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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,125 Reviews)

    Page 10 of 17 • 396 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    Mega Catamaran Charter in Ocho Rios
    Sailing in Ocho Rios · 120 guests

    Mega Catamaran Charter in Ocho Rios

    New
    $2,300/hour
    Fun Memories, Captain & Crew Included
    Sailing in Bávaro · 100 guests

    Fun Memories, Captain & Crew Included

    New
    Superowner
    Best of 2025
    $100/hour
    44' Monohull Day and Multi-day Sailing Charter
    Sailing in Puerto Plata Province · 6 guests

    44' Monohull Day and Multi-day Sailing Charter

    New
    $101/hour
    Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick
    Sailing in Cruz Bay · 12 guests

    Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick

    5.0
    $125/hour
    THE ONE AND ONLY GRADY WHITE FREEDOM
    Fishing in Marathon · 8 guests

    THE ONE AND ONLY GRADY WHITE FREEDOM

    New
    $150/hour
    🛥🥂VIP EXPERIENCE-Prívate Catamaran for bachelorette-birthday in Puerto Plata
    Events in Barrio Las Yaguitas · 60 guests

    🛥🥂VIP EXPERIENCE-Prívate Catamaran for bachelorette-birthday in Puerto Plata

    New
    $170/hour
    Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico
    Sailing in Fajardo · 6 guests

    Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico

    5.0
    $450/hour
    Your Private Yacht for the Day – Lagoon 46 Full-Day Charter
    Sailing in Fajardo · 6 guests

    Your Private Yacht for the Day – Lagoon 46 Full-Day Charter

    New
    $2,730/day
    Private Group Catamaran Cruise in Ocho Rios
    Sailing in Ocho Rios · 40 guests

    Private Group Catamaran Cruise in Ocho Rios

    New
    $1,266/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 2025
    $100/hour
    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!
    Sailing in Anse Marcel · 20 guests

    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!

    New
    $2,931/day
    Saona Island: Private Yacht Tour with Snorkel in DR
    Events in Los Melones · 15 guests

    Saona Island: Private Yacht Tour with Snorkel in DR

    New
    $320/hour
    Private Lunch Tour Deluxe in Curacao
    Sailing in Jan Thiel · 6 guests

    Private Lunch Tour Deluxe in Curacao

    New
    $325/hour
    Private Yacht Day Charter
    Events in Nassau · 12 guests

    Private Yacht Day Charter

    New
    $750/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
    $240/hour
    Instant Book
    Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ
    Powerboats in Punta Cana · 70 guests

    Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ

    New
    $125+/hour
    Set sail with our luxurious Sea Ray 300 Yacht!!
    Powerboats in Sunny Isles Beach · 10 guests

    Set sail with our luxurious Sea Ray 300 Yacht!!

    New
    $200/hour
    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo
    Sailing in Fajardo · 6 guests

    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo

    New
    $583/hour
    All-inclusive Luxury Private Charter - Sailing Cat - St Martin/Anguilla/St Barts
    Sailing in Marigot · 6 guests

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

    New
    $2,990/day
    Luxury 58ft Hanse Velero, Cartagena, Colombia
    Sailing in Cartagena · 12 guests

    Luxury 58ft Hanse Velero, Cartagena, Colombia

    New
    $403/hour
    Fountaine Pajot Catamaran 43ft, Santa Marta, Colombia
    Sailing in Comuna 2 · 30 guests

    Fountaine Pajot Catamaran 43ft, Santa Marta, Colombia

    New
    $210+/hour
    Punta Cana: Ultimate Private Yacht Party with Snorkeling
    Events in Bávaro · 10 guests

    Punta Cana: Ultimate Private Yacht Party with Snorkeling

    New
    $320+/hour
    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo
    Sailing in Fajardo · 12 guests

    Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo

    New
    $450/hour

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. HC

      Heather

      Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick

      Fabulous day with a knowledgeable captain on a very comfortable boat. Captain Rick customized the trip to our group’s every need and preference. He and his assistant Rachel provided an uniquely memorable Caribbean experience we can highly recommend.

    2. Nathan

      Nathan

      Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico

      Great day on the water with a great crew! Service was excellent, food was very good and the boat is comfortable and clean. Really fantastic way to spend a day in PR!

    3. Nathan

      Nathan

      Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico

      Beautiful, comfortable boat with a great sound system and excellent food! The captain and crew were great hosts and we enjoyed every minute of our day!

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