Discover Your Perfect Simpson Bay Beach Rentals by Owner

Simpson Bay Beach Rentals by Owner

10.0 (4 Reviews)
Apartment
Boheme
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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10.0 (3 Reviews)
Apartment
The Lady Bug
  • Air Conditioner
  • Parking
  • View
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More Top-Rated Rentals by Owner in Simpson Bay Beach Area

Why Choose Rent By Owner for your Simpson Bay Beach vacation rental?

What makes our Rentals by Owner 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 Beach Rentals by Owner

Where are the best neighborhoods to stay in Simpson Bay Beach?

When considering where to stay near Simpson Bay Beach, you’ll find that the neighborhood options offer a range of convenient and comfortable accommodations. This area is known for its lively yet relaxed atmosphere, making it an ideal choice for travelers seeking easy access to the stunning shores and vibrant local scene. By choosing a rental by owner in Simpson Bay, you can enjoy personalized amenities and a seamless booking experience, ensuring your stay in this beautiful part of Sint Maarten is both memorable and hassle-free. Whether you prefer a peaceful retreat or a lively hub, the neighborhoods surrounding Simpson Bay Beach provide versatile options to suit your travel needs.

Pelican Key

Located close to the vibrant heart of Simpson Bay, Pelican Key offers a peaceful retreat while providing easy access to the area's popular attractions and beaches. It's an ideal spot for those seeking a tranquil stay with convenient proximity to the region's lively activities.

View 99+ Rentals in Pelican Key

Maho

Maho is renowned for its proximity to the island’s famous airport, offering an exhilarating view of arriving aircraft, yet it remains a great base for exploring the region’s beaches and entertainment options. Here, you can enjoy a lively atmosphere combined with comfortable rental options nearby.

View 451+ Rentals in Maho

Cay Bay

Nestled near the bustling areas of Simpson Bay, Cay Bay provides a tranquil setting with direct access to the region’s beaches and scenic views. It’s perfect for travelers looking for a relaxing stay close to the vibrant local scene.

View 1010+ Rentals in Cay Bay

Almond Grove

Situated within easy reach of the main attractions, Almond Grove offers a quiet neighborhood that complements your Caribbean getaway. It’s an excellent choice for those seeking comfort and convenience in this part of the island.

View 1024+ Rentals in Almond Grove

Indigo Bay

This area offers stunning waterfront views and quick access to the lively town center, making it a superb location for exploring the best of the region’s beaches and nightlife. Stay here for a blend of tranquility and accessibility.

View 62+ Rentals in Indigo Bay

St. Peters

St. Peters provides a peaceful community setting with easy access to the region’s key beaches and attractions, ideal for travelers who value serenity combined with convenience. It’s a wonderful place to unwind after days spent exploring the island.

View 824+ Rentals in St. Peters

Belair

Close to the bustling streets of Philipsburg, Belair offers an inviting environment with quick access to regional beaches, shops, and restaurants. It’s a strategic choice for those wanting both relaxation and activity within reach.

View 31+ Rentals in Belair

South Reward

Bordering the southern part of the island, South Reward presents a peaceful oasis with scenic views and proximity to Simpson Bay’s vibrant attractions. It’s ideal for visitors seeking a serene atmosphere with easy access to the region’s lively amenities.

View 1082+ Rentals in South Reward

Best Times to Visit Simpson Bay Beach

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience, allowing you to enjoy the region's ideal weather and vibrant atmosphere while making the most of your booking through Rent By Owner in Simpson Bay Beach.

Peak Season Highlights

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December to April

During the peak season, you'll experience warm weather and lively beachfront activities that make this time ideal for enjoying Simpson Bay Beach's vibrant atmosphere.

Average Temperature Daytime: around 28-30°C - Nighttime: around 22-24°C
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June to August

The summer months bring high tourist traffic with excellent weather, perfect for sunbathing and water sports along the popular region's shoreline.

Average Temperature Daytime: approximately 29-31°C - Nighttime: around 23-25°C

Off-Season Highlights

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May and November

These shoulder months offer quieter beaches and more relaxed rental options, ideal for travelers seeking a peaceful retreat in the area.

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

This off-peak period sees fewer visitors, making it a great time to find deals on vacation rentals while still enjoying warm weather and calm waters in the region.

Average Temperature Daytime: roughly 28°C - Nighttime: approximately 22°C

Weekly Weather Forecast for Simpson Bay Beach

How to Book Your Simpson Bay Beach vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Beach

More Top-Rated Rentals by Owner in Simpson Bay Beach Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 for refreshing dips under the sun.
  • Relax on a spacious outdoor patio or lounge area with comfortable seating.
  • Take advantage of direct access to the nearby beach for effortless seaside strolls.
  • Utilize outdoor dining spaces, perfect for al fresco meals with scenic views.
  • Make use of lush landscaped gardens that offer a tranquil retreat amid nature.
  • Benefit from outdoor showers to rinse off after beach activities in the region.
  • Access barbecue grills ideal for hosting cookouts in the pleasant outdoor environment.

