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  3. Cottage Rentals

Discover Your Perfect Simpson Bay Cottage Rentals

Simpson Bay Cottage Rentals

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10.0 (1 Review)
Apartment
Island Bliss Condo
  • Air Conditioner
  • Parking
  • Security/Safety
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More Top-Rated Cottage Rentals in Simpson Bay Area

Why Choose Rent By Owner for your Simpson Bay Cottage Rentals?

What makes our Cottage 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 Simpson Bay Cottage Rentals

Where are the best neighborhoods to stay in Simpson Bay?

When exploring Simpson Bay, Sint Maarten, you'll find neighborhoods that offer the perfect balance of vibrant local culture and relaxing seaside ambiance. Staying in this area provides convenient access to the area's lively atmosphere while enjoying the tranquility of nearby beaches. Discover comfortable cottages that make your stay in Simpson Bay both memorable and seamless with dependable amenities and easy booking options.

Pelican Key

This area offers a tranquil retreat with stunning waterfront views, making it an ideal choice for those seeking peaceful surroundings while staying in the region. Enjoy convenient access to local beaches and amenities, enhancing your stay in this relaxing neighborhood.

View 100+ Rentals in Pelican Key

Maho

Known for its vibrant atmosphere and proximity to the famous airport, Maho provides an exciting base where you can experience the lively side of this destination. It’s a perfect spot if you want to be close to entertainment options and enjoy the energetic vibe during your visit.

View 441+ Rentals in Maho

Best Times to Visit Simpson Bay

When should you plan your Cottage Rentals stay?

Choosing the right time to vacation here can significantly enhance your experience, as the region offers optimal weather and lively local events during specific seasons that cater to a variety of preferences for those seeking a memorable getaway.

Peak Season Highlights

spring
December to April

During the peak season, you'll enjoy warm temperatures and lively festivities, making it the perfect time to experience the vibrant atmosphere of this Caribbean destination.

Average Temperature Daytime: 28-30°C - Nighttime: 20-22°C
spring
June to August

The summer months bring sunny weather ideal for beach activities and outdoor exploration, attracting visitors seeking the lively island vibe.

Average Temperature Daytime: 29-31°C - Nighttime: 22-24°C

Off-Season Highlights

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May and November

Shoulder seasons offer fewer crowds and discounted rates, providing a more relaxed atmosphere for enjoying your stay here.

Average Temperature Daytime: 27-29°C - Nighttime: 21-23°C
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September to October

This quieter period corresponds with the region's hurricane season, often resulting in lower rates and less busy beaches for those seeking solitude.

Average Temperature Daytime: 28-30°C - Nighttime: 21-23°C

Weekly Weather Forecast for Simpson Bay

How to Book Your Simpson Bay Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage 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 Simpson Bay

More Top-Rated Cottage Rentals in Simpson Bay Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage 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 after exploring the area.
  • Take advantage of lush gardens or landscaped courtyards for outdoor leisure.
  • Benefit from shaded patios or verandas perfect for outdoor dining or morning coffees.
  • Make use of barbecue grills to host cookouts under the Caribbean sun.
  • Relax on outdoor loungers or sun decks with scenic views of the surrounding region.
  • Utilize nearby walking trails or outdoor spaces for active pursuits and sightseeing.
  • Experience well-maintained outdoor lighting, ideal for evening gatherings in this tropical destination.

Top Attractions Around Simpson Bay

What attractions are nearby?

In this vibrant Caribbean region, you can enjoy a variety of nearby activities such as exploring stunning beaches, engaging in water sports, and discovering local dining options, making your stay in Simpson Bay an unforgettable experience.

