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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,085 Reviews)

    Page 13 of 17 • 391 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Salinas 48 Cruising Catamaran Charter in San Blas Islands, Panama
    Sailing in Guna Yala Comarca · 8 guests

    Salinas 48 Cruising Catamaran Charter in San Blas Islands, Panama

    New
    $3,410/night
    Cruising Catamaran Charter in Falmouth
    Sailing in Falmouth · 40 guests

    Cruising Catamaran Charter in Falmouth

    New
    $1,250/hour
    Sailing Catamaran Leopard 46 in St. Vincent an Grenadines
    Sailing in St. George · 6 guests

    Sailing Catamaran Leopard 46 in St. Vincent an Grenadines

    New
    $150/hour
    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
    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
    $600+/hour
    Instant Book
    Luxury Private Charter - Mojito 44ft Catamaran - St Maarten or Anguilla
    Sailing in Upper Prince's Quarter · 16 guests

    Luxury Private Charter - Mojito 44ft Catamaran - St Maarten or Anguilla

    New
    $2,000/day
    Relaxing Catamaran Charters in Punta Cana
    Sailing in Bávaro · 16 guests

    Relaxing Catamaran Charters in Punta Cana

    New
    $69/hour
    Private Sunset Sail - South Coast of Puerto Rico
    Sailing in Salinas · 6 guests

    Private Sunset Sail - South Coast of Puerto Rico

    New
    $230/hour
    Charter 37' Cruising Monohull In Cartagena, Colombia
    Sailing in Cartagena · 8 guests

    Charter 37' Cruising Monohull In Cartagena, Colombia

    New
    $114+/hour
    45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands
    Sailing in St. Thomas · 12 guests

    45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands

    New
    $2,000/day
    Reggae Catamaran Negril Sail Snorkel and Sunset Tour
    Sailing in West End · 20 guests

    Reggae Catamaran Negril Sail Snorkel and Sunset Tour

    New
    $1,084/hour
    Palm Breeze - 55ft Party Catamaran for rent in Ft. Lauderdale
    Sailing in Fort Lauderdale · 49 guests

    Palm Breeze - 55ft Party Catamaran for rent in Ft. Lauderdale

    New
    $1,200+/hour
    Historic / Educational Private Day Sail - South Coast of Puerto Rico
    Sailing in Salinas · 6 guests

    Historic / Educational Private Day Sail - South Coast of Puerto Rico

    New
    $1,050/day
    Half Day Sailing Cruise Catamaran In Punta cana
    Powerboats in Bávaro · 18 guests

    Half Day Sailing Cruise Catamaran In Punta cana

    New
    $1,300/day
    Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos
    Sailing in Fajardo · 12 guests

    Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos

    New
    $575/hour
    65ft Lagoon Sailing Catamaran VIP Rental in Los Melones, Dominican Republic
    Sailing in Los Melones · 30 guests

    65ft Lagoon Sailing Catamaran VIP Rental in Los Melones, Dominican Republic

    New
    $80/day
    Private sailing and snorkeling charter for 2. A unique and custom tailored trip
    Sailing in Guna Yala Comarca · 2 guests

    Private sailing and snorkeling charter for 2. A unique and custom tailored trip

    New
    $185/night
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Events in Sandy Ground · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    New
    $413/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
    Lagoon 42 Cruising Catamaran for rental
    Sailing in Le Marin · 12 guests

    Lagoon 42 Cruising Catamaran for rental

    New
    $159/hour
    Instant Book
    Private French Built 40'Catamaran in San Blas – All Meals & Skipper Included
    Sailing in Guna Yala Comarca · 6 guests

    Private French Built 40'Catamaran in San Blas – All Meals & Skipper Included

    New
    $1,000/night
    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
    Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. John pick up
    Sailing in Cruz Bay · 6 guests

    Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. John pick up

    New
    $350/hour
    Lagoon 46 Premium Sailing Catamaran in Le Marin, Martinique
    Sailing in Le Marin · 12 guests

    Lagoon 46 Premium Sailing Catamaran in Le Marin, Martinique

    New
    $1,164/day

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