Sint Maarten Winter Rental
House
- Air Conditioner
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- Pet Friendly
Resort
- Air Conditioner
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- Pool
Condo
- Air Conditioner
- Parking
- Pool
Villa
- Air Conditioner
- Parking
- Pet Friendly
Resort
- Air Conditioner
- Parking
- Pool
Villa
- Air Conditioner
- Parking
- Pool
Why Choose Rent By Owner for your Sint Maarten Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Sint Maarten
How to Book Your Sint Maarten Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. 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 Sint Maarten
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental 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
Other Places to Stay in Sint Maarten
Philipsburg
Lowlands
Simpson Bay
Upper Prince's Quarter
Cupecoy
Pelican Key
Little Bay
Beacon Hill
Burgeaux Bay Beach
Cole Bay
Oyster Pond
Sint Maarten Winter Rental Frequently Asked Questions
1. What are the top Winter Rentals in Sint Maarten?
There are a lot of options in Sint Maarten. If you plan on staying in the Sint Maarten area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Sint Maarten:
- Rainbow Beach Club 2 Bedroom Condo - Our Rose in Winter
- The Cliffs 2BR 2.5BA Apt Private Beach Sleeps 5nLuxury Oceanfront Apartment
- Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV.
- Oceanfront villa with breathtaking views–2BR/2BA in Pelican Key, Simpson Bay
- Villa Tamarind - Luxury Oasis - Ocean Views
- Villa Tropicale and paella party
- Villa Amaya - Modern, Pristine Villa, Stunning Ocean Views, Private Pool, Beach
- Luxury Villa - Best View in the Caribbean
- Clean & Fresh: Blessed to have Survived IRMA ~ Beautiful White Sands of Maho Bay
- SPECIAL The Cliff At Cupecoy Beach A Fantastic Value At The Cliff
2. How many Winter Rentals are available in Sint Maarten?
Currently, the total number of properties listed by RBO in 2026 is over 1012 in the Sint Maarten area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Sint Maarten.
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