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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,256 Reviews)

    Page 11 of 18 • 416 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico
    Sailing in Fajardo · 6 guests

    Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico

    5.0
    $450/hour
    Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat
    Sailing in Gros Islet · 10 guests

    Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat

    5.0
    $570/day
    Montego Bay All-inclusive Yacht Experience
    Events in Montego Bay · 10 guests

    Montego Bay All-inclusive Yacht Experience

    New
    Superowner
    $998/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
    Charter a Beautiful Lagoon Catamaran 400 S 2 for 17 people
    Sailing in Cartagena · 17 guests

    Charter a Beautiful Lagoon Catamaran 400 S 2 for 17 people

    New
    $180/hour
    3 courses dinner & sunset cruise on a luxury catamaran up to 12 guests
    Sailing in Nassau · 12 guests

    3 courses dinner & sunset cruise on a luxury catamaran up to 12 guests

    New
    $4,800/hour
    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
    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
    Weekly Caribbean Sailing Cruise from Saint Lucia on 44ft Beneteau Yacht
    Sailing in Rodney Bay · 6 guests

    Weekly Caribbean Sailing Cruise from Saint Lucia on 44ft Beneteau Yacht

    New
    $1,141/day
    Sailing Cruise Guadeloupe to Martinique on Beneteau Oceanis 440
    Sailing in Les Abymes · 10 guests

    Sailing Cruise Guadeloupe to Martinique on Beneteau Oceanis 440

    New
    $228/day
    7 to 21 Days Sailing to the Grenadines aboard Beneteau Oceanis 440 Sailing Yacht
    Sailing in Le Marin · 10 guests

    7 to 21 Days Sailing to the Grenadines aboard Beneteau Oceanis 440 Sailing Yacht

    New
    $228/day
    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
    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
    ⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)
    Events in Miami Beach · 49 guests

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

    New
    Superowner
    $750+/hour
    Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami
    Events in Miami · 14 guests

    Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami

    New
    $350/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
    Private Lunch Tour Deluxe in Curacao
    Sailing in Jan Thiel · 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
    Fun Memories, Captain & Crew Included
    Sailing in Bávaro · 100 guests

    Fun Memories, Captain & Crew Included

    New
    Superowner
    Best of 2026
    $100/hour
    😍SPICE RENTED HER CATAMARANS🛥️💃🏾💕🔥VIP Sailing Catamaran
    Sailing in Punta Cana · 25 guests

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

    New
    $113/hour
    Charter The AKKA 68ft catamaran
    Sailing in Oranjestad-West · 15 guests

    Charter The AKKA 68ft catamaran

    New
    $700/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
    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
    Deal of the Week! Leopard 43Ft Catamaran for Rent in Cartagena, Colombia.
    Powerboats in Cartagena · 25 guests

    Deal of the Week! Leopard 43Ft Catamaran for Rent in Cartagena, Colombia.

    New
    Superowner
    Best of 2026
    $643/hour
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    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. QW

      Quentin

      Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat

      Great Captain you’ll be in trusted hands

    2. Nathan

      Nathan

      Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico

      Great day on the water with a great crew! Service was excellent, food was very good and the boat is comfortable and clean. Really fantastic way to spend a day in PR!

    3. Nathan

      Nathan

      Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico

      Beautiful, comfortable boat with a great sound system and excellent food! The captain and crew were great hosts and we enjoyed every minute of our day!

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