo. Our furry companions deserve a break too, so simply use our search function for pet-friendly vacation rentals to find a perfect property where Spot can join the fun.
Can I rent a house with a pool in Philipsburg?
Dig out your swimwear and swim ring, because there are 283 houses with a private pool in Philipsburg. Book one of these superb vacation homes and let every day be a pool day. Simply enter your dates into Vrbo, then use the “pool” filter to find the ideal place for a splashing good time!
What are popular rental amenities in Philipsburg?
A barbecue grill, tennis and an ocean view top the list of most popular rental amenities in Philipsburg. Whether you plan to travel solo, with your better half or a group of dear friends, Vrbo will help you find a vacation home that matches your style with all the conveniences you’re looking for.
Are there large group vacation rentals in Philipsburg?
Philipsburg has 26 vacation rentals that can accommodate 10 or more guests. These properties come with all the space you need to share good times with friends and family.
Are there vacation rentals in Philipsburg that welcome kids?
With 318 family-friendly vacation rentals available in Philipsburg, now is an awesome time to introduce the kids to the wonders of travel. Simply click on our “Properties good for families” filter to discover stays that feature amenities ideal for vacationing families, like dining rooms, pools, hot tubs and bunk beds.
What are the top attractions for families in Philipsburg?
Keep your kids entertained at these popular family-friendly attractions in Philipsburg:

  • Great Bay Beach
  • Little Bay Beach
  • Sint Maarten Park

Are there one-bedroom vacation rentals in Philipsburg?
Philipsburg has 29 one-bedroom rentals on offer. Often situated in prime areas thanks to their smaller size, a one-bedroom vacation rental is great if you’re getting away with a friend or your partner. And with home comforts like laundry facilities and more privacy than a standard hotel, you’ll be able to chill out while discovering this incredible destination.
Can I find two-bedroom vacation rentals in Philipsburg?
Gather your besties and enjoy total privacy and comfort in one of the 31 two-bedroom vacation homes Philipsburg has to offer.
Are there vacation rentals with WiFi in Philipsburg?
Philipsburg has 113 vacation rentals with WiFi, so you’ll be able to stay connected while you’re traveling. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with your family to sending emails, these Vrbo homes make it a cinch to get online.
How can I find vacation rentals with air conditioning in Philipsburg?
Philipsburg has 315 vacation rentals where you’ll be able to kick back in air-conditioned comfort. To find a stay on Vrbo that has this perk, enter your travel dates and use the convenient filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Philipsburg?
The minimum age allowed can differ across properties on Vrbo, so check the rules of the vacation home in Philipsburg you want to book. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Philipsburg for?
It really depends on the Philipsburg property. To look over a list of options offering extended stays, simply enter your travel dates and number of guests into the Vrbo search page. You can enjoy having the property to yourself, along with home comforts like air conditioning, a kitchen and a yard to play in. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Philipsburg?
Overnight trip or a much-needed extended vacation, Vrbo has some exclusive deals and discounted options in Philipsburg to match your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or see what’s just been added with one of our newly listed homes. Whatever kind of getaway you’re after, you’ll find the perfect place to stay — without blowing your budget.

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