558+ Private Villas and Holiday Rentals in Simpson Bay |
  1. Sint Maarten
  2. Simpson Bay

Simpson Bay Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Simpson Bay

Discover more than 558 vacation rentals available in Simpson Bay. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Simpson Bay.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Simpson Bay, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Simpson Bay. On average, places to stay near Simpson Bay offer 880.45 ft², with nightly prices averaging US $490.

With Casai, finding and comparing holiday rentals in Simpson Bay is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Simpson Bay

Type Count
Holiday Apartments 190
Villas 109
Vacation Homes 83
Cottages 1

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

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Simpson Bay.

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

Top Attractions Around Simpson Bay, SX

Casai offers a large selection of top attractions around Simpson Bay . Research things to do on your vacation before you visit Simpson Bay.


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

Other Places to Stay in Simpson Bay, SX


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 94 Properties
Beacon Hill 74 Properties

Frequently Asked Questions About Simpson Bay?

What are the top holiday rentals in Simpson Bay?

With numerous options available in Simpson Bay, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Simpson Bay:

How many holiday rentals have private pools in Simpson Bay?

Discover a selection of holiday rentals with private pools near Simpson Bay with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Simpson Bay are best for families?

If you're searching for a family-friendly holiday home in Simpson Bay, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Simpson Bay:

How many Casai.com holiday rentals are available in Simpson Bay?

As of 2025, Casai boasts over 558 properties listed in the Simpson Bay area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Simpson Bay.

Nearby Neighborhood (2) 
Neighborhood Property Count
Maho Vacation Rentals in Simpson Bay 436
Pelican Key Vacation Rentals in Simpson Bay 94

People Also Ask

There are 558 Simpson Bay, SX Holiday Rentals

Recently Booked Holiday Rentals in Simpson Bay