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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,312 Reviews)

    Page 12 of 18 • 430 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Fun Memories, Captain & Crew Included
    Sailing in Bávaro · 100 guests

    Fun Memories, Captain & Crew Included

    New
    Superowner
    Best of 2026
    $100/hour
    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
    😎 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
    Private Lunch Tour Deluxe in Curacao
    Sailing in Jan Thiel · 6 guests

    Private Lunch Tour Deluxe in Curacao

    New
    $325/hour
    Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat
    Sailing in Montego Bay · 14 guests

    Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat

    New
    $250/hour
    Deal of the Day! Lagoon 40Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 18 guests

    Deal of the Day! Lagoon 40Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $435/hour
    Instant Book
    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
    All inclusive Bali 4.4 Luxury Catamaran Charter
    Sailing in Nassau · 10 guests

    All inclusive Bali 4.4 Luxury Catamaran Charter

    New
    $720/hour
    Private Saona Island Cruise (All-Inclusive)
    Sailing in Los Melones · 12 guests

    Private Saona Island Cruise (All-Inclusive)

    New
    $169/hour
    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!
    Sailing in Saint Martin · 20 guests

    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!

    New
    $2,880/day
    Cruising Catamaran Charter in Cabarete, Dominican Republic
    Sailing in Cabarete · 80 guests

    Cruising Catamaran Charter in Cabarete, Dominican Republic

    New
    Superowner
    Best of 2026
    $400/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
    All-inclusive Luxury Private Charter - Sailing Cat - St Martin/Anguilla/St Barts
    Sailing in Saint Martin · 6 guests

    All-inclusive Luxury Private Charter - Sailing Cat - St Martin/Anguilla/St Barts

    New
    $2,938/day
    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
    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
    $711/hour
    Instant Book
    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
    Mega Catamaran Charter in Ocho Rios
    Sailing in Ocho Rios · 120 guests

    Mega Catamaran Charter in Ocho Rios

    New
    $2,300/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
    $460/hour
    Instant Book
    Lux Catamaran Fountaine Pajot 40ft
    Sailing in Leeward Settlement · 10 guests

    Lux Catamaran Fountaine Pajot 40ft

    New
    $714+/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
    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
    48ft Sailing Catamaran | Bubble
    Sailing in Miami · 12 guests

    48ft Sailing Catamaran | Bubble

    New
    $423+/hour
    MARTINA Powerboat 40FT in Cartagena de Indias
    Powerboats in Cartagena · 35 guests

    MARTINA Powerboat 40FT in Cartagena de Indias

    New
    $998/day
    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

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