Top Attractions Around Simpson Bay Beach

What attractions are nearby?

Within walking distance from your rental, you can enjoy a variety of activities such as relaxing on the pristine sands, engaging in water sports, or exploring local dining options, all offering an authentic Caribbean experience right here in the region.

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Family Activities

  • Snorkeling Adventures: Discover the vibrant marine life just off the coast, making it a perfect family activity to explore the clear waters of this popular destination.
  • Family Beach Picnics: Enjoy relaxing days on the soft sands with convenient access to local eateries and picnic spots along the shoreline.
  • Watersports for Beginners: Engage in safe and fun water activities like paddleboarding and kayaking suitable for kids and parents alike.
  • Sunset Beach Strolls: Take leisurely walks along the beach during sunset hours, creating memorable moments with your loved ones in this scenic setting.
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Adult Activities

  • Sunset Sailing Tours: Experience the breathtaking Caribbean sunset on a sailing tour that offers stunning views and a relaxing atmosphere in the area.
  • Jet Ski Adventures: Explore the clear waters of Simpson Bay Beach with an exhilarating jet ski ride, perfect for thrill-seekers looking for fun on the waves.
  • Relaxing Spa Treatments: Indulge in rejuvenating spa services offered by local wellness centers to unwind after a day of exploring the region.
  • Dining at Waterfront Restaurants: Savor delicious Caribbean cuisine at waterfront restaurants that offer picturesque views and a vibrant ambiance in this destination.

Simpson Bay Beach Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Ahead: Take advantage of your stay by researching local events and watersports so you can enjoy the best experiences this popular destination has to offer.
  • Choose the Right Rental: Opt for a rental close to the shoreline or with ocean views to maximize relaxation and convenience during your visit.
  • Explore Local Cuisine: Embrace the area's culinary scene by visiting nearby eateries or preparing fresh seafood in your rental’s kitchen.
  • Respect the Environment: Keep the beaches pristine by following local guidelines and minimizing waste, ensuring this stunning destination remains beautiful for others.

Transportation Options

  • Rental Car Services: Local rental car agencies offer convenient options for exploring the vibrant region surrounding Simpson Bay Beach, giving you flexibility and independence during your stay.
  • Taxi and Shuttle Services: Reliable taxi and shuttle services operate throughout the area, providing quick transportation to nearby attractions and the airport with ease.
  • Private Transfers: For a personalized experience, private transfer providers in the region ensure comfortable and efficient rides straight to your Simpson Bay Beach rental by owner property.
  • Public Transit: Although limited, public transit options are available and can be a budget-friendly way to navigate the local area around Simpson Bay Beach.

Local Customs Options

  • Respect for Local Hospitality: Visitors are encouraged to greet locals with friendliness and courtesy, reflecting the warm spirit of this Caribbean destination.
  • Embracing the Island's Culinary Traditions: Tipping generously and trying local dishes demonstrate appreciation for the regional cuisine and cultural customs.
  • Understanding Cultural Dress Codes: When visiting religious sites or attending local events, modest attire is appreciated to show respect for the area's cultural sensitivities.
  • Participating in Community Events: Engaging in local festivals and traditions helps you connect authentically with the area’s vibrant culture and customs.

Frequently Asked Questions About Simpson Bay Beach Rentals by Owner

1. What are the top vacation rentals in Simpson Bay Beach?

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

2. How many Rentbyowner vacation rentals are available in Simpson Bay Beach?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1247 in the Simpson Bay Beach 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 Simpson Bay Beach. 

3. What is the cancellation policy for rentals by owner in Simpson Bay Beach?

Cancellation policies vary depending on the individual host and listing. You should review the specific cancellation terms on the rental's page or contact the property owner directly to understand any fees or deadlines associated with changing or canceling your reservation.

4. How do I find available rental properties by owner in Simpson Bay Beach?

You can browse the listings on our platform, filtering by your preferred travel dates and amenities. Each listing provides detailed information, photos, and contact options so you can easily find a suitable rental here in the region.

5. Are there any additional fees when booking a rental by owner in Simpson Bay Beach?

Additional fees, such as cleaning charges or service fees, are typically outlined in the listing details. Be sure to review all charges before completing your reservation or reach out to the host for clarification.

6. What are the check-in and check-out procedures for rentals by owner in Simpson Bay Beach?

Check-in and check-out times are specified on each listing. Communicate directly with the property owner for detailed instructions regarding key collection, access, and departure procedures to ensure a smooth stay here in the area.

7. Is it possible to secure flexible booking options for rentals in Simpson Bay Beach?

Flexible booking options depend on the individual host's policies. You should look for listings that specify flexible cancellation or arrival dates or contact the host directly to discuss your needs for a more adaptable stay.

More Rentals You May Like Near Simpson Bay Beach

10.0 (31 Reviews)
Apartment
MAHO BEACH VIEW
  • Air Conditioner
  • Parking
  • Pool
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More Top-Rated Rentals by Owner in Simpson Bay Beach Area