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    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,354 Reviews)

    Page 19 of 19 • 439 listings

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    Axe 1 Center Console Boat Rental in Montego Bay, Jamaica
    Events in Montego Bay · 8 guests

    Axe 1 Center Console Boat Rental in Montego Bay, Jamaica

    New
    Snoozed - Active 03 Sep 2026
    The Gallivanders Ultimate Sailing Adventure
    Sailing in Nassau · 12 guests

    The Gallivanders Ultimate Sailing Adventure

    New
    Snoozed - Active 03 Jan 2027
    COME AND SAIL ON THIS BEAUTIFUL ELAN MONOHULL BUILT FOR PERFORMANCE AND COMFORT
    Sailing in Le Marin · 8 guests

    COME AND SAIL ON THIS BEAUTIFUL ELAN MONOHULL BUILT FOR PERFORMANCE AND COMFORT

    New
    Snoozed - Active 12 Apr 2027
    Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1
    Sailing in Fort Lauderdale · 4 guests

    Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1

    New
    Snoozed - Active 02 Aug 2026
    Lagoon 420 Hybrid Eco Friendly Electric Catamaran
    Sailing in Guna Yala Comarca · 4 guests

    Lagoon 420 Hybrid Eco Friendly Electric Catamaran

    New
    Snoozed - Active 27 Mar 2027
    Punta Cana: Tasting the Tides - Rum, Sail and Swim | 4 hrs to full day options
    Sailing in Bávaro · 12 guests

    Punta Cana: Tasting the Tides - Rum, Sail and Swim | 4 hrs to full day options

    New
    Snoozed - Active 03 Jul 2026
    TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter
    Sailing in Wickhams Cay 1 · 20 guests

    TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter

    New
    Snoozed - Active 07 May 2026

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