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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,256 Reviews)

    Page 10 of 18 • 419 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne
    Tours in Miami Beach · 10 guests

    Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne

    New
    Superowner
    $159+/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
    Limited Availability
    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
    Leopard 53 Power Catamaran (25-ft wide deck space)
    Powerboats in Fort Lauderdale · 12 guests

    Leopard 53 Power Catamaran (25-ft wide deck space)

    New
    $400+/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
    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
    Sail from Boynton Beach to Lake Boca
    Sailing in Boynton Beach · 12 guests

    Sail from Boynton Beach to Lake Boca

    New
    Superowner
    $126+/hour
    Sailing catamaran in USVI
    Sailing in Charlotte Amalie · 6 guests

    Sailing catamaran in USVI

    5.0
    $1,300/day
    Twin Island Paradise Snorkel Tour
    Tours in Basseterre · 45 guests

    Twin Island Paradise Snorkel Tour

    New
    $29/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
    $3,121/day
    7 to 21 Days Sailing to the Grenadines aboard Beneteau Oceanis 440 Sailing Yacht
    Sailing in Le Marin · 10 guests

    7 to 21 Days Sailing to the Grenadines aboard Beneteau Oceanis 440 Sailing Yacht

    New
    $231/day
    Sailing Cruise Guadeloupe to Martinique on Beneteau Oceanis 440
    Sailing in Les Abymes · 10 guests

    Sailing Cruise Guadeloupe to Martinique on Beneteau Oceanis 440

    New
    $231/day
    Weekly Caribbean Sailing Cruise from Saint Lucia on 44ft Beneteau Yacht
    Sailing in Rodney Bay · 6 guests

    Weekly Caribbean Sailing Cruise from Saint Lucia on 44ft Beneteau Yacht

    New
    $1,156/day
    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
    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
    $355/hour
    50 Luxury Sailing Catamaran in Miami
    Sailing in Fort Lauderdale · 12 guests

    50 Luxury Sailing Catamaran in Miami

    5.0
    $335/hour
    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
    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
    Punta Cana - PRIVATE BOAT MAX BBQ
    Sailing in Bávaro · 40 guests

    Punta Cana - PRIVATE BOAT MAX BBQ

    New
    $575/hour
    Have an amazing time in Cartagena, Colombia on Beneteau 41 Sailboat
    Sailing in Cartagena · 8 guests

    Have an amazing time in Cartagena, Colombia on Beneteau 41 Sailboat

    New
    Superowner
    $1,220/day
    Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull
    Sailing in Cartagena · 10 guests

    Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull

    New
    Superowner
    $163/hour
    4Hours🎊Birthday-Bachelorette luxury private Boat🛥️🏝️🍾 PARTY in Punta Cana
    Events in Punta Cana · 150 guests

    4Hours🎊Birthday-Bachelorette luxury private Boat🛥️🏝️🍾 PARTY in Punta Cana

    New
    $50/hour
    Puerto Plata Private 6 Hour Catamaran Snorkel and BBQ
    Powerboats in Sosúa · 20 guests

    Puerto Plata Private 6 Hour Catamaran Snorkel and BBQ

    New
    $265/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

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. SA

      Sharon

      50 Luxury Sailing Catamaran in Miami

      Just book it! You will NOT regret it. I promise- it's an amazing experience! The crew (Leornardo and Alina) were awesome and very accommodating! Book with these two!

    2. 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.

    3. Blue

      Blue

      50 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.

    4. erkan

      erkan

      57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

      Crew , boat , owner … they were the best !

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