Villa
10.0(180 Reviews)
5 Bedrooms
14 Guests
Private Pool
Parking
Pool
Balcony/Terrace
CA $780/Night
7 Nights - CA $5,458
Sint Maarten Winter Rentals & Holiday Homes
Discover winter rentals Sint Maarten - We found 968 exact matches
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Compare Winter Rental in Sint Maarten
10.0
House
10.0(2 Reviews)
1 Bedroom
4 Guests
Oceanfront
Hot Tub- Pool
Ocean View
CA $204/Night
7 Nights - CA $1,427
CA $1,313/Night
7 Nights - CA $9,192
Villa
10.0(108 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $1,393/Night
7 Nights - CA $9,748
CA $628/Night
7 Nights - CA $4,398
New
Villa
10.0(92 Reviews)
5 Bedrooms
9 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $2,882/Night
7 Nights - CA $20,175
Apartment
10.0(1 Review)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
Air Conditioner
CA $477/Night
7 Nights - CA $3,336
Apartment
10.0(92 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
CA $960/Night
7 Nights - CA $6,717
House
9.7(3 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $166/Night
7 Nights - CA $1,159
Apartment
10.0(90 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $329/Night
7 Nights - CA $2,303
House
9.7(3 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $213/Night
7 Nights - CA $1,488
Condo
10.0(82 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $939/Night
7 Nights - CA $6,575
CA $812/Night
7 Nights - CA $5,683
Condo
10.0(63 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,007/Night
7 Nights - CA $7,045
Condo
10.0(61 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $1,198/Night
7 Nights - CA $8,383
Condo
10.0(60 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $869/Night
7 Nights - CA $6,085
Condo
10.0(60 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $426/Night
7 Nights - CA $2,983
Villa
10.0(59 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,347/Night
7 Nights - CA $9,426
Villa
10.0(53 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
Kitchen
CA $421/Night
7 Nights - CA $2,947
Villa
10.0(50 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $897/Night
7 Nights - CA $6,282
Condo
10.0(44 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $409/Night
7 Nights - CA $2,862
Condo
10.0(37 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $1,389/Night
7 Nights - CA $9,722
Condo
10.0(36 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $589/Night
7 Nights - CA $4,124
Villa
10.0(34 Reviews)
6 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
Breakfast
CA $1,517/Night
7 Nights - CA $10,619
About Sint Maarten Winter Rental on Casai.ca
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 968 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
Frequently Asked Questions About Sint Maarten Winter Rentals
What are the top rated 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:
- Royal Dream Beachfront Condo- Walk Out to Palm Tree Lined Beach & Pool
- Direct Beachfront 6 BDR/en-suite/maid included. Excellent service. Rare gem (H)
- Villa Crystal Clear - Luxury Villa with Private Pool
- Beach Front Modern Condo on the beach
- Maho Royal Islander, La Terrasse 2br 2ba Beautiful White Sand Beach
- ☀️👙Sea Fan by IRE Vacations - Exquisite Villa With Views from Each Bedroom
- Gorgeous Beachfront Ground Floor 2 Bedroom 2 Bath Condo
- Grand Getaway - Royal Retreats at Maho Beach Studio
- OCEANFRONT 3 Bedroom Condo at Cupecoy Beach Club
- Villa Ocean - Indulge Yourself in Paradise
How much does it cost to rent a place to stay near Sint Maarten in the wintertime?
The average cost for winter rentals in Sint Maarten is $680 per night. Casai has a wide list of great winter places to stay near Sint Maarten that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Sint Maarten that allow pets?
Yes, here are the top cottage/chalet rentals in Sint Maarten that allow you to bring your pet or dog:
- Gorgeous ocean views! Spend your days in pure bliss at a perfect paradise!
- Sublime Stay - Royal Retreats at Maho Beach
- Alizee by Island Properties Online
- DREAM 5-Star Premier BEACHFRONT 3 Bedroom Villa + Private Pool
See all pet-friendly vacation rentals in Sint Maarten on Casai.ca
Do you have any winter rentals in Sint Maarten that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Sint Maarten to find what works for you.
Are there winter accommodations in Sint Maarten that have indoor swimming pools?
As of 2026, the data from Casai.ca shows that there are over 968 private swimming pools or indoor pools accommodations near Sint Maarten along with other great amenities.
Do any winter holiday rentals in Sint Maarten have hot tubs?
About 968 holiday rentals in Sint Maarten boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Sint Maarten?
Yes, there are many luxury places to stay in Sint Maarten for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Sint Maarten with all the best amenities for your next trip.
