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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,280 Reviews)

    Page 11 of 19 • 433 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    Have an amazing time in Cartagena, Colombia on Beneteau 41 Sailboat
    Sailing in Cartagena · 8 guests

    Have an amazing time in Cartagena, Colombia on Beneteau 41 Sailboat

    New
    Superowner
    $1,220/day
    Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull
    Sailing in Cartagena · 10 guests

    Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull

    New
    Superowner
    $163/hour
    Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten
    Sailing in Saint Martin · 8 guests

    Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

    5.0
    $1,000/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
    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
    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
    Montego Bay All-inclusive Yacht Experience
    Events in Montego Bay · 10 guests

    Montego Bay All-inclusive Yacht Experience

    New
    Superowner
    $998/hour
    Private Catamaran to Saona Island – Full-Day All-Inclusive Paradise!
    Powerboats in Bávaro · 50 guests

    Private Catamaran to Saona Island – Full-Day All-Inclusive Paradise!

    New
    $1,480/day
    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
    Punta Cana: Ultimate Private Yacht Party with Snorkeling
    Events in Bávaro · 10 guests

    Punta Cana: Ultimate Private Yacht Party with Snorkeling

    New
    $320+/hour
    50 Luxury Sailing Catamaran in Miami
    Sailing in Fort Lauderdale · 12 guests

    50 Luxury Sailing Catamaran in Miami

    5.0
    $390/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
    50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!
    Sailing in Miami Beach · 42 guests

    50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!

    New
    Superowner
    Best of 2026
    $850/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
    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
    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
    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
    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
    $1,142/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
    ⛵️ 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

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. SA

      Sharon

      50 Luxury Sailing Catamaran in Miami

      Just book it! You will NOT regret it. I promise- it's an amazing experience! The crew (Leornardo and Alina) were awesome and very accommodating! Book with these two!

    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. AS

      Aaron

      Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

      Great time sailing with Robert in Sxm. Food and drinks were great. Only on the boat for two nights but got a lot done for the amount of time we had available.

    4. 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!

    5. Blue

      Blue

      50 Luxury Sailing Catamaran in Miami

      Leo and crew were fantastic, and my friends and I had a blast out on the water! Can't wait to do it again.

    6. MC

      Michael

      Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

      Wonderful day. Highly recommend.

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