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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(1,955 Reviews)

Page 19 of 20468 listings

An Unforgettable Sunset Sailing Evening Aboard Xem3
Sailing in Cartagena · 12 guests

An Unforgettable Sunset Sailing Evening Aboard Xem3

New
$605/hour
Bahia 46 in San Blas Islands
Sailing in Panama City · 8 guests

Bahia 46 in San Blas Islands

New
$1,500/night
Charter this 40' Sailing Catamaran in San Blas, Panama
Sailing in Guna Yala Comarca · 6 guests

Charter this 40' Sailing Catamaran in San Blas, Panama

New
$250/person
Hobie Cat Rental on Cockleshell Bay
Sailing in Saint George Basseterre Parish · 1 guest

Hobie Cat Rental on Cockleshell Bay

New
$100/hour
St John, usvi  private day  sail excursions
Sailing in Charlotte Amalie West · 6 guests

St John, usvi private day sail excursions

New
$175/person
Luxury Sailing Experience in Bocas Del Toro
Sailing in Bocas del Toro Province · 12 guests

Luxury Sailing Experience in Bocas Del Toro

New
$300/hour
Beneteau 50 Sailing Yacht Charter in San Blas Islands
Colón · 10 guests

Beneteau 50 Sailing Yacht Charter in San Blas Islands

New
$1,400/day
6 PAX Cruising Monohull in Cartagena, Colombia
Sailing in Cartagena · 6 guests

6 PAX Cruising Monohull in Cartagena, Colombia

New
$800/day
Alessandra, Pirate Boat Charter in Cartagena, Bolívar
Sailing in Cartagena · 17 guests

Alessandra, Pirate Boat Charter in Cartagena, Bolívar

New
$1,632/day
Charter 48' Privilege - Balindo Cruising Catamaran in Caribe Sur, Venezuela
Sailing in Urbanizacion Molorca · 20 guests

Charter 48' Privilege - Balindo Cruising Catamaran in Caribe Sur, Venezuela

New
$1,197/day
Explore the Ionian Sea with this Cruising Catamaran Rental in Le Robert, Martinique
Sailing in Le Robert · 18 guests

Explore the Ionian Sea with this Cruising Catamaran Rental in Le Robert, Martinique

New
$1,306/day
Charter a Cruising Monohull in Foster Hall, Barbados
Sailing in Less Beholden · 15 guests

Charter a Cruising Monohull in Foster Hall, Barbados

New
$10,667/day
51' Jeanneau Sailing Yacht Charter with Captain in Guna Yala Comarca
Sailing in Guna Yala Comarca · 6 guests

51' Jeanneau Sailing Yacht Charter with Captain in Guna Yala Comarca

New
$170/person
Bavaria 46 CR / 2017 Yacht in Saint Lucia Rodney Bay Marina
Sailing in Gros Islet · 8 guests

Bavaria 46 CR / 2017 Yacht in Saint Lucia Rodney Bay Marina

New
$684/night
Beneteau 413 Yacht Charter in Saint Lucia Rodney Bay Marina
Sailing in Gros Islet · 6 guests

Beneteau 413 Yacht Charter in Saint Lucia Rodney Bay Marina

New
$405/day
Beautiful days with your friends and family on a Brand New Elba 45’ in St. Thomas and St. John, USVI.
Sailing in Charlotte Amalie West · 6 guests

Beautiful days with your friends and family on a Brand New Elba 45’ in St. Thomas and St. John, USVI.

New
$1,715/day
7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne
Sailing in Grande-Terre · 8 guests

7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne

New
$1,088/day
Charter 43ft Sailing Yacht In Hispania, Colombia
Sailing in Cartagena · 8 guests

Charter 43ft Sailing Yacht In Hispania, Colombia

New
$800/day
Private Catamaran Charter In Punta Cana, Dominican Republic
Sailing in El Cortecito · 50 guests

Private Catamaran Charter In Punta Cana, Dominican Republic

New
$350/hour
"Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands
Sailing in Pointe-a-Pitre · 6 guests

"Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands

New
$1,192/person
Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda
Sailing in English Harbour · 6 guests

Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda

5.0
$920/day
51' Neel Cruising Catamaran Rental in Le Marin, Martinique
Sailing in Rivière-Salée · 9 guests

51' Neel Cruising Catamaran Rental in Le Marin, Martinique

New
$1,478/day
Charter 57' Cata Kreyol Cruising Catamaran in Gros-Morne, Martinique
Sailing in Gros-Morne · 27 guests

Charter 57' Cata Kreyol Cruising Catamaran in Gros-Morne, Martinique

New
$1,850/day
Classic Cutter 44' Sailing Boat Charter for Up to 5 People in San Blas islands, Panama
Sailing in Guna Yala Comarca · 5 guests

Classic Cutter 44' Sailing Boat Charter for Up to 5 People in San Blas islands, Panama

New
$185/person