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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,344 Reviews)

    Page 17 of 18 • 431 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    $158/hour
    Nautitech 40 in San Blas Islands
    Sailing in Panama City · 7 guests

    Nautitech 40 in San Blas Islands

    New
    $1,550/night
    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
    $116/hour
    Step into a world of refined elegance aboard Fountaine Pajot Alegria 67
    Sailing in West End, Tortola · 8 guests

    Step into a world of refined elegance aboard Fountaine Pajot Alegria 67

    New
    $10,000/night
    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 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
    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
    $2,918/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
    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
    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
    $481/day
    Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI
    Sailing in Freshwater Pond · 6 guests

    Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI

    New
    $3,666/night
    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
    Sailing Yacht Charter with amazing crew all inclusive
    Sailing in Panama City · 6 guests

    Sailing Yacht Charter with amazing crew all inclusive

    New
    $887/night
    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
    2024 Valentine's Week in BVi 🍹🍸👙🤟
    Sailing in Fisher Estate · 8 guests

    2024 Valentine's Week in BVi 🍹🍸👙🤟

    New
    $92,160/day
    Unwind in Sunlit Luxury: Experience 360° Views Aboard This One-of-a-Kind Yacht!
    Sailing in Stock Island · 12 guests

    Unwind in Sunlit Luxury: Experience 360° Views Aboard This One-of-a-Kind Yacht!

    New
    $325+/hour
    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
    53ft Ocean Voyager Catamaran w/Captain, Rendezvous Bay, Anguilla
    Sailing in Anguilla · 28 guests

    53ft Ocean Voyager Catamaran w/Captain, Rendezvous Bay, Anguilla

    New
    $759/hour
    Explore the British Virgin Islands on a Boston Whaler
    Powerboats in Wickhams Cay 1 · 10 guests

    Explore the British Virgin Islands on a Boston Whaler

    New
    $2,400/day

    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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