How much is a Rental rental for a week in Simpson Bay?

The average price for a weekly Simpson Bay Rental rental found by KAYAK users in the last 2 weeks is $1,225. Though this can obviously vary depending on the time of year of your stay and when you make the booking.

How much is a Rental rental for a month in Simpson Bay?

The average price for a monthly Simpson Bay Rental rental found by KAYAK users in the last 2 weeks is $7,617.

Simpson Bay Vacation Rentals from $68/night

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Best Simpson Bay vacation rentals

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Simpson Bay, St. Maarten

9.3Wonderful(107)

Free Wi-Fi

Pool

$158+

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Charming 1-Bed Studio in Simpson Bay - Beacon Hill

Simpson Bay, St. Maarten

9.6Wonderful(8)

Parking

Free Wi-Fi

Pet friendly

$119+

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Pelican Pearl

Simpson Bay, St. Maarten

8.8Very good(18)

Parking

Free Wi-Fi

Pool

$138+

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Great Ocean View Villa - 1 Bedroom Price Option

Simpson Bay, St. Maarten

$554+

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Maho Beach House - Charming Studio - Beach Access

Simpson Bay, St. Maarten

8.8Very good(25)

Free Wi-Fi

Pet friendly

$212+

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Maho Beach House - Luxe 1 Bedroom - Ocean Hideaway

Simpson Bay, St. Maarten

7.7Good(35)

Free Wi-Fi

Pool

Pet friendly

$381+

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Maho Beach House - Elegant 1 Bedroom, Beach Level

Simpson Bay, St. Maarten

7.7Good(5)

Free Wi-Fi

Pet friendly

$211+

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Cozy 1-BR Balcony apartment in brilliant Maho Beach AC, pool and fitness club.

Simpson Bay, St. Maarten

10Wonderful(1)

$228+

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Your apartment awaits

Simpson Bay, St. Maarten

$73+

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

Simpson Bay, St. Maarten

9.6Wonderful(26)

Free Wi-Fi

$211+

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Condo on the beach La Siesta w/ backup generator; beach and sunsets!

Simpson Bay, St. Maarten

10Wonderful(1)

$327+

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Emerald Apt at Maho Beach

Simpson Bay, St. Maarten

8.7Very good(8)

Parking

Free Wi-Fi

Pool

Pet friendly

$321+

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Flash Sale June-Oct. 2025!! Tropical Gem! Ocean+beach+garden Views + Many Perks!

Simpson Bay, St. Maarten

Free Wi-Fi

Simpson Bay, St. Maarten

Free Wi-Fi

Simpson Bay, St. Maarten

8.0Very good(22)

Parking

Free Wi-Fi

$161+

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Maho Beach House - Grand Studio - Oceanview Suite

Simpson Bay, St. Maarten

6.7Okay(9)

Free Wi-Fi

Pool

Pet friendly

$263+

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Booking Insights

KAYAK’s insights for vacation rentals in Simpson Bay

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Simpson Bay with confidence.

Which month has the cheapest vacation rental rates in Simpson Bay?

Vacation rentals are cheapest in Simpson Bay in November, with average rates of $276. In comparison, December is the most expensive month, with prices at $825.

What is the cheapest day of the week to book a vacation rental in Simpson Bay?

Thursday offers the lowest rates in Simpson Bay, with an average nightly price of $216. The highest prices are found on Sunday, with average rates at $658.

How early should you book a vacation rental in Simpson Bay?

Book at least 38 days before your stay begins to get the best price for your Simpson Bay vacation rental.

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Low season	High season	Average price (weeknight)	Average price (weekend night)
November	December	$361	$526
Cheapest month to stay with an average 50% drop in price.	Most expensive month to stay with an average 50% rise in price.	Average Sun - Thu price over the last 2 weeks.	Average Fri & Sat price over the last 2 weeks.

Pool, adults only, beachfront, and air-conditioned are the most popular vacation rental property amenities in Simpson Bay
Vacation rentals in Simpson Bay are around 65% more expensive than hotels on average. Search here to compare prices for all accommodation types in Simpson Bay.
The best vacation rental properties in Simpson Bay are Flash Sale June-Oct. 2025!! Tropical Gem! Ocean+beach+garden Views + Many Perks! (10.0, 31 reviews), Perfect beach front condo in Simpson Bay Beach 2 bedroom+ Loft, 2.5 Baths. (9.9, 20), and Simpson Bay Beach Modern Apartment. Roof Deck Ocean Views Wifi Satellite Tv. (9.6, 26), based on ratings and reviews from real travelers.
If you’re looking for a cheap vacation rental in Simpson Bay, you should consider visiting during the low season. The cheapest vacation homes in Simpson Bay can be found in November and October.
The cheapest night for renting a vacation home in Simpson Bay is Thursday. In contrast, the most expensive is Sunday.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Simpson Bay for 5 days.
The cheapest Simpson Bay vacation rental found on KAYAK in the last 2 weeks was $172, while the most expensive was $281.

How much is a Rental rental for a week in Simpson Bay?
The average price for a weekly Simpson Bay Rental rental found by KAYAK users in the last 2 weeks is $1,225. Though this can obviously vary depending on the time of year of your stay and when you make the booking.
How much is a Rental rental for a month in Simpson Bay?
The average price for a monthly Simpson Bay Rental rental found by KAYAK users in the last 2 weeks is $7,617.

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Simpson Bay vacation rentals

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Most recommended vacation rentals in Simpson Bay

KAYAK’s insights for vacation rentals in Simpson Bay

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Simpson Bay with confidence.

Which month has the cheapest vacation rental rates in Simpson Bay?

Vacation rentals are cheapest in Simpson Bay in November, with average rates of $276. In comparison, December is the most expensive month, with prices at $825.

What is the cheapest day of the week to book a vacation rental in Simpson Bay?

Thursday offers the lowest rates in Simpson Bay, with an average nightly price of $216. The highest prices are found on Sunday, with average rates at $658.

How early should you book a vacation rental in Simpson Bay?

Book at least 38 days before your stay begins to get the best price for your Simpson Bay vacation rental.

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

KAYAK's top tips for finding Simpson Bay vacation rental deals

FAQs when booking a vacation home in Simpson Bay

How much is a Rental rental for a week in Simpson Bay?

How much is a Rental rental for a month in Simpson Bay?

Where to stay in Simpson Bay?

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