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

The average price for a weekly Simpson Bay vacation rental found by KAYAK users in the last 2 weeks is C$ 2,304.

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

The average price for a monthly Simpson Bay vacation rental found by KAYAK users in the last 2 weeks is C$ 9,872.

What types of vacation rentals are available in Simpson Bay?

There are loads of different property types that you can make your vacation home in Simpson Bay. You’ll find apartments, bungalows, condos, cottages, houses, houseboats and villas.

Are there any pet-friendly vacation rentals in Simpson Bay?

There are a number of dog and pet-friendly Simpson Bay vacation rentals, with around 9% allowing you to bring your pet along with you.

How much is a vacation rental in Simpson Bay for tonight?

In the last 72 hours, users have found Simpson Bay vacation rentals for tonight for as low as C$ 343.

How much is a vacation rental in Simpson Bay for this weekend?

In the last 72 hours, users have found Simpson Bay vacation rentals for this weekend for as low as C$ 375 per night.

How can I find vacation rentals near me in Simpson Bay?

Take a look at our vacation rentals map to find the best vacation rental homes near you.

Simpson Bay Vacation Rentals from C$ 196/night

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Best Simpson Bay vacation rentals

Charming 1-Bed Studio in Simpson Bay - Beacon Hill

9.6 Wonderful

C$ 215+

Parking

Free Wi-Fi

Tradewinds Apartments Simpson Bay

9.2 Wonderful

C$ 333+

Free Wi-Fi

Pool

Maho Beach House - Luxe 1-Bedroom - Ocean View - Simpson Bay - Bedroom

Maho Beach House - Luxe 1-Bedroom - Ocean View

9.5 Wonderful

C$ 483+

Free Wi-Fi

Pelican Pearl - Simpson Bay - Pool

Pelican Pearl

8.8 Very good

C$ 212+

Parking

Free Wi-Fi

Pool

Maho Beach House - Elegant 1 Bedroom - Ocean View - Simpson Bay - Balcony

Maho Beach House - Elegant 1 Bedroom - Ocean View

9.7 Wonderful

C$ 471+

Free Wi-Fi

Pool

Pet friendly

1 BR-Walk out patio and jump in the pool - Simpson Bay - Balcony

1 BR-Walk out patio and jump in the pool

C$ 356+

Free Wi-Fi

Great Ocean View Villa - 1 Bedroom Price Option - Simpson Bay - Balcony

Great Ocean View Villa - 1 Bedroom Price Option

C$ 756+

Oasis 1 Bedroom Apartment Simpson Bay - Simpson Bay - Beach

Oasis 1 Bedroom Apartment Simpson Bay

9 Wonderful

C$ 389+

Parking

Free Wi-Fi

Pool

Pet friendly

Sea View @ La Siesta, Simpson Bay, St. Maarten, N.A. - Simpson Bay - Balcony

Sea View @ La Siesta, Simpson Bay, St. Maarten, N.A.

C$ 969+

Free Wi-Fi

Pool

Villa Cleavage - Simpson Bay

Villa Cleavage

8.3 Very good

C$ 232+

Parking

Free Wi-Fi

Beautiful Maho Condo Steps from the Beach - Simpson Bay

Beautiful Maho Condo Steps from the Beach

7.9 Good

C$ 374+

Simpson Bay Ocean View - Deluxe 1 Bedroom Condo! - Simpson Bay

Simpson Bay Ocean View - Deluxe 1 Bedroom Condo!

C$ 415+

Pool

Pet friendly

Maho Beach House - Studio - Beach Access - Simpson Bay

Maho Beach House - Studio - Beach Access

8.3 Very good

C$ 291+

Free Wi-Fi

Pool

Pet friendly

Maho Beach House - Petite Studio - Beach Access - Simpson Bay

Maho Beach House - Petite Studio - Beach Access

8.7 Very good

C$ 258+

Free Wi-Fi

Pool

Pet friendly

Rest, Relax and Renewbrbrbrbr - Simpson Bay

Rest, Relax and Renewbrbrbrbr

C$ 158+

Maho Beach House - Grand Studio - Oceanview Suite - Simpson Bay

Maho Beach House - Grand Studio - Oceanview Suite

6.8 Okay

C$ 404+

Free Wi-Fi

Pool

Pet friendly

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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 June, with average rates of C$ 155. In comparison, February is the most expensive month, with prices at C$ 6,219.

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

Tuesday offers the lowest rates in Simpson Bay, with an average nightly price of C$ 409. The highest prices are found on Thursday, with average rates at C$ 1,230.

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

Book at least 63 days before your stay begins to get the best price for your Simpson Bay vacation rental.

Find deals

Low season	June
High season	February
Average price (weeknight)	C$ 498
Average price (weekend night)	C$ 624

Cheapest month to stay with an average 88% drop in price.

Most expensive month to stay with an average 382% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

Beachfront, no minors, air-conditioned, and pool are the most popular vacation rental property amenities in Simpson Bay
Vacation rentals in Simpson Bay are around 20% 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 Wow! Wow! Wow!, New Villa Libre` Stunning Inside And Out! (10.0, 20 reviews), Current Discounted Rates! Tropical Gem! Ocean+beach+garden Views + Many Perks!! (10.0, 26), 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 July and October.
The cheapest night for renting a vacation home in Simpson Bay is Tuesday. In contrast, the most expensive is Saturday.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Simpson Bay for 14 days.

See more tips

How much is a vacation rental for a week in Simpson Bay?
The average price for a weekly Simpson Bay vacation rental found by KAYAK users in the last 2 weeks is C$ 2,304.
How much is a vacation rental for a month in Simpson Bay?
The average price for a monthly Simpson Bay vacation rental found by KAYAK users in the last 2 weeks is C$ 9,872.
What types of vacation rentals are available in Simpson Bay?
There are loads of different property types that you can make your vacation home in Simpson Bay. You’ll find apartments, bungalows, condos, cottages, houses, houseboats and villas.
Are there any pet-friendly vacation rentals in Simpson Bay?
There are a number of dog and pet-friendly Simpson Bay vacation rentals, with around 9% allowing you to bring your pet along with you.
How much is a vacation rental in Simpson Bay for tonight?
In the last 72 hours, users have found Simpson Bay vacation rentals for tonight for as low as C$ 343. Search here for similar prices
How much is a vacation rental in Simpson Bay for this weekend?
In the last 72 hours, users have found Simpson Bay vacation rentals for this weekend for as low as C$ 375 per night. Search here for similar prices
How can I find vacation rentals near me in Simpson Bay?
Take a look at our vacation rentals map to find the best vacation rental homes near you.