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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,407 Reviews)

    Page 17 of 20 • 457 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    56' Lagoon Catamaran
    Sailing in Saint Martin · 22 guests

    56' Lagoon Catamaran

    New
    $562/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
    $1,108/day
    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
    $164+/hour
    38' Beneteau Sailing/Diving The Carribbean Sea
    Sailing in Saint Martin · 12 guests

    38' Beneteau Sailing/Diving The Carribbean Sea

    New
    $618/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
    Antigua Barbuda Sailing lessons and expedition!
    Sailing in Jolly Harbour · 10 guests

    Antigua Barbuda Sailing lessons and expedition!

    New
    $1,348/night
    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
    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
    $640/hour
    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
    $498/day
    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 46 Premium Sailing Catamaran in Le Marin, Martinique
    Sailing in Le Marin · 12 guests

    Lagoon 46 Premium Sailing Catamaran in Le Marin, Martinique

    New
    $1,108/day
    Lagoon 500 in San Blas Islands
    Sailing in Panama City · 8 guests

    Lagoon 500 in San Blas Islands

    New
    $2,700/night
    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
    $916/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
    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
    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
    Catamaran Charter In San Blas Panama
    Sailing in Guna Yala Comarca · 10 guests

    Catamaran Charter In San Blas Panama

    New
    $1,236/night
    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
    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
    $835/day
    Explore Grand-Case, Saint Martin Aboard 53ft Ocean Voyager Catamaran - 28 Guests
    Sailing in Saint Martin · 28 guests

    Explore Grand-Case, Saint Martin Aboard 53ft Ocean Voyager Catamaran - 28 Guests

    New
    $618/hour
    Welcome aboard a stunning 2022 Bali Catspace Cruising Catamaran
    Sailing in John's Hole · 8 guests

    Welcome aboard a stunning 2022 Bali Catspace Cruising Catamaran

    New
    $550/hour
    All-inclusive Crewed Charter on 40ft Nautitech Sailing Catamaran in San Blas
    Sailing in Guna Yala Comarca · 7 guests

    All-inclusive Crewed Charter on 40ft Nautitech Sailing Catamaran in San Blas

    New
    $1,000/night
    Nautitech 40 in San Blas Islands
    Sailing in Panama City · 7 guests

    Nautitech 40 in San Blas Islands

    New
    $1,550/night

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