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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,311 Reviews)

    Page 15 of 18 • 430 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    The Gallivanders Ultimate Sailing Adventure
    Sailing in Nassau · 12 guests

    The Gallivanders Ultimate Sailing Adventure

    New
    $430/hour
    Instant Book
    Private Catamaran in San Blas Islands – All Meals & Skipper Included
    Sailing in Guna Yala Comarca · 6 guests

    Private Catamaran in San Blas Islands – All Meals & Skipper Included

    New
    $950/night
    Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas
    Sailing in Key West · 12 guests

    Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas

    New
    $560+/hour
    Caribbean Island-hopping
    Sailing in Le Marin · 10 guests

    Caribbean Island-hopping

    New
    $15+/night
    Instant Book
    Luxury 38' Fountaine Pajot Catamaran Tours & Charters in Cartagena, Colombia
    Sailing in Cartagena · 16 guests

    Luxury 38' Fountaine Pajot Catamaran Tours & Charters in Cartagena, Colombia

    New
    $152/hour
    COME AND SAIL ON THIS BEAUTIFUL ELAN MONOHULL BUILT FOR PERFORMANCE AND COMFORT
    Sailing in Le Marin · 8 guests

    COME AND SAIL ON THIS BEAUTIFUL ELAN MONOHULL BUILT FOR PERFORMANCE AND COMFORT

    New
    $125/hour
    Your dreamed boat in the Caribbeans | 50ft Dufour Sailboat
    Sailing in Le Marin · 8 guests

    Your dreamed boat in the Caribbeans | 50ft Dufour Sailboat

    New
    $248/day
    46ft Fountaine Pajot for 25 people in Taboga ALL INCLUSIVE
    Sailing in Panama City · 25 guests

    46ft Fountaine Pajot for 25 people in Taboga ALL INCLUSIVE

    New
    $468/hour
    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo
    Sailing in Fajardo · 6 guests

    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo

    New
    $350/hour
    Cruising Catamaran Charter in Falmouth
    Sailing in Falmouth · 40 guests

    Cruising Catamaran Charter in Falmouth

    New
    $1,250/hour
    Leopard 46 Catamaran Sailing in Antigua & Barbuda
    Sailing in English Harbour · 6 guests

    Leopard 46 Catamaran Sailing in Antigua & Barbuda

    New
    $1,300/day
    Private Gourmet Sailing Charters on Elegant 50ft Catamaran
    Sailing in Gustavia · 10 guests

    Private Gourmet Sailing Charters on Elegant 50ft Catamaran

    New
    $595+/hour
    Dufour 455 Grand Large - Sloop sail rental in Le Marin
    Sailing in Le Marin · 8 guests

    Dufour 455 Grand Large - Sloop sail rental in Le Marin

    New
    $510/day
    Private Sailing Yacht to Coiba National Park – Overnight Option
    Sailing in Panamá · 6 guests

    Private Sailing Yacht to Coiba National Park – Overnight Option

    New
    $120/hour
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Sailing in Saint Martin · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    New
    $346/hour
    Private Sunset Cruise With Dinner Ocho Rios, Jamaica
    Events in Ocho Rios · 30 guests

    Private Sunset Cruise With Dinner Ocho Rios, Jamaica

    New
    $1,400/hour
    Lagoon 46 Premium Sailing Catamaran in Le Marin, Martinique
    Sailing in Le Marin · 12 guests

    Lagoon 46 Premium Sailing Catamaran in Le Marin, Martinique

    New
    $1,136/day
    Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos
    Sailing in Fajardo · 12 guests

    Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos

    New
    $575/hour
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Sailing in Saint Martin · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    New
    $346/hour
    Punta Cana’s Ultimate Ocean Powerhouse - Luxury Snorkel & Natural Pool Adventure
    Events in Bávaro · 70 guests

    Punta Cana’s Ultimate Ocean Powerhouse - Luxury Snorkel & Natural Pool Adventure

    New
    $325/hour
    Sailing in the Caribbean St. Martin
    Sailing in Saint Martin · 10 guests

    Sailing in the Caribbean St. Martin

    New
    $1,152/day
    Nautitech 43 Cruising Catamaran Rental in San Blas Islands, Panama
    Sailing in Guna Yala Comarca · 6 guests

    Nautitech 43 Cruising Catamaran Rental in San Blas Islands, Panama

    New
    $1,600/night
    It's a Water Planet, Sail it - Beneteau 41S5 Sailboat
    Sailing in Miami · 6 guests

    It's a Water Planet, Sail it - Beneteau 41S5 Sailboat

    New
    $200/hour
    Reggae Catamaran Negril Sail Snorkel and Sunset Tour
    Sailing in West End · 20 guests

    Reggae Catamaran Negril Sail Snorkel and Sunset Tour

    New
    $1,084/hour

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