Insights
Where to stay

Vacation rentals in Simpson Bay

Search and compare Simpson Bay, St. Maarten holiday rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

Travel insights for holiday rentals in Simpson Bay

Use these up-to-date, data-driven insights about booking a holiday rental in Simpson Bay including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Simpson Bay?

The cheapest month to book a vacation rental in Simpson Bay is April ($280). Conversely, the most expensive month to stay in Simpson Bay is May ($1,486).

What is the cheapest day to stay in a vacation rental in Simpson Bay?

The cheapest day to stay in Simpson Bay is Monday ($170). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $465.

How far ahead should you book a vacation rental in Simpson Bay?

Save money by booking a vacation rental at least 65 days before your trip to Simpson Bay. The lowest price found when booking 65 days ahead was $86 per night.

Find deals

Other accommodations in Simpson Bay

Find the perfect holiday rental for your stay in Simpson Bay. There are 307 hotels in Simpson Bay and price data was last updated on 15 December 2025. The average price for a hotel in Simpson Bay is $592/night.
Mary's Boon Beach Resort & Spa
Mary's Boon Beach Resort & Spa

Mary's Boon Beach Resort & Spa

117 Simpson Bay Road, Simpson Bay, St. Maarten
1.3 km from city centre
Free Wi-Fi
Parking
$146
Avg. per night
View Deal
Simpson Bay Resort Marina & Spa
Simpson Bay Resort Marina & Spa

Simpson Bay Resort Marina & Spa

Billy Folly Road 37, Simpson Bay, St. Maarten
2.4 km from city centre
Free Wi-Fi
$173
Avg. per night
View Deal
Cupecoy Beach Club
Cupecoy Beach Club

Cupecoy Beach Club

#7 Rhine Road, Simpson Bay, St. Maarten
1.8 km from city centre
Free Wi-Fi
Air conditioning
$670
Avg. per night
View Deal
Simpson Bay Beach Modern Apartment. Roof Deck Ocean Views Wifi Satellite Tv.
Simpson Bay Beach Modern Apartment. Roof Deck Ocean Views Wifi Satellite Tv.

Simpson Bay Beach Modern Apartment. Roof Deck Ocean Views Wifi Satellite Tv.

Simpson Bay, St. Maarten
1.6 km from city centre
Air conditioning
$220
Avg. per night
View Deal

Where to stay in Simpson Bay

Explore different neighbourhoods and areas within Simpson Bay to find the perfect location for your stay. Map data was last updated on 15 December 2025.
Whether you're visiting Simpson Bay for leisure or business, utilize the map to find vacation rentals close to your ideal location. More information on a given vacation rental can be accessed by clicking the vacation rental's name within the map.

Facts about staying in Simpson Bay

Find useful tips and insights about staying in Simpson Bay to help you make the most of your experience. FAQs were last updated on 15 December 2025.

  • How much does a holiday rental in Simpson Bay cost?

    The average cost for a holiday rental in Simpson Bay is $593/night. A good holiday rental deal in Simpson Bay would be for $504/night or less. The cheapest rental deal found recently by our users was $71/night. If you’re flexible with your travel dates, then try to avoid booking May, the most expensive month of the year. Booking November is the cheapest month to book a holiday rental in Simpson Bay.

  • Are there any Aparthotel holiday rentals in Simpson Bay?

    Yes, there are 4 Aparthotel holiday rentals in Simpson Bay. According to our data, The Hills Residence is currently the most popular Aparthotel rental in the city.

Find better results for your stay in Simpson Bay