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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,318 Reviews)

    Page 10 of 18 • 432 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Sailing Adventure on Bay in Miami on Tartan Sailboat!
    Sailing in Key Biscayne · 6 guests

    Sailing Adventure on Bay in Miami on Tartan Sailboat!

    5.0
    $100/hour
    Sailing catamaran in USVI
    Sailing in Charlotte Amalie · 6 guests

    Sailing catamaran in USVI

    5.0
    $1,300/day
    Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ
    Sailing in Punta Cana · 70 guests

    Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ

    New
    $125+/hour
    Cruising Catamaran Rental in Puerto Plata, Puerto Plata
    Sailing in Barrio Las Yaguitas · 80 guests

    Cruising Catamaran Rental in Puerto Plata, Puerto Plata

    1.0
    Superowner
    Best of 2026
    $183/hour
    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
    Maxicat 65ft Private Party Catamaran in Cartagena
    Sailing in Cartagena · 80 guests

    Maxicat 65ft Private Party Catamaran in Cartagena

    New
    Superowner
    $838/hour
    Clear Kayak Mangrove Cay Eco Venture 2-hour tour
    Adventures in Leeward Settlement · 10 guests

    Clear Kayak Mangrove Cay Eco Venture 2-hour tour

    New
    $200/hour
    All-inclusive Luxury Shared Charter - Power Cat - St Martin
    Caribbean · 10 guests

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

    New
    $414/day
    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
    Punta Cana - FAMILY BOAT
    Sailing in Bávaro · 200 guests

    Punta Cana - FAMILY BOAT

    New
    $160/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
    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
    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
    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
    Sailing in Fort Lauderdale · 12 guests

    Luxury Catamaran Party | Lagoon 50

    New
    $300/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
    🛥🥂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
    Charter The AKKA 68ft catamaran
    Sailing in Oranjestad-West · 15 guests

    Charter The AKKA 68ft catamaran

    New
    $700/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
    Twin Island Paradise Snorkel Tour
    Tours in Basseterre · 45 guests

    Twin Island Paradise Snorkel Tour

    New
    $29/hour
    44 Luxury Catamaran BIG BEN
    Sailing in Leeward Settlement · 18 guests

    44 Luxury Catamaran BIG BEN

    New
    $875+/hour
    Punta Cana - PARTY BOAT (ADULT ONLY)
    Sailing in Bávaro · 200 guests

    Punta Cana - PARTY BOAT (ADULT ONLY)

    New
    $984/hour
    Ocho Rios Private Sunset Catamaran with Dinner & Open Bar
    Powerboats in Ocho Rios · 100 guests

    Ocho Rios Private Sunset Catamaran with Dinner & Open Bar

    New
    $817/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

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. GS

      Grant

      Sailing Adventure on Bay in Miami on Tartan Sailboat!

      Wonderful experience. The boat functioned perfectly and was a blast. Great communication from the owner Don.

    2. RH

      Roger

      Sailing Adventure on Bay in Miami on Tartan Sailboat!

      Great vessel. Well maintained. Up to date equipment. Very relaxed.

    3. Evan

      Evan

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

      Amazing people to deal with ! Highly recommend

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