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Simpson Bay, Sint Maarten Boat Rentals

Page 1 of 359 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
Luxurious & spacious 55ft Motor Yacht,discover Anguilla,Sint Maarten,St Martin
Events in Simpson Bay · 12 guests

Luxurious & spacious 55ft Motor Yacht,discover Anguilla,Sint Maarten,St Martin

5.0
$278/hour
Luxurious 55ft private Motor Yacht around Saint Martin, Sint Maarten, Anguilla
Events in Marigot · 12 guests

Luxurious 55ft private Motor Yacht around Saint Martin, Sint Maarten, Anguilla

5.0
$278/hour
Luxury Private Charter - 50ft Pajot Catamaran | St Martin - Anguilla
Powerboats in Cole Bay · 28 guests

Luxury Private Charter - 50ft Pajot Catamaran | St Martin - Anguilla

5.0
$2,900/day
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
$1,998/day
Private Luxury Catamaran Day Charter (All-inclusive) in St. Maarten
Sailing in Cole Bay · 10 guests

Private Luxury Catamaran Day Charter (All-inclusive) in St. Maarten

5.0
$2,395/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

5.0
$950/day
Charter Formula III Open 32 in Philipsburg, Sint Maarten
Powerboats in Cole Bay · 10 guests

Charter Formula III Open 32 in Philipsburg, Sint Maarten

5.0
$135+/hour
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
Luxury Catamaran Trips in St Maarten and Surrounding Islands
Sailing in Simpson Bay · 22 guests

Luxury Catamaran Trips in St Maarten and Surrounding Islands

5.0
$475/hour
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
$190/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

New
$1,150/day
 Luxury Catamaran Private Day Charter with 4-Course Gourmet Lunch
Powerboats in Simpson Bay · 12 guests

Luxury Catamaran Private Day Charter with 4-Course Gourmet Lunch

5.0
$2,390/night
New Leopard 53 SAINT MARTIN
Powerboats in Marigot · 12 guests

New Leopard 53 SAINT MARTIN

5.0
$450/hour
St Martin Luxury Catamaran Shared Day Charter with 4-Course Gourmet Lunch
Powerboats in Simpson Bay · 10 guests

St Martin Luxury Catamaran Shared Day Charter with 4-Course Gourmet Lunch

New
$365/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
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500/day
Adventures in the Caribbean
Sailing in Simpson Bay · 10 guests

Adventures in the Caribbean

New
$500/hour
Boat Charter in Sint Maarten
Powerboats in Lowlands · 12 guests

Boat Charter in Sint Maarten

5.0
$213/hour
Private powercat 40 around saint martin, pinel, tintamarre and anguilla
Powerboats in Simpson Bay · 12 guests

Private powercat 40 around saint martin, pinel, tintamarre and anguilla

New
$278/hour
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
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
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
Beneteau 48 Motor Yacht Charter St Martin | St Barths | Anguilla
Events in Marigot · 10 guests

Beneteau 48 Motor Yacht Charter St Martin | St Barths | Anguilla

New
$600/hour

Simpson Bay Reviews

  1. BB

    Bob

    Luxurious 55ft private Motor Yacht around Saint Martin, Sint Maarten, Anguilla

    We spent a wonderful six hours boating with Jordan and his sister Cloey (sp) and in our group of six, several considered it their favorite activity during our 10 day Caribbean trip! Both Captain and First Mate are friendly, attentive, knowledgeable and nice people. Snacks and an open bar and soft drinks are available. We had several snorkeling opportunities and a wonderful lunch beach side in Grand Case. The boat is not a bright, shiny speed boat but a super comfortable trawler with ample room on several levels. This was well worth the time and money. Thanks Jordan and Cloey.

  2. SB

    Steven

    New Leopard 53 SAINT MARTIN

    If you happen to have the pleasure of traveling to Saint Maarten and you want an aquatic adventure that is top notch and destined to become the highlight of your trip, you need to book with this captain. He met us at the entrance and promptly chauffeured us to the stunning catarman yacht. The yacht was immaculate and had plenty of space for our party of four! They supplied delicious eats including a charcuterie board and fruit. We brought our own liquor but they had a fully stocked bar and chasers available. He accommodated our every request and ensured we had an amazing time. We made four stops along the gorgeous Saint Maarten coastline. It was a trip to remember!

  3. CP

    Christine

    Luxurious 55ft private Motor Yacht around Saint Martin, Sint Maarten, Anguilla

    We had an incredible time aboard this beautiful yacht! The vessel itself was stunning—clean, spacious, and perfect for relaxing or soaking up the sun. What truly made the experience exceptional, though, were our amazing captains, Jordan and Chloe. They were so friendly, professional, and made us feel completely at ease from the moment we stepped on board. They went above and beyond to make our trip special, serving us delicious drinks and tasty snacks throughout. Every detail was taken care of with such warmth and care. We couldn’t have asked for a better experience—highly recommend to anyone looking for a perfect day on the water!

  4. PM

    Paul

    Luxury Private Charter - 50ft Pajot Catamaran | St Martin - Anguilla

    We had an amazing day on the boat. Crew was fantastic, boat was clean and spacious. Plenty of drinks, snacks, and water toys. It was the best day of our week in SXM.

  5. TS

    Tyler

    Luxurious & spacious 55ft Motor Yacht,discover Anguilla,Sint Maarten,St Martin

    Jordan and Chloe are amazing hosts. They were incredibly accommodating for our families and did an outstanding job finding a bay out of the wind for us to enjoy. The water toys were a huge hit with our kids and the boat was neat, organized, clean and comfortable for our group of ten. Chloe makes a mean pina colada and Jordan is a very thoughtful and knowledgeable captain. We can’t recommend them enough. Unforgettable time for our families.

  6. JR

    Jessica

    Luxury Private Charter - 50ft Pajot Catamaran | St Martin - Anguilla

    Jonathan and the entire crew were extraordinary. They went above and beyond in every aspect of our trip. From basic amenities like towels, snorkeling gear, food, and beverages; to their great attitudes and personalities, we couldn’t be happier. There were even some personal touches and surprises that made our already wonderful day extra special. They had a tough job with our large group and wide array of ages, and everyone said it was one of the best days they’ve ever had.