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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,407 Reviews)

    Page 14 of 20 • 457 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private Saona Island Cruise (All-Inclusive)
    Sailing in Los Melones · 12 guests

    Private Saona Island Cruise (All-Inclusive)

    New
    $169/hour
    Private Group Catamaran Cruise in Ocho Rios
    Sailing in Ocho Rios · 40 guests

    Private Group Catamaran Cruise in Ocho Rios

    New
    $1,266/hour
    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
    Ultra luxe Full Day Yacht Charter to Negril!
    Events in Montego Bay · 10 guests

    Ultra luxe Full Day Yacht Charter to Negril!

    New
    Superowner
    $1,625/hour
    7 to 21 Days Sailing to the Grenadines aboard Beneteau Oceanis 440 Sailing Yacht
    Sailing in Le Marin · 10 guests

    7 to 21 Days Sailing to the Grenadines aboard Beneteau Oceanis 440 Sailing Yacht

    New
    $225/day
    All-inclusive Luxury Shared Charter - Power Cat - St Martin
    Caribbean · 10 guests

    All-inclusive Luxury Shared Charter - Power Cat - St Martin

    New
    $403/day
    74ft Sunreef Sailing Catamaran In The Bahamas
    Sailing in Black Point · 13 guests

    74ft Sunreef Sailing Catamaran In The Bahamas

    New
    $1,690/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
    Premium Catamaran Experience Around St Martin - Vogue
    Powerboats in Saint Martin · 12 guests

    Premium Catamaran Experience Around St Martin - Vogue

    New
    $2,843/day
    Limited Availability
    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale
    Powerboats in Fort Lauderdale · 12 guests

    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale

    New
    $330/hour
    Charter Your Pirate Ship In The Bahamas
    Events in Nassau · 300 guests

    Charter Your Pirate Ship In The Bahamas

    New
    Superowner
    $2,500/hour
    Fountaine Pajot Belize 43 Sailing Catamaran in Cartagena, Bolívar
    Sailing in Cartagena · 30 guests

    Fountaine Pajot Belize 43 Sailing Catamaran in Cartagena, Bolívar

    New
    Superowner
    $313/hour
    Exclusive Getaway with Sea Ray 180 Bow Rider Sport to Cuna de Los Nidos!
    Powerboats in Punta Cana · 80 guests

    Exclusive Getaway with Sea Ray 180 Bow Rider Sport to Cuna de Los Nidos!

    New
    Superowner
    Best of 2026
    $15/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
    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
    Private Boat Rental La Morronga Bravo 41' Luxury Finishes
    Powerboats in Cartagena · 15 guests

    Private Boat Rental La Morronga Bravo 41' Luxury Finishes

    New
    $965/day
    45ft Lagoon 450F Sailing Catamaran, Key West with Captain
    Sailing in Key West · 13 guests

    45ft Lagoon 450F Sailing Catamaran, Key West with Captain

    New
    $739+/hour
    55' Nisi Catamaran – Private Bahamas Day Charter- Gratuity and Tax included
    Powerboats in Nassau · 15 guests

    55' Nisi Catamaran – Private Bahamas Day Charter- Gratuity and Tax included

    New
    $1,385+/hour
    Luxurious 72' Azimut: Tender and Water Toys Serving Around South Florida
    Events in North Bay Village · 12 guests

    Luxurious 72' Azimut: Tender and Water Toys Serving Around South Florida

    New
    $950+/hour
    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
    BRAND NEW 2025 Lagoon 43 Luxury Catamaran with AC price include 2 guests
    Sailing in Guna Yala Comarca · 8 guests

    BRAND NEW 2025 Lagoon 43 Luxury Catamaran with AC price include 2 guests

    New
    $2,600/night
    Leopard 51' Power Catamaran from St Martin to Anguilla
    Powerboats in Saint Martin · 12 guests

    Leopard 51' Power Catamaran from St Martin to Anguilla

    New
    $2,932/day
    Sailing Classic Yacht 1980 Swan 47 in Caribbean Waters
    Sailing in Saint George's · 7 guests

    Sailing Classic Yacht 1980 Swan 47 in Caribbean Waters

    New
    $60/hour
    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

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