Name: Tradewinds at Simpson Bay
Rating: 9.4

Where to stay in Simpson Bay

Pelican Key

While visiting Pelican Key, you might make a stop by sights like Flamingo Beach and Lay Bay Beach.

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

£107

includes taxes & fees

17 May - 18 May

Stay at this 4-star beach resort in Simpson Bay. Enjoy free Wi-Fi, free parking and 6 outdoor pools. Our guests praise the pool and the helpful staff in their ...

8.8/10 Excellent! (1,074 reviews)

"All the staff were professional and friendly. The dinning options are great, you can either eat in or have it delivered to your room."

Reviewed on 28 Apr 2025

The Morgan Resort Spa Village

2 Beacon Hill Road, Simpson Bay

Fully refundableReserve now, pay when you stay

£280

includes taxes & fees

14 May - 15 May

Stay at this 4-star spa resort in Simpson Bay. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the pool and the restaurant in their ...

8.8/10 Excellent! (1,661 reviews)

"The staff was Amazing! Super friendly and Helpful! I needed a last min trip to drug store in the pouring rain and they were able to take me on one of their airport drop offs so I wouldnt get soaked!!! Great stay Thanks again!"

Reviewed on 28 Apr 2025

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay

£99

includes taxes & fees

11 May - 12 May

Stay at this 3.5-star beach resort in Simpson Bay. Enjoy free Wi-Fi, free parking and a beach locale. Our guests praise the pool and the helpful staff in their ...

9/10 Wonderful! (1,008 reviews)

"Everything was great, location and beach were awesome. Would stay again"

Reviewed on 28 Apr 2025

See all 424 properties in Simpson Bay

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hilton Vacation Club Royal Palm St. Maarten

115 Welfare Road, Simpson Bay

Stay at this 3.5-star beach resort in Simpson Bay. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the helpful staff and the property ...

8.8/10 Excellent! (1,010 reviews)

"Great place to vacation with family"

Reviewed on 23 Apr 2025

The Hills Residence

69 Welfare Rd, Simpson Bay, Sint Maarten

Stay at this 3-star aparthotel in Simpson Bay. Enjoy free Wi-Fi, free parking and 4 outdoor pools. Popular attractions Maho Beach and Orient Bay Beach are located ...

9/10 Wonderful! (23 reviews)

"I loved staying at The Hills because it was very centric, easy to move around. The property has an amazing view with a pool, beautiful decor comfortable bed. I love it all. I will recommend it. I am staying here again."

Reviewed on 17 Mar 2025

Tradewinds at Simpson Bay

23 Simpson Bay Road, Simpson Bay, Sint Maarten

Stay at this 3.5-star beach condo in Simpson Bay. Enjoy free Wi-Fi, a beach locale and Netflix. Popular attractions Maho Beach and Orient Bay Beach are located ...

9.4/10 Exceptional! (25 reviews)

"This is a great vacation spot in Simpson Bay. My wife and I celebrated our 25th here. The location and views are perfect. Walking distance to everything Simpson Bay and a great starting point for the whole island ( you need a car). Accommodations are as they look in the photos and the owners are ..."

Reviewed on 19 Apr 2025

See all properties in Simpson Bay

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Kim Sha Beach

4.5/5(2 reviews)

Why not spend a care-free afternoon at Kim Sha Beach during your travels in Simpson Bay? Visit the shops and lively bars in this romantic area.

Hollywood Casino

Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.

Simpson Bay Beach

4/5(1 review)

Why not spend a lazy afternoon at Simpson Bay Beach during your trip to Simpson Bay? Visit the shops and lively bars in this romantic area.

Flamingo Beach

Why not spend a lazy afternoon at Flamingo Beach during your trip to Simpson Bay? Stroll along the beautiful beaches or visit the shops in this romantic area.

Lay Bay Beach

Why not spend a lazy afternoon at Lay Bay Beach during your trip to Simpson Bay?

Dunes Casino

Why not roll the dice with a visit to Dunes Casino during your visit to Beacon Hill? Stroll along the seaside in this romantic area or visit its top-notch restaurants.