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Holiday hires in Simpson Bay

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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 ($421). Conversely, the most expensive month to stay in Simpson Bay is May ($2,232).

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

The cheapest day to stay in Simpson Bay is Monday ($255). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $699.

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 $129 per night.

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Other accommodations in Simpson Bay

Find the perfect holiday rental for your stay in Simpson Bay. There are 309 hotels in Simpson Bay and price data was last updated on 12 December 2025. The average price for a hotel in Simpson Bay is $889/night.
Simpson Bay Suites
Simpson Bay Suites

Simpson Bay Suites

3D Billy Fully RD, Simpson Bay, St. Maarten
2.8 km from city centre
Free Wi-Fi
Parking
$204
Avg. per night
View Deal
The Atrium Beach Resort and Spa Sint Marteen Ascend Hotel Collection
The Atrium Beach Resort and Spa Sint Marteen Ascend Hotel Collection

The Atrium Beach Resort and Spa Sint Marteen Ascend Hotel Collection

6 Billy Folly Road, Simpson Bay, St. Maarten
2.7 km from city centre
Free Wi-Fi
Parking
$242
Avg. per night
View Deal
Baker's Suites
Baker's Suites

Baker's Suites

Spinel Road #2, Simpson Bay, St. Maarten
2.7 km from city centre
Free Wi-Fi
Parking
$302
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
$1,038
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
$330
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 12 December 2025.
Use the map to find holiday rentals in Simpson Bay that are close to the points of interest you'll be frequenting. Clicking on a holiday rental name will take you to a page with pricing, reviews, and more useful information.

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 12 December 2025.

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

    $890 per night is how much a holiday rental in Simpson Bay costs, on average. $107 per night was the cheapest price recently found by our users, though anything for $757 per night or less is a good deal. Keep in mind that Simpson Bay holiday rental prices fluctuate throughout the year: the most expensive month to book is May, and the cheapest time to book is November.

  • Are there any Aparthotel holiday rentals in Simpson Bay?

    If you’re looking to book a Aparthotel holiday rental in Simpson Bay, then you have 4 to choose from. We recommend looking at The Hills Residence as it’s currently the most popular Aparthotel rental among our users.

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