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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,407 Reviews)

    Page 10 of 20 • 457 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
    $530/hour
    Instant Book
    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
    Sailing live aboard Charter in Montego Bay, Jamaica
    Sailing in Montego Bay · 15 guests

    Sailing live aboard Charter in Montego Bay, Jamaica

    5.0
    $950/day
    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
    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
    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
    Sunset Cruise on Cartagena Bay Aboard 48' Leopard Catamaran with DJ and Open Bar
    Sailing in Cartagena · 30 guests

    Sunset Cruise on Cartagena Bay Aboard 48' Leopard Catamaran with DJ and Open Bar

    New
    $120/hour
    🟢🍾Ocean Escape: Snorkel, Sip & Celebrate with Open Bar & Music☀️
    Powerboats in Punta Cana · 500 guests

    🟢🍾Ocean Escape: Snorkel, Sip & Celebrate with Open Bar & Music☀️

    New
    Superowner
    Best of 2026
    $15/hour
    Private 40ft Catamaran Charter to Rosario Islands, Cartagena
    Sailing in Cartagena · 15 guests

    Private 40ft Catamaran Charter to Rosario Islands, Cartagena

    New
    $3,799/day
    Instant Book
    Luxury 52 Catamaran With AC - Price include 2 People
    Sailing in Guna Yala Comarca · 8 guests

    Luxury 52 Catamaran With AC - Price include 2 People

    5.0
    $2,700/day
    🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️
    Tours in Dominican Republic · 40 guests

    🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

    New
    Superowner
    Best of 2026
    $75/hour
    Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)
    Events in Bávaro · 100 guests

    Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

    5.0
    $240/hour
    60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!
    Powerboats in Bávaro · 200 guests

    60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!

    New
    Superowner
    Best of 2026
    $16/hour
    Maxicat 65ft Private Party Catamaran in Cartagena
    Sailing in Cartagena · 80 guests

    Maxicat 65ft Private Party Catamaran in Cartagena

    New
    Superowner
    $838/hour
    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
    Punta Cana - FAMILY BOAT
    Sailing in Bávaro · 200 guests

    Punta Cana - FAMILY BOAT

    New
    $160/hour
    An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena
    Sailing in Cartagena · 23 guests

    An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena

    New
    Superowner
    $231/hour
    Cruising Catamaran Rental in Puerto Plata, Puerto Plata
    Sailing in Barrio Las Yaguitas · 80 guests

    Cruising Catamaran Rental in Puerto Plata, Puerto Plata

    1.0
    Superowner
    Best of 2026
    $183/hour
    Private 47ft Power Catamaran to Saona Island – Full-Day All-Inclusive Experience
    Sailing in Los Melones · 35 guests

    Private 47ft Power Catamaran to Saona Island – Full-Day All-Inclusive Experience

    New
    $850/hour
    Instant Book
    Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch
    Powerboats in Sosúa · 70 guests

    Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch

    New
    $242/hour
    Instant Book
    Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia
    Sailing in Cartagena · 80 guests

    Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia

    New
    Superowner
    $5,000/day
    Limited Availability
    57' Fountaine Pajot Sailing Catamaran - A Luxury Experience
    Sailing in Fort Lauderdale · 12 guests

    57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

    5.0
    $450/hour
    Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience
    Events in Sosúa · 25 guests

    Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience

    New
    $135/hour
    Dunn’s River Falls Private Catamaran Cruise – Ocho Rios
    Powerboats in Ocho Rios · 100 guests

    Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

    New
    $654/hour

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. DP

      Dawn

      Luxury 52 Catamaran With AC - Price include 2 People

      ⭐⭐⭐⭐⭐ An unforgettable experience in San Blas, Panama! The Italian-owned boat exceeded all expectations. The food was divine, reflecting true Italian finesse, and the service was impeccable. Every moment aboard was filled with warmth, comfort, and authentic hospitality. A must-try for anyone seeking a remarkable sailing adventure in paradise!

    2. Lisa

      Lisa

      Sailing live aboard Charter in Montego Bay, Jamaica

      It was my first time using the service and Chris was always available when I had a question. My clients had a great time.

    3. Evan

      Evan

      Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

      Amazing people to deal with ! Highly recommend

    4. erkan

      erkan

      57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

      Crew , boat , owner … they were the best !

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