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Rent a Sailboat in Philipsburg

Add dates to find your ideal boat for the best price
Top trending Sailboats in Philipsburg
How we rank results
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Rental Sailboat Jeanneau 53 Sint Maarten
Sint Maarten
4.9
(5)

Jeanneau - 53 |

(2011)
Skipper mandatory
Superowners
Sailboats
10 people · 16 m

From
$101
 / day

Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Rental Sailboat Sunsail 44 SO Marigot
Marigot

- Sunsail 44 SO | 4 cabins

(2022)
Without captain
Superowners
Sailboats
10 people · 4 cabins · 10 berths · 13 m

From
$530
 / day

Special offer
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
Superowners
Sailboat
8 hours · For groups of up to 10 people
Fuel included

From
$1,236

38 sailboats available
How we rank results
Rental Sailboat Moorings 464PC Marigot
Rental Sailboat Moorings 464PC Marigot
Rental Sailboat Moorings 464PC Marigot
Rental Sailboat Moorings 464PC Marigot
Rental Sailboat Moorings 464PC Marigot
Rental Sailboat Moorings 464PC Marigot
Marigot
New

- Moorings 464PC | 4 cabins

(2024)
Skipper optional
Superowners
Sailboats
8 people · 4 cabins · 8 berths · 14 m

From
$1,518
 / day

Special offer
Rental Sailboat DUFOUR 460 GL with watermaker Saint Martin
Rental Sailboat DUFOUR 460 GL with watermaker Saint Martin
Rental Sailboat DUFOUR 460 GL with watermaker Saint Martin
Rental Sailboat DUFOUR 460 GL with watermaker Saint Martin
Rental Sailboat DUFOUR 460 GL with watermaker Saint Martin
Saint Martin

DUFOUR - 460 GL with watermaker | 5 cabins

(2019)
Skipper optional
Sailboats
12 people · 5 cabins · 10 berths · 14.2 m

From
$352
 / day

Rental Sailboat BENETEAU OCEANIS 51.1 Saint Martin
Rental Sailboat BENETEAU OCEANIS 51.1 Saint Martin
Rental Sailboat BENETEAU OCEANIS 51.1 Saint Martin
Rental Sailboat BENETEAU OCEANIS 51.1 Saint Martin
Rental Sailboat BENETEAU OCEANIS 51.1 Saint Martin
Rental Sailboat BENETEAU OCEANIS 51.1 Saint Martin
Saint Martin

BENETEAU - OCEANIS 51.1 | 6 cabins

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

From
$451
 / day

Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Rental Sailboat Dufour Yachts Dufour 460 GL Liberty Saint Martin
Saint Martin

Dufour Yachts - Dufour 460 GL Liberty | 4 cabins

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

From
$292
 / day

Rental Sailboat BENETEAU OCEANIS 48 Saint Martin
Rental Sailboat BENETEAU OCEANIS 48 Saint Martin
Rental Sailboat BENETEAU OCEANIS 48 Saint Martin
Rental Sailboat BENETEAU OCEANIS 48 Saint Martin
Rental Sailboat BENETEAU OCEANIS 48 Saint Martin
Rental Sailboat BENETEAU OCEANIS 48 Saint Martin
Rental Sailboat BENETEAU OCEANIS 48 Saint Martin
Saint Martin
0.0
(1)

BENETEAU - OCEANIS 48 | 4 cabins

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

From
$1,345
 / day

Rental Sailboat Moorings 44.3 Marigot
Rental Sailboat Moorings 44.3 Marigot
Rental Sailboat Moorings 44.3 Marigot
Rental Sailboat Moorings 44.3 Marigot
Rental Sailboat Moorings 44.3 Marigot
Rental Sailboat Moorings 44.3 Marigot
Marigot
New

- Moorings 44.3 | 3 cabins

(2025)
Skipper optional
Superowners
Sailboats
7 people · 3 cabins · 7 berths · 13 m

From
$594
 / day

Special offer
Rental Sailboat Kirie - Feeling 446 Marigot
Rental Sailboat Kirie - Feeling 446 Marigot
Rental Sailboat Kirie - Feeling 446 Marigot
Rental Sailboat Kirie - Feeling 446 Marigot
Rental Sailboat Kirie - Feeling 446 Marigot
Rental Sailboat Kirie - Feeling 446 Marigot
Marigot
4.9
(13)

Kirie - Feeling - 446 | 3 cabins

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

From
$471
 / day

Rental Sailboat JEANNEAU Sun Odyssey 519 with watermaker & A/C - PLUS Saint Martin
Rental Sailboat JEANNEAU Sun Odyssey 519 with watermaker & A/C - PLUS Saint Martin
Rental Sailboat JEANNEAU Sun Odyssey 519 with watermaker & A/C - PLUS Saint Martin
Rental Sailboat JEANNEAU Sun Odyssey 519 with watermaker & A/C - PLUS Saint Martin
Rental Sailboat JEANNEAU Sun Odyssey 519 with watermaker & A/C - PLUS Saint Martin
Rental Sailboat JEANNEAU Sun Odyssey 519 with watermaker & A/C - PLUS Saint Martin
Saint Martin

JEANNEAU - Sun Odyssey 519 with watermaker & A/C - PLUS | 6 cabins

(2018)
Skipper optional
Sailboats
13 people · 6 cabins · 11 berths · 15.8 m

From
$382
 / day

Rental Sailboat Dufour Yachts Dufour 412 GL Saint Martin
Saint Martin

Dufour Yachts - Dufour 412 GL | 3 cabins

(2021)
Skipper optional
Sailboats
8 people · 3 cabins · 8 berths · 12.7 m

From
$314
 / day

Rental Sailboat Bénéteau Oceanis 40.1 - 3 cab. Saint Martin
Rental Sailboat Bénéteau Oceanis 40.1 - 3 cab. Saint Martin
Rental Sailboat Bénéteau Oceanis 40.1 - 3 cab. Saint Martin
Rental Sailboat Bénéteau Oceanis 40.1 - 3 cab. Saint Martin
Rental Sailboat Bénéteau Oceanis 40.1 - 3 cab. Saint Martin
Rental Sailboat Bénéteau Oceanis 40.1 - 3 cab. Saint Martin
Rental Sailboat Bénéteau Oceanis 40.1 - 3 cab. Saint Martin
Saint Martin

Bénéteau - Oceanis 40.1 - 3 cab. | 3 cabins

(2023)
Skipper optional
Sailboats
8 people · 3 cabins · 8 berths · 12 m

From
$332
 / day

Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Rental Sailboat Dufour Yachts Dufour 500 GL - 5 cab. Saint Martin
Saint Martin

Dufour Yachts - Dufour 500 GL - 5 cab. | 5 cabins

(2016)
Skipper optional
Sailboats
10 people · 5 cabins · 10 berths · 14.8 m

From
$299
 / day

Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Rental Sailboat Beneteau Oceanis 38 Marigot
Marigot

Beneteau - Oceanis 38 | 3 cabins

(2014)
Skipper optional
Sailboats
8 people · 3 cabins · 7 berths · 11 m

From
$370
 / day

Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Relax in Gustavia: 9 hours of sunshine on a sailboat
Gustavia, Saint Barthélemy

Relax in Gustavia: 9 hours of sunshine on a sailboat

Skipper included
Sailboat
9 hours · For groups of up to 8 people
Flexible cancellation

From
$2,118

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