Villa
10.0(178 Reviews)
5 Bedrooms
5 Baths
12 Guests
4500 ft²
Private Pool
Parking
Pool
Ocean View
US $499/Night
7 Nights - US $3,491
Sint Maarten Winter Rental
10.0
House
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
505.9 ft²
Oceanfront
Hot Tub- Parking
- Pool
US $144/Night
7 Nights - US $1,011
US $930/Night
7 Nights - US $6,510
Condo
10.0(162 Reviews)
3 Bedrooms
3 Baths
6 Guests
4500 ft²
- Private Pool
- Oceanfront
Breakfast- Parking
US $817/Night
7 Nights - US $5,716
Apartment
10.0(1 Review)
2 Bedrooms
3 Baths
5 Guests
1130.21 ft²
- Hot Tub
- Parking
- Pool
View
US $445/Night
7 Nights - US $3,115
Condo
10.0(155 Reviews)
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $296/Night
7 Nights - US $2,074
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
1550 ft²
- Parking
- Pool
Balcony/Terrace
Air Conditioner
US $338/Night
7 Nights - US $2,363
Villa
10.0(150 Reviews)
4 Bedrooms
3 Baths
10 Guests
3500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
US $701/Night
7 Nights - US $4,907
Apartment
9.7(3 Reviews)
1 Bedroom
1 Bath
3 Guests
1248.61 ft²
Private Beach- Oceanfront
- Parking
- Pool
US $313/Night
7 Nights - US $2,190
Villa
10.0(127 Reviews)
2 Bedrooms
3 Baths
6 Guests
1500 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $310/Night
7 Nights - US $2,170
House
9.5(2 Reviews)
1 Bedroom
1 Bath
4 Guests
505.9 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $151/Night
7 Nights - US $1,054
Villa
10.0(123 Reviews)
6 Bedrooms
7 Baths
12 Guests
8000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $1,783/Night
7 Nights - US $12,480
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.
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
Simpson Bay
Philipsburg
Upper Prince's Quarter
Cupecoy
Pelican Key
Beacon Hill
Burgeaux Bay Beach
Little Bay
Cole Bay
Indigo Bay
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:
- Amazing Beachfront Condo in Simpson Bay -Walk Out Beach/Pool
- Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI, Live TV.
- Luxury 5 star Indigo Bay Villa w/Pool-Walk to Beach
- Villa Amaya - Modern, Pristine Villa, Stunning Ocean Views, Private Pool, Beach
- Luxury Villa - Best View in the Caribbean
- Clean & Fresh: Beautiful White Sands of Maho Bay with views of planes landing
- OCEAN FRONT 3 BEDROOM PENTHOUSE UNIT. STAY IN LUXURY.
- Perfect beach front condo in Simpson Bay Beach 2 bedroom+ Loft, 2.5 Baths.
- Direct Beachfront 6 BDR/en-suite/maid included. Excellent service. Rare gem (O)
- LUXURY and MODERN 3BR On the Beach - CUPECOY
2. How many Winter Rentals are available in Sint Maarten?
Currently, the total number of properties listed by RBO in 2026 is over 979 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
Villa
9.3(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
3003.13 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Parking
US $575/Night
7 Nights - US $4,025
Villa
10.0(108 Reviews)
3 Bedrooms
3 Baths
7 Guests
5000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $782/Night
7 Nights - US $5,472
Villa
10.0(108 Reviews)
4 Bedrooms
4 Baths
8 Guests
4000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $586/Night
7 Nights - US $4,103
Apartment
10.0(92 Reviews)
3 Bedrooms
3 Baths
8 Guests
4000 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $771/Night
7 Nights - US $5,397
Apartment
10.0(90 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $228/Night
7 Nights - US $1,596
Condo
10.0(82 Reviews)
2 Bedrooms
2 Baths
4 Guests
3067 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $641/Night
7 Nights - US $4,485
Villa
10.0(75 Reviews)
3 Bedrooms
3 Baths
6 Guests
3000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $715/Night
7 Nights - US $5,008
Villa
10.0(64 Reviews)
4 Bedrooms
3 Baths
8 Guests
4306 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,849/Night
7 Nights - US $12,944
Condo
10.0(63 Reviews)
3 Bedrooms
3 Baths
6 Guests
2280 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $682/Night
7 Nights - US $4,773
Condo
10.0(60 Reviews)
2 Bedrooms
2 Baths
4 Guests
1680 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $455/Night
7 Nights - US $3,185
Condo
10.0(60 Reviews)
2 Bedrooms
2 Baths
5 Guests
1600 ft²
- Hot Tub
- Parking
- Pool
Spa
US $370/Night
7 Nights - US $2,590
Condo
10.0(60 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $316/Night
7 Nights - US $2,212
