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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,366 Reviews)

    Page 14 of 18 • 432 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private Catamaran Sail & Snorkel in Negril – Open Bar, Snacks & Music
    Sailing in Negril · 60 guests

    Private Catamaran Sail & Snorkel in Negril – Open Bar, Snacks & Music

    New
    $930+/hour
    45ft Lagoon 450F Sailing Catamaran, Key West with Captain
    Sailing in Key West · 13 guests

    45ft Lagoon 450F Sailing Catamaran, Key West with Captain

    New
    $739+/hour
    Sailing Classic Yacht 1980 Swan 47 in Caribbean Waters
    Sailing in Saint George's · 7 guests

    Sailing Classic Yacht 1980 Swan 47 in Caribbean Waters

    New
    $60/hour
    BRAND NEW 2025 Lagoon 43 Luxury Catamaran with AC price include 2 guests
    Sailing in Guna Yala Comarca · 8 guests

    BRAND NEW 2025 Lagoon 43 Luxury Catamaran with AC price include 2 guests

    New
    $2,600/night
    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale
    Powerboats in Fort Lauderdale · 12 guests

    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale

    New
    $330/hour
    Saona Island: Private Yacht Tour with Snorkel in DR
    Events in Los Melones · 15 guests

    Saona Island: Private Yacht Tour with Snorkel in DR

    New
    $320/hour
    Massive Luxury 51ft Lagoon Catamaran In Fort Lauderdale
    Sailing in Fort Lauderdale · 12 guests

    Massive Luxury 51ft Lagoon Catamaran In Fort Lauderdale

    New
    $375/hour
    ''Valentine'' Sea Ray SDX Series Deck Boat Rental in Fort Myers, Florida
    Powerboats in Fort Myers · 12 guests

    ''Valentine'' Sea Ray SDX Series Deck Boat Rental in Fort Myers, Florida

    New
    $535/hour
    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo
    Sailing in Fajardo · 12 guests

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

    New
    $450/hour
    Leopard 51' Power Catamaran from St Martin to Anguilla
    Powerboats in Saint Martin · 12 guests

    Leopard 51' Power Catamaran from St Martin to Anguilla

    New
    $3,033/day
    Relaxing Catamaran Charters in Punta Cana
    Sailing in Bávaro · 16 guests

    Relaxing Catamaran Charters in Punta Cana

    New
    $69/hour
    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
    Bahamas Sunset Cruise
    Powerboats in Nassau · 8 guests

    Bahamas Sunset Cruise

    New
    $350/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
    55' Nisi Catamaran – Private Bahamas Day Charter- Gratuity and Tax included
    Powerboats in Nassau · 15 guests

    55' Nisi Catamaran – Private Bahamas Day Charter- Gratuity and Tax included

    New
    $1,385+/hour
    "The Cats Meow" Custom Cats Catamaran
    Sailing in Sunny Isles Beach · 12 guests

    "The Cats Meow" Custom Cats Catamaran

    New
    $591/hour
    53' Leopard Power Catamaran – Private Bahamas Day Charter
    Sailing in Nassau · 15 guests

    53' Leopard Power Catamaran – Private Bahamas Day Charter

    New
    $1,160+/hour
    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
    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
    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
    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

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