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$ 1,559.

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$ 6,682.

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$ 179.

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$ 130/night

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Best Simpson Bay vacation rentals

Charming 1-Bed Studio in Simpson Bay - Beacon Hill

Simpson Bay, St. Maarten

9.6Wonderful(8)

Parking

Free Wi-Fi

C$ 208+

Check availability

Tradewinds Apartments Simpson Bay

Simpson Bay, St. Maarten

9.2Wonderful(93)

Free Wi-Fi

Pool

C$ 213+

Check availability

Maho Beach House - Luxe 1-Bedroom - Ocean View

Simpson Bay, St. Maarten

Free Wi-Fi

Simpson Bay, St. Maarten

8.8Very good(17)

Parking

Free Wi-Fi

Pool

C$ 183+

Check availability

Maho Beach House - Petite Studio - Beach Access

Simpson Bay, St. Maarten

8.7Very good(30)

Free Wi-Fi

Pool

Pet friendly

C$ 183+

Check availability

1 BR-Walk out patio and jump in the pool

Simpson Bay, St. Maarten

Free Wi-Fi

C$ 345+

Check availability

Maho Beach House - Elegant 1 Bedroom - Ocean View

Simpson Bay, St. Maarten

9.7Wonderful(3)

Free Wi-Fi

Pool

Pet friendly

C$ 363+

Check availability

Oasis 1 Bedroom Apartment Simpson Bay

Simpson Bay, St. Maarten

C$ 343+

Check availability

Great Ocean View Villa - 1 Bedroom Price Option

Simpson Bay, St. Maarten

C$ 784+

Check availability

Perfect beach front condo in Simpson Bay Beach 2 bedroom+ Loft, 2.5 Baths.

Simpson Bay, St. Maarten

9.8Wonderful(15)

Free Wi-Fi

Pool

C$ 574+

Check availability

Eduardo's Inn

Simpson Bay, St. Maarten

Free Wi-Fi

Simpson Bay, St. Maarten

8.2Very good(21)

Parking

Free Wi-Fi

C$ 223+

Check availability

Beautiful Maho Condo Steps from the Beach

Simpson Bay, St. Maarten

7.9Good(24)

C$ 360+

Check availability

Maho Beach House - Studio - Beach Access

Simpson Bay, St. Maarten

8.4Very good(24)

Free Wi-Fi

Pool

Pet friendly

C$ 208+

Check availability

Simpson Bay Ocean View - Deluxe 1 Bedroom Condo!

Simpson Bay, St. Maarten

Pool

Pet friendly

C$ 400+

Check availability

Rest, Relax and Renewbrbrbrbr

Simpson Bay, St. Maarten

C$ 152+

Check availability

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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.

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

Wednesday offers the lowest rates in Simpson Bay, with an average nightly price of C$ 298. The highest prices are found on Friday, with average rates at C$ 911.

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

Book at least 74 days before your stay begins to get the best price for your Simpson Bay vacation rental.

Find deals

Low season	September
High season	February
Average price (weeknight)	C$ 371
Average price (weekend night)	C$ 429

Cheapest month to stay with an average 86% drop in price.

Most expensive month to stay with an average 431% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

Beachfront, air-conditioned, pool, and no minors are the most popular vacation rental property amenities in Simpson Bay
Vacation rentals in Simpson Bay are around 35% 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 3 Br/3 Bath. Sint Maarten Direct Beachfront With Pool! Rates Start At 225/Nt!! (9.8, 23), 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 September and August.
The cheapest night for renting a vacation home in Simpson Bay is Wednesday. In contrast, the most expensive is Friday.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Simpson Bay for 17 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$ 1,559.
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$ 6,682.
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$ 179. 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.