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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,086 Reviews)

    Page 12 of 17 • 391 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private boat rental La Morronga Bravo 41' luxury finishes
    Powerboats in Cartagena · 15 guests

    Private boat rental La Morronga Bravo 41' luxury finishes

    New
    $842/day
    Cruising Catamaran Rental in St Kitts-Nevis
    Sailing in Basseterre · 40 guests

    Cruising Catamaran Rental in St Kitts-Nevis

    New
    $1,045/day
    Charter 47ft Sailing Yacht In Cartagena, Colombia
    Sailing in El Centro · 12 guests

    Charter 47ft Sailing Yacht In Cartagena, Colombia

    New
    $94+/hour
    Private Catamaran for Large Groups – Snorkeling, BBQ & Open Bar in Punta Cana
    Powerboats in Bávaro · 120 guests

    Private Catamaran for Large Groups – Snorkeling, BBQ & Open Bar in Punta Cana

    New
    $208+/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
    Bahamas Sunset Cruise
    Powerboats in Nassau · 8 guests

    Bahamas Sunset Cruise

    New
    $350/hour
    Private Catamaran Charter - Knot at Work 40 - Discover the beautiful St Maarten
    Sailing in Upper Prince's Quarter · 12 guests

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

    New
    $350/hour
    Charter The Arusun 65ft catamaran
    Sailing in Oranjestad-West · 20 guests

    Charter The Arusun 65ft catamaran

    New
    $700/hour
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Sailing in Marigot · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    New
    $352/hour
    ''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
    50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay
    Sailing in Nassau · 12 guests

    50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

    New
    $1,375/hour
    Private Catamaran to Saona Island – Full-Day All-Inclusive Paradise!
    Powerboats in Bávaro · 50 guests

    Private Catamaran to Saona Island – Full-Day All-Inclusive Paradise!

    New
    $1,480/day
    Private Group Catamaran Sail Snorkeling Adventure in Ocho Rios, Jamaica
    Sailing in Ocho Rios · 60 guests

    Private Group Catamaran Sail Snorkeling Adventure in Ocho Rios, Jamaica

    New
    $1,080/hour
    Charter this 45ft Sailing Yacht in Cartagena, Bolívar
    Sailing in Cartagena · 12 guests

    Charter this 45ft Sailing Yacht in Cartagena, Bolívar

    New
    $176+/hour
    44' Catamaran Charter in Panama, Panama
    Sailing in Panama City · 12 guests

    44' Catamaran Charter in Panama, Panama

    New
    $850/hour
    Sailing yacht Catamaran (Cat 42 Ps/Ft), Lagoon 420, Dominican Republic, Samana
    Sailing in El Centro · 20 guests

    Sailing yacht Catamaran (Cat 42 Ps/Ft), Lagoon 420, Dominican Republic, Samana

    New
    $145+/hour
    Bahamas Adventure : Boat + Captain + Chef + Meals + Excursions + Toys + Fuel
    Sailing in George Town · 6 guests

    Bahamas Adventure : Boat + Captain + Chef + Meals + Excursions + Toys + Fuel

    New
    $200+/hour
    COME AND SAIL ON THIS BEAUTIFUL ELAN MONOHULL BUILT FOR PERFORMANCE AND COMFORT
    Sailing in Pointe-a-Pitre · 8 guests

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

    New
    $252/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
    Lagoon 42 Sailing Catamaran
    Sailing in Guna Yala Comarca · 8 guests

    Lagoon 42 Sailing Catamaran

    New
    $1,320/night
    Sailboat Gemini Beneteau 50ps, Panama, San Blas
    Sailing in Panama City · 8 guests

    Sailboat Gemini Beneteau 50ps, Panama, San Blas

    New
    $85/hour
    Charter this 55' Sailboat in Santa Marta, Colombia
    Sailing in Comuna 2 · 22 guests

    Charter this 55' Sailboat in Santa Marta, Colombia

    New
    $114+/hour
    Sailing in the Caribbean St. Martin
    Sailing in Marigot · 10 guests

    Sailing in the Caribbean St. Martin

    New
    $1,174/day

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