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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,245 Reviews)

    Page 15 of 19 • 433 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Rent This Lux Sea Ray 33’ Miami Experience
    Events in Miami · 12 guests

    Rent This Lux Sea Ray 33’ Miami Experience

    New
    $130+/hour
    Bachelorette Catamaran in Punta Cana – All Inclusive (3 Hours or 6 Hours)
    Powerboats in El Cortecito · 100 guests

    Bachelorette Catamaran in Punta Cana – All Inclusive (3 Hours or 6 Hours)

    New
    $373+/hour
    Private Group Catamaran Sail Snorkeling Adventure in Ocho Rios, Jamaica
    Sailing in Ocho Rios · 60 guests

    Private Group Catamaran Sail Snorkeling Adventure in Ocho Rios, Jamaica

    New
    $1,080/hour
    Beach Catamaran and Windsurf Rental in Playa Blanca Beach
    Sailing in Rio Hato · 1 guest

    Beach Catamaran and Windsurf Rental in Playa Blanca Beach

    New
    $55/hour
    THE ONE AND ONLY GRADY WHITE FREEDOM
    Fishing in Marathon · 8 guests

    THE ONE AND ONLY GRADY WHITE FREEDOM

    New
    $150/hour
    Caribbean Island-hopping
    Sailing in Le Marin · 10 guests

    Caribbean Island-hopping

    New
    $15+/night
    Instant Book
    It's a Water Planet, Sail it - Beneteau 41S5 Sailboat
    Sailing in Miami · 6 guests

    It's a Water Planet, Sail it - Beneteau 41S5 Sailboat

    New
    $200/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
    $350/hour
    Leopard 46 Catamaran Sailing in Antigua & Barbuda
    Sailing in English Harbour · 6 guests

    Leopard 46 Catamaran Sailing in Antigua & Barbuda

    New
    $1,300/day
    Welcome aboard a stunning 2022 Bali 42 Cruising Catamaran
    Sailing in John's Hole · 8 guests

    Welcome aboard a stunning 2022 Bali 42 Cruising Catamaran

    New
    $550/hour
    Nautitech 43 Cruising Catamaran Rental in San Blas Islands, Panama
    Sailing in Guna Yala Comarca · 6 guests

    Nautitech 43 Cruising Catamaran Rental in San Blas Islands, Panama

    New
    $1,600/night
    Luxury 38' Fountaine Pajot Catamaran Tours & Charters in Cartagena, Colombia
    Sailing in Cartagena · 16 guests

    Luxury 38' Fountaine Pajot Catamaran Tours & Charters in Cartagena, Colombia

    New
    $203/hour
    Limited Availability
    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
    46ft Fountaine Pajot for 25 people in Taboga ALL INCLUSIVE
    Sailing in Panama City · 25 guests

    46ft Fountaine Pajot for 25 people in Taboga ALL INCLUSIVE

    New
    $468/hour
    Cruising Catamaran Charter in Falmouth
    Sailing in Falmouth · 40 guests

    Cruising Catamaran Charter in Falmouth

    New
    $1,250/hour
    Your dreamed boat in the Caribbeans | 50ft Dufour Sailboat
    Sailing in Le Marin · 8 guests

    Your dreamed boat in the Caribbeans | 50ft Dufour Sailboat

    New
    $250/day
    Dufour 455 Grand Large - Sloop sail rental in Le Marin
    Sailing in Le Marin · 8 guests

    Dufour 455 Grand Large - Sloop sail rental in Le Marin

    New
    $516/day
    Punta Cana’s Ultimate Ocean Powerhouse - Luxury Snorkel & Natural Pool Adventure
    Events in Bávaro · 70 guests

    Punta Cana’s Ultimate Ocean Powerhouse - Luxury Snorkel & Natural Pool Adventure

    New
    $325/hour
    Boat Tours in Panama
    Sailing in Panama City · 70 guests

    Boat Tours in Panama

    1.0
    $125/day
    Private Sunset Cruise With Dinner Ocho Rios, Jamaica
    Events in Ocho Rios · 30 guests

    Private Sunset Cruise With Dinner Ocho Rios, Jamaica

    New
    $1,400/hour
    VIP Private Yacht Negril Jamaica | Azimut 54 Flybridge
    Events in Negril · 15 guests

    VIP Private Yacht Negril Jamaica | Azimut 54 Flybridge

    New
    $1,150/hour
    Private Luxury Yacht Experience in Montego Bay
    Events in Montego Bay · 12 guests

    Private Luxury Yacht Experience in Montego Bay

    New
    $450/hour
    Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas
    Sailing in Key West · 12 guests

    Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas

    New
    $560+/hour
    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

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