Simpson Bay Ski Chalets
Condo
10.0(158 Reviews)
3 Bedrooms
3 Baths
6 Guests
4500 ft²
Private Pool
Oceanfront
Pool
Ocean View
CA $1,008/Night
7 Nights - CA $7,055
Apartment
10.0(4 Reviews)
4 Bedrooms
6 Baths
8 Guests
1700.7 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
CA $1,176/Night
7 Nights - CA $8,235
Condo
9.6(47 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $307/Night
7 Nights - CA $2,148
Villa
10.0(113 Reviews)
3 Bedrooms
3 Baths
6 Guests
1200 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $403/Night
7 Nights - CA $2,818
House
10.0(1 Review)
5 Bedrooms
5 Baths
10 Guests
13993.08 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $1,123/Night
7 Nights - CA $7,858
Apartment
10.0(89 Reviews)
3 Bedrooms
3 Baths
8 Guests
4000 ft²
Hot Tub- Ocean View
- Balcony/Terrace
View
CA $894/Night
7 Nights - CA $6,255
Apartment
10.0(1 Review)
1 Bedroom
2 Baths
6 Guests
1700.7 ft²
Pet Friendly
Parking
Air Conditioner
Internet
CA $665/Night
7 Nights - CA $4,658
Condo
10.0(81 Reviews)
2 Bedrooms
2 Baths
4 Guests
3067 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
CA $790/Night
7 Nights - CA $5,534
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
- Parking
- Air Conditioner
- Internet
Child Friendly
CA $304/Night
7 Nights - CA $2,128
Villa
10.0(75 Reviews)
3 Bedrooms
3 Baths
6 Guests
3000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $890/Night
7 Nights - CA $6,228
Villa
10.0(1 Review)
1 Bedroom
3 Baths
8 Guests
1700.7 ft²
- Pool
- Balcony/Terrace
- View
- Parking
CA $797/Night
7 Nights - CA $5,580
Villa
10.0(63 Reviews)
4 Bedrooms
3 Baths
8 Guests
4306 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $2,318/Night
7 Nights - CA $16,227
Why Choose Rent By Owner for your Simpson Bay Ski Chalets?
What makes our Ski Chalets 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 Simpson Bay
How to Book Your Simpson Bay Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. 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 Simpson Bay
Common Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets 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 Simpson Bay
Kim Sha Beach
Flamingo Beach
Simpson Bay Beach
Hollywood Casino
Lay Bay Beach
Dunes Casino
Pelican Key
Beacon Hill
Frequently Asked Questions About Simpson Bay Rental Ski Chalets
1. What are the top Ski Chalets in Simpson Bay?
There are a lot of options in Simpson Bay. If you plan on staying in the Simpson Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Simpson Bay:
- Villa Seaclusion accommodates 18 guests 9 beds 5 villas Ocean view pool
- Beach Front Modern Condo on the beach
- UNBRIDLED Le Papillon: Beachfront Elegance with Backup Generator
- very nice condo full equiped
- Villa Bonjour water front villa next to Maho
- SIMPSON BAY on the beach 2 BR, 2.5 bath, panoramic ocean view, pool, GENERATOR
- Sea View @ La Siesta, Simpson Bay, St. Maarten, N.A.
- Gorgeous Beachfront Ground Floor 2 Bedroom 2 Bath Condo
- Paradise in the West Indies
- Ocean Breeze at Le Papillon; Modern with steps to the Beach! Backup Generator!
2. How many Ski Chalets are available in Simpson Bay?
Currently, the total number of properties listed by RBO in 2026 is over 704 in the Simpson Bay area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Simpson Bay.
More Rentals You May Like Near Simpson Bay
Apartment
9.8(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1603.82 ft²
Private Beach- Oceanfront
Spa- Pool
CA $757/Night
7 Nights - CA $5,297
Condo
10.0(60 Reviews)
3 Bedrooms
3 Baths
6 Guests
2280 ft²
Fireplace/Heating- Pool
- Ocean View
- Balcony/Terrace
CA $854/Night
7 Nights - CA $5,977
Condo
10.0(60 Reviews)
2 Bedrooms
2 Baths
4 Guests
1680 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
CA $722/Night
7 Nights - CA $5,055
Apartment
10.0(57 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $220/Night
7 Nights - CA $1,538
Villa
10.0(53 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $403/Night
7 Nights - CA $2,824
Villa
10.0(44 Reviews)
3 Bedrooms
2 Baths
6 Guests
2153 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $1,049/Night
7 Nights - CA $7,341
Apartment
10.0(42 Reviews)
2 Bedrooms
2 Baths
4 Guests
2151 ft²
- Ocean View
- Balcony/Terrace
- View
Kitchen
CA $557/Night
7 Nights - CA $3,896
Condo
10.0(37 Reviews)
3 Bedrooms
3 Baths
6 Guests
2800 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
CA $1,095/Night
7 Nights - CA $7,667
Condo
10.0(36 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $482/Night
7 Nights - CA $3,375
Condo
10.0(31 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $456/Night
7 Nights - CA $3,192
Condo
10.0(29 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $798/Night
7 Nights - CA $5,584
Condo
10.0(29 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $308/Night
7 Nights - CA $2,155
