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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,379 Reviews)

    Page 12 of 19 • 439 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Hunter 450 Passage Yacht - Sail From Key Biscayne
    Sailing in Key Biscayne · 10 guests

    Hunter 450 Passage Yacht - Sail From Key Biscayne

    New
    Superowner
    $250/hour
    Punta Cana - PARTY BOAT (ADULT ONLY)
    Sailing in Bávaro · 200 guests

    Punta Cana - PARTY BOAT (ADULT ONLY)

    New
    $984/hour
    Clear Kayak Mangrove Cay Eco Venture 2-hour tour
    Adventures in Leeward Settlement · 10 guests

    Clear Kayak Mangrove Cay Eco Venture 2-hour tour

    New
    $200/hour
    4Hours🎊Birthday-Bachelorette luxury private Boat🛥️🏝️🍾 PARTY in Punta Cana
    Events in Punta Cana · 150 guests

    4Hours🎊Birthday-Bachelorette luxury private Boat🛥️🏝️🍾 PARTY in Punta Cana

    New
    $50/hour
    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami
    Events in Miami · 13 guests

    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami

    New
    $250/hour
    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!
    Sailing in Saint Martin · 20 guests

    Full day Anguilla Tour with Lagoon 450 Cruising Catamaran!

    New
    $2,862/day
    Puerto Plata Private 6 Hour Catamaran Snorkel and BBQ
    Powerboats in Sosúa · 20 guests

    Puerto Plata Private 6 Hour Catamaran Snorkel and BBQ

    New
    $265/hour
    Instant Book
    Private Sunset Proposal Experience – All Inclusive (For 2 People)
    Sailing in El Cortecito · 6 guests

    Private Sunset Proposal Experience – All Inclusive (For 2 People)

    New
    $1,060/hour
    Instant Book
    Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish
    Sailing in Negril · 100 guests

    Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish

    New
    $1,800/hour
    Sunset cruise on a luxury catamaran up to 20 guests
    Sailing in Nassau · 20 guests

    Sunset cruise on a luxury catamaran up to 20 guests

    New
    $933/hour
    ⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)
    Events in Miami Beach · 49 guests

    ⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)

    New
    Superowner
    $750+/hour
    Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ
    Sailing in Punta Cana · 70 guests

    Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ

    New
    $125+/hour
    Instant Book
    Private Lunch Tour Deluxe in Curacao
    Sailing in Santa Barbara Plantation · 6 guests

    Private Lunch Tour Deluxe in Curacao

    New
    $299/hour
    😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎
    Events in Sosúa · 18 guests

    😎 For Exclusive Party Yacth in Cabarete, Puerto Plata 😎

    New
    Superowner
    Best of 2026
    $75/hour
    Charter The AKKA 68ft catamaran
    Sailing in Oranjestad-West · 15 guests

    Charter The AKKA 68ft catamaran

    New
    $700/hour
    Luxe 75ft Sailing Catamaran Serving Key West & Miami Florida
    Events in Key West · 12 guests

    Luxe 75ft Sailing Catamaran Serving Key West & Miami Florida

    New
    $14,750/night
    Fun Memories, Captain & Crew Included
    Sailing in Bávaro · 100 guests

    Fun Memories, Captain & Crew Included

    New
    Superowner
    Best of 2026
    $100/hour
    Party Boat that can host 150 people in La Romana, Dominican Republic
    Events in La Romana · 150 guests

    Party Boat that can host 150 people in La Romana, Dominican Republic

    New
    Superowner
    Best of 2026
    $100/hour
    Punta Cana: Ultimate Private Yacht Party with Snorkeling
    Events in Bávaro · 10 guests

    Punta Cana: Ultimate Private Yacht Party with Snorkeling

    New
    $320+/hour
    Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises
    Events in Miami · 14 guests

    Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises

    New
    $250/hour
    All inclusive Bali 4.4 Luxury Catamaran Charter
    Sailing in Nassau · 10 guests

    All inclusive Bali 4.4 Luxury Catamaran Charter

    New
    $720/hour
    😍SPICE RENTED HER CATAMARANS🛥️💃🏾💕🔥VIP Sailing Catamaran
    Sailing in Punta Cana · 25 guests

    😍SPICE RENTED HER CATAMARANS🛥️💃🏾💕🔥VIP Sailing Catamaran

    New
    $113/hour
    💥 51' Leopard + 1 FREE Extra Hour in Cartagena, Colombia 💥
    Powerboats in Cartagena · 35 guests

    💥 51' Leopard + 1 FREE Extra Hour in Cartagena, Colombia 💥

    New
    Superowner
    Best of 2026
    $843+/hour
    Instant Book
    Catamaran Lagoon 62’ 2019 for a week in BVI
    Sailing in John's Hole · 8 guests

    Catamaran Lagoon 62’ 2019 for a week in BVI

    New
    Superowner
    $10,500/day

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