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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (1,986 Reviews)

    Page 3 of 16 • 369 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Let's go Sailing in Miami!
    Sailing in Miami · 6 guests

    Let's go Sailing in Miami!

    5.0
    $45+/hour
    Instant Book
    Jeanneau Sun Odyssey for an Intimate Cruise in Montego Bay
    Sailing in Montego Bay · 4 guests

    Jeanneau Sun Odyssey for an Intimate Cruise in Montego Bay

    5.0
    $417/hour
    Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico
    Sailing in San Juan · 6 guests

    Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

    4.9
    Superowner
    $198/hour
    Instant Book
    ALL FEES INCLUDED! Endeavor 43 Sailboat Charter out of Miami.
    Sailing in Miami · 4 guests

    ALL FEES INCLUDED! Endeavor 43 Sailboat Charter out of Miami.

    5.0
    Superowner
    $75+/hour
    Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
    Sailing in Miami Beach · 42 guests

    Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

    4.7
    Superowner
    Best of 2025
    $900/hour
    Sunset Sail in Bay of Santa Marta, Magdalena
    Sailing in Comuna 2 · 12 guests

    Sunset Sail in Bay of Santa Marta, Magdalena

    5.0
    $125/hour
    Instant Book
    Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island
    Tours in Fajardo · 6 guests

    Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island

    5.0
    Superowner
    Best of 2025
    $1,500/day
    Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
    Sailing in Fajardo · 6 guests

    Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

    4.9
    $995/day
    Instant Book
    Sailing Hobie Cat Rental in Noord, Aruba
    Sailing in Oranjestad-West · 4 guests

    Sailing Hobie Cat Rental in Noord, Aruba

    4.4
    $89/hour
    48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil
    Sailing in Miami · 13 guests

    48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

    5.0
    $187+/hour
    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura
    Sailing in Nassau · 40 guests

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    5.0
    Best of 2025
    $960/hour
    Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica
    Sailing in Ocho Rios · 40 guests

    Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica

    5.0
    $1,560/hour
    Luxury Lagoon 440 Sailing Catamaran in Key West
    Sailing in Key West · 6 guests

    Luxury Lagoon 440 Sailing Catamaran in Key West

    5.0
    $250/hour
    Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
    Sailing in Cartagena · 45 guests

    Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

    4.9
    Superowner
    Best of 2025
    $300/hour
    Tuna Yacht 38FT for island hopping in Cartagena Cholon Baru Islas del Rosario
    Events in Cartagena · 12 guests

    Tuna Yacht 38FT for island hopping in Cartagena Cholon Baru Islas del Rosario

    5.0
    Best of 2025
    $1,290/day
    Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max
    Powerboats in Fort Lauderdale · 6 guests

    Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max

    4.8
    Superowner
    $113+/hour
    Instant Book
    sunbathe and relax on our island in the middle of the ocean
    Events in Punta Cana · 100 guests

    sunbathe and relax on our island in the middle of the ocean

    3.7
    Superowner
    Best of 2025
    $50/hour
    Discover Miami on this Sea Ray Yacht Charter
    Events in Miami · 12 guests

    Discover Miami on this Sea Ray Yacht Charter

    5.0
    $100/hour
    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay
    Sailing in Collectivity of Saint Martin · 12 guests

    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

    4.9
    $1,161/day
    🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.
    Events in Sosúa · 150 guests

    🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.

    4.4
    $300/hour
    46' Oyster Sailboat in St. Thomas, Virgin Islands
    Sailing in St. Thomas · 6 guests

    46' Oyster Sailboat in St. Thomas, Virgin Islands

    5.0
    $197+/hour
    DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY
    Events in Uvero Alto · 80 guests

    DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY

    5.0
    $50/hour
    🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.
    Events in Sosúa · 150 guests

    🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.

    5.0
    $425/hour
    Sailing Catamaran Yacht for up to 24 Guests in Aruba
    Sailing in Oranjestad-West · 24 guests

    Sailing Catamaran Yacht for up to 24 Guests in Aruba

    4.5
    Superowner
    Best of 2025
    $600/hour
    Instant Book

    Sailing Reviews in Caribbean

    1. FA

      Funmi

      Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica

      Great communication from George and the team, we had a fantastic experience and the catamaran was lovely, and clean. Staff were polite and engaging everyone had a fun time! Thanks so much George 🙏🏾

    2. MM

      Martina

      Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

      You don’t need to think twice, just simply book. We throughly enjoyed our experience from start to finish. I will definitely be returning. Thank you for having us !

    3. SP

      Shelby

      ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

      Rebecca was amazing to work with. She answered all our questions and had us booked ASAP. Max & Mi on the boat made the trip fantastic.

    4. ML

      Michelle

      Jeanneau Sun Odyssey for an Intimate Cruise in Montego Bay

      Sailing with the Captain and his son was really nice. They are friendly and professional, very accommodating. The vibe was amazing, from the tasty drinks, to the delicious sushi. My family had a great time snorkeling.

    5. MG

      Melanie

      46' Oyster Sailboat in St. Thomas, Virgin Islands

      Shana and Nick were the best captains! Served lunch and delicious cocktails! Snorkeling and a relaxing sail. Perfect day!

    6. MJ

      Mollie

      48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

      What a wonderful day with a great captain and a great boat.

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