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    All listings in Florida

    Incredible sailboat rentals in Florida, United States.

    4.9
    (924 Reviews)

    Page 4 of 5 • 104 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Sail From Key Biscayne $195/Hr - $40/Person
    Sailing in Key Biscayne · 6 guests

    Sail From Key Biscayne $195/Hr - $40/Person

    New
    Superowner
    Best of 2023
    $195hour
    Bay Boat Dolphin/Shelling Adventures in Marco Island, Florida
    Powerboats in Marco Island · 6 guests

    Bay Boat Dolphin/Shelling Adventures in Marco Island, Florida

    5.0
    $99hour
    2018 Regal 42' Luxury Yacht for Day Charter or Sunset Cruise
    Events in Aventura · 8 guests

    2018 Regal 42' Luxury Yacht for Day Charter or Sunset Cruise

    5.0
    $334-$350hour
    64' Luxury Horizon Sport Yacht Rental in Fort Myers Beach, Florida
    Events in Fort Myers Beach · 12 guests

    64' Luxury Horizon Sport Yacht Rental in Fort Myers Beach, Florida

    New
    $500-$825hour
    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
    $1,400day
    Sailing Cataraman 48ft "Bubble"
    Sailing in Miami · 12 guests

    Sailing Cataraman 48ft "Bubble"

    New
    $177person
    Sea Ray 270 SDX Luxury Deck Boat Rental in Riverview, Florida
    Powerboats in Riverview · 10 guests

    Sea Ray 270 SDX Luxury Deck Boat Rental in Riverview, Florida

    New
    $160hour
    Hunter 336 Sailing Yacht Charter in Palm Beach, Florida
    Sailing in North Palm Beach · 4 guests

    Hunter 336 Sailing Yacht Charter in Palm Beach, Florida

    New
    $125hour
    55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida
    Events in Tampa · 13 guests

    55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida

    New
    $801hour
    2016 Bali Sailing Cataraman 45ft
    Events in Sunny Isles Beach · 12 guests

    2016 Bali Sailing Cataraman 45ft

    New
    $270-$400hour
    "Thea Marie" Yacht Charter in Riviera Beach, FL
    Sailing in Riviera Beach · 49 guests

    "Thea Marie" Yacht Charter in Riviera Beach, FL

    New
    $1,288hour
    ''Aloan at Last''r Mega Yacht Rental in Sarasota, Florida
    Events in Sarasota · 13 guests

    ''Aloan at Last''r Mega Yacht Rental in Sarasota, Florida

    New
    $1,690hour
    Tampa Bay - Clearwater Area with a perfect & elegant Carver Mariner 38 x 190$/h
    Powerboats in Tampa · 12 guests

    Tampa Bay - Clearwater Area with a perfect & elegant Carver Mariner 38 x 190$/h

    New
    $250hour
    Luxury Sailing Yacht In The Bahamas With Captain Shane!
    Sailing in Fort Lauderdale · 6 guests

    Luxury Sailing Yacht In The Bahamas With Captain Shane!

    New
    $299person
    Day Sail, Sun Rise & Sun Set, Special Event Guided Charter, Si hablo Español
    Sailing in Aventura · 7 guests

    Day Sail, Sun Rise & Sun Set, Special Event Guided Charter, Si hablo Español

    New
    $130-$150hour
    ''Remarkable I'' 54ft Aquila Powercat Rental in Palmetto, Florida
    Sailing in Palmetto · 13 guests

    ''Remarkable I'' 54ft Aquila Powercat Rental in Palmetto, Florida

    New
    $1,147hour
    ''Valentine'' Sea Ray SDX Series Deck Boat Rental in Fort Myers, Florida
    Powerboats in Fort Myers · 12 guests

    ''Valentine'' Sea Ray SDX Series Deck Boat Rental in Fort Myers, Florida

    New
    $535hour
    "Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West
    Sailing in Key West · 6 guests

    "Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West

    New
    $351hour
    "The Cats Meow" Custom Cats Catamaran
    Sailing in Sunny Isles Beach · 12 guests

    "The Cats Meow" Custom Cats Catamaran

    New
    $591hour
    9425 US Hwy 41 S, Riverview, FL 33578
    Tampa · 3 guests

    9425 US Hwy 41 S, Riverview, FL 33578

    New
    $60day
    Hakuna Matata - Party Catamaran in South Florida
    Powerboats in West Palm Beach · 43 guests

    Hakuna Matata - Party Catamaran in South Florida

    New
    $1,000hour
    Single Paddle Kayak
    Adventures in Ellenton · 1 guest

    Single Paddle Kayak

    New
    $25hour
    Palm Breeze - 55ft Party Catamaran for rent in Ft. Lauderdale
    Sailing in Fort Lauderdale · 49 guests

    Palm Breeze - 55ft Party Catamaran for rent in Ft. Lauderdale

    New
    $1,200-$1,266hour
    Experience the Magic of Charm! | Luxury Private Catamaran Charter Service in South Florida and the Bahamas
    Miami · 12 guests

    Experience the Magic of Charm! | Luxury Private Catamaran Charter Service in South Florida and the Bahamas

    New
    $300hour

    Top Destinations Nearby

    Sailing Reviews in Florida

    1. Patricia

      Patricia

      Bay Boat Dolphin/Shelling Adventures in Marco Island, Florida

      We had a great afternoon on the water with Jonallen. He was kind and courteous and knew all of the places to go for a good time. Even the teenagers in our group had a blast and they’re not always easy to please! It was an awesome experience and I’d recommend to anyone who’s looking for a fun time on the water.

    2. Robyn

      Robyn

      Bay Boat Dolphin/Shelling Adventures in Marco Island, Florida

      JonAllen is an outstanding young man with superior captain skills. Very accommodating from the moment we met him. Carried our items to the boat, offered towels, drinks and pleasant conversation. Extremely well versed in the areas water ways. We travel to the area many times per year and I am certain JonAllen will be hearing from us often. Absolutely will not be disappointed!

    3. RP

      Robert

      Bay Boat Dolphin/Shelling Adventures in Marco Island, Florida

      A fantastic boat. First class service, the boat was delivered to the boat ramp and off we went. Fishing and dolphin watching. I highly recommend this boat and Jon and I’ll be renting his boat again soon !!!

    4. sm

      shar

      2018 Regal 42' Luxury Yacht for Day Charter or Sunset Cruise

      Wallace and his wife were incredible hosts. Friendly, on time and flexible. The boat was beautiful with a fly bridge that allowed for great views of the Intra coastal. Would definitely charter again.

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