Discover Your Perfect Philipsburg Vacation Homes

Philipsburg Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Philipsburg Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Philipsburg Vacation Rentals

Where are the best neighborhoods to stay in Philipsburg?

When selecting a neighborhood to stay in within Philipsburg, Sint Maarten, you'll find that each area offers its own unique charm and convenient access to the island’s vibrant attractions. Whether you prefer the lively atmosphere of the downtown district or a more relaxed coastal setting, there are options to suit every travel style. Staying in a well-located neighborhood ensures you’re close to beautiful beaches, local shops, and authentic dining experiences, all while enjoying the comfort and reliability of carefully curated vacation rentals. Explore your ideal neighborhood and experience the best of what Sint Maarten has to offer during your unforgettable getaway.

Madame's Estate

This neighborhood offers tranquil surroundings and scenic views, making it a desirable choice for travelers seeking peaceful accommodations in the region. It’s ideal for those wanting a relaxing stay close to local attractions.

View 1054+ Rentals in Madame's Estate

Fort William

Known for its historical significance and central location, this area provides easy access to the vibrant parts of the destination while maintaining a charming, old-world atmosphere for a memorable stay.

View 1015+ Rentals in Fort William

Hope Estate

Offering a blend of scenic beauty and convenience, Hope Estate is perfect for visitors who want to explore the region’s natural landscapes while enjoying comfortable accommodations nearby.

View 777+ Rentals in Hope Estate

Sucker Garden

Set in a lush environment, Sucker Garden appeals to guests looking for a serene retreat with easy access to outdoor activities and local points of interest.

View 796+ Rentals in Sucker Garden

Vineyard

Surrounded by lush vineyards, this neighborhood provides a picturesque setting for relaxing stays, ideal for those wanting to experience the charm of the area's countryside.

View 780+ Rentals in Vineyard

Belair

Located conveniently close to the heart of the region, Belair offers easy access to city amenities while providing quiet, comfortable retreats for your vacation.

View 31+ Rentals in Belair

Point Blanche

Situated near key transportation routes, this area is suitable for travelers who prioritize accessibility and proximity to main attractions during their stay.

View 28+ Rentals in Point Blanche

Indigo Bay

Known for its scenic coastal views, Indigo Bay is perfect for guests seeking a tranquil seaside escape with convenient access to the region’s beaches and outdoor activities.

View 62+ Rentals in Indigo Bay

Best Times to Visit Philipsburg

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit this vibrant Caribbean destination can enhance your experience, allowing you to enjoy ideal weather and availability when booking your preferred vacation rentals here.

Peak Season Highlights

spring
December to April

This period marks the high season when the weather is ideal for outdoor activities and beach lounging, attracting many visitors seeking the perfect Caribbean getaway.

Average Temperature Daytime: around 82°F (28°C) - Nighttime: about 74°F (23°C)
spring
June to August

Summer months bring vibrant local festivals and lively atmosphere, making it a popular time for travelers looking to enjoy the region’s festive spirit.

Average Temperature Daytime: approximately 88°F (31°C) - Nighttime: roughly 79°F (26°C)

Off-Season Highlights

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May and November

During these shoulder months, you can experience fewer crowds and more affordable rates, ideal for exploring the area at a relaxed pace.

Average Temperature Daytime: around 85°F (29°C) - Nighttime: about 76°F (24°C)
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September and October

These months typically see lower visitor numbers due to the increased chance of rain, offering a quieter, more tranquil stay in the region.

Average Temperature Daytime: roughly 86°F (30°C) - Nighttime: approximately 77°F (25°C)

Weekly Weather Forecast for Philipsburg

How to Book Your Philipsburg Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Philipsburg

More Top-Rated Vacation Rentals in Philipsburg Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor swimming pool to relax in the tropical climate.
  • Take advantage of spacious patios or decks for outdoor dining and entertaining.
  • Benefit from lush garden areas or landscaped yards perfect for outdoor leisure.
  • Make use of outdoor grills or barbecue facilities to prepare local cuisine.
  • Relax on loungers or sunbeds with scenic views of the surrounding area.
  • Access common outdoor spaces such as shared courtyards or open-air lounges.
  • Participate in water sports equipment rentals like kayaks or paddleboards, readily available nearby.

Top Attractions Around Philipsburg

What attractions are nearby?

While staying in this vibrant destination, you can enjoy nearby activities such as exploring beautiful beaches, shopping at colorful local markets, and experiencing lively nightlife—all easily accessible from your comfortable vacation rentals.

