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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,289 Reviews)

    Page 10 of 18 • 428 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)
    Events in Bávaro · 100 guests

    Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

    5.0
    $240/hour
    All-inclusive Luxury Shared Charter - Power Cat - St Martin
    Powerboats in Simpson Bay · 10 guests

    All-inclusive Luxury Shared Charter - Power Cat - St Martin

    New
    $415/day
    46 Sport Bridge Yacht
    Events in Miami Beach · 12 guests

    46 Sport Bridge Yacht

    New
    $240+/hour
    Maxicat 65ft Private Party Catamaran in Cartagena
    Sailing in Cartagena · 80 guests

    Maxicat 65ft Private Party Catamaran in Cartagena

    New
    Superowner
    $838/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
    Punta Cana - FAMILY BOAT
    Sailing in Bávaro · 200 guests

    Punta Cana - FAMILY BOAT

    New
    $160/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
    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
    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
    $40/hour
    🛥🥂VIP EXPERIENCE-Prívate Catamaran for bachelorette-birthday in Puerto Plata
    Events in Barrio Las Yaguitas · 60 guests

    🛥🥂VIP EXPERIENCE-Prívate Catamaran for bachelorette-birthday in Puerto Plata

    New
    $170/hour
    Twin Island Paradise Snorkel Tour
    Tours in Basseterre · 45 guests

    Twin Island Paradise Snorkel Tour

    New
    $29/hour
    Knot at Work 40 - Private Catamaran Charter - Discover the beautiful St Maarten
    Sailing in Upper Prince's Quarter · 12 guests

    Knot at Work 40 - Private Catamaran Charter - Discover the beautiful St Maarten

    New
    $1,850/day
    Charter The AKKA 68ft catamaran
    Sailing in Oranjestad-West · 15 guests

    Charter The AKKA 68ft catamaran

    New
    $700/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
    Luxury Catamaran Party | Lagoon 50
    Sailing in Fort Lauderdale · 12 guests

    Luxury Catamaran Party | Lagoon 50

    New
    $300/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
    Punta Cana - PARTY BOAT (ADULT ONLY)
    Sailing in Bávaro · 200 guests

    Punta Cana - PARTY BOAT (ADULT ONLY)

    New
    $984/hour
    Hunter 450 Passage Yacht - Sail From Key Biscayne
    Sailing in Key Biscayne · 10 guests

    Hunter 450 Passage Yacht - Sail From Key Biscayne

    New
    Superowner
    $250/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
    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
    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
    Punta Cana: Ultimate Private Yacht Party with Snorkeling
    Events in Bávaro · 10 guests

    Punta Cana: Ultimate Private Yacht Party with Snorkeling

    New
    $320+/hour
    Power in Las Galeras
    Sailing in Las Galeras · 10 guests

    Power in Las Galeras

    New
    $1,580/day
    Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten
    Sailing in Lowlands · 8 guests

    Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

    5.0
    $1,000/day

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. AS

      Aaron

      Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

      Great time sailing with Robert in Sxm. Food and drinks were great. Only on the boat for two nights but got a lot done for the amount of time we had available.

    2. Evan

      Evan

      Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

      Amazing people to deal with ! Highly recommend

    3. MC

      Michael

      Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

      Wonderful day. Highly recommend.

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