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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,379 Reviews)

    Page 16 of 19 • 439 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Unforgettable Day Charter - Bali 4.6 Sailing Catamaran in Bahamas for 10 Guests
    Sailing in Nassau · 10 guests

    Unforgettable Day Charter - Bali 4.6 Sailing Catamaran in Bahamas for 10 Guests

    New
    $1,350/hour
    Sailing adventure in San blas
    Sailing in Guna Yala Comarca · 8 guests

    Sailing adventure in San blas

    New
    $550/day
    Boat Tours in Panama
    Sailing in Panama City · 70 guests

    Boat Tours in Panama

    1.0
    $125/day
    Caribbean Island-hopping
    Sailing in Portsmouth · 10 guests

    Caribbean Island-hopping

    New
    $150/hour
    Private Sunset Cruise With Dinner Ocho Rios, Jamaica
    Events in Ocho Rios · 30 guests

    Private Sunset Cruise With Dinner Ocho Rios, Jamaica

    New
    $1,400/hour
    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
    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
    Limited Availability
    42ft Orc San Blas Cruising Catamaran in Guna Yala Comarca
    Sailing in Guna Yala Comarca · 6 guests

    42ft Orc San Blas Cruising Catamaran in Guna Yala Comarca

    New
    $1,130+/day
    38' Beneteau Sailing/Diving The Carribbean Sea
    Sailing in Saint Martin · 12 guests

    38' Beneteau Sailing/Diving The Carribbean Sea

    New
    $631/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 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
    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
    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
    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
    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
    $246/day
    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
    Antigua Barbuda Sailing lessons and expedition!
    Sailing in Jolly Harbour · 10 guests

    Antigua Barbuda Sailing lessons and expedition!

    New
    $1,376/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
    $508/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
    $631/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
    $1,130/day
    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
    $1,130/day
    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

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