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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,354 Reviews)

    Page 13 of 19 • 440 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Deal of the Week! Lagoon 44Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 23 guests

    Deal of the Week! Lagoon 44Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $460/hour
    Instant Book
    Mega Catamaran Charter in Ocho Rios
    Sailing in Ocho Rios · 120 guests

    Mega Catamaran Charter in Ocho Rios

    New
    $2,300/hour
    All inclusive Bali 4.4 Luxury Catamaran Charter
    Sailing in Nassau · 10 guests

    All inclusive Bali 4.4 Luxury Catamaran Charter

    New
    $720/hour
    Leopard 51 Power Catamaran In Anguilla
    Powerboats in Sandy Ground · 12 guests

    Leopard 51 Power Catamaran In Anguilla

    New
    $1,752/hour
    Premium Catamaran Experience - Vogue Sint Maarten
    Powerboats in Saint Martin · 12 guests

    Premium Catamaran Experience - Vogue Sint Maarten

    New
    $1,168/hour
    Leopard 51 Power Catamaran In Sint Maarten/Anguilla-Includes Seabob, jet board
    Powerboats in Saint Martin · 12 guests

    Leopard 51 Power Catamaran In Sint Maarten/Anguilla-Includes Seabob, jet board

    New
    $1,285/hour
    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo
    Sailing in Fajardo · 12 guests

    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo

    New
    $450/hour
    Deal of the Week! Leopard 51 Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 35 guests

    Deal of the Week! Leopard 51 Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $779/hour
    Instant Book
    Catamaran Lagoon 450 from Marina Puerto del Rey in Fajardo
    Sailing in Fajardo · 12 guests

    Catamaran Lagoon 450 from Marina Puerto del Rey in Fajardo

    New
    $699/hour
    MARTINA Powerboat 40FT in Cartagena de Indias
    Powerboats in Cartagena · 35 guests

    MARTINA Powerboat 40FT in Cartagena de Indias

    New
    $998/day
    48ft Sailing Catamaran | Bubble
    Sailing in Miami · 12 guests

    48ft Sailing Catamaran | Bubble

    New
    $423+/hour
    Private Catamaran Sail & Snorkel in Negril – Open Bar, Snacks & Music
    Sailing in Negril · 60 guests

    Private Catamaran Sail & Snorkel in Negril – Open Bar, Snacks & Music

    New
    $930+/hour
    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo
    Sailing in Fajardo · 6 guests

    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo

    New
    $583/hour
    Private Group Catamaran Cruise in Ocho Rios
    Sailing in Ocho Rios · 40 guests

    Private Group Catamaran Cruise in Ocho Rios

    New
    $1,266/hour
    Ultra luxe Full Day Yacht Charter to Negril!
    Events in Montego Bay · 10 guests

    Ultra luxe Full Day Yacht Charter to Negril!

    New
    Superowner
    $1,625/hour
    BRAND NEW 2025 Lagoon 43 Luxury Catamaran with AC price include 2 guests
    Sailing in Guna Yala Comarca · 8 guests

    BRAND NEW 2025 Lagoon 43 Luxury Catamaran with AC price include 2 guests

    New
    $2,600/night
    Exclusive Getaway with Sea Ray 180 Bow Rider Sport to Cuna de Los Nidos!
    Powerboats in Punta Cana · 80 guests

    Exclusive Getaway with Sea Ray 180 Bow Rider Sport to Cuna de Los Nidos!

    New
    Superowner
    Best of 2026
    $15/hour
    Charter Your Pirate Ship In The Bahamas
    Events in Nassau · 300 guests

    Charter Your Pirate Ship In The Bahamas

    New
    Superowner
    $2,500/hour
    45ft Lagoon | Somewhere
    Sailing in Key West · 12 guests

    45ft Lagoon | Somewhere

    New
    $740+/hour
    Captained Luxury Lagoon 560 Catamaran In The Bahamas
    Sailing in Nassau · 25 guests

    Captained Luxury Lagoon 560 Catamaran In The Bahamas

    New
    $1,050/hour
    Fountaine Pajot Belize 43 Sailing Catamaran in Cartagena, Bolívar
    Sailing in Cartagena · 30 guests

    Fountaine Pajot Belize 43 Sailing Catamaran in Cartagena, Bolívar

    New
    Superowner
    $313/hour
    Saona Island: Private Yacht Tour with Snorkel in DR
    Events in Los Melones · 15 guests

    Saona Island: Private Yacht Tour with Snorkel in DR

    New
    $320/hour
    Sailing Classic Yacht 1980 Swan 47 in Caribbean Waters
    Sailing in Saint George's · 7 guests

    Sailing Classic Yacht 1980 Swan 47 in Caribbean Waters

    New
    $60/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

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