Pontoon in Florida Keys

8 boats available

The best out of 8 deals in Florida Keys - enter dates to check availability

Top Pontoon in Florida Keys

  • 26 ft
    •
    up to 6
    3 Hour Trip – Fun in the Sun (AM)
    Join us for a fun day in the sun! We would love to customize your 3-hour trip just for you. We can swim, use the waterslide, and enjoy some fun fishing! Please note we do not visit sandbars and we do not provide Snorkel equipment
    Instant Confirmation
    Price for up to 6 people
    US $599
  • 23 ft
    •
    up to 6
    4 Hour – Vitamin Sea Tour
    Departure time is flexible! We will set a destination on our Vitamin Sea Tour and recharge your senses with a day of relaxation, sun, and ocean breeze! This unforgettable tour is designed to give you a much-needed dose of adventure and tranquility on the open waters. You deserve some downtime. Our Barletta Tritoon boat offers the feeling of a cozy living room on the ocean.
    Price for up to 6 people
    US $650
  • 25 ft
    •
    up to 24
    6 Hour – Large Groups 7-12 Guests
    6Hrs Famous Islamorada Sandbar with add-ons - Snorkel, Sightsee, and Bar Hop/Booze Cruise, with all the floats, paddleboards, & coolers. BEST DAY EVER for your Large Group. NOTE: USCG Law restricts private boat captains to limit 6 passengers or fewer WHILE DRIVING. Although our largest boats can physically hold 12-13 guests, our trip adds on transport boats for the ride to locations and includes the biggest boats for everyone to board all together while anchored. Price includes all 2 boats and minimum tip
    Price for up to 24 people
    US $2,250
  • 24 ft
    •
    up to 6
    2 Hr – Sunset Cruise
    A personalized, guided sunset cruise through the Everglades and Florida Bay. Enjoy stunning views, peaceful waters, and the warmth of the setting sun as you explore the wild beauty of Key Largo.
    Per person
    US $74
  • 28 ft
    •
    up to 6
    1 Hour Excursion
    Pick and choose any combination of excursions from Eco-Tour Sandbar Sunset Moonrise / Evening Diving Fishing Shrimping Every charter is PRIVATE and custom tailored to YOUR needs including departure times. Availability is based upon reservations. Open 7 days week 7am - 10pm. We have plenty of cooler space for any drinks or snacks you want to bring along. Enjoy our spacious and CLEAN tour boat 'Aloha Friday' where everyday is FRIDAY. Come experience the VERY best of Key Largo with Living Aloha Excursions!
    Price for up to 6 people
    US $375
  • 40 ft
    •
    up to 34
    4 Hour Boat Cruise
    Cruise the beautiful waters of Islamorada on a relaxing 4-hour private boat tour. Perfect for swimming, sightseeing, or just unwinding with your group. The boat includes an onboard restroom for added comfort, and ice is provided—just bring your favorite drinks and snacks. A 21% gratuity is expected for your captain.
    Instant Confirmation
    Price for up to 34 people
    US $2,500
  • 23 ft
    •
    up to 6

    Poppa Toon

    Islamorada
    2 Hr – Sunset Experience
    Experience the breathtaking beauty of an Islamorada sunset from the comfort of a luxurious pontoon boat. Set sail across the tranquil waters of the Florida Keys as the sun dips below the horizon, painting the sky in stunning shades of color. Relax and unwind with your loved ones as you cruise along the scenic coastline, taking in the sights and sounds of this tropical paradise.
    Instant Confirmation
    Price for up to 6 people
    US $575
  • 4 ft
    •
    up to 8
    8 Hour – Islands and Sandbars
    Spend an unforgettable day exploring the beautiful waters around Stock Island on this 8 Hour – Islands and Sandbars adventure. Visit hidden islands, relax on stunning sandbars, and island-hop through the best spots the area has to offer while enjoying a full day of tropical exploration. A delicious Cuban sandwich is included for each guest, making this the perfect combination of adventure, relaxation, and local flavor.
    Price for up to 8 people
    US $1,000

What boaters said about Pontoon

  • 5.0
    /5
    (4 Hour – Customers Choice AM Trip)

    We had such a great time!

    The owner and captain/crew was absolutely awesome! The pontoon was very spacious and comfortable, the pictures don't do it justice. We snorkled at Sombrerro Reef. We saw plenty of Yellowtail, Barracuda and even saw a Nurse Shark. We caught tons of fish to bring back to the house and made some awesome fish tacos for dinner. Would book again if we come back to the keys.
    Karen B.
    Karen B.
    Reviewed on Jun 3, 2026
  • 5.0
    /5
    (4 Hour Trip – Fun in the Sun (AM))

    So much fun!

    We enjoyed our time on the pontoon! Captain Casey was great! She is very knowledgeable of the marine life and water ways!
    Jennifer S.
    Jennifer S.
    Reviewed on Jul 18, 2025
  • 5.0
    /5
    (4 Hour – Boat Trip (AM))

    Captain James took great care of my family. Took us to a great spot to release my wife's ashes and took the time to show and explain things to my overly inquisitive grandsons. Definitely recommend

    Captain James took great care of my family. Took us to a great spot to release my wife's ashes and took the time to show and explain things to my overly inquisitive grandsons. Definitely recommend
    Mark P.
    Mark P.
    Reviewed on Oct 17, 2026
  • 5.0
    /5
    (8 Hour – Boating Adventure (AM))

    A day well spent, great for a special group outing

    We spent a day with Captain Carlos- great trip, and he was very accommodating to our group of 10. One thing to note- the boat did hold all of us, but may be a more comfortable ride with 8. Highly recommend a full day of cruising, as a half a day is too short.
    Jill E.
    Jill E.
    Reviewed on Oct 19, 2026
  • 5.0
    /5
    (4 hour - Sunset Cruise)

    Amazing time

    Awesome Captain, immaculate boat and outstanding experience. Highly recommend
    David T.
    David T.
    Reviewed on Oct 17, 2026