Sint Maarten Winter Rental
House
10.0(159 Reviews)
4 Bedrooms
3 Baths
10 Guests
6000 ft²
Private Pool
Pool
Ocean View
Balcony/Terrace
CA $1,414/Night
7 Nights - CA $9,895
House
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
495.14 ft²
Oceanfront- Pool
- Ocean View
View
CA $209/Night
7 Nights - CA $1,465
Resort
8.8(1000 Reviews)
1 Bath
Spa- Pool
- Ocean View
- Balcony/Terrace
CA $1,008/Night
7 Nights - CA $7,054
Condo
10.0(158 Reviews)
3 Bedrooms
3 Baths
6 Guests
4500 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,005/Night
7 Nights - CA $7,033
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
1550 ft²
- Pool
- Balcony/Terrace
Parking
Air Conditioner
CA $469/Night
7 Nights - CA $3,285
Condo
10.0(154 Reviews)
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Private Pool
- Oceanfront
Hot Tub- Spa
CA $381/Night
7 Nights - CA $2,666
Apartment
9.5(2 Reviews)
1 Bedroom
1 Bath
3 Guests
1248.61 ft²
Private Beach- Oceanfront
- Pool
- Ocean View
CA $435/Night
7 Nights - CA $3,044
Villa
10.0(143 Reviews)
4 Bedrooms
3 Baths
10 Guests
3500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $852/Night
7 Nights - CA $5,967
Villa
9.3(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
3003.13 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Spa
CA $799/Night
7 Nights - CA $5,595
Villa
10.0(124 Reviews)
2 Bedrooms
3 Baths
6 Guests
1500 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $409/Night
7 Nights - CA $2,861
House
9.0(1 Review)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $199/Night
7 Nights - CA $1,392
Condo
10.0(121 Reviews)
2 Bedrooms
3 Baths
4 Guests
1750 ft²
- Oceanfront
- Spa
- Pool
- Ocean View
CA $453/Night
7 Nights - CA $3,171
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
Lowlands
Philipsburg
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:
- The Cliffs 2BR 2.5BA Apt Private Beach Sleeps 5nLuxury Oceanfront Apartment
- Oceanfront villa with breathtaking views–2BR/2BA in Pelican Key, Simpson Bay
- Villa Tropicale and paella party
- Villa Tamarind - Luxury Oasis - Spectacular Views
- luxury quiet 2 bedrooms private pool breathtaking view
- Villa Amaya - Modern, Pristine Villa, Stunning Ocean Views, Private Pool, Beach
- Luxury 5 star Indigo Bay Villa w/Pool-Walk to Beach
- Luxury Villa - Best View in the Caribbean
- Beach - Private Heated Pool - 2 Master King Bedrooms - Auto Generator Power
- Le Papillon on the beach
2. How many Winter Rentals are available in Sint Maarten?
Currently, the total number of properties listed by RBO in 2026 is over 1004 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
Resort
8.9(329 Reviews)
1 Bath
18 Guests
1115.86 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Spa
CA $754/Night
7 Nights - CA $5,280
Villa
10.0(113 Reviews)
3 Bedrooms
3 Baths
6 Guests
1200 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $401/Night
7 Nights - CA $2,810
Villa
10.0(106 Reviews)
3 Bedrooms
3 Baths
7 Guests
5000 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
CA $1,373/Night
7 Nights - CA $9,613
Villa
10.0(104 Reviews)
4 Bedrooms
4 Baths
8 Guests
4000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $718/Night
7 Nights - CA $5,030
Apartment
10.0(89 Reviews)
3 Bedrooms
3 Baths
8 Guests
4000 ft²
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
CA $891/Night
7 Nights - CA $6,235
Apartment
10.0(88 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $196/Night
7 Nights - CA $1,369
Condo
10.0(81 Reviews)
2 Bedrooms
2 Baths
4 Guests
3067 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
CA $788/Night
7 Nights - CA $5,516
Villa
10.0(75 Reviews)
3 Bedrooms
3 Baths
6 Guests
3000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $887/Night
7 Nights - CA $6,209
Condo
10.0(60 Reviews)
3 Bedrooms
3 Baths
6 Guests
2280 ft²
Fireplace/Heating- Pool
- Ocean View
- Balcony/Terrace
CA $851/Night
7 Nights - CA $5,958
Condo
10.0(60 Reviews)
2 Bedrooms
2 Baths
4 Guests
1680 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
CA $720/Night
7 Nights - CA $5,039
Villa
10.0(59 Reviews)
3 Bedrooms
4 Baths
6 Guests
4400 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $941/Night
7 Nights - CA $6,591
Condo
10.0(59 Reviews)
3 Bedrooms
2 Baths
4 Guests
1400 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $399/Night
7 Nights - CA $2,793
