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Simpson Bay, Sint Maarten Boat Rentals

Page 1 of 352 listings

Charter our 34 ft Apache performance in Sint Maarten or Anguilla
Powerboats in Cole Bay · 10 guests

Charter our 34 ft Apache performance in Sint Maarten or Anguilla

4.9
$150/hour
Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends
Sailing in Simpson Bay · 20 guests

Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

5.0
$2,091/day
Leopard Powercat 51ft 2018 From Saint Martin, Marigot
Powerboats in Marigot · 12 guests

Leopard Powercat 51ft 2018 From Saint Martin, Marigot

5.0
$3,091/day
Charter Formula III Open 32 in St Maarten
Powerboats in Cole Bay · 10 guests

Charter Formula III Open 32 in St Maarten

5.0
$135+/hour
Luxury Private Charters Sint Maarten | St Martin - Anguilla - St Barths
Powerboats in Cole Bay · 12 guests

Luxury Private Charters Sint Maarten | St Martin - Anguilla - St Barths

5.0
$950/day
Luxury Private Catamaran Charter – All-Inclusive from St. Maarten
Sailing in Cole Bay · 16 guests

Luxury Private Catamaran Charter – All-Inclusive from St. Maarten

5.0
$2,095/day
All-inclusive Luxury Private Day Charter - Power Catamaran - St Martin/Anguilla
Powerboats in Simpson Bay · 12 guests

All-inclusive Luxury Private Day Charter - Power Catamaran - St Martin/Anguilla

5.0
$2,312/day
Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten
Sailing in Cole Bay · 12 guests

Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

5.0
$1,500/day
All-inclusive Luxury Private Charter - Power Cat - St Martin/Anguilla/St Barths
Powerboats in Simpson Bay · 12 guests

All-inclusive Luxury Private Charter - Power Cat - St Martin/Anguilla/St Barths

5.0
$2,312+/day
The Best Day Sail in St. Maarten
Sailing in Simpson Bay · 30 guests

The Best Day Sail in St. Maarten

5.0
$129/day
Boat charter service based in St Maarten/St Martin/Anguilla/St Barts
Powerboats in Cole Bay · 10 guests

Boat charter service based in St Maarten/St Martin/Anguilla/St Barts

5.0
$165/hour
All-inclusive Luxury Shared Charter - Power Cat - St Martin
Powerboats in Simpson Bay · 10 guests

All-inclusive Luxury Shared Charter - Power Cat - St Martin

New
$417/day
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500/day
Cruising Catamaran Charter for Up to 65 People in St Maarten
Sailing in Simpson Bay · 65 guests

Cruising Catamaran Charter for Up to 65 People in St Maarten

5.0
$1,800/day
Boat Charter in Sint Maarten
Powerboats in Lowlands · 12 guests

Boat Charter in Sint Maarten

5.0
$213/hour
New Leopard 53 SAINT MARTIN
Powerboats in Marigot · 12 guests

New Leopard 53 SAINT MARTIN

5.0
$450/hour
Sunseeker 52 Motor Yacht Charter in Sint Maarten
Events in Lowlands · 10 guests

Sunseeker 52 Motor Yacht Charter in Sint Maarten

5.0
$2,800/day
Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull
Sailing in Simpson Bay · 10 guests

Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

5.0
$1,200/day
Luxury Private Charters Sint Maarten | St Martin - Anguilla - St Barths
Powerboats in Cole Bay · 12 guests

Luxury Private Charters Sint Maarten | St Martin - Anguilla - St Barths

New
$1,150/day
Deep Sea Fishing (Half Day) in St Maarten onboard 38ft Power Cat
Fishing in Cole Bay · 8 guests

Deep Sea Fishing (Half Day) in St Maarten onboard 38ft Power Cat

5.0
$195/hour
Private Charters In Simpson Bay or Philipsburg
Sailing in Simpson Bay · 30 guests

Private Charters In Simpson Bay or Philipsburg

5.0
$3,300/day
Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten
Sailing in Lowlands · 8 guests

Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

5.0
$1,000/day
Princess V53 Motor Yacht Available In Marigot, Saint-Martin
Events in Marigot · 10 guests

Princess V53 Motor Yacht Available In Marigot, Saint-Martin

5.0
$465/hour
120' ISA Yacht, YCM120 | Luxury Yacht in BVI & USVI | Winter 2025
Events in Marigot · 13 guests

120' ISA Yacht, YCM120 | Luxury Yacht in BVI & USVI | Winter 2025

New
$2,200/hour

Simpson Bay Reviews

  1. CM

    Cory

    Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

    Book Garth now. This was such a great trip. The boat and stops are great. We had a blast!

  2. NJ

    Nautica

    Charter our 34 ft Apache performance in Sint Maarten or Anguilla

    Nick was very responsive and made it easy for us to book our trip. Our captain Tony was very knowledgable about the French and Dutch sides of the island and took us to several different locations that we really enjoyed. The boat was also in great condition and looked great in our photographs. We highly recommend booking with Nick. It was a great experience.

  3. CR

    Catherine

    Charter our 34 ft Apache performance in Sint Maarten or Anguilla

    This was the highlight of our trip. We got to see places off the beaten path and also experienced spots we didn’t know existed. Captain gave us a wonderful tour of the island and great detail of its history. Totally professional, the boat was very comfortable with a sun canopy and plenty of drinks offered. We will be back!

  4. JK

    John

    Charter our 34 ft Apache performance in Sint Maarten or Anguilla

    Nick, and his Captain Tony, provided our group of ten adults a great day on the water. Taking us to a number of stops around Anguilla. He provided some interesting information about the area we were in. He even extended our day by an hour to help us avoid the crazy St Martin afternoon traffic!

  5. JW

    Jennifer

    Charter our 34 ft Apache performance in Sint Maarten or Anguilla

    We couldn’t have asked for a better day with Nick! From explaining to our taxi driver how to get to the dock to a sparklingly clean boat and stocked cooler, it was a perfect day on the water. Nick took us to all the beautiful beaches along the island and always asked us what we wanted to do (sightsee, snorkel, swim, etc) to make sure we were enjoying. We also hadn’t brought food with us, and he recommended a beach bar he could call ahead for pickup so we wouldn’t lose any boat time which was perfect. He also was available beforehand on WhatsApp to make sure we knew where we were going and to confirm the pickup time and place before we headed over. Would definitely recommend to anyone visiting wanting to see more from the water.

  6. khadijah

    khadijah

    Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

    Overall great experience. Communication could have been better but overall my crew had an amazing time. Drinks were good staff was friendly. They took us to Anguilla and we pretty much had a private beach and pool experience and amazing food. Best day of our trip.