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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,354 Reviews)

    Page 15 of 19 • 439 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Events in Sandy Ground · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    New
    $409/hour
    THE ONE AND ONLY GRADY WHITE FREEDOM
    Fishing in Marathon · 8 guests

    THE ONE AND ONLY GRADY WHITE FREEDOM

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

    Caribbean Island-hopping

    New
    $15+/night
    Instant Book
    Rent The only Custom Pirate ship in Miami for a unique experience!
    Events in Miami · 85 guests

    Rent The only Custom Pirate ship in Miami for a unique experience!

    New
    $1,200/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 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
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Sailing in Saint Martin · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    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
    Leopard 46 Catamaran Sailing in Antigua & Barbuda
    Sailing in English Harbour · 6 guests

    Leopard 46 Catamaran Sailing in Antigua & Barbuda

    New
    $1,300/day
    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
    Limited Availability
    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale
    Powerboats in Fort Lauderdale · 12 guests

    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale

    New
    $330/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
    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
    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
    $251/day
    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
    Cruising Catamaran Charter in Falmouth
    Sailing in Falmouth · 40 guests

    Cruising Catamaran Charter in Falmouth

    New
    $1,250/hour
    Private Sailing Yacht to Coiba National Park – Overnight Option
    Sailing in Panamá · 6 guests

    Private Sailing Yacht to Coiba National Park – Overnight Option

    New
    $120/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
    Private Gourmet Sailing Charters on Elegant 50ft Catamaran
    Sailing in Gustavia · 10 guests

    Private Gourmet Sailing Charters on Elegant 50ft Catamaran

    New
    $595+/hour
    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
    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

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