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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,379 Reviews)

    Page 13 of 19 • 439 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Lagoon 46 Catamaran - Luxury Private Charter in St Maarten or Anguilla
    Caribbean · 16 guests

    Lagoon 46 Catamaran - Luxury Private Charter in St Maarten or Anguilla

    New
    $294+/hour
    45' Large Lagoon Catamaran | Private Luxury Charter | Fort Lauderdale
    Sailing in Fort Lauderdale · 12 guests

    45' Large Lagoon Catamaran | Private Luxury Charter | Fort Lauderdale

    New
    $350/hour
    Axe 1 Center Console Boat Rental in Montego Bay, Jamaica
    Events in Montego Bay · 8 guests

    Axe 1 Center Console Boat Rental in Montego Bay, Jamaica

    New
    $750/hour
    💥 43' Leopard + 1 FREE Extra Hour in Cartagena, Colombia 💥
    Powerboats in Cartagena · 25 guests

    💥 43' Leopard + 1 FREE Extra Hour in Cartagena, Colombia 💥

    New
    Superowner
    Best of 2026
    $709+/hour
    Instant Book
    Luxury Party Boat Catamaran in Punta Cana
    Events in Punta Cana · 150 guests

    Luxury Party Boat Catamaran in Punta Cana

    New
    Superowner
    Best of 2026
    $80/hour
    💥 40' Lagoon + 1 FREE Extra Hour in Cartagena, Colombia 💥
    Powerboats in Cartagena · 18 guests

    💥 40' Lagoon + 1 FREE Extra Hour in Cartagena, Colombia 💥

    New
    Superowner
    Best of 2026
    $471+/hour
    Instant Book
    Spectacular 51-foot Lagoon Catamaran In Cartagena
    Sailing in Cartagena · 40 guests

    Spectacular 51-foot Lagoon Catamaran In Cartagena

    New
    Superowner
    $430/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
    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
    $172/hour
    Private Saona Island Cruise (All-Inclusive)
    Sailing in Los Melones · 12 guests

    Private Saona Island Cruise (All-Inclusive)

    New
    $169/hour
    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
    💥 44' Lagoon + 1 FREE Extra Hour in Cartagena, Colombia 💥
    Powerboats in Cartagena · 23 guests

    💥 44' Lagoon + 1 FREE Extra Hour in Cartagena, Colombia 💥

    New
    Superowner
    Best of 2026
    $452/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
    $3,434/day
    💥 47' Leopard + 1 FREE Extra Hour in Cartagena, Colombia 💥
    Powerboats in Cartagena · 35 guests

    💥 47' Leopard + 1 FREE Extra Hour in Cartagena, Colombia 💥

    New
    Superowner
    Best of 2026
    $771+/hour
    Instant Book
    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
    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
    All-inclusive Luxury Shared Charter - Power Cat - St Martin
    Caribbean · 10 guests

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

    New
    $411/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
    $229/day
    74ft Sunreef Sailing Catamaran In The Bahamas
    Sailing in Black Point · 13 guests

    74ft Sunreef Sailing Catamaran In The Bahamas

    New
    $1,690/hour
    Private Boat Rental La Morronga Bravo 41' Luxury Finishes
    Powerboats in Cartagena · 15 guests

    Private Boat Rental La Morronga Bravo 41' Luxury Finishes

    New
    $965/day
    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
    Premium Catamaran Experience Around St Martin - Vogue
    Powerboats in Saint Martin · 12 guests

    Premium Catamaran Experience Around St Martin - Vogue

    New
    $2,896/day

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