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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,085 Reviews)

    Page 14 of 17 • 391 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    Dufour 455 Grand Large - Sloop sail rental in Le Marin
    Sailing in Le Marin · 8 guests

    Dufour 455 Grand Large - Sloop sail rental in Le Marin

    New
    $523/day
    Luxury Catamaran Charter In Grenada and The Grenadines
    Sailing in Saint George's · 10 guests

    Luxury Catamaran Charter In Grenada and The Grenadines

    New
    $200/hour
    CARLOTTA -Classic cruises, single-handed sailing courses or photo sailing trips
    Sailing in Le Marin · 8 guests

    CARLOTTA -Classic cruises, single-handed sailing courses or photo sailing trips

    New
    $130+/hour
    60ft Sea Ray Power MegaYacht Rental in Cartagena, Bolívar
    Sailing in Cartagena · 16 guests

    60ft Sea Ray Power MegaYacht Rental in Cartagena, Bolívar

    New
    $3,350/day
    Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. Thomas pick up
    Sailing in Charlotte Amalie · 6 guests

    Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. Thomas pick up

    New
    $350/hour
    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
    $350/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
    $963/day
    Nautitech 43 Cruising Catamaran Rental in San Blas Islands, Panama
    Sailing in Guna Yala Comarca · 6 guests

    Nautitech 43 Cruising Catamaran Rental in San Blas Islands, Panama

    New
    $1,600/night
    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
    $1,165/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
    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
    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
    $113/day
    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
    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
    $487/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
    Boat Tours in Panama
    Sailing in Panama City · 70 guests

    Boat Tours in Panama

    1.0
    $125/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
    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
    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
    Charter the 50' Cruising Monohull In Cartagena, Colombia
    Sailing in Cartagena · 10 guests

    Charter the 50' Cruising Monohull In Cartagena, Colombia

    New
    $110+/hour
    Antigua Barbuda Sailing lessons and expedition!
    Sailing in Jolly Harbour · 10 guests

    Antigua Barbuda Sailing lessons and expedition!

    New
    $1,417/night

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