565+ Luxury Vacation Rentals & Cabins in Simpson Bay |
  1. Sint Maarten
  2. Simpson Bay

Simpson Bay Cabin Rentals

About Simpson Bay Vacation Rentals

There are more than 565 incredible getaway rentals that are available in Simpson Bay. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.ca and uncover great stays in Simpson Bay.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.ca in Simpson Bay, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Simpson Bay. Places to stay near Simpson Bay are 854.35 ft² on average, with prices averaging CA $686 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of travel memories in Simpson Bay. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

Show more
Show less

Top Cabin Rentals, Cottages, and Holiday Home Rentals in Simpson Bay

Type Count
Holiday Apartments 192
Villas 110
Vacation Homes 87
B&B 1
Unique Vacation Rentals 1
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Simpson Bay

★ Pro Tip: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Simpson Bay with Cabinns.ca.

Weather in Simpson Bay, SX

View the weather forecast for Simpson Bay before booking your Simpson Bay Vacation Rentals to confirm your best time to go.

December - February
High 85°F       Low 69°F
March - May
High 87°F       Low 72°F
June - August
High 89°F       Low 76°F
September - November
High 88°F       Low 73°F

Activities Simpson Bay Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Simpson Bay. Discover Top Attractions For Your Next Outdoor Adventure.


Kim Sha Beach
Simpson Bay Beach
Flamingo Beach
Dunes Casino
Hollywood Casino
Lay Bay Beach
Maho Beach
Mullet Bay Beach
American University of the Caribbean
Great Bay Beach
Guana Bay Beach
Cupecoy Beach
Dawn Beach
University of St. Martin
Fort Amsterdam
Starz City Casino
Philipsburg Courthouse
Mullet Bay
Little Bay Beach

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Flamingo Beach 1,514 Properties
Kim Sha Beach 1,511 Properties
Simpson Bay Beach 1,504 Properties
Hollywood Casino 1,460 Properties
Lay Bay Beach 1,438 Properties
Dunes Casino 1,401 Properties
Pelican Key 99 Properties
Beacon Hill 75 Properties

Complexes around Simpson Bay, SX


The Villas At Simpson Bay Resort Marina 6 Properties
Bella Vita 4 Properties
Villa Beach Secrets 3 Properties
Flamingo Beach Resort Simpson Bay 2 Properties
Beach Casino Resort Water Sports Tennis 1 Properties
Mary Beach Cottage Ocean 1 Properties

Frequently Asked Questions About Simpson Bay?

What are the top cabins, lake houses & summer homes in Simpson Bay?

We provide an array of great vacation destinations in Simpson Bay. If you are looking to stay in or around the Simpson Bay area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Simpson Bay:

How many cabin rentals and resorts have private pools in Simpson Bay?

We have 93 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Simpson Bay. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Simpson Bay is best for families?

Searching for a family-friendly cabin in Simpson Bay? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Simpson Bay?

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2025 is over 565 in the Simpson Bay area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca can provide you with a diverse amount of choices of the best luxury stays in Simpson Bay.

Nearby Neighborhood (2) 
Neighborhood Property Count
Maho Rental Cabins and Private Getaways in Simpson Bay 441
Pelican Key Rental Cabins and Private Getaways in Simpson Bay 99

People Also Ask

Finding the best prices in Simpson Bay

There are 15 hotels in Simpson Bay 21 resorts, and 389 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Simpson Bay