Discover Your Perfect Upper Prince's Quarter Vacation Homes

Best Vacation Homes in Upper Prince's Quarter

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Upper Prince's Quarter Luxury Rentals

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Find More Upper Prince's Quarter Villas, Resorts, & Rentals on BedroomVillas

Upper Prince's Quarter Pet Friendly Vacation Rentals

9.6 (10 Reviews)
Apartment
The Tree House
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Upper Prince's Quarter 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 Upper Prince's Quarter Vacation Rentals

Where are the best neighborhoods to stay in Upper Prince's Quarter?

Exploring the neighborhoods around Upper Prince's Quarter in Philipsburg, Sint Maarten, you’ll find a welcoming area perfectly suited for your next getaway. Staying within this vibrant district offers easy access to the island’s stunning beaches and lively local scene, making it an ideal choice for travelers seeking convenience and comfort. As you choose your vacation rental in the area, you'll enjoy the authentic Caribbean atmosphere combined with the reliable, seamless booking experience that ensures a memorable stay on this beautiful island.

Sucker Garden

This neighborhood offers a tranquil retreat within the region, making it an ideal spot for those seeking a peaceful stay close to local conveniences. Its serene atmosphere complements your search for comfortable vacation rentals here.

View 796+ Rentals in Sucker Garden

Hope Estate

Nestled in the area’s lush surroundings, Hope Estate provides a scenic setting perfect for relaxing and enjoying the natural beauty of this destination. It’s a popular choice for travelers looking for scenic views and convenient access to nearby amenities.

View 777+ Rentals in Hope Estate

Red Pond Estates

Offering privacy and a sense of exclusivity, Red Pond Estates is a sought-after location for visitors who want to experience the region’s upscale side. It’s an excellent base for exploring the local attractions while enjoying the comfort of well-appointed vacation rentals.

View 671+ Rentals in Red Pond Estates

Vineyard

Surrounded by lush landscapes, Vineyard is perfect for guests who appreciate scenic views and a quiet atmosphere. Its proximity to key points of interest makes it an appealing spot for booking your preferred accommodations.

View 780+ Rentals in Vineyard

Tamarind Hill Estates

This neighborhood features elevated settings and beautiful views, ideal for travelers looking for a peaceful yet accessible location. It’s a favorite among those seeking serene vacation rentals with scenic surroundings.

View 661+ Rentals in Tamarind Hill Estates

Middle Region

Located centrally, the Middle Region offers easy access to the area's main attractions, making it a practical choice for travelers wanting convenience along with comfortable lodging options.

View 828+ Rentals in Middle Region

Dawn Beach Estates

Just steps from the beach, Dawn Beach Estates provides a prime location for sun-seekers and beach lovers. Here, you’ll find vacation rentals that combine comfort with stunning ocean views.

View 30+ Rentals in Dawn Beach Estates

Point Blanche

This historic neighborhood offers a mix of cultural charm and scenic views, making it a compelling choice for travelers wanting to immerse themselves in the area's local character while enjoying top-tier accommodations.

View 28+ Rentals in Point Blanche

Best Times to Visit Upper Prince's Quarter

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here ensures you enjoy the region's best weather and local events, making your stay in Upper Prince's Quarter, Philipsburg, Sint Maarten truly memorable.

Peak Season Highlights

spring
December to April (Dry Season)

This is the peak season when the region experiences warm, sunny weather ideal for outdoor activities.

Average Temperature Daytime: around 82°F to 86°F - Nighttime: about 74°F to 78°F
summer
June to August (Summer Peak)

During summer months, you can enjoy lively events and vibrant local culture, making it a popular time to visit.

Average Temperature Daytime: approximately 85°F to 89°F - Nighttime: roughly 77°F to 81°F

Off-Season Highlights

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May and November (Pre- and Post-Rainy Season)

These shoulder months offer fewer crowds and more affordable rates while still providing pleasant weather.

Average Temperature Daytime: around 80°F to 84°F - Nighttime: about 73°F to 76°F
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September to October (Rainy Season)

The region sees occasional showers during these months, making it a quieter time for travel and ideal for exploring at a relaxed pace.

Average Temperature Daytime: approximately 81°F to 83°F - Nighttime: roughly 75°F to 77°F

Weekly Weather Forecast for Upper Prince's Quarter

How to Book Your Upper Prince's Quarter 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 Upper Prince's Quarter

More Top-Rated Vacation Rentals in Upper Prince's Quarter 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 during your stay in the area.
  • Take advantage of lush gardens and landscaped outdoor spaces for leisurely strolls or outdoor dining.
  • Make use of spacious patios or verandas perfect for basking in the Caribbean sun.
  • Benefit from outdoor grilling facilities to enjoy local flavors with family and friends.
  • Utilize shaded outdoor lounge areas for rest and socializing amid tropical surroundings.
  • Access nearby beaches and waterfronts for swimming, sunbathing, or water sports.
  • Make the most of outdoor recreational amenities like tennis courts or fitness areas, if available on-site.

Top Attractions Around Upper Prince's Quarter

What attractions are nearby?

