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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,344 Reviews)

    Page 13 of 18 • 431 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private Sunset Cruise in St. Lucia on Beneteau Oceanis 440 Yacht
    Sailing in Gros Islet · 10 guests

    Private Sunset Cruise in St. Lucia on Beneteau Oceanis 440 Yacht

    New
    $175/hour
    Mega Catamaran Charter in Ocho Rios
    Sailing in Ocho Rios · 120 guests

    Mega Catamaran Charter in Ocho Rios

    New
    $2,300/hour
    Party Catamaran Rental🎉Best 2021-2022 Awards in Punta Cana, Dominican Republic
    Powerboats in Macao · 80 guests

    Party Catamaran Rental🎉Best 2021-2022 Awards in Punta Cana, Dominican Republic

    New
    Superowner
    Best of 2026
    $275/hour
    Deal of the Week! Leopard 47 Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 35 guests

    Deal of the Week! Leopard 47 Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $771+/hour
    Instant Book
    Leopard 51' Power Catamaran from and around Anguilla
    Powerboats in Sandy Ground · 18 guests

    Leopard 51' Power Catamaran from and around Anguilla

    New
    $3,499/day
    Private Catamaran Tour in Punta Cana: Party Boat+Snorkeling
    Sailing in Bávaro · 60 guests

    Private Catamaran Tour in Punta Cana: Party Boat+Snorkeling

    New
    $180+/hour
    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
    $452/hour
    Instant Book
    Premium Catamaran Experience Around St Martin - Vogue
    Powerboats in Saint Martin · 12 guests

    Premium Catamaran Experience Around St Martin - Vogue

    New
    $2,951/day
    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
    Private overnight Charter on a Luxurious Fountaine Pajot 47 up to 8 guests
    Sailing in Nassau · 9 guests

    Private overnight Charter on a Luxurious Fountaine Pajot 47 up to 8 guests

    New
    $3,715+/night
    Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests
    Sailing in Key West · 6 guests

    Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests

    New
    $150/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
    74ft Sunreef Sailing Catamaran In The Bahamas
    Sailing in Black Point · 13 guests

    74ft Sunreef Sailing Catamaran In The Bahamas

    New
    $1,690/hour
    Charter the Cruising Monohull in Las Terrenas, Samana
    Sailing in Las Terrenas · 10 guests

    Charter the Cruising Monohull in Las Terrenas, Samana

    New
    $1,586/day
    All-inclusive Luxury Shared Charter - Power Cat - St Martin
    Caribbean · 10 guests

    All-inclusive Luxury Shared Charter - Power Cat - St Martin

    New
    $419/day
    Limited Availability
    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale
    Powerboats in Fort Lauderdale · 12 guests

    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale

    New
    $330/hour
    Massive Luxury 51ft Lagoon Catamaran In Fort Lauderdale
    Sailing in Fort Lauderdale · 12 guests

    Massive Luxury 51ft Lagoon Catamaran In Fort Lauderdale

    New
    $375/hour
    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
    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
    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
    Luxurious 72' Azimut: Tender and Water Toys Serving Around South Florida
    Events in North Bay Village · 12 guests

    Luxurious 72' Azimut: Tender and Water Toys Serving Around South Florida

    New
    $950+/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

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