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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,379 Reviews)

    Page 17 of 19 • 439 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Island Dreams on a Luxury Contender 40' Center Console
    Powerboats in Fajardo · 8 guests

    Island Dreams on a Luxury Contender 40' Center Console

    New
    $225+/hour
    Sailing Lagoon 42 Premium (Crewed and Bareboat Charter Options!) in Le Marin
    Sailing in Le Marin · 12 guests

    Sailing Lagoon 42 Premium (Crewed and Bareboat Charter Options!) in Le Marin

    New
    $933/day
    Lagoon 450 - Catamaran sail rental in Le Marin - Martinique
    Sailing in Le Marin · 12 guests

    Lagoon 450 - Catamaran sail rental in Le Marin - Martinique

    New
    $850/day
    Salinas 48 Cruising Catamaran Charter in San Blas Islands, Panama
    Sailing in Guna Yala Comarca · 8 guests

    Salinas 48 Cruising Catamaran Charter in San Blas Islands, Panama

    New
    $3,410/night
    Welcome aboard a stunning 2022 Bali Catspace Cruising Catamaran
    Sailing in John's Hole · 8 guests

    Welcome aboard a stunning 2022 Bali Catspace Cruising Catamaran

    New
    $550/hour
    Private sailing and snorkeling charter for 2. A unique and custom tailored trip
    Sailing in Guna Yala Comarca · 2 guests

    Private sailing and snorkeling charter for 2. A unique and custom tailored trip

    New
    $185/night
    Catamaran Charter In San Blas Panama
    Sailing in Guna Yala Comarca · 10 guests

    Catamaran Charter In San Blas Panama

    New
    $1,259/night
    All-inclusive Crewed Charter on 40ft Nautitech Sailing Catamaran in San Blas
    Sailing in Guna Yala Comarca · 7 guests

    All-inclusive Crewed Charter on 40ft Nautitech Sailing Catamaran in San Blas

    New
    $1,000/night
    Nautitech 40 in San Blas Islands
    Sailing in Panama City · 7 guests

    Nautitech 40 in San Blas Islands

    New
    $1,550/night
    The Stars are Calling aboard Bali 5.4 Sailing Catamaran in British Virgin Island
    Sailing in West End, Tortola · 10 guests

    The Stars are Calling aboard Bali 5.4 Sailing Catamaran in British Virgin Island

    New
    $5,142/night
    Montecarlo 43’ private sailing boat in San Blas Islands
    Sailing in Guna Yala Comarca · 2 guests

    Montecarlo 43’ private sailing boat in San Blas Islands

    New
    $275/night
    Sailing in the Caribbean St. Martin
    Sailing in Saint Martin · 10 guests

    Sailing in the Caribbean St. Martin

    New
    $1,145/day
    Lagoon 42 Cruising Catamaran for rent in Le Marin, Martinique
    Sailing in Le Marin · 12 guests

    Lagoon 42 Cruising Catamaran for rent in Le Marin, Martinique

    New
    $155/hour
    Jeannuea Internacional 51" Sailboat - Jump onboard and relax!
    Sailing in San Andrés · 6 guests

    Jeannuea Internacional 51" Sailboat - Jump onboard and relax!

    New
    $425/night
    Sail in Luxury: Smack Offers Space, Style, and Seamless Comfort
    Sailing in Stock Island · 12 guests

    Sail in Luxury: Smack Offers Space, Style, and Seamless Comfort

    New
    $260+/hour
    VIP Private Yacht Negril Jamaica | Azimut 54 Flybridge
    Events in Negril · 15 guests

    VIP Private Yacht Negril Jamaica | Azimut 54 Flybridge

    New
    $1,150/hour
    Amazing new power catamaran for Coiba's amazing Pacific island paradise
    Powerboats in Boca Chica · 8 guests

    Amazing new power catamaran for Coiba's amazing Pacific island paradise

    New
    $3,150+/night
    Yacht charter in San Blas Islands |Alubat — Ovni 435 (2003) Sailboat
    Sailing in Guna Yala Comarca · 2 guests

    Yacht charter in San Blas Islands |Alubat — Ovni 435 (2003) Sailboat

    New
    $472/day
    Private Catamaran in San Blas Islands – All Meals & Skipper Included
    Sailing in Guna Yala Comarca · 6 guests

    Private Catamaran in San Blas Islands – All Meals & Skipper Included

    New
    $950/night
    2021 Lagoon 46 Sailing Catamaran Based in Saint Martin / Saint Barthélémy
    Sailing in Saint Martin · 12 guests

    2021 Lagoon 46 Sailing Catamaran Based in Saint Martin / Saint Barthélémy

    New
    $2,862/day
    Your Private Yacht for the Day – Lagoon 42 Full-Day Charter
    Sailing in Fajardo · 6 guests

    Your Private Yacht for the Day – Lagoon 42 Full-Day Charter

    New
    $2,500/day
    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 Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports
    Powerboats in Fajardo · 6 guests

    Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports

    New
    $650/day
    Sail aboard our wonderful Jeanneau Sun Odyssey Sailboat and discover San Blas
    Sailing in Guna Yala Comarca · 12 guests

    Sail aboard our wonderful Jeanneau Sun Odyssey Sailboat and discover San Blas

    New
    $113/hour

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