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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,280 Reviews)

    Page 10 of 19 • 433 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    57' Fountaine Pajot Sailing Catamaran - A Luxury Experience
    Sailing in Fort Lauderdale · 12 guests

    57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

    5.0
    $450/hour
    39ft Sea Ray Motor Yacht in Punta Cana, La Altagracia
    Events in Bávaro · 12 guests

    39ft Sea Ray Motor Yacht in Punta Cana, La Altagracia

    New
    $1,910/day
    An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena
    Sailing in Cartagena · 23 guests

    An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena

    New
    Superowner
    $231/hour
    Charter the yacht of your dreams Jeanneau 54 Cruising Monohull in Cartagena
    Sailing in Cartagena · 14 guests

    Charter the yacht of your dreams Jeanneau 54 Cruising Monohull in Cartagena

    New
    Superowner
    $200/hour
    Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience
    Events in Sosúa · 25 guests

    Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience

    New
    $135/hour
    Dunn’s River Falls Private Catamaran Cruise – Ocho Rios
    Powerboats in Ocho Rios · 100 guests

    Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

    New
    $654/hour
    Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia
    Sailing in Cartagena · 80 guests

    Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia

    New
    Superowner
    $5,000/day
    Sail from Boynton Beach to Lake Boca
    Sailing in Boynton Beach · 12 guests

    Sail from Boynton Beach to Lake Boca

    New
    Superowner
    $126+/hour
    Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling
    Sailing in Montego Bay · 60 guests

    Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

    New
    $1,176/hour
    Twin Island Paradise Snorkel Tour
    Tours in Basseterre · 45 guests

    Twin Island Paradise Snorkel Tour

    New
    $29/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
    Sailing catamaran in USVI
    Sailing in Charlotte Amalie · 6 guests

    Sailing catamaran in USVI

    5.0
    $1,300/day
    Luxury Catamaran Party Lagoon 50 in Fort Lauderdale, Florida
    Sailing in Fort Lauderdale · 12 guests

    Luxury Catamaran Party Lagoon 50 in Fort Lauderdale, Florida

    New
    $370/hour
    BOOK NOW 🏆 5-Star Private Luxury Yacht: All-Inclusive Captain & Crew
    Water Sports in Macao · 110 guests

    BOOK NOW 🏆 5-Star Private Luxury Yacht: All-Inclusive Captain & Crew

    New
    Superowner
    Best of 2026
    $17/hour
    St. Barth Boat tour with Lagoon 450 Cruising Catamaran!
    Sailing in Saint Martin · 20 guests

    St. Barth Boat tour with Lagoon 450 Cruising Catamaran!

    New
    $3,082/day
    Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat
    Sailing in Gros Islet · 10 guests

    Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat

    New
    $571/day
    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami
    Events in Miami · 13 guests

    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami

    New
    $250/hour
    Leopard 53 Power Catamaran Available in Anguilla
    Powerboats in Sandy Ground · 13 guests

    Leopard 53 Power Catamaran Available in Anguilla

    New
    $4,909/day
    46' Monohull Sailing Private Charter in Charlotte Amalie
    Sailing in St. Thomas · 6 guests

    46' Monohull Sailing Private Charter in Charlotte Amalie

    New
    $200/hour
    Punta Cana - PRIVATE BOAT MAX BBQ
    Sailing in Bávaro · 40 guests

    Punta Cana - PRIVATE BOAT MAX BBQ

    New
    $575/hour
    Charter The AKKA 68ft catamaran
    Sailing in Oranjestad-West · 15 guests

    Charter The AKKA 68ft catamaran

    New
    $700/hour
    Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia
    Sailing in Cartagena · 12 guests

    Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia

    New
    Superowner
    $150/hour
    Lagoon 62’ 2019 Cruising Catamaran Rental in Nassau, New Providence
    Sailing in Nassau · 10 guests

    Lagoon 62’ 2019 Cruising Catamaran Rental in Nassau, New Providence

    New
    Superowner
    $1,331/hour
    Punta Cana - PARTY BOAT (ADULT ONLY)
    Sailing in Bávaro · 200 guests

    Punta Cana - PARTY BOAT (ADULT ONLY)

    New
    $984/hour

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. TL

      Tanya

      46' Monohull Sailing Private Charter in Charlotte Amalie

      Captain Fancy and Lindsey were awesome!! We loved every minute of it. Pedro the pirate dog was so sweet. I would post pictures but not sure how. I don’t see an option.

    2. erkan

      erkan

      57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

      Crew , boat , owner … they were the best !

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