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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,280 Reviews)

    Page 13 of 19 • 433 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
    Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe
    Sailing in Hanover Parish · 120 guests

    Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe

    New
    $700/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
    $842/day
    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
    Unforgettable Day Charter - Bali 4.6 Sailing Catamaran in Bahamas for 10 Guests
    Sailing in Nassau · 10 guests

    Unforgettable Day Charter - Bali 4.6 Sailing Catamaran in Bahamas for 10 Guests

    New
    $1,350/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
    All-inclusive Luxury Shared Charter - Power Cat - St Martin
    Caribbean · 10 guests

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

    New
    $410/day
    52' Catamaran - Sunset Cruise Private Charter at Simpson Bay
    Caribbean · 32 guests

    52' Catamaran - Sunset Cruise Private Charter at Simpson Bay

    New
    $550/day
    Deal of the Week! Leopard 51 Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 35 guests

    Deal of the Week! Leopard 51 Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $766/hour
    Instant Book
    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
    74ft Sunreef Sailing Catamaran In The Bahamas
    Sailing in Black Point · 13 guests

    74ft Sunreef Sailing Catamaran In The Bahamas

    New
    $1,690/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
    Private Sunset Cruise in St. Lucia on Beneteau Oceanis 440 Yacht
    Sailing in Gros Islet · 10 guests

    Private Sunset Cruise in St. Lucia on Beneteau Oceanis 440 Yacht

    New
    $171/hour
    Leopard 51 Power Catamaran In Anguilla
    Powerboats in Sandy Ground · 12 guests

    Leopard 51 Power Catamaran In Anguilla

    New
    $3,425/day
    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
    Charter Your Pirate Ship In The Bahamas
    Events in Nassau · 300 guests

    Charter Your Pirate Ship In The Bahamas

    New
    Superowner
    $2,500/hour
    Miami Catamaran Charter | 48ft Sailing Yacht ⚓ • July 4th Available 🇺🇸
    Sailing in Miami · 12 guests

    Miami Catamaran Charter | 48ft Sailing Yacht ⚓ • July 4th Available 🇺🇸

    New
    $426+/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
    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
    65ft Pershing Yacht for Luxury Charter and Miami Fun!
    Events in Miami · 13 guests

    65ft Pershing Yacht for Luxury Charter and Miami Fun!

    New
    $450/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
    Luxury 45ft Lagoon Catamaran Key West 🛥️⚓
    Sailing in Key West · 13 guests

    Luxury 45ft Lagoon Catamaran Key West 🛥️⚓

    New
    $739+/hour
    Limited Availability
    Private Luxury Yacht Experience in Montego Bay
    Events in Montego Bay · 12 guests

    Private Luxury Yacht Experience in Montego Bay

    New
    $450/hour

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