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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,407 Reviews)

    Page 16 of 20 • 457 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    🏆Best Boat 2025🏆 Private Boat 3H with Unlimited drinks and Sand-bar in DR
    Events in Bávaro · 60 guests

    🏆Best Boat 2025🏆 Private Boat 3H with Unlimited drinks and Sand-bar in DR

    New
    $184+/hour
    Private Group Catamaran Sail Snorkeling Adventure in Ocho Rios, Jamaica
    Sailing in Ocho Rios · 60 guests

    Private Group Catamaran Sail Snorkeling Adventure in Ocho Rios, Jamaica

    New
    $1,080/hour
    Performance Sailing Catamaran Adventure
    Sailing in Saint Barthélemy · 6 guests

    Performance Sailing Catamaran Adventure

    New
    $169/hour
    Leopard 53' Power Catamaran from and around Anguilla
    Powerboats in Sandy Ground · 18 guests

    Leopard 53' Power Catamaran from and around Anguilla

    New
    $4,607/day
    Sailing adventure Puerto Rico
    Sailing in Culebra Pueblo · 8 guests

    Sailing adventure Puerto Rico

    New
    $290/hour
    Charter The Arusun 65ft catamaran
    Sailing in Oranjestad-West · 20 guests

    Charter The Arusun 65ft catamaran

    New
    $700/hour
    Boat tour Sailboat 40 feet Saint Martin
    Sailing in Saint Martin · 6 guests

    Boat tour Sailboat 40 feet Saint Martin

    New
    $130/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
    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
    $195/hour
    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
    Unforgettable Crewed Charters on 42' Seawind 1260, Grenadines
    Sailing in St. George · 6 guests

    Unforgettable Crewed Charters on 42' Seawind 1260, Grenadines

    New
    $1,200/day
    Leopard 46 Catamaran Sailing in Antigua & Barbuda
    Sailing in English Harbour · 6 guests

    Leopard 46 Catamaran Sailing in Antigua & Barbuda

    New
    $1,300/day
    Cruising Catamaran Charter in Falmouth
    Sailing in Falmouth · 40 guests

    Cruising Catamaran Charter in Falmouth

    New
    $1,250/hour
    46' Lagoon Sailing Catamaran | Key West Sunsets, Sandbars & Dry Tortugas
    Sailing in Key West · 12 guests

    46' Lagoon Sailing Catamaran | Key West Sunsets, Sandbars & Dry Tortugas

    New
    $635+/hour
    Boat Tours in Panama
    Sailing in Panama City · 70 guests

    Boat Tours in Panama

    1.0
    $125/day
    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
    Sail this cruising catamaran Nautitech 48 in Cartagena, Colombia
    Sailing in Cartagena · 30 guests

    Sail this cruising catamaran Nautitech 48 in Cartagena, Colombia

    New
    $2,200/day
    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
    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
    42ft Orc San Blas Cruising Catamaran in Guna Yala Comarca
    Sailing in Guna Yala Comarca · 6 guests

    42ft Orc San Blas Cruising Catamaran in Guna Yala Comarca

    New
    $1,108+/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
    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
    $242/day
    Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1
    Sailing in Fort Lauderdale · 4 guests

    Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1

    New
    $50/hour
    Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe
    Sailing in Hanover Parish · 120 guests

    Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe

    New
    $700/hour

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