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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,382 Reviews)

    Page 9 of 19 • 442 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private 41' Power Catamaran Cartagena in Rosario Islands & Cholón
    Sailing in Cartagena · 20 guests

    Private 41' Power Catamaran Cartagena in Rosario Islands & Cholón

    New
    $340/hour
    Private 26ft Family Friendly Speedboat Charter in Aruba
    Powerboats in Oranjestad-West · 10 guests

    Private 26ft Family Friendly Speedboat Charter in Aruba

    New
    $200/hour
    Instant Book
    Private 42-Foot Sailing Catamaran Charter in Bocas del Toro
    Sailing in Bocas del Toro Province · 22 guests

    Private 42-Foot Sailing Catamaran Charter in Bocas del Toro

    New
    $199/hour
    Isla Saona 60ft Private Yacht – Full Day Luxury Tour
    Powerboats in La Romana · 20 guests

    Isla Saona 60ft Private Yacht – Full Day Luxury Tour

    New
    $1,820/day
    Instant Book
    Private 3-Hour Sunset Catamaran Cruise to Media Luna Pool
    Sailing in Dominican Republic · 45 guests

    Private 3-Hour Sunset Catamaran Cruise to Media Luna Pool

    New
    $1,100/hour
    Private 40ft Catamaran Charter in Miches, El Seibo: Snorkeling & Lunch
    Sailing in Dominican Republic · 35 guests

    Private 40ft Catamaran Charter in Miches, El Seibo: Snorkeling & Lunch

    New
    $1,050/hour
    Private 52ft Catamaran Charter in St. Maarten with Lunch & Open Bar
    Caribbean · 8 guests

    Private 52ft Catamaran Charter in St. Maarten with Lunch & Open Bar

    New
    $700/hour
    Private Catamaran in Punta Cana – Natural Pool & Beach Stop
    Sailing in Bávaro · 37 guests

    Private Catamaran in Punta Cana – Natural Pool & Beach Stop

    New
    $250+/hour
    50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay
    Sailing in Nassau · 12 guests

    50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

    5.0
    $1,375/hour
    Private Bravo VIP Double Deck Catamaran with Waterslide for 80 Guests in Sosúa
    Sailing in Sosúa · 80 guests

    Private Bravo VIP Double Deck Catamaran with Waterslide for 80 Guests in Sosúa

    New
    $250+/hour
    Private Double-Deck Party Catamaran with Waterslide in Sosúa
    Sailing in Sosúa · 80 guests

    Private Double-Deck Party Catamaran with Waterslide in Sosúa

    New
    $220+/hour
    Private 44ft Catamaran in La Romana – Saona or Catalina – Up to 20 Guests
    Sailing in La Romana · 20 guests

    Private 44ft Catamaran in La Romana – Saona or Catalina – Up to 20 Guests

    New
    $225/hour
    Instant Book
    Private 63ft Luxury Catamaran in La Romana – Saona or Catalina – Up to 35 Guests
    Sailing in La Romana · 35 guests

    Private 63ft Luxury Catamaran in La Romana – Saona or Catalina – Up to 35 Guests

    New
    $570/hour
    Instant Book
    Puerto Plata Party Catamaran Jacuzzi Slide Barbecue and Bar
    Sailing in Sosúa · 20 guests

    Puerto Plata Party Catamaran Jacuzzi Slide Barbecue and Bar

    New
    $425/hour
    Instant Book
    Puerto Plata Private Sunset Catamaran Cruise with Open Bar and BBQ
    Sailing in Sosúa · 10 guests

    Puerto Plata Private Sunset Catamaran Cruise with Open Bar and BBQ

    New
    $260/hour
    Instant Book
    51ft Beneteau Cyclades Crewed Sailing Charter in St. John, U.S. Virgin Islands
    Sailing in St. John · 8 guests

    51ft Beneteau Cyclades Crewed Sailing Charter in St. John, U.S. Virgin Islands

    New
    $1,990/day
    3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel
    Powerboats in Sosúa · 15 guests

    3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

    New
    $332/hour
    Instant Book
    Private Sail tour to Les Saintes with Skipper Sailing teacher
    Sailing in Saint Charles · 9 guests

    Private Sail tour to Les Saintes with Skipper Sailing teacher

    5.0
    $1,371/day
    🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️
    Sailing in Barrio Las Yaguitas · 18 guests

    🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️

    New
    Superowner
    Best of 2026
    $75/hour
    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull
    Caribbean · 10 guests

    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

    5.0
    $1,200/day
    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
    $530/hour
    Instant Book
    Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami
    Events in Miami · 14 guests

    Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami

    New
    $350/hour
    Sail from Delray Beach to Lake Boca
    Sailing in Delray Beach · 12 guests

    Sail from Delray Beach to Lake Boca

    1.0
    Superowner
    $125+/hour
    Bachelorette Dancing Party In Luxury Cruise in Punta Cana, La Altagracia
    Events in Bávaro · 200 guests

    Bachelorette Dancing Party In Luxury Cruise in Punta Cana, La Altagracia

    New
    Superowner
    Best of 2026
    $17/hour

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. MW

      MAESHEN

      Private Sail tour to Les Saintes with Skipper Sailing teacher

      Une journée de Rêve à ne pas manquer! Le voilier porte bien son nom!!! La croisière était super! On a vraiment aimé voir la Guadeloupe depuis la mer. Avec possibilité de prendre la barre et d'aider avec les voiles. Nous avons déjà fait du voilier, mais jamais participer, donc c'était une bonne expérience. Skipper m très sympa et intéressant et nous avons appris beaucoup sur la Guadeloupe et le voilier. Apéro et repas aussi très bon😊. Vous ne regretterez pas! Je recommande! Vraiment belle journée!

    2. CT

      Cassie

      Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

      We had a great experience with Garth and Byron! They shared lots of fun information about the island and we had a great day of snorkeling and sailing. Would definitely recommend for a group of 6-8 versus jumping on a big boat with lots of people.

    3. Kurt

      Kurt

      Private Sail tour to Les Saintes with Skipper Sailing teacher

      Oliver is a great captain and knows how to create a wonderful and safe experience. I highly recommend you consider a sailing trip with Oliver.

    4. PG

      Paul

      50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

      If you have the chance to book this charter. DO IT! 5* service all around! What a special day. Cannot recommend this charter more!

    5. JR

      Janell

      Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

      Garth and Byron really made sure that we had a good time! I would definitely use them again when I come back to St Martin!

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