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Rent a Sailboat in Simpson Bay

Add dates to find your ideal boat for the best price
Top trending Sailboats in Simpson Bay
How we rank results
Sint Maarten
New

Hanse - 418 | 9 people

(2020)
Skipper optional
Sailboats
9 people · 3 cabins · 9 berths · 12 m

From
$688
 / day

Marigot
4.9
(12)

Kirie - Feeling - 446 | 4 people

(1989)
Skipper optional
Super owner
Sailboats
4 people · 3 cabins · 4 berths · 14 m
Fuel included

From
$482
 / day

Full-day sailboat rental in Simpson Bay
Full-day sailboat rental in Simpson Bay
Full-day sailboat rental in Simpson Bay
Full-day sailboat rental in Simpson Bay
Full-day sailboat rental in Simpson Bay
Simpson Bay, Sint Maarten
5.0
(1)

Full-day sailboat rental in Simpson Bay

Skipper included
Super owner
Sailboat
8 hours · For groups of up to 10 people
Fuel included

From
$1,266

42 sailboats available
How we rank results
Marigot
New

- Moorings 41.3 | 7 people

(2024)
Skipper optional
Super owner
Sailboats
7 people · 3 cabins · 7 berths · 12 m

From
$542
 / day

Special offer
Marigot
New

- Moorings 42.3 | 7 people

(2024)
Skipper optional
Super owner
Sailboats
7 people · 3 cabins · 7 berths · 12 m

From
$573
 / day

Special offer
Marigot
New

Chantier naval aixois - Ketch | 10 people

(1989)
Skipper mandatory
Sailboats
10 people · 2 cabins · 6 berths · 12 m

From
$517
 / day

Marigot, Marigot Port
4.3
(7)

Beneteau - First 38 | 12 people

(1984)
With Skipper
Sailboats
12 people · 3 cabins · 8 berths · 12 m
Fuel included
Flexible cancellation

From
$568
 / day

Saint Martin
0.0
(0)

BENETEAU - OCEANIS 51.1 | 12 people

(2019)
Skipper optional
Sailboats
12 people · 6 cabins · 12 berths · 15.9 m

From
$521
 / day

Saint Martin
0.0
(1)

BENETEAU - OCEANIS 48 | 4 people

(2011)
Skipper optional
Sailboats
4 people · 4 cabins · 8 berths · 15 m

From
$861
 / day

Saint Martin
4.7
(2)

Jeanneau - Sun Odyssey 45.2 | 4 people

(2003)
Skipper mandatory
Sailboats
4 people · 3 cabins · 5 berths · 13.8 m

From
$362
 / day

Saint Martin
0.0
(0)

Dufour Yachts - Dufour 460 GL Liberty | 10 people

(2018)
Skipper optional
Sailboats
10 people · 4 cabins · 10 berths · 14.2 m

From
$415
 / day

Saint Martin
5.0
(1)

Jeanneau - Sun Odyssey 40 | 6 people

(2003)
With Skipper
Sailboats
6 people · 3 cabins · 6 berths · 12 m
Fuel included

From
$86
 / day

Marigot
5.0
(3)

Jeanneau - 53 | 8 people

(2011)
Without captain
Sailboats
8 people · 2 cabins · 4 berths · 16 m
Fuel included

From
$86
 / day

Gustavia
New

Hanse - 445 | 8 people

(2013)
With Skipper
Sailboats
8 people · 3 cabins · 8 berths · 13.4 m
Flexible cancellation

From
$1,205
 / day

Gustavia
New

Bavaria - Bavaria45 cruiser | 4 people

(2010)
With Skipper
Sailboats
4 people · 2 cabins · 4 berths · 14.3 m
Fuel included

From
$964
 / day

Saint Barthélemy
0.0
(0)

Beneteau - First 40.7 | 10 people

(2008)
Skipper mandatory
Super owner
Sailboats
10 people · 3 cabins · 10 berths · 12.9 m
Fuel included

From
$1,033
 / day

Saint Barthélemy
5.0
(4)

JEANNEAU - SUN ODYSSEY 52.2 | 2 people

(2001)
Skipper optional
Super owner
Sailboats
2 people · 3 cabins · 6 berths · 15 m

From
$999
 / day

Relax in Saint Barthélemy: 9h of sun on a sailboat
Relax in Saint Barthélemy: 9h of sun on a sailboat
Relax in Saint Barthélemy: 9h of sun on a sailboat
Relax in Saint Barthélemy: 9h of sun on a sailboat
Relax in Saint Barthélemy: 9h of sun on a sailboat
Relax in Saint Barthélemy: 9h of sun on a sailboat
Relax in Saint Barthélemy: 9h of sun on a sailboat
Saint Barthélemy

Relax in Saint Barthélemy: 9h of sun on a sailboat

With skipper
Super owner
Sailboat
9 hours · For groups of up to 10 people

From
$1,205

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