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Simpson Bay, Sint Maarten Boat Rentals

Page 1 of 361 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
Superowner
$353/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
$353/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
$294/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
$2,119/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
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 20m CANTIERI OPERA Yacht for Private Charter Anguilla
Events in Marigot · 30 guests

Luxury 20m CANTIERI OPERA Yacht for Private Charter Anguilla

New
$706+/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
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
Superowner
$294/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 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
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
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
Adventures in the Caribbean
Sailing in Simpson Bay · 10 guests

Adventures in the Caribbean

New
$500/hour
New Leopard 53 SAINT MARTIN
Powerboats in Marigot · 12 guests

New Leopard 53 SAINT MARTIN

5.0
$450/hour
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500/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
Boat Charter in Sint Maarten
Powerboats in Lowlands · 12 guests

Boat Charter in Sint Maarten

5.0
$213/hour

Simpson Bay Reviews

  1. AK

    Andrew

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

    Outstanding trip with Jordan and Chloe. Took us to the best spots and great drinks and service. It was the highlight of our trip and we rented and boat with them for 2 days. Be sure to rent the underwater scooter as that is a lot of fun. We will be back

  2. AK

    Andrew

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

    Great day on the water. Jordan and Chloe were fantastic. We went to great spots and our margarita glasses were never empty. Recommend getting the underwater scooter. We re booked them for another day with new itinerary. Best part of our vacation

  3. ER

    Eva

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

    Where do I start? Jordan and Chloe were responsive and attentive from the beginning so I had no qualms booking with them the same day they sent over the quote. The boat is beautiful and as advertised. It was easy to navigate around on the boat while on the water. They even decorated for my boyfriend’s birthday which was awesome. We chose the lobster for lunch and were not disappointed- the scallop appetizer and lobster were amazing. Drinks (piña coladas) were great as well. Highlight of our vacation and I’m glad I saved it for the last day. Will definitely book with them the next time we visit.

  4. Sundeep

    Sundeep

    Luxury Catamaran Trips in St Maarten and Surrounding Islands

    Simply incredible! Captain Neil and his crew provided an outstanding experience for our buddy's 40th birthday celebration (16 of us!). The service was impeccable – drinks were always topped up, and we felt incredibly well taken care of. The boat itself is super comfortable and spacious. We were greeted with an endless array of freshly baked croissants and bakery items, and lunch was hands down the best meal we had on the water, all prepared right on board by the chef. This is definitely one of my favorite charters and an unforgettable day. Thank you Capt Neil and crew.

  5. 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.

  6. 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!