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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,382 Reviews)

    Page 15 of 19 • 442 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Luxury Sailboat in Panama for Pearl Islands or Taboga
    Sailing in Panama City · 20 guests

    Luxury Sailboat in Panama for Pearl Islands or Taboga

    New
    $600/hour
    Morgan 41 Classic Sailboat for Charter in Key West
    Sailing in Key West · 6 guests

    Morgan 41 Classic Sailboat for Charter in Key West

    New
    $351/hour
    Mojito 44ft Catamaran - Luxury Private Charter - St Maarten or Anguilla
    Caribbean · 16 guests

    Mojito 44ft Catamaran - Luxury Private Charter - St Maarten or Anguilla

    New
    $2,100/day
    "The Cats Meow" Custom Cats Catamaran
    Sailing in Sunny Isles Beach · 12 guests

    "The Cats Meow" Custom Cats Catamaran

    New
    $591/hour
    Half Day Sailing Cruise Catamaran In Punta cana
    Powerboats in Bávaro · 18 guests

    Half Day Sailing Cruise Catamaran In Punta cana

    New
    $1,300/day
    55ft Party Catamaran for rent in Ft. Lauderdale
    Sailing in Fort Lauderdale · 49 guests

    55ft Party Catamaran for rent in Ft. Lauderdale

    New
    $1,200+/hour
    Don't Worry 45ft Catamaran - Luxury Private Charter - St Maarten or Anguilla
    Caribbean · 16 guests

    Don't Worry 45ft Catamaran - Luxury Private Charter - St Maarten or Anguilla

    New
    $2,350/day
    A Week Of Escaping Everyday Life Aboard Saint Sophie
    Sailing in Tortola · 10 guests

    A Week Of Escaping Everyday Life Aboard Saint Sophie

    New
    $4,000/night
    Welcome Aboard Athena, A Beautifully Appointed 2022 Lagoon 50
    Sailing in St. Thomas · 10 guests

    Welcome Aboard Athena, A Beautifully Appointed 2022 Lagoon 50

    New
    $4,572/night
    Step aboard Sea Monkeys, a 2022 Fountaine Pajot Elba 45 Cruising Catamaran
    Sailing in West End, Tortola · 6 guests

    Step aboard Sea Monkeys, a 2022 Fountaine Pajot Elba 45 Cruising Catamaran

    New
    $2,500/night
    Miami Sunset Sailing Cruise with Open Bar, Appetizers, DJ on 60ft Catamaran
    Sailing in Miami Beach · 49 guests

    Miami Sunset Sailing Cruise with Open Bar, Appetizers, DJ on 60ft Catamaran

    New
    $1,500/hour
    Bachelorette Catamaran in Punta Cana – All Inclusive (3 Hours or 6 Hours)
    Powerboats in El Cortecito · 100 guests

    Bachelorette Catamaran in Punta Cana – All Inclusive (3 Hours or 6 Hours)

    New
    $373+/hour
    Instant Book
    Private 65ft Catamaran for Charter Trips in Montego Bay
    Sailing in Montego Bay · 40 guests

    Private 65ft Catamaran for Charter Trips in Montego Bay

    New
    $1,365/hour
    Lagoon 46 Luxury Catamaran with AC price include 2 guests
    Sailing in Guna Yala Comarca · 8 guests

    Lagoon 46 Luxury Catamaran with AC price include 2 guests

    New
    $2,600/day
    🏆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
    Sailing Catamaran Leopard 46 in St. Vincent an Grenadines
    Sailing in St. George · 6 guests

    Sailing Catamaran Leopard 46 in St. Vincent an Grenadines

    New
    $150/hour
    Charter The Arusun 65ft catamaran
    Sailing in Oranjestad-West · 20 guests

    Charter The Arusun 65ft catamaran

    New
    $700/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
    $171/hour
    Leopard 53' Power Catamaran from and around Anguilla
    Powerboats in Sandy Ground · 18 guests

    Leopard 53' Power Catamaran from and around Anguilla

    New
    $4,684/day
    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
    $199/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

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