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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,317 Reviews)

    Page 11 of 18 • 430 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    Private Catamaran Sail & Snorkel in Negril – Open Bar, Snacks & Music
    Sailing in Negril · 60 guests

    Private Catamaran Sail & Snorkel in Negril – Open Bar, Snacks & Music

    New
    $930+/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
    St. Barth Boat tour with Lagoon 450 Cruising Catamaran!
    Sailing in Saint Martin · 20 guests

    St. Barth Boat tour with Lagoon 450 Cruising Catamaran!

    New
    $3,111/day
    Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten
    Sailing in Saint Martin · 8 guests

    Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

    5.0
    $1,000/day
    46' Monohull Sailing Private Charter in Charlotte Amalie
    Sailing in St. Thomas · 6 guests

    46' Monohull Sailing Private Charter in Charlotte Amalie

    New
    $200/hour
    Private Catamaran Tour in Punta Cana: Party Boat+Snorkeling
    Sailing in Bávaro · 60 guests

    Private Catamaran Tour in Punta Cana: Party Boat+Snorkeling

    New
    $180+/hour
    50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!
    Sailing in Miami Beach · 42 guests

    50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!

    New
    Superowner
    Best of 2026
    $850/hour
    Puerto Plata Private 6 Hour Catamaran Snorkel and BBQ
    Powerboats in Sosúa · 20 guests

    Puerto Plata Private 6 Hour Catamaran Snorkel and BBQ

    New
    $265/hour
    Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia
    Sailing in Cartagena · 12 guests

    Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia

    New
    Superowner
    $150/hour
    Have an amazing time in Cartagena, Colombia on Beneteau 41 Sailboat
    Sailing in Cartagena · 8 guests

    Have an amazing time in Cartagena, Colombia on Beneteau 41 Sailboat

    New
    Superowner
    $1,220/day
    Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull
    Sailing in Cartagena · 10 guests

    Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull

    New
    Superowner
    $163/hour
    Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling
    Sailing in Montego Bay · 60 guests

    Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

    New
    $1,176/hour
    😍SPICE RENTED HER CATAMARANS🛥️💃🏾💕🔥VIP Sailing Catamaran
    Sailing in Punta Cana · 25 guests

    😍SPICE RENTED HER CATAMARANS🛥️💃🏾💕🔥VIP Sailing Catamaran

    New
    $113/hour
    Montego Bay All-inclusive Yacht Experience
    Events in Montego Bay · 10 guests

    Montego Bay All-inclusive Yacht Experience

    New
    Superowner
    $998/hour
    Deal of the Week! Leopard 43Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 25 guests

    Deal of the Week! Leopard 43Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $654/hour
    Instant Book
    Lagoon 62’ 2019 Cruising Catamaran Rental in Nassau, New Providence
    Sailing in Nassau · 10 guests

    Lagoon 62’ 2019 Cruising Catamaran Rental in Nassau, New Providence

    New
    Superowner
    $1,331/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
    Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish
    Sailing in Negril · 100 guests

    Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish

    New
    $1,800/hour
    46 Sport Bridge Yacht
    Events in Miami Beach · 12 guests

    46 Sport Bridge Yacht

    New
    $240+/hour
    3 courses dinner & sunset cruise on a luxury catamaran up to 12 guests
    Sailing in Nassau · 12 guests

    3 courses dinner & sunset cruise on a luxury catamaran up to 12 guests

    New
    $4,800/hour
    ⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)
    Events in Miami Beach · 49 guests

    ⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)

    New
    Superowner
    $750+/hour
    Private Catamaran to Saona Island – Full-Day All-Inclusive Paradise!
    Powerboats in Bávaro · 50 guests

    Private Catamaran to Saona Island – Full-Day All-Inclusive Paradise!

    New
    $1,480/day

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. TL

      Tanya

      46' Monohull Sailing Private Charter in Charlotte Amalie

      Captain Fancy and Lindsey were awesome!! We loved every minute of it. Pedro the pirate dog was so sweet. I would post pictures but not sure how. I don’t see an option.

    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. AS

      Aaron

      Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

      Great time sailing with Robert in Sxm. Food and drinks were great. Only on the boat for two nights but got a lot done for the amount of time we had available.

    4. 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!

    5. MC

      Michael

      Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

      Wonderful day. Highly recommend.

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