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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,175 Reviews)

    Page 17 of 18 • 432 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports
    Powerboats in Fajardo · 6 guests

    Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports

    New
    $650/day
    Instant Book
    Nautitech 40 in San Blas Islands
    Sailing in Panama City · 7 guests

    Nautitech 40 in San Blas Islands

    New
    $1,550/night
    Jamaican Party Boat In Punta Cana Noahs Ark
    Sailing in Bávaro · 50 guests

    Jamaican Party Boat In Punta Cana Noahs Ark

    New
    $265/hour
    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
    Lagoon 450 - Catamaran sail rental in Le Marin - Martinique
    Sailing in Le Marin · 12 guests

    Lagoon 450 - Catamaran sail rental in Le Marin - Martinique

    New
    $864/day
    Book your dream vacation on the Lagoon 51 Athena Blu
    Sailing in Upper Prince's Quarter · 10 guests

    Book your dream vacation on the Lagoon 51 Athena Blu

    New
    $2,457/day
    Premium Catamaran Charter in Santa Marta - 48ft Nautitech
    Events in Comuna 2 · 30 guests

    Premium Catamaran Charter in Santa Marta - 48ft Nautitech

    New
    $220/hour
    Sweden Yachts 38 Day Sail Fort Lauderdale, Si hablo Español
    Sailing in Aventura · 6 guests

    Sweden Yachts 38 Day Sail Fort Lauderdale, Si hablo Español

    New
    $130+/hour
    Amazing beautifully crafted 40-foot-private day sail excursions in St John,USVI
    Sailing in Charlotte Amalie West · 6 guests

    Amazing beautifully crafted 40-foot-private day sail excursions in St John,USVI

    New
    $250/hour
    Instant Book
    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
    15 Days14 Nights Cruise To The Islands Of The Wind - Antilles
    Sailing in Pointe-a-Pitre · 6 guests

    15 Days14 Nights Cruise To The Islands Of The Wind - Antilles

    New
    $37,529/day
    Helia 44 Catamaran: Your Gateway to Adventure and Comfort on the Open Seas
    Sailing in Oranjestad-West · 4 guests

    Helia 44 Catamaran: Your Gateway to Adventure and Comfort on the Open Seas

    New
    $1,584/night
    Explore the British Virgin Islands on a Boston Whaler
    Powerboats in Wickhams Cay 1 · 10 guests

    Explore the British Virgin Islands on a Boston Whaler

    New
    $2,400/day
    Captained Charter on 47ft
    Sailing in Coclé Province · 8 guests

    Captained Charter on 47ft

    5.0
    $2,000/day
    Bahia 46 in San Blas Islands
    Sailing in Panama City · 8 guests

    Bahia 46 in San Blas Islands

    New
    $1,500/night
    Bali Catspace 40 ft Catamaran in Ft Lauderdale for charter to Florida Keys
    Sailing in Fort Lauderdale · 12 guests

    Bali Catspace 40 ft Catamaran in Ft Lauderdale for charter to Florida Keys

    New
    $1,400/day
    Private Catamaran Cruise in Punta Cana, Dominican Republic
    Sailing in Punta Cana · 34 guests

    Private Catamaran Cruise in Punta Cana, Dominican Republic

    New
    $273+/hour
    Luxury Sailing Experience – The Ultimate Caribbean Adventure
    Sailing in Cruz Bay · 6 guests

    Luxury Sailing Experience – The Ultimate Caribbean Adventure

    New
    $250/hour
    Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI
    Sailing in Freshwater Pond · 6 guests

    Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI

    New
    $3,666/night
    Romantic Sunset Sailing in La Boquilla, Bolívar
    Sailing in La Boquilla · 4 guests

    Romantic Sunset Sailing in La Boquilla, Bolívar

    New
    $260/hour
    Luxury Catamaran 38ft private charter for up to 15 people in Cartagena
    Powerboats in Cartagena · 15 guests

    Luxury Catamaran 38ft private charter for up to 15 people in Cartagena

    New
    $170/hour
    Yacht Charter in Split Lagoon 46 Catamaran
    Sailing in Florida · 13 guests

    Yacht Charter in Split Lagoon 46 Catamaran

    New
    $802+/hour
    2024 Valentine's Week in BVi 🍹🍸👙🤟
    Sailing in Fisher Estate · 8 guests

    2024 Valentine's Week in BVi 🍹🍸👙🤟

    New
    $92,160/day
    Performance Sailing Catamaran Adventure
    Sailing in Saint Barthélemy · 6 guests

    Performance Sailing Catamaran Adventure

    New
    $174/hour

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. FO

      Fernando

      Captained Charter on 47ft

      Was the best trip ever! Really recommend this trip and hope soon have a weekend trip in this catamaran

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