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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,255 Reviews)

    Page 14 of 18 • 416 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    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
    🏆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
    Instant Book
    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
    The Stars are Calling aboard Bali 5.4 Sailing Catamaran in British Virgin Island
    Sailing in West End, Tortola · 10 guests

    The Stars are Calling aboard Bali 5.4 Sailing Catamaran in British Virgin Island

    New
    $5,142/night
    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
    Sailing adventure in San blas
    Sailing in Guna Yala Comarca · 8 guests

    Sailing adventure in San blas

    New
    $550/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
    Leopard 51 Power Catamaran In Sint Maarten/Anguilla-Includes Seabob, jet board
    Powerboats in Saint Martin · 12 guests

    Leopard 51 Power Catamaran In Sint Maarten/Anguilla-Includes Seabob, jet board

    New
    $2,509/day
    55' Nisi Catamaran – Private Bahamas Day Charter- Gratuity and Tax included
    Powerboats in Nassau · 15 guests

    55' Nisi Catamaran – Private Bahamas Day Charter- Gratuity and Tax included

    New
    $1,385+/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
    Performance Sailing Catamaran Adventure
    Sailing in Saint Barthélemy · 6 guests

    Performance Sailing Catamaran Adventure

    New
    $171/hour
    Unforgettable Crewed Charters on 42' Seawind 1260, Grenadines
    Sailing in St. George · 6 guests

    Unforgettable Crewed Charters on 42' Seawind 1260, Grenadines

    New
    $1,200/day
    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
    Beneteau Oceanis 41 for sailing adventures in San Blas Islands
    Sailing in Guna Yala Comarca · 3 guests

    Beneteau Oceanis 41 for sailing adventures in San Blas Islands

    New
    $225/day
    Explore Grand-Case, Saint Martin Aboard 53ft Ocean Voyager Catamaran - 28 Guests
    Sailing in Saint Martin · 28 guests

    Explore Grand-Case, Saint Martin Aboard 53ft Ocean Voyager Catamaran - 28 Guests

    New
    $627/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
    42ft Orc San Blas Cruising Catamaran in Guna Yala Comarca
    Sailing in Guna Yala Comarca · 6 guests

    42ft Orc San Blas Cruising Catamaran in Guna Yala Comarca

    New
    $1,124+/day
    Boat tour Sailboat 40 feet Saint Martin
    Sailing in Saint Martin · 6 guests

    Boat tour Sailboat 40 feet Saint Martin

    New
    $130/hour
    Charter The Arusun 65ft catamaran
    Sailing in Oranjestad-West · 20 guests

    Charter The Arusun 65ft catamaran

    New
    $700/hour
    38' Beneteau Sailing/Diving The Carribbean Sea
    Sailing in Saint Martin · 12 guests

    38' Beneteau Sailing/Diving The Carribbean Sea

    New
    $627/day
    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
    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

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