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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,245 Reviews)

    Page 12 of 19 • 433 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Fun Memories, Captain & Crew Included
    Sailing in Bávaro · 100 guests

    Fun Memories, Captain & Crew Included

    New
    Superowner
    Best of 2026
    $100/hour
    😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎
    Events in Sosúa · 18 guests

    😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎

    New
    Superowner
    Best of 2026
    $75/hour
    Catamaran Lagoon 450 from Marina Puerto del Rey in Fajardo
    Sailing in Fajardo · 12 guests

    Catamaran Lagoon 450 from Marina Puerto del Rey in Fajardo

    New
    $699/hour
    Private Lunch Tour Deluxe in Curacao
    Sailing in Santa Barbara Plantation · 6 guests

    Private Lunch Tour Deluxe in Curacao

    New
    $325/hour
    46ft Luxury Sailing Catamaran in Miami
    Sailing in Fort Lauderdale · 12 guests

    46ft Luxury Sailing Catamaran in Miami

    5.0
    $300/hour
    Deal of the Week! Leopard 43Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 25 guests

    Deal of the Week! Leopard 43Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $654/hour
    Party Boat that can host 150 people in La Romana, Dominican Republic
    Events in La Romana · 150 guests

    Party Boat that can host 150 people in La Romana, Dominican Republic

    New
    Superowner
    Best of 2026
    $100/hour
    46 Sport Bridge Yacht
    Events in Miami Beach · 12 guests

    46 Sport Bridge Yacht

    New
    $240+/hour
    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!
    Sailing in Saint Martin · 20 guests

    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!

    New
    $2,911/day
    Deal of the Day! Lagoon 40Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 18 guests

    Deal of the Day! Lagoon 40Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $435/hour
    Cruising Catamaran Charter in Cabarete, Dominican Republic
    Sailing in Cabarete · 80 guests

    Cruising Catamaran Charter in Cabarete, Dominican Republic

    New
    Superowner
    Best of 2026
    $400/hour
    Private overnight Charter on a Luxurious Fountaine Pajot 47 up to 8 guests
    Sailing in Nassau · 9 guests

    Private overnight Charter on a Luxurious Fountaine Pajot 47 up to 8 guests

    New
    $3,715+/night
    Catamaran Lagoon 62’ 2019 for a week in BVI
    Sailing in John's Hole · 8 guests

    Catamaran Lagoon 62’ 2019 for a week in BVI

    New
    Superowner
    $10,500/day
    Luxury Party Boat Catamaran in Punta Cana
    Events in Punta Cana · 150 guests

    Luxury Party Boat Catamaran in Punta Cana

    New
    Superowner
    Best of 2026
    $80/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
    Charter a Beautiful Lagoon Catamaran 400 S 2 for 17 people
    Sailing in Cartagena · 17 guests

    Charter a Beautiful Lagoon Catamaran 400 S 2 for 17 people

    New
    $180/hour
    Sailing in the Caribbean with Bavaria 44 AC Cruising Monohull
    Sailing in Parham Town · 10 guests

    Sailing in the Caribbean with Bavaria 44 AC Cruising Monohull

    New
    $100/hour
    Deal of the Week! Leopard 47 Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 35 guests

    Deal of the Week! Leopard 47 Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $711/hour
    Spectacular 51-foot Lagoon Catamaran In Cartagena
    Sailing in Cartagena · 40 guests

    Spectacular 51-foot Lagoon Catamaran In Cartagena

    New
    Superowner
    $430/hour
    Party Catamaran Rental🎉Best 2021-2022 Awards in Punta Cana, Dominican Republic
    Powerboats in Macao · 80 guests

    Party Catamaran Rental🎉Best 2021-2022 Awards in Punta Cana, Dominican Republic

    New
    Superowner
    Best of 2026
    $275/hour
    Mega Catamaran Charter in Ocho Rios
    Sailing in Ocho Rios · 120 guests

    Mega Catamaran Charter in Ocho Rios

    New
    $2,300/hour
    Private Saona Island Cruise (All-Inclusive)
    Sailing in Los Melones · 12 guests

    Private Saona Island Cruise (All-Inclusive)

    New
    $169/hour
    Deal of the Week! Lagoon 44Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 23 guests

    Deal of the Week! Lagoon 44Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $460/hour
    Premium Catamaran Experience - Vogue Sint Maarten
    Powerboats in Saint Martin · 12 guests

    Premium Catamaran Experience - Vogue Sint Maarten

    New
    $2,329/day

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. Blue

      Blue

      46ft Luxury Sailing Catamaran in Miami

      Leo and crew were fantastic, and my friends and I had a blast out on the water! Can't wait to do it again.

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