We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

05/24/2024  ± 2 days

Simpson Bay, Sint Maarten Boat Rentals

Page 1 of 360 listings

Spacious 55ft Motor Yacht perfect to discover Anguilla with your family
Events in Simpson Bay · 12 guests

Spacious 55ft Motor Yacht perfect to discover Anguilla with your family

5.0
$268hour
Charter our 34 ft Apache performance in Sint Maarten or Anguilla
Powerboats in Cole Bay · 12 guests

Charter our 34 ft Apache performance in Sint Maarten or Anguilla

5.0
$150hour
SCHAEFER V33 Luxury speedboat 34ft charter from Marigot, Saint Martin
Powerboats in Marigot · 8 guests

SCHAEFER V33 Luxury speedboat 34ft charter from Marigot, Saint Martin

5.0
$1,275day
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
Best of 2023
$1,929day
Luxurious 55ft  private American Trawler around St Martin, Anguilla, Pinel
Events in Marigot · 12 guests

Luxurious 55ft private American Trawler around St Martin, Anguilla, Pinel

4.5
$1,608day
Deep Sea Fishing Charter in St. Maarten with Captain Rudy
Fishing in Simpson Bay · 6 guests

Deep Sea Fishing Charter in St. Maarten with Captain Rudy

New
$169hour
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
$188hour
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
$2,395day
ORA Power Catamaran Leopard 53PC from Saint Martin, Marigot
Events in Marigot · 13 guests

ORA Power Catamaran Leopard 53PC from Saint Martin, Marigot

New
$3,076day
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
$230person
Fishing Charter in Simpson Bay
Fishing in Simpson Bay · 6 guests

Fishing Charter in Simpson Bay

4.7
$163-$169hour
Boat tour Sailboat 40 feet Saint Martin
Sailing in Marigot · 6 guests

Boat tour Sailboat 40 feet Saint Martin

New
$165person
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
$1,150day
Luxury Catamaran Day cruises with 4-Course Gourmet Lunch
Powerboats in Simpson Bay · 12 guests

Luxury Catamaran Day cruises with 4-Course Gourmet Lunch

5.0
$360hour
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
$550hour
Lagoon 450 S Power Catamaran Luxury Day Charters with 4-Course Gourmet Lunch
Events in Simpson Bay · 12 guests

Lagoon 450 S Power Catamaran Luxury Day Charters with 4-Course Gourmet Lunch

5.0
$2,280day
Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten
Sailing in Cole Bay · 16 guests

Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

New
$1,500day
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
$1,200day
LEOPARD POWERCAT 51ft 2018 from Saint Martin, Marigot
Powerboats in Marigot · 12 guests

LEOPARD POWERCAT 51ft 2018 from Saint Martin, Marigot

New
$2,851day
Boat Charter in Sint Maarten
Powerboats in Lowlands · 12 guests

Boat Charter in Sint Maarten

5.0
$213hour
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500day
Sunseeker 52 Motor Yacht Charter in Sint Maarten
Events in Lowlands · 10 guests

Sunseeker 52 Motor Yacht Charter in Sint Maarten

5.0
$2,800day
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
$825day
Private Charters In Simpson Bay or Philipsburg
Sailing in Simpson Bay · 30 guests

Private Charters In Simpson Bay or Philipsburg

5.0
$3,300day

Simpson Bay Reviews

  1. Nicole

    Nicole

    Spacious 55ft Motor Yacht perfect to discover Anguilla with your family

    I had the best experience! Jordan and V made my birthday vacation so much fun! If you are thinking about yachting in in SXM you should book them. The drinks were good, the floating bed and pool were a great way to experience the ocean! As nervous as I was my friends and I had an amazing time. They made sure we were enjoying ourselves throughout the full day charter we booked. Jordan took us to an island in Anguilla where I had the biggest lobster I’ve ever seen! I give them 10 stars if I could! Thank you for making us feel welcomed and allowing us ti turn up!!! A time was had! Xo

  2. RP

    Ron

    Luxurious 55ft private American Trawler around St Martin, Anguilla, Pinel

    The boat was AMAZING, the pictures do it no justice. The captain and host were the BEST !!!! They were so nice and helpful. They were funny and so polite. The drinks made on the boat were to die for. 10/10 will recommend.

  3. DV

    Diamond

    Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

    Look no further- Book Today! The boat is super fabulous, the Captain is so friendly and nice and Rebecca makes the best drinks. They cater to your every need and make your trip so memorable. We truly had a blast!!

  4. DS

    Dana

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

    I celebrated my 36th birthday with 7 of my close friends and family. This experience was a real treat! We had an unforgettable trip to Anguilla filled with great vibes, great food, unlimited drinks, paddle boarding, snorkeling, and more. 11/10

  5. JF

    Joanna

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

    We had an amazing time! The catamaran is clean, spacious and beautiful. The captain and Diane were the best and took very good care of us! The drink options available were good!! The light breakfast and lunch served were fresh and delicious! I highly recommend them, don't hesitate to book!

  6. JR

    Janell

    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

    Garth and Byron really made sure that we had a good time! I would definitely use them again when I come back to St Martin!