1. St. Martin
  2. Simpson Bay
  3. Rentals by Owner

Discover Your Perfect Simpson Bay Rentals by Owner

Simpson Bay Rentals by Owner

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10.0 (4 Reviews)
Villa
O SUN
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Simpson Bay Area

Why Choose Rent By Owner for your Simpson Bay 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.

Best Times to Visit Simpson Bay

When should you plan your Rentals by Owner stay?

Timing your vacation to this tropical destination ensures you enjoy the best weather and vibrant local experiences, allowing you to make the most of your rental by owner experience here in Simpson Bay, St. Martin.

Peak Season Highlights

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December to April

During the peak season, you'll experience ideal weather conditions—warm days and pleasant nights—that make this destination perfect for outdoor activities and beach relaxation.

Average Temperature Daytime: 28-30°C - Nighttime: 22-24°C
spring
July to August

The summer months attract visitors seeking vibrant local events and lively atmosphere, with warm temperatures that enhance your stay in the region.

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

Off-Season Highlights

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May to June

During this shoulder period, you may find fewer crowds while still enjoying warm weather, making it an excellent time to explore rental options with more flexibility.

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

This off-peak season offers a quieter atmosphere with occasional showers, providing a relaxed environment ideal for those looking to avoid the busy travel periods here.

Average Temperature Daytime: 27-28°C - Nighttime: 21-22°C

Weekly Weather Forecast for Simpson Bay

How to Book Your Simpson Bay 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

More Top-Rated Rentals by Owner in Simpson Bay 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 to relax and unwind in the warm Caribbean sunshine.
  • Take advantage of lush, landscaped gardens perfect for lounging or outdoor dining with friends and family.
  • Make the most of spacious patios or verandas designed for alfresco meals and evening gatherings.
  • Benefit from outdoor grilling facilities to prepare delicious meals while enjoying the scenic surroundings.
  • Relax on comfortable lounge chairs by the poolside, ideal for soaking up the sun during your stay here.
  • Utilize shaded pergolas or covered terraces that provide comfortable outdoor seating options.
  • Explore well-maintained pathways and gardens that connect you with the natural beauty of this tropical region.

Top Attractions Around Simpson Bay

What attractions are nearby?

When staying in this vibrant area, you can enjoy a variety of nearby activities, from relaxing on beautiful beaches to exploring lively local restaurants and shops just minutes from your rental by owner.

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Family Activities

  • Maho Beach: Enjoy a family day watching planes land and take off right over your head at this iconic spot, perfect for creating unforgettable memories in the region.
  • Simpson Bay Lagoon: Spend time exploring the calm waters with family-friendly kayaking or boat tours, ideal for experiencing the area's natural beauty safely.
  • Indigo Bay Beach: Relax and play on the soft sands of this tranquil beach, offering a safe environment for children to splash and build sandcastles.
  • Leisure World Water Park: Have a fun-filled day at the nearby water park, featuring kid-friendly rides and attractions that guarantee hours of entertainment for younger travelers.
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Adult Activities

  • Sailing and Yacht Charters: Experience the thrill of exploring the region’s waters with a private sailing or yacht charter, offering stunning views and a luxurious adventure.
  • Scuba Diving and Snorkeling: Discover vibrant marine life and coral reefs in the clear waters surrounding this destination, perfect for underwater exploration enthusiasts.
  • Jet Skiing and Water Sports: Enjoy high-energy water activities along the coastline, providing an exciting way to see the area’s scenic shoreline from the water.
  • Spa and Wellness Retreats: Indulge in relaxing spa treatments at local wellness centers, ideal for unwinding after a day of adventures in the region.

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Simpson Bay Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Take advantage of the area's diverse cuisine by trying popular restaurants and fresh seafood eateries nearby your rental to fully experience the regional flavors.
  • Utilize your rental’s proximity to beaches: Make the most of the stunning coastal views and relax on the sandy shores just minutes from your accommodation in this destination.
  • Plan excursions during off-peak hours: To enjoy a more tranquil experience at attractions and scenic spots, visit early or later in the day when the region tends to be less crowded.
  • Engage with local hosts and neighbors: Connecting with community members can provide insider tips and enhance your stay, making it more authentic and memorable.

Transportation Options

  • Rental Cars: You can easily rent a vehicle to explore the area at your own pace, with numerous rental agencies conveniently located nearby.
  • Taxis and Rideshare Services: Taxis and popular rideshare options offer reliable transportation around this vibrant destination, providing an effortless way to get around.
  • Public Buses: Budget-friendly public buses connect key spots within the region, making it simple to navigate without a car.
  • Water Taxis and Ferries: Water-based transportation options provide scenic routes across the bay, ideal for experiencing this coastal town from the water.

Local Customs Options

  • Local Greetings: When visiting here, it's customary to greet others with a warm smile or a friendly handshake, reflecting the welcoming spirit of the community.
  • Dining Etiquette: Sharing meals is a cherished tradition in the region, so be prepared to enjoy local dishes together and accept invitations to dine as a sign of good manners.
  • Respect for Festivals: Participating respectfully in local festivals and celebrations shows your appreciation for the area's vibrant cultural heritage.
  • Environmental Respect: Protecting the natural beauty of this destination by avoiding littering and respecting marine life is highly valued by residents and visitors alike.

Frequently Asked Questions About Simpson Bay Rentals by Owner

1. What are the top vacation rentals 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 Vacation Rentals in Simpson Bay:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1362 in the Simpson Bay 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. 

3. How do I find the most accurate cancellation policy for my rental by owner in Simpson Bay?

To view the cancellation policy, carefully read the listing details or contact the property owner directly. Each rental may have different terms, so verifying this information before booking ensures a smooth experience.

4. What amenities are typically included in rentals by owner in this area?

Amenities vary by property, but most rentals here offer essential features such as Wi-Fi, kitchen facilities, and air conditioning. Specific amenities are listed on each property page, so review those details or reach out to the owner for confirmation.

5. Are there any additional fees I should expect when booking a rental directly from an owner in the region?

Additional fees can include cleaning charges or service fees. These details are usually disclosed in the listing or during the booking process. Always review the total cost before confirming your reservation.

6. What is the best way to contact the property owner for special requests or questions about my stay?

You can communicate directly through the messaging system provided on the booking platform. For specific inquiries or requests, reaching out to the owner early helps ensure your needs are accommodated.

7. How do I ensure my booking at a rental by owner in this destination is secure and reliable?

Booking through a reputable platform provides verified listings and secure payment methods. Always read reviews, confirm licensing or registration if available, and communicate with the owner to clarify any concerns before finalizing your reservation.

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More Top-Rated Rentals by Owner in Simpson Bay Area