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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,354 Reviews)

    Page 12 of 19 • 439 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Punta Cana 60' Private Luxury Power Catamaran to Catalina Island
    Powerboats in Punta Cana · 65 guests

    Punta Cana 60' Private Luxury Power Catamaran to Catalina Island

    New
    $471/hour
    😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎
    Events in Sosúa · 18 guests

    😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎

    New
    Superowner
    Best of 2026
    $75/hour
    Private Lunch Tour Deluxe in Curacao
    Sailing in Santa Barbara Plantation · 6 guests

    Private Lunch Tour Deluxe in Curacao

    New
    $325/hour
    Knot at Work 40 - Private Catamaran Charter - Discover the beautiful St Maarten
    Caribbean · 12 guests

    Knot at Work 40 - Private Catamaran Charter - Discover the beautiful St Maarten

    New
    $1,850/day
    46ft Luxury Sailing Catamaran in Miami
    Sailing in Fort Lauderdale · 12 guests

    46ft Luxury Sailing Catamaran in Miami

    5.0
    $300/hour
    Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat
    Sailing in Montego Bay · 14 guests

    Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat

    New
    $250/hour
    Party Boat that can host 150 people in La Romana, Dominican Republic
    Events in La Romana · 150 guests

    Party Boat that can host 150 people in La Romana, Dominican Republic

    New
    Superowner
    Best of 2026
    $100/hour
    Deal of the Day! Lagoon 40Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 18 guests

    Deal of the Day! Lagoon 40Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $435/hour
    Instant Book
    Private overnight Charter on a Luxurious Fountaine Pajot 47 up to 8 guests
    Sailing in Nassau · 9 guests

    Private overnight Charter on a Luxurious Fountaine Pajot 47 up to 8 guests

    New
    $3,715+/night
    Luxury Lagoon 620 Essence Sailing Catamaran in The Bahamas
    Sailing in Nassau · 25 guests

    Luxury Lagoon 620 Essence Sailing Catamaran in The Bahamas

    New
    $1,225/hour
    46 Sport Bridge Yacht
    Events in Miami Beach · 12 guests

    46 Sport Bridge Yacht

    New
    $240+/hour
    Authentic Caribbean Sailing Aboard a 43ft Grand Soleil
    Sailing in Saint Martin · 6 guests

    Authentic Caribbean Sailing Aboard a 43ft Grand Soleil

    New
    $95/hour
    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!
    Sailing in Saint Martin · 20 guests

    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!

    New
    $2,920/day
    Cruising Catamaran Charter in Cabarete, Dominican Republic
    Sailing in Cabarete · 80 guests

    Cruising Catamaran Charter in Cabarete, Dominican Republic

    New
    Superowner
    Best of 2026
    $400/hour
    Beneteau Oceanis Yacht 62 - Miami Charter with Captain for up to 10 Guests
    Sailing in North Bay Village · 10 guests

    Beneteau Oceanis Yacht 62 - Miami Charter with Captain for up to 10 Guests

    New
    $800+/hour
    Catamaran Lagoon 62’ 2019 for a week in BVI
    Sailing in John's Hole · 8 guests

    Catamaran Lagoon 62’ 2019 for a week in BVI

    New
    Superowner
    $10,500/day
    Luxury Party Boat Catamaran in Punta Cana
    Events in Punta Cana · 150 guests

    Luxury Party Boat Catamaran in Punta Cana

    New
    Superowner
    Best of 2026
    $80/hour
    Deal of the Week! Leopard 47 Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 35 guests

    Deal of the Week! Leopard 47 Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $711/hour
    Instant Book
    All-inclusive Luxury Private Charter - Sailing Cat - St Martin/Anguilla/St Barts
    Sailing in Saint Martin · 6 guests

    All-inclusive Luxury Private Charter - Sailing Cat - St Martin/Anguilla/St Barts

    New
    $2,978/day
    Spectacular 51-foot Lagoon Catamaran In Cartagena
    Sailing in Cartagena · 40 guests

    Spectacular 51-foot Lagoon Catamaran In Cartagena

    New
    Superowner
    $430/hour
    Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe
    Sailing in Hanover Parish · 120 guests

    Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe

    New
    $700/hour
    Private Saona Island Cruise (All-Inclusive)
    Sailing in Los Melones · 12 guests

    Private Saona Island Cruise (All-Inclusive)

    New
    $169/hour
    Party Catamaran Rental🎉Best 2021-2022 Awards in Punta Cana, Dominican Republic
    Powerboats in Macao · 80 guests

    Party Catamaran Rental🎉Best 2021-2022 Awards in Punta Cana, Dominican Republic

    New
    Superowner
    Best of 2026
    $275/hour
    Charter the Cruising Monohull in Las Terrenas, Samana
    Sailing in Las Terrenas · 10 guests

    Charter the Cruising Monohull in Las Terrenas, Samana

    New
    $1,586/day

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. Blue

      Blue

      46ft Luxury Sailing Catamaran in Miami

      Leo and crew were fantastic, and my friends and I had a blast out on the water! Can't wait to do it again.

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