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Family Activities

  • Fort Amsterdam Tour: Explore the historic fort that offers stunning panoramic views and insights into the area's colonial past, making it a captivating outing for families seeking educational fun.
  • Beach Day at Great Bay Beach: Relax on this picturesque beach with calm waters ideal for swimming and building sandcastles, perfect for creating family memories in a scenic, safe environment.
  • Museum Tour at Sint Maarten Museum: Discover local history and culture through engaging exhibits that entertain children and inform adults, all within an accessible location in the region.
  • Shopping and Strolling in the Boardwalk Area: Enjoy leisurely walks along the lively waterfront, where you can shop for souvenirs and indulge in local treats while experiencing the vibrant atmosphere of this destination.
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Adult Activities

  • Sailing and Yacht Tours: Experience the vibrant maritime scene with sailing excursions that showcase the region’s stunning coastlines and offer a relaxing way to explore the waters surrounding here.
  • Shopping at Front Street: Discover local craftsmanship and international brands along this bustling street, perfect for indulging in retail therapy after a day at the beach.
  • Cuisine and Dining Experiences: Savor a variety of culinary delights at local restaurants that reflect the diverse flavors of this destination and provide an authentic taste of the area.
  • Historical and Cultural Exploration: Visit key landmarks and museums to gain insight into the rich heritage that has shaped this region and enrich your understanding of the local community.

Other Places to Stay in Philipsburg

Sint Maarten
Sint Maarten Vacation Rentals
Great Bay Beach
Great Bay Beach Vacation Rentals
Madame's Estate
Madame's Estate Vacation Rentals
Philipsburg Boardwalk
Philipsburg Boardwalk Vacation Rentals
Vineyard
Vineyard Vacation Rentals
Upper Prince's Quarter
Upper Prince's Quarter Vacation Rentals
Little Bay
Little Bay Vacation Rentals
Maho
Maho Vacation Rentals
Indigo Bay
Indigo Bay Vacation Rentals
Cay Bay Hill
Cay Bay Hill Vacation Rentals
Belair
Belair Vacation Rentals
Point Blanche
Point Blanche Vacation Rentals
More Places to Stay Near Philipsburg

Philipsburg Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Outdoor Activities Early: Take advantage of the region’s beautiful weather by scheduling your outdoor excursions during the cooler parts of the day to enjoy the scenic views and vibrant atmosphere without the midday heat.
  • Explore Local Cuisine: Immerse yourself in the area's culinary scene by trying popular local dishes, which can be conveniently enjoyed at nearby restaurants or prepared in your vacation rental kitchen for a true taste of the region.
  • Use Convenient Transportation Options: Maximize your stay by utilizing the local transportation services or rental bikes available here to easily access popular spots and avoid parking hassles.
  • Book Accommodation Close to Key Attractions: Secure a well-located vacation rental within easy reach of the region’s top sites to make the most of your time exploring this destination’s vibrant culture and natural beauty.

Transportation Options

  • Car Rentals: Renting a car here gives you the flexibility to explore this vibrant destination at your own pace, with many providers offering convenient pickup options near popular vacation rentals.
  • Taxis and Rideshare Services: Taxis and popular rideshare apps are readily available in the area, offering quick and reliable transportation for shorter trips around this lively region.
  • Public Buses: The local bus system provides an affordable way to navigate throughout the destination, connecting you to key points of interest from your rental accommodation.
  • Ferries: Ferries offer scenic transit options between here and nearby islands, making it easy to plan day trips during your stay at one of the region’s premium vacation rentals.

Local Customs Options

  • Greeting Handshakes: It is customary here to exchange friendly handshakes as a sign of welcome and respect when meeting new people in the local community.
  • Respect for Local Dress Codes: You will find that dressing modestly, especially when visiting religious sites or traditional establishments, shows your appreciation for the area's cultural customs.
  • Celebrating Carnival: Participating in or observing vibrant Carnival festivities is a cherished tradition that highlights the region’s lively spirit and cultural pride.
  • Local Cuisine Etiquette: When enjoying meals at local eateries, sharing dishes and engaging with hosts demonstrates good manners and an appreciation for regional culinary customs.

Frequently Asked Questions About Philipsburg?

1. What are the top vacation rentals in Philipsburg?

There are a lot of options in Philipsburg. If you plan on staying in the Philipsburg area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Philipsburg:

2. How many vacation rentals have private pools in Philipsburg?

There are 129 vacation rentals with private pools near Philipsburg. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Philipsburg are best for families?

If you are looking for a family-friendly vacation home in Philipsburg, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Philipsburg:

4. How many Rentbyowner vacation rentals are available in Philipsburg?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 542 in the Philipsburg area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Philipsburg. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property, so it’s important to review the specific listing details and contact the owner directly to understand the terms before booking.

6. Are there any fees or additional costs I should be aware of when booking a vacation rental here?

Additional fees, such as cleaning or service charges, are typically outlined in the listing. To get a complete understanding of the total cost, please refer to the property details or reach out to the owner.

7. How can I ensure my preferred dates are available for booking?

Availability depends on the property's current reservation schedule. You can check real-time availability on the listing page or contact the owner for confirmation and assistance with your desired dates.

8. What amenities are usually included in vacation rentals here?

Amenities vary between properties but commonly include essentials like Wi-Fi, air conditioning, and fully equipped kitchens. For specific amenities, consult the detailed listing or contact the host directly.

9. Is there local support available if I encounter issues during my stay?

Most hosts offer support during your visit, and some listings include contact information for local management. Ensure you review the listing details or communicate with the owner to know what assistance is available during your stay.