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Tradewinds at Simpson Bay

3.5 star property
3.5-star beachfront condo near Maho Beach

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Photo gallery for Tradewinds at Simpson Bay

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 covered outdoor seating area with wicker furniture, a hanging chair, and a view of the sea with boats.
A modern living room with a white sofa, a round dining table with chairs, a kitchen area with white cabinets and appliances, and a wooden ceiling.
A modern kitchen with a central island, bar stools, a potted plant, and a wooden door.

Reviews

9.6 out of 10
Exceptional

Popular amenities

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

Explore the area

View in a 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.)
    ‪4 min drive‬

Room options

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 Twin Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

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
  • 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

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
  • 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

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

UNIT 8

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

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
  • Free WiFi

View all photos for UNIT10

UNIT10 | Private kitchen

UNIT10

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

About the area

Simpson Bay

On the beach.Your stay at this Simpson Bay condo places you within a 10-minute walk of Simpson Bay Beach and Kim Sha Beach. Also, Market Garden Supermarket is within half a mile (1 km) and Paradise Plaza is within 2 miles (3 km).
View more Condo rentals in Simpson BayOpens in a new window

What's nearby

  • Simpson Bay Beach - 1 min walk - 0.2 km
  • Market Garden Supermarket - 16 min walk - 1.4 km
  • Paradise Plaza - 1 min drive - 1.2 km
  • Flamingo Beach - 2 min drive - 1.6 km
  • Hollywood Casino - 2 min drive - 1.6 km

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

3.5-star beachfront condo near Maho Beach
Tradewinds at Simpson Bay offers its guests an outdoor pool. Public spaces have free WiFi.

This 3.5-star Simpson Bay condo is smoke free.

  • 10 guestrooms or units
  • No smoking on site
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.

Similar properties

Exterior
Simpson Bay Resort, Marina & Spa
Pelican Key
  • On private beach
  • Pool
  • Spa
  • Kids pool
4.5 out of 5, Wonderful, 1,832 reviews
The price is CA $324
CA $398 total
includes taxes & fees
Jun 28 - Jun 29
Simpson Bay Resort, Marina & Spa

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

  • No pets 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. No onsite parking is available. This property accepts Visa, Mastercard, American Express, and cash. This property reserves the right to pre-authorize the guest's credit card prior to arrival. For guests' safety, the property includes a smoke detector in each accommodation. The 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 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

How close is Tradewinds at Simpson Bay to the airport?

Tradewinds at Simpson Bay is 2.7 mi (14-min drive) away from the Princess Juliana Intl. Airport (SXM) airport, the closest popular airport to the property.

Does Tradewinds at Simpson Bay have an airport shuttle?

Airport shuttle services are not available at Tradewinds at Simpson Bay.

How close is Tradewinds at Simpson Bay to the beach?

This condo is on the beach. Don't forget your sunscreen!

Does Tradewinds at Simpson Bay offer free breakfast?

Tradewinds at Simpson Bay does not offer free breakfast.

Is there a casino at Tradewinds at Simpson Bay?

No, there is no casino at this condo, but Paradise Plaza (18-min walk) and Hollywood Casino (19-min walk) are nearby.

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

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

Is there free parking at Tradewinds at Simpson Bay?

Free parking is not available at this condo.

Does Tradewinds at Simpson Bay have a pool?

Tradewinds at Simpson Bay features an outdoor pool.

Does Tradewinds at Simpson Bay have a spa?

There are no spa services available at this condo.

How close is Tradewinds at Simpson Bay to downtown Simpson Bay?

Tradewinds at Simpson Bay is 0.1 mi away from Simpson Bay.

Tradewinds at Simpson Bay Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 38 out of 47 reviews
Rating 8 - Good. 6 out of 47 reviews
Rating 6 - Okay. 2 out of 47 reviews
Rating 4 - Poor. 0 out of 47 reviews
Rating 2 - Terrible. 1 out of 47 reviews

9.4/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

Reviews

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
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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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