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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
$285/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

4.9
$285/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
$2,049/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
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 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 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
$1,500/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
$950/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
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
Sailing Catamaran Amari - Overnight Charter All Inclusive Fully Crewed
Sailing in Simpson Bay · 6 guests

Sailing Catamaran Amari - Overnight Charter All Inclusive Fully Crewed

New
$3,360+/night
Boat Charter in Sint Maarten
Powerboats in Lowlands · 12 guests

Boat Charter in Sint Maarten

5.0
$213/hour
Adventures in the Caribbean
Sailing in Simpson Bay · 10 guests

Adventures in the Caribbean

New
$500/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
Boat tour Sailboat 40 feet Saint Martin
Sailing in Marigot · 6 guests

Boat tour Sailboat 40 feet Saint Martin

New
$140/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
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. 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!

  2. 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.

  3. 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.

  4. MW

    Mike

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

    Everything about this trip went really well. Communication and planning was easy, we adjusted the itinerary based on the weather conditions and the boat itself and all the water toys were great. Jordan and Chloe were great hosts and nothing was too much trouble to make our day special. Would definitely recommend.

  5. 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.

  6. JH

    Jeff

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

    This was our best day on vacation! Jordan and Chloe were perfect hosts. They were very welcoming from the very beginning. We were worried that our 82 year old family member would struggle but they made it so easy! From the snacks to drinks they were always on top of it. They have everything you need for the perfect day out on the water. They have floating chairs, a floating pad to sit on, snorkeling gear, and a really fun Sea Bob! Jordan took us to a really nice snorkeling area where we saw all kinds of tropical fish and even saw some squid! They have blue tooth speakers so you can enjoy your music while relaxing on padded bow! The view was spectacular and Jordan and Chloe made that happen! If you are deciding on a boat to rent for the day you should definitely choose this one!