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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 March ($546). Conversely, the most expensive month to stay in Simpson Bay is November ($3,948).

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

The cheapest day to stay in Simpson Bay is Friday ($481). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is $1,363.

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

Save money by booking a vacation rental at least 74 days before your trip to Simpson Bay. The lowest price found when booking 74 days ahead was $98 per night.
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Other accommodations in Simpson Bay

Find the perfect holiday rental for your stay in Simpson Bay. There are 342 hotels in Simpson Bay and price data was last updated on 6 June 2025. The average price for a hotel in Simpson Bay is $927/night.
Show all 342 stays
Vicky's Keys - Hostel
Vicky's Keys - Hostel

Vicky's Keys - Hostel

The Keys Road 2-8, Lane 3, Philipsburg, St. Maarten
1.2 km from city centre
Free Wi-Fi
Air conditioning
$155
Avg. per night
View Deal
The Horny Toad Guest House
The Horny Toad Guest House

The Horny Toad Guest House

2 Vlaun Drive, Simpson Bay, St. Maarten
1.7 km from city centre
Free Wi-Fi
Parking
$292
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
$472
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 6 June 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 6 June 2025.

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

    $928 per night is how much a holiday rental in Simpson Bay costs, on average. $129 per night was the cheapest price recently found by our users, though anything for $847 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 November, and the cheapest time to book is January.

  • 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 Horny Toad Guest House as it’s currently the most popular Aparthotel rental among our users.

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