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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,245 Reviews)

    Page 14 of 19 • 433 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    ''Valentine'' Sea Ray SDX Series Deck Boat Rental in Fort Myers, Florida
    Powerboats in Fort Myers · 12 guests

    ''Valentine'' Sea Ray SDX Series Deck Boat Rental in Fort Myers, Florida

    New
    $535/hour
    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
    $233/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
    $233/day
    Unforgettable Crewed Charters on 42' Seawind 1260, Grenadines
    Sailing in St. George · 6 guests

    Unforgettable Crewed Charters on 42' Seawind 1260, Grenadines

    New
    $1,200/day
    Beneteau Oceanis 41 for sailing adventures in San Blas Islands
    Sailing in Guna Yala Comarca · 3 guests

    Beneteau Oceanis 41 for sailing adventures in San Blas Islands

    New
    $185/day
    🏆Best Boat 2025🏆 Private Boat 3H with Unlimited drinks and Sand-bar in DR
    Events in Bávaro · 60 guests

    🏆Best Boat 2025🏆 Private Boat 3H with Unlimited drinks and Sand-bar in DR

    New
    $184+/hour
    Instant Book
    Performance Sailing Catamaran Adventure
    Sailing in Saint Barthélemy · 6 guests

    Performance Sailing Catamaran Adventure

    New
    $175/hour
    Bahamas Sunset Cruise
    Powerboats in Nassau · 8 guests

    Bahamas Sunset Cruise

    New
    $350/hour
    Luxury Sailboat in Panama for Pearl Islands or Taboga
    Sailing in Panama City · 20 guests

    Luxury Sailboat in Panama for Pearl Islands or Taboga

    New
    $600/hour
    Luxury Lagoon 620 Essence Sailing Catamaran in The Bahamas
    Sailing in Nassau · 25 guests

    Luxury Lagoon 620 Essence Sailing Catamaran in The Bahamas

    New
    $1,225/hour
    Lagoon 46 Luxury Catamaran with AC price include 2 guests
    Sailing in Guna Yala Comarca · 8 guests

    Lagoon 46 Luxury Catamaran with AC price include 2 guests

    New
    $2,600/day
    Charter The Arusun 65ft catamaran
    Sailing in Oranjestad-West · 20 guests

    Charter The Arusun 65ft catamaran

    New
    $700/hour
    "Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West
    Sailing in Key West · 6 guests

    "Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West

    New
    $351/hour
    "The Cats Meow" Custom Cats Catamaran
    Sailing in Sunny Isles Beach · 12 guests

    "The Cats Meow" Custom Cats Catamaran

    New
    $591/hour
    Half Day Sailing Cruise Catamaran In Punta cana
    Powerboats in Bávaro · 18 guests

    Half Day Sailing Cruise Catamaran In Punta cana

    New
    $1,300/day
    Don't Worry 45 - Luxury Private Charter - St Maarten or Anguilla
    Caribbean · 16 guests

    Don't Worry 45 - Luxury Private Charter - St Maarten or Anguilla

    New
    $2,350/day
    55ft Party Catamaran for rent in Ft. Lauderdale
    Sailing in Fort Lauderdale · 49 guests

    55ft Party Catamaran for rent in Ft. Lauderdale

    New
    $1,200+/hour
    Private 65ft Catamaran for Charter Trips in Montego Bay
    Sailing in Montego Bay · 40 guests

    Private 65ft Catamaran for Charter Trips in Montego Bay

    New
    $1,365/hour
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Events in Sandy Ground · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    New
    $407/hour
    Sailing Catamaran Leopard 46 in St. Vincent an Grenadines
    Sailing in St. George · 6 guests

    Sailing Catamaran Leopard 46 in St. Vincent an Grenadines

    New
    $150/hour
    Mojito 44ft Catamaran - Luxury Private Charter - St Maarten or Anguilla
    Caribbean · 16 guests

    Mojito 44ft Catamaran - Luxury Private Charter - St Maarten or Anguilla

    New
    $2,100/day
    38' Beneteau Sailing/Diving The Carribbean Sea
    Sailing in Saint Martin · 12 guests

    38' Beneteau Sailing/Diving The Carribbean Sea

    New
    $640/day
    Rent The only Custom Pirate ship in Miami for a unique experience!
    Events in Miami · 85 guests

    Rent The only Custom Pirate ship in Miami for a unique experience!

    New
    $1,200/hour
    Bachelorette Catamaran in Punta Cana – All Inclusive (3 Hours or 6 Hours)
    Powerboats in El Cortecito · 100 guests

    Bachelorette Catamaran in Punta Cana – All Inclusive (3 Hours or 6 Hours)

    New
    $373+/hour

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