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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,125 Reviews)

    Page 11 of 17 • 397 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    The Gallivanders Ultimate Sailing Adventure
    Sailing in Nassau · 12 guests

    The Gallivanders Ultimate Sailing Adventure

    New
    $397/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 2025
    $80/hour
    Isla Saona Private Yacht – Luxury Full-Day Tour
    Powerboats in Bávaro · 20 guests

    Isla Saona Private Yacht – Luxury Full-Day Tour

    New
    $1,820/day
    Spectacular 51-foot Lagoon Catamaran In Cartagena
    Sailing in Cartagena · 40 guests

    Spectacular 51-foot Lagoon Catamaran In Cartagena

    New
    Superowner
    Best of 2025
    $450/hour
    AMAZING 65 FOOT CATAMARAN IN CARTAGENA COLOMBIA
    Events in Cartagena · 56 guests

    AMAZING 65 FOOT CATAMARAN IN CARTAGENA COLOMBIA

    New
    $3,000/day
    Private Yacht Cruise
    Events in Nassau · 12 guests

    Private Yacht Cruise

    New
    $850/hour
    Private Charter Leopard 43 Catamaran in St Lucia
    Sailing in Rodney Bay · 20 guests

    Private Charter Leopard 43 Catamaran in St Lucia

    New
    $1,500/day
    😍SPICE RENTED HER CATAMARANS🛥️💃🏾💕🔥VIP Sailing Catamaran
    Sailing in Punta Cana · 25 guests

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

    New
    $113/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 2025
    $275/hour
    40ft Catamaran Lagoon, Cartagena, Colombia
    Sailing in Cartagena · 23 guests

    40ft Catamaran Lagoon, Cartagena, Colombia

    New
    $185+/hour
    Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music
    Powerboats in Bávaro · 70 guests

    Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music

    New
    $255/hour
    Snorkeling in Turks and Caicos Islands
    Tours in The Bight Settlement · 6 guests

    Snorkeling in Turks and Caicos Islands

    New
    $448/hour
    Catamaran Lagoon 62’ 2019 for a week in Bahamas. Nassau, Exumas and more
    Sailing in Nassau · 8 guests

    Catamaran Lagoon 62’ 2019 for a week in Bahamas. Nassau, Exumas and more

    New
    Superowner
    $1,320/hour
    2021 HOBIE CAT Sailing and Snorkeling trip 3 hours 2 persons with instructor
    Sailing in Collectivity of Saint Martin · 2 guests

    2021 HOBIE CAT Sailing and Snorkeling trip 3 hours 2 persons with instructor

    New
    $100/hour
    Deal of the Week! Leopard 43 Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 25 guests

    Deal of the Week! Leopard 43 Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    $207/hour
    Instant Book
    Curacao Private Romantic Sunset Tour 2p
    Sailing in Jan Thiel · 2 guests

    Curacao Private Romantic Sunset Tour 2p

    New
    $250/hour
    Charter a Cruising Monohull in Les Trois-Îlets, Martinique
    Sailing in Les Trois-Îlets · 8 guests

    Charter a Cruising Monohull in Les Trois-Îlets, Martinique

    New
    $939/day
    Ultra luxe Full Day Yacht Charter to Negril!
    Events in Montego Bay · 10 guests

    Ultra luxe Full Day Yacht Charter to Negril!

    New
    Superowner
    Best of 2025
    $1,625/hour
    Lagoon 43 Sailing Catamaran in El Porvenir, Panama
    Sailing in Guna Yala Comarca · 8 guests

    Lagoon 43 Sailing Catamaran in El Porvenir, Panama

    New
    $1,560/night
    Boat tour Sailboat 40 feet Saint Martin
    Sailing in Marigot · 6 guests

    Boat tour Sailboat 40 feet Saint Martin

    New
    $140/hour
    🏆Best Boat 2025🏆 Private Boat 3H with Unlimited drinks and Sand-bar in DR
    Events in Bávaro · 60 guests

    🏆Best Boat 2025🏆 Private Boat 3H with Unlimited drinks and Sand-bar in DR

    New
    $184+/hour
    Luxury Private Charter - Don't Worry 45ft - Around St Maarten or Anguilla
    Sailing in Upper Prince's Quarter · 16 guests

    Luxury Private Charter - Don't Worry 45ft - Around St Maarten or Anguilla

    New
    $2,200/day
    Charter 36' Gulet In Santa Marta, Colombia
    Sailing in Comuna 2 · 8 guests

    Charter 36' Gulet In Santa Marta, Colombia

    New
    $114+/hour

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