Condo

Tradewinds at Simpson Bay

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Photo gallery for Tradewinds at Simpson Bay

A deck with lounge chairs, a pool, and a view of boats at sunset.
A terrace with wicker furniture, a glass table, and a hanging chair overlooking a marina with boats and a sunset.
A rooftop pool area with lounge chairs, a small pool, and a view of sailboats at sunset.
A modern hotel room with a large sliding glass door leading to a balcony with a pool and a view of the sea.
A modern living room with a sofa, a coffee table, and a wicker chair. There is a glass door leading to a balcony with a view of the sea and boats.

Reviews

9.4 out of 10
Exceptional

Highlights

  • White sand beach
    Step onto rare, powdery white sand beach near you.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • On beach
  • Outdoor pool
  • Yard
  • Free Wi-Fi in public areas
  • Air-conditioning
  • Kitchen

Explore the area

View map
23 Simpson Bay Road, Simpson Bay, Sint Maarten
  • Place, Simpson Bay Beach
    ‪1 min walk‬
  • Place, Flamingo Beach
    ‪2 min drive‬
  • Place, Hollywood Casino
    ‪2 min drive‬
  • Airport, Philipsburg (SXM-Princess Juliana Intl.)
    ‪5 min drive‬

Choose your unit

View all photos for UNIT 1

A modern living room with a sofa, dining table, and chairs. There is a TV mounted on the wall and a window with curtains.

UNIT 1

  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 2 Single Beds and 1 Double Sofa Bed

View all photos for UNIT 2

A modern living room with a sofa, a coffee table, and a wicker chair. There is a glass door leading to a balcony with a view of the sea and boats.

UNIT 2

  • Garden view
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for UNIT 3

A neatly made bed with white bedding and two blue and white patterned pillows. There are two bedside tables, one with a lamp and the other with a small wooden tray.

UNIT 3

  • Ocean view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed

View all photos for UNIT 4

A modern kitchen with a central island, bar stools, a dining area with a wicker chair, and a view of the garden through the sliding doors.

UNIT 4

  • Garden view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for UNIT 5

A hotel room with a sofa, a bed, a small table, a plant, and a view of the outside.

UNIT 5

  • Garden view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed

View all photos for UNIT 6

A modern kitchen with a white countertop, a built-in oven, and a view of the sea through a glass door.

UNIT 6

  • Ocean view
  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 2 Single Beds and 1 Double Sofa Bed

View all photos for UNIT 7

A hotel room with a large bed, a view of the sea through a sliding door, and a balcony with a railing.

UNIT 7

  • Ocean view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed

View all photos for UNIT 8

A hotel room with a bed, a chair, a table, and a view of boats on the water through an open door.

UNIT 8

  • Ocean view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed

View all photos for UNIT 9

A modern kitchen with a central island, bar stools, a potted plant, and a wooden door.

UNIT 9

  • Ocean view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for UNIT10

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a wooden door.

UNIT10

  • Garden view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed

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Frequently asked questions

Does Tradewinds at Simpson Bay have a pool?

Yes, this property has an outdoor pool.

Is Tradewinds at Simpson Bay pet-friendly?

No, pets are not allowed at this property.

How much is parking at Tradewinds at Simpson Bay?

This property doesn't offer parking.

What time is check-in at Tradewinds at Simpson Bay?

Check-in start time: 2:00 PM; check-in end time: 10:00 PM.

What time is check-out at Tradewinds at Simpson Bay?

Checkout is at 10:30 AM.

Where is Tradewinds at Simpson Bay located?

Nestled on the beach, this Simpson Bay condo building is steps from Simpson Bay Beach and 2.6 mi (4.1 km) from Maho Beach. Kim Sha Beach and Market Garden Supermarket are also within 15 minutes.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on selected room rates because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

Tradewinds at Simpson Bay Reviews

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 40 out of 50 reviews
Rating 8 - Good. 7 out of 50 reviews
Rating 6 - Okay. 2 out of 50 reviews
Rating 4 - Poor. 0 out of 50 reviews
Rating 2 - Terrible. 1 out of 50 reviews

9.6/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

10/10

Check-in

9.6/10

Communication

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Great communication…very friendly and hospitable 😊….cant wait to come back
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Friendly and helpful staff! Great location with everything you need, for a good price. Really enjoyed my stay and will definitely book if I visit Sint Maarten again.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Attentive staff, clean, accommodating
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
It was a clean and nice place.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
great staff ....location location location close to everything great dinner spot next door secrets restaurant ..accessible to everything ! 5 minutes drive from airport !!!! definitely can't wait to go back
Stayed 3 nights in Apr 2026
Verified review

8/10 Good

Liked: Cleanliness, amenities, property conditions & facilities, communication
This was a great stay, in the middle of everything and walking distance to all restaurants. The room was clean will stay here again and I do recommend.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Was an amazing stay definitely recommend this place !
Stayed 4 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Beautiful ocean view ! Clean & managed very well. Excellent convenient location .
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Friendly staff clean room and common areas
Stayed 2 nights in Feb 2026
Verified review

6/10 Okay

Liked: Check-in, communication, listing accuracy
Fairly nice property with a great view of the ocean. Unparalleled access to restaurants, shopping, etc.
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
We enjoyed the stay to the fullest
Stayed 10 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Wonderful place to stay. Hugo being on site was very nice who went above and beyond plus the owner Adrian stepped when we had a power outage. We 100% recommend this place and can't wait to return.
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
It was a perfect location with an ocean view. Near the lively strip of restaurants and bars. A perfect spot for 1st timers because it is impossible to get lost. Everything in the unit was operational and comfortable. We had no issues with our stay
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Wonderful view, decent location and great host!
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
We did 4/17-4/20. Location to all most everything night life bar food next door to the secret restaurant food is really good there.the ocean view is great in the morning n sunset. Walk out of your room to the pool
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Nice appartment with amazing view. The sound of the wave was so relaxing. The kitchen is well equiped so we prapared our breakfast and had a few takeout.
Stayed 2 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
It’s beautiful and all the restaurants are across the way!
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities, communication
Very nice host with incredibly fast responses to questions. I would stay there again.
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Cute and quiet hotel. Plenty of privacy. Short walk to the strip with restaurants and bars. Little parking options but worth the stay!!
Stayed 2 nights in Feb 2025
Verified review

8/10 Good

Liked: Cleanliness, property conditions & facilities, communication
Well cared for, and though out, interesting location, cooperative and helpful landlords, I would use this location on another list to island.
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
The property management was very hospitable (Hugo).
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities, communication
Very beautiful place. And walking distance from restaurants and bars. Street itself is not great though.
Stayed 3 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Hotel was super good, Hugo is a manager of the property He was excellent person, helpful and kind, thanks Hugo for make us feeling as We are at home, hotel was nice, quiet very clean and in my next stay in St. Martin, for sure I’ll be back to Tradewinds. I recommend this Hotel.
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Adrian and the manager were very accommodating and the stay was amazing. Close to everything and can walk to shops and restaurants. We got the 2 bedroom first floor unit and it was very clean and smell good. Definitely recommend to families, couples etc.
Stayed 3 nights in Feb 2025
Verified review

10/10 Excellent

Liked: Cleanliness, room comfort, communication

A biz trip with a pool and very cool apartment

I was staying for two days of business. But the apartment is very well located on Simpson bay. Close to the beach, shops, bars and restaurants.
Stayed 2 nights in Mar 2025