Within this vibrant area, you can enjoy a variety of outdoor activities and explore local attractions that showcase the beauty and culture of Sint Maarten, providing an ideal setting for a memorable stay near your vacation rentals.

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Family Activities

  • Scenic Beach Days: Spend quality time with your family enjoying the beautiful sandy beaches here, perfect for swimming, building sandcastles, and relaxing under the sun.
  • Snorkeling Adventures: Discover vibrant marine life just off the coast, making snorkeling a fun and educational activity for children and adults alike in this region.
  • Historical Tours: Explore local history through guided tours that showcase the area's rich cultural heritage, offering an engaging experience for the whole family.
  • Local Markets and Artisan Shops: Browse colorful markets filled with handmade crafts and local produce, providing a delightful way to enjoy authentic regional flavors and souvenirs.
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Adult Activities

  • Sailing Excursions: Experience a relaxing day on the water by taking a sailing trip around the region’s scenic coastlines and vibrant marine life.
  • Beach Hopping: Discover pristine beaches nearby, where you can unwind, swim, or enjoy beachside dining with stunning views of the Caribbean Sea.
  • Island Tours: Join an organized tour to explore the natural beauty and cultural highlights of this destination’s surrounding islands.
  • Nightlife Experiences: Enjoy the lively nightlife scene in the area, with bars and entertainment venues offering a taste of local music and cuisine.

Other Places to Stay in Upper Prince's Quarter

Sucker Garden
Sucker Garden Vacation Rentals
Vineyard
Vineyard Vacation Rentals
Hope Estate
Hope Estate Vacation Rentals
Guana Bay Beach
Guana Bay Beach Vacation Rentals
Red Pond Estates
Red Pond Estates Vacation Rentals
Gibb's Bay Beach
Gibb's Bay Beach Vacation Rentals
Tamarind Hill Estates
Tamarind Hill Estates Vacation Rentals
Oyster Pond
Oyster Pond Vacation Rentals
Dawn Beach Estates
Dawn Beach Estates Vacation Rentals
Point Blanche
Point Blanche Vacation Rentals
More Places to Stay Near Upper Prince's Quarter

Upper Prince's Quarter Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Local Markets: Take time to visit the vibrant markets nearby to enjoy authentic regional products and craft souvenirs that enhance your stay.
  • Plan Water-Based Activities: Make the most of the region's pristine beaches by scheduling snorkeling, sailing, or relaxing seaside walks directly from your rental.
  • Discover Nearby Dining Options: Seek out local eateries and beachfront restaurants to experience the region’s culinary delights and lively atmosphere.
  • Arrange Convenient Transportation: Consider renting a scooter or car to effortlessly explore the area’s scenic spots and hidden gems during your holiday.

Transportation Options

  • Rental Car Services: You can conveniently rent a vehicle here to explore the region at your own pace, with numerous local providers offering flexible options for your stay.
  • Taxis and Private Transfers: Reliable taxi services and private transfers are available to take you directly from the airport or around the area, ensuring a comfortable journey to your vacation rental.
  • Public Buses: Affordable and accessible, public buses connect key points in the region, making it easy for you to travel between popular destinations without hassle.
  • Bike Rentals: For an eco-friendly and scenic way to explore, bike rentals are a popular choice, allowing you to enjoy the area's beautiful landscapes at your leisure.

Local Customs Options

  • Local Festivals: Participating in vibrant festivals like Saint Martin's Carnival offers an authentic glimpse into the area's rich cultural heritage.
  • Traditional Cuisine: Sampling regional dishes such as conch fritters and johnny cakes allows you to experience the local flavors unique to this Caribbean destination.
  • Maritime Customs: Observing traditional boat parades and fishing practices highlights the community's deep connection to the sea.
  • Respectful Dress Code: Wearing modest attire when visiting religious sites or participating in cultural events shows respect for local customs here.

Frequently Asked Questions About Upper Prince's Quarter?

1. What are the top vacation rentals in Upper Prince's Quarter?

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

2. How many vacation rentals have private pools in Upper Prince's Quarter?

There are 218 vacation rentals with private pools near Upper Prince's Quarter. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Upper Prince's Quarter are best for families?

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

4. How many Rentbyowner vacation rentals are available in Upper Prince's Quarter?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 538 in the Upper Prince's Quarter 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 Upper Prince's Quarter. 

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

Cancellation policies vary by listing, so it's important to review the specific terms outlined on the property page or contact the host directly for detailed information.

6. How do I ensure my booking in Philipsburg is secure and confirmed?

Once you select your preferred property, you can confirm your reservation through our secure booking system, which verifies availability and provides confirmation details promptly.

7. Are there any fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning or service charges are typically listed within the property details or during the checkout process; always review these before finalizing your reservation.

8. Can I get assistance if I encounter issues during my stay in this region?

Yes, our support team is available to help resolve any concerns or questions that arise during your stay, with contact details provided upon booking confirmation.

9. What amenities are generally available in vacation rentals in this destination?

Most listings include essential amenities like Wi-Fi, air conditioning, and kitchen facilities, but it’s advisable to check the specific property details for a complete list of what’s offered.

Upper Prince's Quarter Top Rated Vacation Rentals

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