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Condo

Tradewinds at Simpson Bay

Photo gallery for Tradewinds at Simpson Bay

Exterior
Beach
Exterior
Room
Beach/ocean view

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Pool
  • Kitchen
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

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

Choose your unit

View all photos for UNIT 1

Living area

UNIT 1

  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 2 Single Beds and 1 Double Sofa Bed
  • Free Wi-Fi

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Beach/ocean view

UNIT 2

  • Garden view
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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Room

UNIT 3

  • Ocean view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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Courtyard view

UNIT 4

  • Garden view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

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Courtyard view

UNIT 5

  • Garden view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for UNIT 6

Beach/ocean view

UNIT 6

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

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Room

UNIT 7

  • Ocean view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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Room

UNIT 8

  • Ocean view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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Private kitchen

UNIT 9

  • Ocean view
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for UNIT10

Private kitchen

UNIT10

  • Garden view
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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About the area

Simpson Bay

Located in Simpson Bay, Tradewinds at Simpson Bay is on the beach. The area's natural beauty can be seen at Maho Beach and Mullet Bay Beach.

What's nearby

  • Simpson Bay Beach - 1 min walk - 0.2 km
  • Paradise Plaza - 16 min walk - 1.4 km
  • Hollywood Casino - 16 min walk - 1.4 km
  • Flamingo Beach - 18 min walk - 1.5 km
  • Lay Bay Beach - 19 min walk - 1.7 km

Getting around

  • Philipsburg (SXM-Princess Juliana Intl.) - 14 min drive

Restaurants

  • ‪Secret Seafood House - ‬1 min walk
  • ‪Palapa Hidden Oasis SXM - ‬6 min walk
  • ‪Balls - ‬6 min walk
  • ‪Goat Fish Restaurant - ‬4 min walk
  • ‪Charlie's Bistro - ‬4 min walk

About this property

Tradewinds at Simpson Bay

This smoke-free condo building features an outdoor pool and free Wi-Fi in public areas. Each condo features a kitchen with a fridge and a dishwasher, plus free WiFi and a Smart TV with Netflix. A private garden, a TV and a safe are among the other amenities available to guests.
Tradewinds at Simpson Bay offers 10 air-conditioned accommodations with a safe and an iron/ironing board. Each accommodation is individually furnished and decorated. Accommodation at this 3.5-star condo has kitchens with fridges, kitchenware and utensils and dishwashers. Bathrooms include a shower.

Guests can surf the web using complimentary wireless Internet access. 32-inch Smart televisions come with Netflix.

Recreational amenities at the condo include an outdoor pool.

Policies

Check-in

Check-in start time: 2:00 PM; check-in end time: 10:00 PM
Minimum check-in age - 15

Check-out

Check-out before 10:30 AM

Special check-in instructions

There is no front desk at this property
Guests must contact the property in advance for check-in instructions; access will be through a private entrance
To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Access methods

Private entrance

Pets

Pets not allowed

Children and extra beds

Children are welcome

Payment types

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards and cash
This property reserves the right to pre-authorise the guest's credit card prior to arrival.
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is professionally cleaned

National rating

This property does not have a Sint Maarten Tourist Board rating. For the benefit of our customers, we have provided a rating based on our ratings system.

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 Flamingo Beach are also within 1 mile (2 km).

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. 37 out of 46 reviews
Rating 8 - Good. 6 out of 46 reviews
Rating 6 - Okay. 2 out of 46 reviews
Rating 4 - Poor. 0 out of 46 reviews
Rating 2 - Terrible. 1 out of 46 reviews

9.4/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

10/10

Check-in

9.6/10

Communication

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Sabina

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

10/10 Excellent

Manpreet

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

10/10 Excellent

Rene

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

10/10 Excellent

Andreas

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

10/10 Excellent

Shiwen

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

10/10 Excellent

hanan

Liked: Cleanliness, amenities, property conditions & facilities, communication
This place is amazing. Great price. Super helpful and flexible owner and staff. They truly did everything to help and make my stay perfect. The room was clean. The bed was very comfortable. There's beautiful sunset view from this property. Great seafood restaurant next door. I'll definitely be back. 10 out of 10
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Jessica

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

10/10 Excellent

Matthew

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

10/10 Excellent

Roosgini

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

8/10 Good

Brian

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

10/10 Excellent

David

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
Verified

10/10 Excellent

Cristian

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

10/10 Excellent

Valerie

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

10/10 Excellent

Jeroen

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

10/10 Excellent

Anette

Liked: Cleanliness, amenities, property conditions & facilities, communication
This was our second year at Tradewinds and won’t be our last. Love staying here. Peaceful, relaxing and love just watching the boats and hearing the waves. Near everything but not bothered by large groups. Love this place.
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Susan

Liked: Cleanliness, amenities, property conditions & facilities, communication
Tradewinds was a great place to stay. it was close to dining and grocery shopping. It was very clean and Hugo was very helpful if you needed anything. It was beautiful to watch the sunset from the deck.
Stayed 14 nights in Feb 2025
Verified

10/10 Excellent

ROGER IVAN

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

10/10 Excellent

David

Liked: Cleanliness, amenities, property conditions & facilities, communication
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 attentive to all needs. Fully recommend. You won’t go wrong.
Stayed 6 nights in Apr 2025
Verified

10/10 Excellent

Antoine

Liked: Cleanliness, amenities, property conditions & facilities, communication
Very drop was the view and the space was amazing
Stayed 2 nights in Mar 2024
Verified

10/10 Excellent

Sonica

Liked: Cleanliness, amenities, property conditions & facilities, communication
Tradewinds Apartments is at a location where basically everything this accessible. Communication with the staff was warm and easy going.
Verified

10/10 Excellent

Akima

Liked: Cleanliness, amenities, property conditions & facilities, communication
The room was spacious and spotless . The staff were attentive and went out of their way to ensure that we were comfortable. Nothing was too much trouble.Will be back excellent stay
Stayed 5 nights in Apr 2024
Verified

10/10 Excellent

Tamika

Liked: Cleanliness, amenities, property conditions & facilities, communication
Thoroughly impressed!!!!! Modern furnishings comfortable clean space, the restaurant next door has amazing food and drinks Leo and Nita were so hospitable. The ambiance the views everything was spectacular it really feels like a home away from home. The owners communicated well and were very hospitable . This is a hidden gem I will definitely be back
Stayed 5 nights in Apr 2024
Verified

10/10 Excellent

Anthony

Liked: Cleanliness, amenities, property conditions & facilities, communication
Michael was a great host. Went above and beyond when we arrived. Responded quick to any questions or concerns. Highly recommend.
Stayed 3 nights in Dec 2023
Verified

6/10 Okay

Rosanna

Liked: Communication
Stayed in unit 4 which was a cozy garden view studio. The unit was nice, however there were certain minor things that require updating. The trash can in the bathroom was very rusty as was the coffee maker and kettle. There was a hole in the bathroom ceiling and a few cracks and chipping paint throughout the unit. Overall my stay was comfortable. I would give the property another try but book a different unit with an ocean view.
Stayed 3 nights in Jan 2024
Verified

2/10 Terrible

PatrickDriscoll

Disliked: Communication
We never received an actual address went to two other locations with the same name and after an hour and a half had to find another hotel. The phone number given was not answered. Someone indicated that a physical address was provided back in September. I just looked for it and cannot find it. More importantly is that no one answered the phone number nor returned our call to locate the little known hotel. Subsequent emails and one received that changed our room did not include the actual address and provided a phone number that was not being attended.
Stayed 1 night in Oct 2020