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Entire condo

Tradewinds at Simpson Bay

3.5 star property

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Close to Mullet Bay Beach, Tradewinds at Simpson Bay has plenty to offer. Stay connected with free in-room WiFi.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Pool
  • Kitchen
  • Free Wi-Fi
  • 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

UNIT 1

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

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UNIT 2 | 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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In-room safe, individually decorated, individually furnished

UNIT 3

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

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UNIT 4 | Courtyard view

UNIT 4

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

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UNIT 5 | Courtyard view

UNIT 5

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

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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

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 Wi-Fi

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 Wi-Fi

View all photos for UNIT 9

UNIT 9 | Private kitchen

UNIT 9

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

View all photos for UNIT10

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

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 - 1.4 km
  • Simpson Bay Beach
    1 min walk - 0.2 km
  • Market Garden Supermarket
    11 min walk - 0.9 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

  • Condo near Mullet Bay Beach
  • Tradewinds at Simpson Bay provides everything that you need. Guests can connect to free in-room WiFi.
  • You'll also enjoy perks such as:
    • An outdoor pool
    • Smoke-free property
  • Room features
  • All rooms are individually furnished, and have comforts such as air conditioning, as well as perks such as free WiFi and safes.
  • Other amenities include:
    • Showers and shampoo
    • 32-inch Smart TVs with Netflix and streaming services
    • Private gardens, wardrobes/cupboards and kitchens

Similar properties

Exterior
Simpson Bay Resort, Marina & Spa
Pelican Key
  • On private beach
  • Pool
  • Spa
  • Kids’ pool
9.0 out of 10, Wonderful, 1,757 reviews
The price is NZ$420
includes taxes & fees
15 June - 16 June
Simpson Bay Resort, Marina & Spa
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 transport

  • No on-site 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 lift
  • Smoke-free property

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

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

We should mention

This property does not have any lifts

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 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.

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Reviews

Tradewinds at Simpson Bay Reviews

9.6

Exceptional

9.4

Cleanliness

9.6

Amenities

9.8

Property conditions & facilities
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

Reviews

Verified

10/10 Excellent

Laporsha

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

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

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

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

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

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

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

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

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

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

Laercio

Liked: Cleanliness, amenities, communication
O espaço interno do apartamento é ótimo, a limpeza impecável, a gentileza e prestatividade do Sr. Hugo fez toda a diferença para tornar nossa estadia muito agradável, com certeza iremos voltar neste estabelecimento.
Stayed 3 nights in Nov 2025
Verified

8/10 Good

Mathias Juul

Liked: Cleanliness, amenities, communication
Lejligheden var rummelig med smuk udsigt og et dejligt udemiljø. Dog var internettet ubrugeligt.
Stayed 2 nights in Nov 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

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

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

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

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

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

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

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

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

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