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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,411 Reviews)

    Page 17 of 20 • 460 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos
    Sailing in Fajardo · 12 guests

    Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos

    New
    $575/hour
    Sail Bocas del Toro Aboard 40ft Beneteau Oceanis 40 with Captain Included
    Sailing in Bocas del Toro Province · 8 guests

    Sail Bocas del Toro Aboard 40ft Beneteau Oceanis 40 with Captain Included

    New
    $112+/hour
    Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1
    Sailing in Fort Lauderdale · 4 guests

    Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1

    New
    $50/hour
    Your dreamed boat in the Caribbeans | 50ft Dufour Sailboat
    Sailing in Le Marin · 8 guests

    Your dreamed boat in the Caribbeans | 50ft Dufour Sailboat

    New
    $240/day
    Lagoon 560 S2 Catamaran | Luxury Cruising Edition From Anguilla
    Sailing in Saint Martin · 22 guests

    Lagoon 560 S2 Catamaran | Luxury Cruising Edition From Anguilla

    New
    $635/hour
    Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe
    Sailing in Hanover Parish · 120 guests

    Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe

    New
    $700/hour
    Caribbean Island-hopping
    Sailing in Portsmouth · 10 guests

    Caribbean Island-hopping

    New
    $150/hour
    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
    $1,099/day
    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
    La Peregrina Beneteau 58ft Sailing Yacht Charter for 12 people
    Sailing in Cartagena · 12 guests

    La Peregrina Beneteau 58ft Sailing Yacht Charter for 12 people

    New
    $163+/hour
    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
    Antigua Barbuda Sailing lessons and expedition!
    Sailing in Jolly Harbour · 10 guests

    Antigua Barbuda Sailing lessons and expedition!

    New
    $1,338/night
    38' Beneteau Sailing/Diving The Carribbean Sea
    Sailing in Saint Martin · 12 guests

    38' Beneteau Sailing/Diving The Carribbean Sea

    New
    $613/day
    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
    $494/day
    Catamaran Charter In San Blas Panama
    Sailing in Guna Yala Comarca · 10 guests

    Catamaran Charter In San Blas Panama

    New
    $1,226/night
    Lagoon 500 in San Blas Islands
    Sailing in Panama City · 8 guests

    Lagoon 500 in San Blas Islands

    New
    $2,700/night
    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
    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
    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
    $1,099/day
    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
    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
    $909/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

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