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Simpson Bay, Sint Maarten Boat Rentals

Page 1 of 367 listings

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
Superowner
$290/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
Superowner
$290/hour
Private powercat 40 around saint martin, pinel, tintamarre and anguilla
Powerboats in Marigot · 12 guests

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

5.0
Superowner
$290/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

5.0
Superowner
$290/hour
Charter Formula III Open 32 in St Maarten
Powerboats in Cole Bay · 10 guests

Charter Formula III Open 32 in St Maarten

5.0
$130+/hour
Instant Book
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
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 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
Leopard Powercat 51ft 2018 From Saint Martin, Marigot
Powerboats in Marigot · 12 guests

Leopard Powercat 51ft 2018 From Saint Martin, Marigot

5.0
$3,088/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
$2,310/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
$2,310+/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
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
ORA Power Catamaran Leopard 53PC from Saint Martin, Marigot
Events in Marigot · 13 guests

ORA Power Catamaran Leopard 53PC from Saint Martin, Marigot

5.0
$4,295/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
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
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
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500/day
Boat Charter in Sint Maarten
Powerboats in Cole Bay · 12 guests

Boat Charter in Sint Maarten

5.0
$213/hour
Leopard Power Catamaran 51ft - 2018 model from Saint Martin, Anse Marcel
Powerboats in Marigot · 12 guests

Leopard Power Catamaran 51ft - 2018 model from Saint Martin, Anse Marcel

5.0
$3,088/day
Sunseeker 52 Motor Yacht Charter in Sint Maarten
Events in Marigot · 10 guests

Sunseeker 52 Motor Yacht Charter in Sint Maarten

5.0
$2,800/day
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
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
 165'/50m Oceanfast | Winter in The Caribbean
Events in Marigot · 12 guests

165'/50m Oceanfast | Winter in The Caribbean

New
$3,250/hour

Simpson Bay Reviews

  1. MS

    Margaux

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

    Super journée en mer ☀️🌊 Un énorme merci pour cette expérience incroyable ! Le catamaran était parfait, l’ambiance au top et que dire de l’équipage… juste génial 👌 Service impeccable, attentionné et toujours de bonne humeur — et professionnel! On recommande à 100 % et on reviendra sans hésiter 🙌

  2. TY

    Tim

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

    Captain Jordan is knowledgeable and super friendly. An absolute gem. Chloe, our steward and chef, was at our becken call for food or drink. She was kind and caring and almost felt like she was one our group. We would absolutely use OBC again an it will always be with Jordan and Chloe!

  3. RC

    Rocco

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

    Our captain did an amazing job navigating the rough seas. Everyone felt comfortable and enjoyed the experience. His recommendations for beaches to visit and how to experience the most of our time at the Anguilla beaches was perfect. He also made a great recommendation for lunch as well. He was very accommodating to our request as well. Chloe, the first mate was incredible. She made fantastic drinks, maintained the boat and was always there to assist our group in any way. Thank you both for a great day.

  4. Rina

    Rina

    ORA Power Catamaran Leopard 53PC from Saint Martin, Marigot

    From start to finish, this yacht rental exceeded every expectation. The boat was spotless, beautifully maintained, and even more stunning in person than in the photos. Every detail felt thoughtfully prepared — from the comfortable seating areas to the fully stocked amenities. The captain and crew were incredibly professional, friendly, and attentive. They made us feel completely relaxed and taken care of the entire time. Safety was clearly a priority, but so was making sure we had an unforgettable experience. The ride itself was smooth and luxurious. Whether we were cruising, swimming, or just enjoying the views, everything felt effortless and special. It was the perfect balance of fun and elegance. I would absolutely book again without hesitation. If you’re considering renting this yacht — do it. It’s worth every penny and truly a 5-star experience!

  5. KA

    Kylee

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

    This was a wonderful day on the water with our family of 20 ages ranging from 18 months to 65. The boat was so nice, clean and the staff taking care of us were awesome. Great communication pre-excursion and as a travel agent myself I will be highly recommending this to my clients. Would definitely do this again. Our family would say it was the highlight of our trip. Thanks so much for a great day!!

  6. Jocelyn

    Jocelyn

    PRIVATE POWERCAT 40 AROUND SAINT MARTIN, PINEL, TINTAMARRE AND ANGUILLA

    If we could give Captain Joe and Chloe, 100 stars, we would. We had the best time with them on the boat, they showed us all around the island, their hospitality is unmatched. We enjoyed it so much, we ended up booking the boat for two days instead of one. I would highly recommend them for the best experience in Saint Maarten!