Title: Adventure Vacations in Sint Maarten 2026 | Expedia.ca

![](https://images.trvl-media.com/place/602829/904d6c1a-f901-4bb5-a277-ae4c807f73b8.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Sint Maarten Adventure Vacations

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## Flight and Adventure hotel deals in Sint Maarten

Price found within the past 48 hours. Click for updated prices.

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,309

per person

Mar 19 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

Clean rooms and resort. Staff was friendly. Check-in could have been a little more detailed ie resort map so we knew where courts, towels etc were. Beach was smaller than I had anticipated but there was always chairs available for use. Beach bar food and sports bar food was excellent. Aqua Marine catamaran tour around the island was great!

Reviewed on Jan 15, 2026

![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Villas at Simpson Bay Resort

Pelican Key

CA $1,519

per person

Mar 19 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

The room was spotless and staff was very courteous.

Reviewed on Jan 12, 2026

![Oyster Bay Beach Resort](https://images.trvl-media.com/lodging/2000000/1100000/1095400/1095348/00eb22aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oyster Bay Beach Resort

Oyster Pond

CA $2,109

per person

Feb 15 - Feb 19

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Philipsburg (SXM)

8.6/10 Excellent! (952 reviews)

I LIKE THE QUIETNESS OF THE HOTEL IT WAS ALSO CLEAN STAFF WAS CORDIAL/PLEASANT THIS IS 2026 WELCOME GUEST WITH A SMALL BOTTLE YOU GUYS CAN DO BETTER. I WOULD STILL STAY THERE THE ROOM WAS SPACIUOS AND CLEAN

Reviewed on Jan 15, 2026

![Holland House Beach Hotel](https://images.trvl-media.com/lodging/2000000/1170000/1160500/1160500/ef6e99b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holland House Beach Hotel

Downtown Philipsburg

CA $2,059

per person

Feb 21 - Feb 26

found 7 hours ago

Roundtrip flight included

Montreal (YMQ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,002 reviews)

We loved everything about The Holland House ❤️

Reviewed on Jan 14, 2026

![Divi Little Bay Beach Resort](https://images.trvl-media.com/lodging/1000000/480000/470900/470827/e8112429_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Divi Little Bay Beach Resort

CA $1,589

per person

Mar 19 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Philipsburg (SXM)

8.4/10 Very Good! (1,002 reviews)

Staff was courteous

Reviewed on Jan 15, 2026

Don't see what you're looking for?

See all available trips from Columbus to Sint Maarten

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-16/2026-02-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Adventure holidays in Sint Maarten

Price found within the past 48 hours. Click for updated prices.

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,309

per person

Mar 19 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

Clean rooms and resort. Staff was friendly. Check-in could have been a little more detailed ie resort map so we knew where courts, towels etc were. Beach was smaller than I had anticipated but there was always chairs available for use. Beach bar food and sports bar food was excellent. Aqua Marine catamaran tour around the island was great!

Reviewed on Jan 15, 2026

![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Villas at Simpson Bay Resort

Pelican Key

CA $1,519

per person

Mar 19 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

The room was spotless and staff was very courteous.

Reviewed on Jan 12, 2026

![Divi Little Bay Beach Resort](https://images.trvl-media.com/lodging/1000000/480000/470900/470827/e8112429_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Divi Little Bay Beach Resort

CA $1,589

per person

Mar 19 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Philipsburg (SXM)

8.4/10 Very Good! (1,002 reviews)

Staff was courteous

Reviewed on Jan 15, 2026

Don't see what you're looking for?

See all available trips from Columbus to Sint Maarten

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-16/2026-02-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Adventure holidays in Sint Maarten

Price found within the past 48 hours. Click for updated prices.

![Princess Heights Luxury Boutique Condo Hotel](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/3eb207bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,107

per person

Mar 19 - Mar 23

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Philipsburg (SXM)

9.2/10 Wonderful! (973 reviews)

Room was cleaned immaculately. Staff was so helpful with any questions that we had or requests. They left a complimentary bottle of wine in our room for New Year’s Eve. We thoroughly enjoyed our stay.

Reviewed on Jan 11, 2026

![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Villas at Simpson Bay Resort

Pelican Key

CA $1,565

per person

Mar 19 - Mar 23

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

The room was spotless and staff was very courteous.

Reviewed on Jan 12, 2026

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,271

per person

Mar 19 - Mar 23

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

Clean rooms and resort. Staff was friendly. Check-in could have been a little more detailed ie resort map so we knew where courts, towels etc were. Beach was smaller than I had anticipated but there was always chairs available for use. Beach bar food and sports bar food was excellent. Aqua Marine catamaran tour around the island was great!

Reviewed on Jan 15, 2026

Don't see what you're looking for?

See all available trips from Columbus to Sint Maarten

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-16/2026-02-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Adventure Hotels in Sint Maarten

![Divi Little Bay Beach Resort](https://images.trvl-media.com/lodging/1000000/480000/470900/470827/e8112429_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Divi Little Bay Beach Resort

Little Bay Road Philipsburg 

- 8 min drive from Maho Beach

CA $703

CA $885 total

Jan 26 - Jan 27

includes taxes & fees

Book a stay at this beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms ...

8.2/10 Very Good! (1,005 reviews)

I will be coming back 🙌🙌🙌

Reviewed on Jan 9, 2026

[](https://expedia.ca/Philipsburg-Hotels-Divi-Little-Bay-Beach-Resort.h470827.Hotel-Information)

![Hilton Vacation Club Flamingo Beach St. Maarten](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/67b50717_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay 

- 27 min walk from Maho Beach

CA $412

CA $469 total

Feb 15 - Feb 16

includes taxes & fees

Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...

9/10 Wonderful! (1,403 reviews)

Everything great! Staff very helpful.

Reviewed on Jan 12, 2026

[](https://expedia.ca/Simpson-Bay-Hotels-Flamingo-Beach-Resort-By-Diamond-Resorts.h796441.Hotel-Information)

![Hilton Vacation Club Royal Palm St. Maarten](https://images.trvl-media.com/lodging/1000000/810000/807900/807815/ddd10394_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Vacation Club Royal Palm St. Maarten

115 Welfare Road Simpson Bay 

- 25 min walk from Maho Beach

CA $559

CA $623 total

Feb 12 - Feb 13

includes taxes & fees

Book a stay at this beach aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...

9/10 Wonderful! (1,169 reviews)

This was our second time here the location is fantastic except for the night club across the street it’s walkable to many shops grocery store and restaurants it’s on the Dutch side it’s an amazing property

Reviewed on Jan 10, 2026

[](https://expedia.ca/Simpson-Bay-Hotels-Royal-Palm-Beach-Resort-By-Diamond-Resorts.h807815.Hotel-Information)

[See all 1,644 properties in Sint Maarten](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=6143274)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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