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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (1,883 Reviews)

    Page 13 of 16 • 380 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    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
    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
    Island Dreams on a Luxury Contender 40' Center Console
    Powerboats in Fajardo · 8 guests

    Island Dreams on a Luxury Contender 40' Center Console

    New
    $225+/hour
    Sailing in the Caribbean St. Martin
    Sailing in Marigot · 10 guests

    Sailing in the Caribbean St. Martin

    New
    $1,167/day
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Sailing in Marigot · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    New
    $350/hour
    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
    Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1
    Sailing in Fort Lauderdale · 4 guests

    Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1

    New
    $50/hour
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Events in Sandy Ground · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    New
    $408/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
    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
    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 42 Cruising Catamaran for rental
    Sailing in Le Marin · 12 guests

    Lagoon 42 Cruising Catamaran for rental

    New
    $158/hour
    Instant Book
    Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI
    Sailing in Freshwater Pond · 6 guests

    Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI

    New
    $3,666/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
    Luxury Catamaran Charter In Grenada and The Grenadines
    Sailing in Saint George's · 10 guests

    Luxury Catamaran Charter In Grenada and The Grenadines

    New
    $200/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
    $1,151/day
    60ft Sea Ray Power MegaYacht Rental in Cartagena, Bolívar
    Sailing in Cartagena · 16 guests

    60ft Sea Ray Power MegaYacht Rental in Cartagena, Bolívar

    New
    $3,350/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
    $517/day
    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
    Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. Thomas pick up
    Sailing in Charlotte Amalie · 6 guests

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

    New
    $350/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
    Sailing Lagoon 42 Premium (Crewed and Bareboat Charter Options!) in Le Marin
    Sailing in Le Marin · 12 guests

    Sailing Lagoon 42 Premium (Crewed and Bareboat Charter Options!) in Le Marin

    New
    $951/day

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