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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,366 Reviews)

    Page 17 of 18 • 432 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    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
    $279/night
    Nautitech 40 in San Blas Islands
    Sailing in Panama City · 7 guests

    Nautitech 40 in San Blas Islands

    New
    $1,550/night
    Sailing in the Caribbean St. Martin
    Sailing in Saint Martin · 10 guests

    Sailing in the Caribbean St. Martin

    New
    $1,162/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
    $157/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
    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
    $115/hour
    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
    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
    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
    $479/day
    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
    $2,906/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
    Captained Charter on 47ft
    Sailing in Coclé Province · 8 guests

    Captained Charter on 47ft

    5.0
    $2,000/day
    Private Sailing Yacht to Coiba National Park – Overnight Option
    Sailing in Panamá · 6 guests

    Private Sailing Yacht to Coiba National Park – Overnight Option

    New
    $120/hour
    2024 Valentine's Week in BVi 🍹🍸👙🤟
    Sailing in Fisher Estate · 8 guests

    2024 Valentine's Week in BVi 🍹🍸👙🤟

    New
    $92,160/day
    Come and enjoy the Spanish Virgin Island onboard 38ft Hunter Marine
    Sailing in Fajardo · 6 guests

    Come and enjoy the Spanish Virgin Island onboard 38ft Hunter Marine

    New
    $200/hour
    Sailing Yacht Charter with amazing crew all inclusive
    Sailing in Panama City · 6 guests

    Sailing Yacht Charter with amazing crew all inclusive

    New
    $883/night
    Beneteau 50 Sailing Yacht Charter in San Blas Islands
    Colón · 10 guests

    Beneteau 50 Sailing Yacht Charter in San Blas Islands

    New
    $1,400/day
    Romantic Sunset Sailing in La Boquilla, Bolívar
    Sailing in La Boquilla · 4 guests

    Romantic Sunset Sailing in La Boquilla, Bolívar

    New
    $260/hour

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. FO

      Fernando

      Captained Charter on 47ft

      Was the best trip ever! Really recommend this trip and hope soon have a weekend trip in this catamaran

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