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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,354 Reviews)

    Page 14 of 19 • 440 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Performance Sailing Catamaran Adventure
    Sailing in Saint Barthélemy · 6 guests

    Performance Sailing Catamaran Adventure

    New
    $175/hour
    52' Catamaran - Sunset Cruise Private Charter at Simpson Bay
    Caribbean · 32 guests

    52' Catamaran - Sunset Cruise Private Charter at Simpson Bay

    New
    $550/day
    🏆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
    ''Valentine'' Sea Ray SDX Series Deck Boat Rental in Fort Myers, Florida
    Powerboats in Fort Myers · 12 guests

    ''Valentine'' Sea Ray SDX Series Deck Boat Rental in Fort Myers, Florida

    New
    $535/hour
    Limited Availability
    Massive Luxury 51ft Lagoon Catamaran In Fort Lauderdale
    Sailing in Fort Lauderdale · 12 guests

    Massive Luxury 51ft Lagoon Catamaran In Fort Lauderdale

    New
    $375/hour
    Relaxing Catamaran Charters in Punta Cana
    Sailing in Bávaro · 16 guests

    Relaxing Catamaran Charters in Punta Cana

    New
    $69/hour
    65ft Pershing Yacht for Luxury Charter and Miami Fun!
    Events in Miami · 13 guests

    65ft Pershing Yacht for Luxury Charter and Miami Fun!

    New
    $450/hour
    Lagoon 46 Luxury Catamaran with AC price include 2 guests
    Sailing in Guna Yala Comarca · 8 guests

    Lagoon 46 Luxury Catamaran with AC price include 2 guests

    New
    $2,750/day
    Bahamas Sunset Cruise
    Powerboats in Nassau · 8 guests

    Bahamas Sunset Cruise

    New
    $350/hour
    Luxury Sailboat in Panama for Pearl Islands or Taboga
    Sailing in Panama City · 20 guests

    Luxury Sailboat in Panama for Pearl Islands or Taboga

    New
    $600/hour
    Charter The Arusun 65ft catamaran
    Sailing in Oranjestad-West · 20 guests

    Charter The Arusun 65ft catamaran

    New
    $700/hour
    "Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West
    Sailing in Key West · 6 guests

    "Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West

    New
    $351/hour
    "The Cats Meow" Custom Cats Catamaran
    Sailing in Sunny Isles Beach · 12 guests

    "The Cats Meow" Custom Cats Catamaran

    New
    $591/hour
    38' Beneteau Sailing/Diving The Carribbean Sea
    Sailing in Saint Martin · 12 guests

    38' Beneteau Sailing/Diving The Carribbean Sea

    New
    $642/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
    Don't Worry 45 - Luxury Private Charter - St Maarten or Anguilla
    Caribbean · 16 guests

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

    New
    $2,350/day
    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
    55ft Party Catamaran for rent in Ft. Lauderdale
    Sailing in Fort Lauderdale · 49 guests

    55ft Party Catamaran for rent in Ft. Lauderdale

    New
    $1,200+/hour
    Private 65ft Catamaran for Charter Trips in Montego Bay
    Sailing in Montego Bay · 40 guests

    Private 65ft Catamaran for Charter Trips in Montego Bay

    New
    $1,365/hour
    Mojito 44ft Catamaran - Luxury Private Charter - St Maarten or Anguilla
    Caribbean · 16 guests

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

    New
    $2,100/day
    Rent This Lux Sea Ray 33’ Miami Experience
    Events in Miami · 12 guests

    Rent This Lux Sea Ray 33’ Miami Experience

    New
    $130+/hour
    Boat tour Sailboat 40 feet Saint Martin
    Sailing in Saint Martin · 6 guests

    Boat tour Sailboat 40 feet Saint Martin

    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
    28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
    Sailing in Saint Martin · 28 guests

    28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

    New
    $397/hour

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