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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,320 Reviews)

    Page 17 of 19 • 434 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    All-inclusive Crewed Charter on 40ft Nautitech Sailing Catamaran in San Blas
    Sailing in Guna Yala Comarca · 7 guests

    All-inclusive Crewed Charter on 40ft Nautitech Sailing Catamaran in San Blas

    New
    $1,000/night
    Catamaran Charter In San Blas Panama
    Sailing in Guna Yala Comarca · 10 guests

    Catamaran Charter In San Blas Panama

    New
    $1,269/night
    Sail aboard our wonderful Jeanneau Sun Odyssey Sailboat and discover San Blas
    Sailing in Guna Yala Comarca · 12 guests

    Sail aboard our wonderful Jeanneau Sun Odyssey Sailboat and discover San Blas

    New
    $114/hour
    Nautitech 40 in San Blas Islands
    Sailing in Panama City · 7 guests

    Nautitech 40 in San Blas Islands

    New
    $1,550/night
    Lagoon 450 - Catamaran sail rental in Le Marin - Martinique
    Sailing in Le Marin · 12 guests

    Lagoon 450 - Catamaran sail rental in Le Marin - Martinique

    New
    $857/day
    2021 Lagoon 46 Sailing Catamaran Based in Saint Martin / Saint Barthélémy
    Sailing in Saint Martin · 12 guests

    2021 Lagoon 46 Sailing Catamaran Based in Saint Martin / Saint Barthélémy

    New
    $2,884/day
    Yacht charter in San Blas Islands |Alubat — Ovni 435 (2003) Sailboat
    Sailing in Guna Yala Comarca · 2 guests

    Yacht charter in San Blas Islands |Alubat — Ovni 435 (2003) Sailboat

    New
    $475/day
    Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports
    Powerboats in Fajardo · 6 guests

    Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports

    New
    $650/day
    Instant Book
    Amazing new power catamaran for Coiba's amazing Pacific island paradise
    Powerboats in Boca Chica · 8 guests

    Amazing new power catamaran for Coiba's amazing Pacific island paradise

    New
    $3,150+/night
    7 Day Cruise Aboard 47ft Cruising Catamaran in Sainte-Anne, Guadeloupe
    Sailing in Sainte-Anne · 8 guests

    7 Day Cruise Aboard 47ft Cruising Catamaran in Sainte-Anne, Guadeloupe

    New
    $111/day
    Helia 44 Catamaran: Your Gateway to Adventure and Comfort on the Open Seas
    Sailing in Oranjestad-West · 4 guests

    Helia 44 Catamaran: Your Gateway to Adventure and Comfort on the Open Seas

    New
    $1,584/night
    Step into a world of refined elegance aboard Fountaine Pajot Alegria 67
    Sailing in West End, Tortola · 8 guests

    Step into a world of refined elegance aboard Fountaine Pajot Alegria 67

    New
    $10,000/night
    Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI
    Sailing in Freshwater Pond · 6 guests

    Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI

    New
    $3,666/night
    28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN IN SAINT MARTIN
    Events in Saint Martin · 28 guests

    28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN IN SAINT MARTIN

    New
    $392/hour
    Captained Charter on 47ft
    Sailing in Coclé Province · 8 guests

    Captained Charter on 47ft

    5.0
    $2,000/day
    Sweden Yachts 38 Day Sail Fort Lauderdale, Si hablo Español
    Sailing in Aventura · 6 guests

    Sweden Yachts 38 Day Sail Fort Lauderdale, Si hablo Español

    New
    $130+/hour
    Private Catamaran Cruise in Punta Cana, Dominican Republic
    Sailing in Punta Cana · 34 guests

    Private Catamaran Cruise in Punta Cana, Dominican Republic

    New
    $273+/hour
    Your Private Yacht for the Day – Lagoon 46 Full-Day Charter
    Sailing in Fajardo · 6 guests

    Your Private Yacht for the Day – Lagoon 46 Full-Day Charter

    New
    $2,730/day
    Book your dream vacation on the Lagoon 51 Athena Blu
    Caribbean · 10 guests

    Book your dream vacation on the Lagoon 51 Athena Blu

    New
    $2,442/day
    Romantic Sunset Sailing in La Boquilla, Bolívar
    Sailing in La Boquilla · 4 guests

    Romantic Sunset Sailing in La Boquilla, Bolívar

    New
    $260/hour
    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
    2024 Valentine's Week in BVi 🍹🍸👙🤟
    Sailing in Fisher Estate · 8 guests

    2024 Valentine's Week in BVi 🍹🍸👙🤟

    New
    $92,160/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
    Beneteau 50 Sailing Yacht Charter in San Blas Islands
    Colón · 10 guests

    Beneteau 50 Sailing Yacht Charter in San Blas Islands

    New
    $1,400/day

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. FO

      Fernando

      Captained Charter on 47ft

      Was the best trip ever! Really recommend this trip and hope soon have a weekend trip in this catamaran

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