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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,320 Reviews)

    Page 16 of 19 • 434 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    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
    Sailing in the Caribbean St. Martin
    Sailing in Saint Martin · 10 guests

    Sailing in the Caribbean St. Martin

    New
    $1,154/day
    It's a Water Planet, Sail it - Beneteau 41S5 Sailboat
    Sailing in Miami · 6 guests

    It's a Water Planet, Sail it - Beneteau 41S5 Sailboat

    New
    $200/hour
    Luxury Lagoon 620 Essence Sailing Catamaran in The Bahamas
    Sailing in Nassau · 25 guests

    Luxury Lagoon 620 Essence Sailing Catamaran in The Bahamas

    New
    $1,225/hour
    65ft Searay Power Mega Yacht Rental in Miami, Florida
    Sailing in Miami · 13 guests

    65ft Searay Power Mega Yacht Rental in Miami, Florida

    New
    $450/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
    Boat Tours in Panama
    Sailing in Panama City · 70 guests

    Boat Tours in Panama

    1.0
    $125/day
    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
    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
    $940/day
    Bali 4.0 Catana Power Catamaran – Perfect Escape
    Powerboats in Hollywood · 13 guests

    Bali 4.0 Catana Power Catamaran – Perfect Escape

    New
    $300/hour
    Antigua Barbuda Sailing lessons and expedition!
    Sailing in Jolly Harbour · 10 guests

    Antigua Barbuda Sailing lessons and expedition!

    New
    $1,384/night
    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
    $1,137/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
    Come and enjoy the Spanish Virgin Island onboard 38ft Hunter Marine
    Sailing in Fajardo · 6 guests

    Come and enjoy the Spanish Virgin Island onboard 38ft Hunter Marine

    New
    $200/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
    Jeannuea Internacional 51" Sailboat - Jump onboard and relax!
    Sailing in Cartagena · 6 guests

    Jeannuea Internacional 51" Sailboat - Jump onboard and relax!

    New
    $170/hour
    Your Private Yacht for the Day – Lagoon 42 Full-Day Charter
    Sailing in Fajardo · 6 guests

    Your Private Yacht for the Day – Lagoon 42 Full-Day Charter

    New
    $2,500/day
    Welcome aboard a stunning 2022 Bali 42 Cruising Catamaran
    Sailing in John's Hole · 8 guests

    Welcome aboard a stunning 2022 Bali 42 Cruising Catamaran

    New
    $550/hour
    Lagoon 50 in San Blas Islands
    Sailing in Panama City · 8 guests

    Lagoon 50 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
    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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