What types of holiday rentals are available in Simpson Bay?

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

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

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

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

In the last 72 hours, users have found Simpson Bay holiday rentals for tonight for as low as £97.

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

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

Simpson Bay Holiday Rentals from £38/night

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Best Simpson Bay holiday rentals

Charming 1-Bed Studio in Simpson Bay - Beacon Hill

Simpson Bay, St. Maarten

9.6Wonderful(8)

Parking

Free Wi-Fi

Air conditioning

£112+

Check availability

Tradewinds Apartments Simpson Bay

Simpson Bay, St. Maarten

9.2Wonderful(93)

Free Wi-Fi

Pool

Air conditioning

£115+

Check availability

Maho Beach House - Luxe 1-Bedroom - Ocean View

Simpson Bay, St. Maarten

9.5Wonderful(29)

Free Wi-Fi

Air conditioning

£184+

Check availability

Pelican Pearl

Simpson Bay, St. Maarten

8.8Very Good(17)

Parking

Free Wi-Fi

Pool

Air conditioning

£98+

Check availability

Maho Beach House - Petite Studio - Beach Access

Simpson Bay, St. Maarten

8.7Very Good(30)

Free Wi-Fi

Pool

Pet-friendly

Air conditioning

£99+

Check availability

1 BR-Walk out patio and jump in the pool

Simpson Bay, St. Maarten

Free Wi-Fi

£186+

Check availability

Maho Beach House - Elegant 1 Bedroom - Ocean View

Simpson Bay, St. Maarten

9.7Wonderful(3)

Free Wi-Fi

Pool

Pet-friendly

Air conditioning

£196+

Check availability

Oasis 1 Bedroom Apartment Simpson Bay

Simpson Bay, St. Maarten

Air conditioning

£185+

Check availability

Great Ocean View Villa - 1 Bedroom Price Option

Simpson Bay, St. Maarten

£422+

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

Air conditioning

£309+

Check availability

Eduardo's Inn

Simpson Bay, St. Maarten

Free Wi-Fi

Simpson Bay, St. Maarten

8.2Very Good(21)

Parking

Free Wi-Fi

Air conditioning

£120+

Check availability

Beautiful Maho Condo Steps from the Beach

Simpson Bay, St. Maarten

7.9Good(24)

£194+

Check availability

Maho Beach House - Studio - Beach Access

Simpson Bay, St. Maarten

8.4Very Good(24)

Free Wi-Fi

Pool

Pet-friendly

Air conditioning

£112+

Check availability

Simpson Bay Ocean View - Deluxe 1 Bedroom Condo!

Simpson Bay, St. Maarten

Pool

Pet-friendly

Air conditioning

£216+

Check availability

Rest, Relax and Renewbrbrbrbr

Simpson Bay, St. Maarten

£82+

Check availability

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KAYAK’s insights for holiday 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 October, with average rates of £74. In comparison, November is the most expensive month, with prices at £522.

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 £116. The highest prices are found on Friday, with average rates at £576.

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	March
High season	May
Average price (weeknight)	£156
Average price (weekend night)	£112

Cheapest month to stay with an average 64% drop in price.

Most expensive month to stay with an average 91% 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 holiday rental property amenities in Simpson Bay
Holiday rentals in Simpson Bay are around 47% more expensive than hotels on average. Search here to compare prices for all accommodation types in Simpson Bay.
The best holiday 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 travellers.
If you’re looking for a cheap holiday rental in Simpson Bay, you should consider visiting during the low season. The cheapest holiday homes in Simpson Bay can be found in March and October.
The cheapest night for renting a holiday home in Simpson Bay is Friday. In contrast, the most expensive is Tuesday.
Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Simpson Bay for 9 days.

See more tips

What types of holiday rentals are available in Simpson Bay?
There are loads of different property types that you can make your holiday home in Simpson Bay. You’ll find apartments, bungalows, condos, cottages, houses, houseboats and villas.
Are there any pet-friendly holiday rentals in Simpson Bay?
There are a number of dog and pet-friendly Simpson Bay holiday rentals, with around 9% allowing you to bring your pet along with you.
How much is a holiday rental in Simpson Bay for tonight?
In the last 72 hours, users have found Simpson Bay holiday rentals for tonight for as low as £97. Search here for similar prices
How can I find holiday rentals near me in Simpson Bay?
Take a look at our holiday rentals map to find the best holiday rental homes near you.

See more FAQs

Simpson Bay holiday rentals

KAYAK searches hundreds of travel sites at once for holiday home deals in Simpson Bay

Best Simpson Bay holiday rentals

Most recommended holiday rentals in Simpson Bay

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Property Types

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KAYAK’s insights for holiday 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 October, with average rates of £74. In comparison, November is the most expensive month, with prices at £522.

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 £116. The highest prices are found on Friday, with average rates at £576.

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.

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

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

FAQs when booking a holiday home in Simpson Bay

What types of holiday rentals are available in Simpson Bay?

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

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

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

Where to stay in Simpson Bay?

Everything you need to know for your stay in Simpson Bay

Hotels near airports in Simpson Bay

Complete your trip to Simpson Bay

Other popular hotel destinations

Stays in Simpson Bay