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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,407 Reviews)

    Page 13 of 20 • 457 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎
    Events in Sosúa · 18 guests

    😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎

    New
    Superowner
    Best of 2026
    $75/hour
    Luxe 75ft Sailing Catamaran Serving Key West & Miami Florida
    Events in Key West · 12 guests

    Luxe 75ft Sailing Catamaran Serving Key West & Miami Florida

    New
    $14,750/night
    Charter The AKKA 68ft catamaran
    Sailing in Oranjestad-West · 15 guests

    Charter The AKKA 68ft catamaran

    New
    $700/hour
    Party Boat that can host 150 people in La Romana, Dominican Republic
    Events in La Romana · 150 guests

    Party Boat that can host 150 people in La Romana, Dominican Republic

    New
    Superowner
    Best of 2026
    $100/hour
    Fun Memories, Captain & Crew Included
    Sailing in Bávaro · 100 guests

    Fun Memories, Captain & Crew Included

    New
    Superowner
    Best of 2026
    $100/hour
    Punta Cana: Ultimate Private Yacht Party with Snorkeling
    Events in Bávaro · 10 guests

    Punta Cana: Ultimate Private Yacht Party with Snorkeling

    New
    $320+/hour
    Turks & Caicos Private Sunrise 27' Sea Ray Boat Charter
    Powerboats in The Bight Settlement · 10 guests

    Turks & Caicos Private Sunrise 27' Sea Ray Boat Charter

    New
    $525/hour
    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami
    Events in Miami · 13 guests

    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami

    New
    $250/hour
    😍SPICE RENTED HER CATAMARANS🛥️💃🏾💕🔥VIP Sailing Catamaran
    Sailing in Punta Cana · 25 guests

    😍SPICE RENTED HER CATAMARANS🛥️💃🏾💕🔥VIP Sailing Catamaran

    New
    $113/hour
    Catamaran Lagoon 62’ 2019 for a week in BVI
    Sailing in John's Hole · 8 guests

    Catamaran Lagoon 62’ 2019 for a week in BVI

    New
    Superowner
    $10,500/day
    💥 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
    $355+/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
    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
    💥 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
    $385+/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
    💥 51' Leopard + 1 FREE Extra Hour in Cartagena, Colombia 💥
    Powerboats in Cartagena · 35 guests

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

    New
    Superowner
    Best of 2026
    $422+/hour
    Instant Book
    💥 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
    $235+/hour
    Instant Book
    Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises
    Events in Miami · 14 guests

    Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises

    New
    $250/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
    $169/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
    $226/hour
    Instant Book
    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
    Leopard 51' Power Catamaran from and around Anguilla
    Powerboats in Sandy Ground · 18 guests

    Leopard 51' Power Catamaran from and around Anguilla

    New
    $3,371/day

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