Insights
Where to stay

Holiday hires 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 October ($464). Conversely, the most expensive month to stay in Simpson Bay is November ($2,516).

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

The cheapest day to stay in Simpson Bay is Thursday ($634). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $1,360.

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

Save money by booking a vacation rental at least 38 days before your trip to Simpson Bay. The lowest price found when booking 38 days ahead was $104 per night.
Find deals

Other accommodations in Simpson Bay

Find the perfect holiday rental for your stay in Simpson Bay. There are 505 hotels in Simpson Bay and price data was last updated on 25 July 2025. The average price for a hotel in Simpson Bay is $865/night.
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
$153
Avg. per night
View Deal
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
$183
Avg. per night
View Deal
The Atrium Beach Resort and Spa Ascend Hotel Collection
The Atrium Beach Resort and Spa Ascend Hotel Collection

The Atrium Beach Resort and Spa Ascend Hotel Collection

6 Billy Folly Road, Simpson Bay, St. Maarten
2.7 km from city centre
Free Wi-Fi
Parking
$174
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
$194
Avg. per night
View Deal
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
$204
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 25 July 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 25 July 2025.

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

    $865 per night is how much a holiday rental in Simpson Bay costs, on average. $78 per night was the cheapest price recently found by our users, though anything for $796 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.

Find better results for your stay in Simpson Bay

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $76 and Hotels Under $151. Discover hotel discounts now and make your hotel reservation today.