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Family Activities

  • Snorkeling Adventures: Explore the vibrant underwater world just off the coast, where you can experience colorful marine life suitable for all ages.
  • Beach Play and Relaxation: Spend quality time with your family on the sandy shores of the area, enjoying sunbathing, sandcastle building, or gentle sea breezes.
  • Boat Tours and Excursions: Embark on a scenic boat tour to discover nearby islands and secluded beaches, perfect for creating memorable family moments.
  • Local Dining Experiences: Savor delicious dishes at family-friendly restaurants that showcase regional flavors and offer welcoming atmospheres in this destination.
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Adult Activities

  • Sailing and Boat Tours: Experience the region’s stunning coastline firsthand by booking a sailing adventure or boat tour, offering breathtaking views and a relaxing day on the water.
  • Scuba Diving and Snorkeling: Discover vibrant marine life and coral reefs in this tropical destination, making it an ideal spot for both beginners and experienced divers.
  • Dining at Local Restaurants: Indulge in the region's culinary delights by visiting local eateries that serve fresh seafood and Caribbean-inspired dishes.
  • Nightlife and Entertainment: Enjoy vibrant nightlife options, including bars and live music venues, perfect for unwinding after a day of exploring here.

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Simpson Bay Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Book your accommodations well in advance to secure the best cottages and enjoy priority access to popular spots here.
  • Explore Local Cuisine: Take time to indulge in the authentic flavors of the region by visiting nearby eateries and experiencing the local culinary scene.
  • Discover the Area: Use your stay as a chance to explore beyond your cottage, uncovering hidden gems and scenic spots around this vibrant destination.
  • Respect the Environment: Help preserve the beauty of the region by practicing responsible tourism and adhering to eco-friendly guidelines during your visit.

Transportation Options

  • Taxi Services: Reliable taxis are readily available to transport you around Simpson Bay, offering convenient point-to-point trips for easy access to local attractions and your chosen cottages.
  • Car Rentals: Renting a car provides the flexibility to explore the region at your own pace, with numerous rental agencies serving the Sint Maarten area near Simpson Bay.
  • Public Buses: The area's public bus system offers an affordable and practical way to navigate the local scene, connecting key spots within Simpson Bay and surrounding neighborhoods.
  • Water Taxis and Ferries: For scenic travel across the water, water taxis and ferries operate frequently, providing stunning views of the Caribbean while reaching nearby islands and beaches.

Local Customs Options

  • Greeting Customs: Locals often greet visitors with a warm smile and a friendly "Bon Bini," embracing the island's welcoming spirit.
  • Dress Code: Casual and lightweight clothing is customary, especially when enjoying outdoor activities or dining at local establishments.
  • Celebration of Festivals: Participating in vibrant festivals such as Carnival offers insight into the region's rich cultural traditions and community values.
  • Respect for Local Cuisine: Appreciating traditional foods and engaging with vendors respectfully contributes to authentic cultural experiences here.

Simpson Bay Cottage Rentals Frequently Asked Questions

1. What are the top Cottages in Simpson Bay?

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

2. How many Cottages are available in Simpson Bay?

Currently, the total number of properties listed by RBO in 2026 is over 1 in the Simpson Bay area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Simpson Bay. 

3. What is the cancellation policy for cottages in this area?

The cancellation policy varies by listing. Please review the specific cottage's terms on the listing page or contact the owner directly to understand the cancellation and refund options available.

4. Are there any additional fees or charges when booking a cottage here?

Additional fees, such as cleaning fees or service charges, are typically detailed on the property listing. Be sure to review these details carefully or reach out to the owner for clarification before completing your reservation.

5. How do I confirm my reservation at a cottage in this destination?

Reservation confirmation is usually sent after completing the booking process online. For any questions or special requests, contacting the property owner directly can help ensure your stay is secured properly.

6. What amenities can I expect in cottages around this region?

While amenities vary by property, most cottages offer essential features like Wi-Fi, air conditioning, and kitchen facilities. Check each listing for specific amenities included with your chosen cottage.

7. Is it possible to modify or extend my stay once booked?

Modifications or extensions depend on the owner's policies and availability. Contact the property owner directly through the booking platform to discuss possible changes to your reservation.

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More Top-Rated Cottage Rentals in Simpson Bay Area