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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,276 Reviews)

    Page 16 of 19 • 438 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    Punta Cana’s Ultimate Ocean Powerhouse - Luxury Snorkel & Natural Pool Adventure
    Events in Bávaro · 70 guests

    Punta Cana’s Ultimate Ocean Powerhouse - Luxury Snorkel & Natural Pool Adventure

    New
    $325/hour
    Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas
    Sailing in Key West · 12 guests

    Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas

    New
    $560+/hour
    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
    Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat
    Sailing in Gros Islet · 10 guests

    Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat

    New
    $576/day
    Reggae Catamaran Negril Sail Snorkel and Sunset Tour
    Sailing in West End · 20 guests

    Reggae Catamaran Negril Sail Snorkel and Sunset Tour

    New
    $1,084/hour
    Lagoon 46 Premium Sailing Catamaran in Le Marin, Martinique
    Sailing in Le Marin · 12 guests

    Lagoon 46 Premium Sailing Catamaran in Le Marin, Martinique

    New
    $1,136/day
    Private Gourmet Sailing Charters on Elegant 50ft Catamaran
    Sailing in Gustavia · 10 guests

    Private Gourmet Sailing Charters on Elegant 50ft Catamaran

    New
    $595+/hour
    Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests
    Sailing in Key West · 6 guests

    Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests

    New
    $150/hour
    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
    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
    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
    $1,136/day
    Sailing in the Caribbean St. Martin
    Sailing in Saint Martin · 10 guests

    Sailing in the Caribbean St. Martin

    New
    $1,152/day
    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
    $939/day
    Antigua Barbuda Sailing lessons and expedition!
    Sailing in Jolly Harbour · 10 guests

    Antigua Barbuda Sailing lessons and expedition!

    New
    $1,383/night
    Limited Availability
    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale
    Powerboats in Fort Lauderdale · 12 guests

    Luxury 39ft Lagoon Catamaran for 12 in Fort Lauderdale

    New
    $330/hour
    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
    $856/day
    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
    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
    Reserve the Luxury Tiara Power in Road Town, Tortola
    Powerboats in Wickhams Cay 1 · 12 guests

    Reserve the Luxury Tiara Power in Road Town, Tortola

    New
    $2,900/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
    $156/hour
    Luxury Sailing Catamaran for up to10 guests
    Sailing in St. Thomas · 12 guests

    Luxury Sailing Catamaran for up to10 guests

    New
    $1,500/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
    $2,880/day
    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

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