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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (1,883 Reviews)

    Page 14 of 16 • 381 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    $947/day
    65ft Searay Power Mega Yacht Rental in Miami, Florida
    Sailing in Miami · 13 guests

    65ft Searay Power Mega Yacht Rental in Miami, Florida

    New
    $450/hour
    Instant Book
    Lagoon 450 - Catamaran Charter in Le Marin - Premium - Air conditioned
    Sailing in Le Marin · 12 guests

    Lagoon 450 - Catamaran Charter in Le Marin - Premium - Air conditioned

    New
    $1,146/day
    Jeannuea Internacional 51" Sailboat - Jump onboard and relax!
    Sailing in Guna Yala Comarca · 4 guests

    Jeannuea Internacional 51" Sailboat - Jump onboard and relax!

    New
    $100/hour
    Limited Availability
    50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay
    Sailing in Nassau · 12 guests

    50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

    New
    $1,375/hour
    46ft Fountaine Pajot for 25 people in Taboga ALL INCLUSIVE
    Sailing in Panama City · 25 guests

    46ft Fountaine Pajot for 25 people in Taboga ALL INCLUSIVE

    New
    $468/hour
    Sail onboard 43' Wooden Yawl "Cimmaron" Classic Sailboat in US Virgin Islands!
    Sailing in Cruz Bay · 12 guests

    Sail onboard 43' Wooden Yawl "Cimmaron" Classic Sailboat in US Virgin Islands!

    New
    $1,200/day
    98ft Lagoon Fontaine Pajot Sailing Catamaran Rental in Los Melones, Dominican Republic
    Sailing in Los Melones · 100 guests

    98ft Lagoon Fontaine Pajot Sailing Catamaran Rental in Los Melones, Dominican Republic

    New
    $80/day
    Sail this cruising catamaran Nautitech 48 in Cartagena, Colombia
    Sailing in Cartagena · 30 guests

    Sail this cruising catamaran Nautitech 48 in Cartagena, Colombia

    New
    $2,200/day
    Yacht charter in San Blas Islands |Alubat — Ovni 435 (2003) Sailboat
    Sailing in Guna Yala Comarca · 10 guests

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

    New
    $479/day
    Boat Tours in Panama
    Sailing in Panama City · 70 guests

    Boat Tours in Panama

    1.0
    $125/day
    Premium Catamaran Charter in Santa Marta - 48ft Nautitech
    Events in Comuna 2 · 30 guests

    Premium Catamaran Charter in Santa Marta - 48ft Nautitech

    New
    $220/hour
    Charter 47' Aguamarina Catamaran in Margarita island
    Tours in Federal Dependencies of Venezuela · 60 guests

    Charter 47' Aguamarina Catamaran in Margarita island

    New
    $100/hour
    7 Day Cruise Aboard 47ft Cruising Catamaran in Sainte-Anne, Guadeloupe
    Sailing in Sainte-Anne · 8 guests

    7 Day Cruise Aboard 47ft Cruising Catamaran in Sainte-Anne, Guadeloupe

    New
    $112/day
    Bali 4.0 – Unmatched comfort for your perfect escape!
    Powerboats in Miami · 13 guests

    Bali 4.0 – Unmatched comfort for your perfect escape!

    New
    $280/hour
    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
    Instant Book
    Antigua Barbuda Sailing lessons and expedition!
    Sailing in Jolly Harbour · 10 guests

    Antigua Barbuda Sailing lessons and expedition!

    New
    $1,394/night
    Catamaran Charter In San Blas Panama
    Sailing in Guna Yala Comarca · 10 guests

    Catamaran Charter In San Blas Panama

    New
    $1,278/night
    Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina
    Sailing in Gros Islet · 8 guests

    Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina

    New
    $729/night
    Charter the 50' Cruising Monohull In Cartagena, Colombia
    Sailing in Cartagena · 10 guests

    Charter the 50' Cruising Monohull In Cartagena, Colombia

    New
    $110+/hour
    Crewed Charter on 55ft Lagoon Sailing Catamaran in San Blas Islands, Panama
    Sailing in Guna Yala Comarca · 8 guests

    Crewed Charter on 55ft Lagoon Sailing Catamaran in San Blas Islands, Panama

    New
    $300/day
    Private Charter Catamaran up to 6 passengers
    Sailing in Fajardo · 6 guests

    Private Charter Catamaran up to 6 passengers

    New
    $400/hour
    Lagoon 50 in San Blas Islands
    Sailing in Panama City · 8 guests

    Lagoon 50 in San Blas Islands

    New
    $2,700/night
    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS
    Sailing in Grand Case · 16 guests

    LAGOON 51 SAILING CATAMARAN - 2023 - 16 GUESTS

    New
    $349/hour

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