See all properties
Entire condo

Tradewinds at Simpson Bay

3.5 star property

Choose dates to view prices

Photo gallery for Tradewinds at Simpson Bay

Exterior - Tradewinds at Simpson Bay (Simpson Bay)
Exterior - Tradewinds at Simpson Bay (Simpson Bay)
UNIT 8 | Living area | Smart TV, Netflix, streaming services - Tradewinds at Simpson Bay (Simpson Bay)
UNIT 7 | Beach/ocean view - Tradewinds at Simpson Bay (Simpson Bay)
UNIT 2 | In-room safe, individually decorated, individually furnished - Tradewinds at Simpson Bay (Simpson Bay)
Close to Mullet Bay Beach, Tradewinds at Simpson Bay has plenty to offer. Stay connected with free in-room WiFi.

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Pool
  • Kitchen
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Room options

Available filters for rooms
Showing 10 of 10 rooms

View all photos for UNIT 1

UNIT 1 | Living area | Smart TV, Netflix, streaming services

UNIT 1

  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 2 Twin Beds and 1 Double Sofa Bed
  • Free WiFi

View all photos for UNIT 2

UNIT 2 | Beach/ocean view

UNIT 2

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

View all photos for UNIT 3

In-room safe, individually decorated, individually furnished

UNIT 3

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

View all photos for UNIT 4

UNIT 4 | Courtyard view

UNIT 4

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

View all photos for UNIT 5

UNIT 5 | Courtyard view

UNIT 5

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

View all photos for UNIT 6

UNIT 6 | Beach/ocean view

UNIT 6

  • Ocean view
  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 2 Twin Beds and 1 Double Sofa Bed
  • Free WiFi

View all photos for UNIT 7

UNIT 7 | In-room safe, individually decorated, individually furnished

UNIT 7

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

View all photos for UNIT 8

UNIT 8 | In-room safe, individually decorated, individually furnished

UNIT 8

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

View all photos for UNIT 9

UNIT 9 | Private kitchen | Fridge, dishwasher, cookware/dishes/utensils

UNIT 9

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

View all photos for UNIT10

UNIT10 | Private kitchen | Fridge, dishwasher, cookware/dishes/utensils

UNIT10

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

About the neighborhood

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. Visit our Simpson Bay travel guide
View more Condo Rentals in Simpson Bay
Map
23 Simpson Bay Road, Simpson Bay, Sint Maarten

What's nearby

  • Hollywood Casino
    Hollywood Casino
    16 min walk - 0.9 miles
  • Simpson Bay Beach
    1 min walk - 0.1 miles
  • Paradise Plaza
    16 min walk - 0.9 miles
  • Flamingo Beach
    18 min walk - 1.0 mile
  • Lay Bay Beach
    19 min walk - 1.0 mile

Getting around

  • Princess Juliana Intl. Airport (SXM)
    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

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Tradewinds at Simpson Bay

This smoke-free condo building features an outdoor pool and free WiFi in public areas. Each condo features a kitchen with a refrigerator and a dishwasher, plus free WiFi and a Smart TV with Netflix. A private yard, a TV, and a safe are among the other amenities available to guests.
Tradewinds at Simpson Bay offers 10 air-conditioned accommodations with safes and irons/ironing boards. Each accommodation is individually furnished and decorated. Accommodations at this 3.5-star condo have kitchens with refrigerators, cookware/dishes/utensils, and dishwashers. Bathrooms include showers.

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

Recreational amenities at the condo include an outdoor pool.

Similar properties

Outdoor pool, sun loungers
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
9.2 out of 10, Wonderful, 1,532 reviews
Hilton Vacation Club Flamingo Beach St. Maarten
Compare similar properties

Property amenities

Beach

  • On a white sand beach

Pool/Spa

  • Outdoor pool

Internet

  • Available in the condo: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • No onsite parking available

Kitchen

  • Cookware, dishware, and utensils
  • Dishwasher
  • Refrigerator

Bedrooms

  • Bedsheets provided

Bathroom

  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • 32-inch smart TV
  • Netflix
  • Streaming services

Outdoor areas

  • Yard

Laundry

  • Laundry detergent

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • No elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Safe

Location highlights

  • Near the ocean
  • On the waterfront

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • 10 units
  • Individual decor
  • Individual furnishings

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

Property 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-authorize 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 there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is professionally cleaned

We should mention

This property does not have elevators

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 rating system.

Property is also known as

Tradewinds At Simpson Simpson
Tradewinds at Simpson Bay Condo
Tradewinds at Simpson Bay Simpson Bay
Tradewinds at Simpson Bay Condo Simpson Bay

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?

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?

Check-out 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 mi (2 km).

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

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

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

Tradewinds at Simpson Bay Reviews

9.4

Exceptional

9.4

Cleanliness

9.6

Amenities

9.8

Property conditions & facilities
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

Reviews

Verified

10/10 Excellent

Gina

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

10/10 Excellent

Susan

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

10/10 Excellent

Niariah

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

10/10 Excellent

randy

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

6/10 Okay

Aja

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

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

Catherine Ann

Liked: Cleanliness, check-in, communication, listing accuracy
Our stay at Tradewinds Resort in Simpson Bay, Sint Maarten was absolutely incredible. From the moment we arrived, the hosts made us feel completely welcome but we especially have to give a huge shoutout to Hugo. He was truly exceptional. Hugo went above and beyond in every way possible. He was incredibly friendly, attentive, and always ready to help with anything we needed. Whether it was recommendations, assistance around the property, or just making sure we were comfortable, he made our entire experience that much better. The property itself was spotless and beautifully maintained. Everything was clean, comfortable, and thoughtfully prepared for guests. You can tell a lot of care goes into keeping the resort in top condition. Between the amazing hospitality especially from Hugo and the pristine accommodations, this was easily one of the best stays we’ve had. We highly recommend Tradewinds Resort and would absolutely return without hesitation!
Stayed 4 nights in Mar 2026
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

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

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

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

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

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

10/10 Excellent

Joseph

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

8/10 Good

PEGGY

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

10/10 Excellent

Shaniefa

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