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Simpson Bay, Sint Maarten Boat Rentals

Page 1 of 357 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
$272/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
$272/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
$1,957/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
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
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
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
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 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
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
 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
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
Boat tour Sailboat 40 feet Saint Martin
Sailing in Marigot · 6 guests

Boat tour Sailboat 40 feet Saint Martin

New
$140/hour
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
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
$550/hour
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

Simpson Bay Reviews

  1. 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!

  2. NS

    Nancy

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

    Jordan and Chloe were wonderful hosts, super attentive, and we had an excellent day on the Oceane! The boat was clean and well stocked with everything we needed, our lunch was delicious, and we snorkeled and saw some really cool fish. It was a perfect day to relax and enjoy the crystal clear carribean waters. We highly recommend and hope to come back and visit again soon!

  3. Aliyanna

    Aliyanna

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

    This Charter was such a good time! Not only were we able to enjoy the open bar but the views and boat ride itself was so enjoyable! We came for my bachelorette trip and it did not disappoint! 🥰 Jordan and Chloe were amazing and made the time so funnn!!

  4. VN

    Viktoriya

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

    We had an absolutely wonderful time on the boat! We have a large family with ages ranging from 2 years old to 83 years old, and everyone enjoyed themselves. The layout of the boat is very comfortable, from a private cabin with a bathroom, to a covered room with couches and open deck spaces in the front and the back. Theres plenty of water play equipment for a great time on the water. Chloe and Jordan were extremely accomodating. The drinks and light snacks were perfect for a half day on the water. The Captain took us to some beautiful stops, where we got to snorkel and even see some sea turtles. And on the way back we saw a pod of dolphins! We highly recommend Jordan and Chloe for your next boat adventure!

  5. SL

    Samantha

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

    We had a great day on the water with Jordan and Chloe! The weather was a bit up and down but they made every effort to make our day as perfect as possible! They had plenty of drinks and Chloe made the BEST bloody Mary’s! They made reservations for us for lunch and it was also fantastic. We would absolutely book them again!

  6. JW

    Jasmine

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

    BOOK THIS BOAT & CREW!! We had the absolute best day with them. The boat and experience exceeded our expectations & gave lifetime island visitors a totally new and unique day. All of the drinks and snacks were delicious, including Chloe bringing us fruit in the ocean! They ferried us to an amazing lunch spot, pointed out all kinds of great places to visit, and provided an updated itinerary when it was windy on the day of our trip! Super knowledgeable, clean, professional, fun staff & a great day for our family! We had 12 people including a baby and didn’t feel cramped at all. It was a great time and I highly recommend booking this boat!!