Sint Maarten Winter Rental
4500 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
£404/Night
For 7 Nights £2,831
1248.61 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Beach
- Oceanfront
- Pool
£232/Night
For 7 Nights £1,625
1 Bathroom
Ocean View
Resort
- Spa
- Pool
- Ocean View
£484/Night
For 7 Nights £3,389
6000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Pool
- Ocean View
£810/Night
For 7 Nights £5,668
3003.13 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Beach
- Oceanfront
- Hot Tub
£427/Night
For 7 Nights £2,987
4500 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Private Pool
- Oceanfront
- Pool
£536/Night
For 7 Nights £3,754
1115.86 ft²
18 Guests
1 Bathroom
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
£403/Night
For 7 Nights £2,819
1800 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Oceanfront
- Hot Tub
£210/Night
For 7 Nights £1,467
656.6 ft²
32 Guests
1 Bathroom
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
£185/Night
For 7 Nights £1,292
3500 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
£471/Night
For 7 Nights £3,294
415.49 ft²
12 Guests
10 Bedrooms
5 Bathrooms
Free Cancellation
House
- Oceanfront
- Skiing
- Ocean View
£95/Night
For 7 Nights £662
1500 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
£221/Night
For 7 Nights £1,546
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
Indigo Bay
Cay Bay Hill
Frequently Asked Questions About Sint Maarten Winter Rentals
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
- Oceanfront villa with breathtaking views–2BR/2BA in Pelican Key, Simpson Bay
- Villa Tamarind - Luxury Oasis - Spectacular Views
- Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access
- Villa Amaya - Modern, Pristine Villa, Stunning Ocean Views, Private Pool, Beach
- It’s all about the view - Ocean front 3 bedroom end unit with backup generator!
- Luxury Villa - Best View in the Caribbean
- Le Papillon on the beach
- Clean & Fresh: Beautiful White Sands of Maho Bay with views of planes landing
- 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 985 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.
More Rentals You May Like Near Sint Maarten
796.53 ft²
15 Guests
5 Bathrooms
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
£162/Night
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8000 ft²
12 Guests
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7 Bathrooms
Ocean View
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- Ocean View
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6 Guests
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Ocean View
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7 Guests
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3 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Pool
£698/Night
For 7 Nights £4,886
4000 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
£376/Night
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600 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Pool
- Oceanfront
- Hot Tub
£177/Night
For 7 Nights £1,242
4000 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Hot Tub
- Ocean View
- Balcony/Terrace
£481/Night
For 7 Nights £3,370
3067 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
£421/Night
For 7 Nights £2,945
4400 ft²
6 Guests
3 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£503/Night
For 7 Nights £3,518
2280 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
£454/Night
For 7 Nights £3,181
1680 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Hot Tub
- Fireplace/Heating
£372/Night
For 7 Nights £2,602
1600 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Spa
- Pool
£263/Night
For 7 Nights £1,841
