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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,344 Reviews)

    Page 16 of 18 • 431 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    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
    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
    $517/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
    $642/hour
    Antigua Barbuda Sailing lessons and expedition!
    Sailing in Jolly Harbour · 10 guests

    Antigua Barbuda Sailing lessons and expedition!

    New
    $1,400/night
    Jeanneau Sun Odyssey 45 Sailboat for Private Yacht Experience in Saint Thomas
    Sailing in Anna's Retreat · 12 guests

    Jeanneau Sun Odyssey 45 Sailboat for Private Yacht Experience in Saint Thomas

    New
    $232/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
    $1,151/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
    $951/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
    $1,151/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
    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
    $867/day
    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
    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
    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 500 in San Blas Islands
    Sailing in Panama City · 8 guests

    Lagoon 500 in San Blas Islands

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

    Catamaran Charter In San Blas Panama

    New
    $1,284/night
    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
    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
    The Stars are Calling aboard Bali 5.4 Sailing Catamaran in British Virgin Island
    Sailing in West End, Tortola · 10 guests

    The Stars are Calling aboard Bali 5.4 Sailing Catamaran in British Virgin Island

    New
    $5,142/night
    Sailing in the Caribbean St. Martin
    Sailing in Saint Martin · 10 guests

    Sailing in the Caribbean St. Martin

    New
    $1,167/day
    Montecarlo 43’ private sailing boat in San Blas Islands
    Sailing in Guna Yala Comarca · 2 guests

    Montecarlo 43’ private sailing boat in San Blas Islands

    New
    $280/night

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