Where the pontoon meets the party!

Mini Pontoon Rentals

Small boats. Big vibes. Our self-guided mini pontoons put you in the captain’s seat for a safe, easy cruise to the Haulover Sandbar. Want the VIP treatment? We also offer private group tours during the week to destinations like Peanut Island, the Islamorada Sandbar, and island hopping in the Florida Keys. Reserve your boat today before they’re all gone—availability at the sandbar fills up fast!

BOOK YOUR BOAT!
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About Us

“From local sandbars to custom tours, we make getting on the water easy.”

At Pirate Flag Pontoons, we believe the best days in South Florida happen on the water — and you don’t need a captain’s license (or a mega yacht) to enjoy them.

We offer guided, or self-guided, 2-person mini pontoon rentals that give you the freedom to cruise to the famous Islamorada Sandbar on your own terms, or take a Sunset Cruise in Key Largo. Our boats are easy to operate, safe, and designed for chill vibes. Whether you’re looking for a spontaneous weekend escape or just want to drop anchor and unwind, we make it simple, fun, and affordable.

We’re a small local business — not a big marina. That means every rental is personal, every boat is cared for, and every guest matters.

Pirate Flag Pontoons is owned and operated by a South Florida native who’s spent a lifetime exploring the waters from West Palm Beach down to Key West. When you rent with us, you’re tapping into years of local know-how and the kind of experience that only comes from growing up on these shores.

You don’t need experience to feel like a captain — just sunscreen, a playlist, and a sense of adventure.

Where the pontoon meets the party — we’ll see you at the sandbar. 🏴‍☠️

Information about our pontoon rentals

🛥 What We Offer

Our 2-person mini pontoons are compact, stable, and incredibly easy to operate — no boating experience or license required.

These boats are perfect for cruising to the sandbar or exploration, dropping anchor, and soaking up the sun. Each pontoon comes equipped with:

  • A 55 lb thrust electric trolling motor
  • Large Bimini Top
  • Two 360-degree swivel seats w/ cupholders (fits large Stanley) and caddy
  • A soft-sided cooler
  • Mesh bag clipped to the Bimini top for your essentials
  • Swim ladder & anchor
  • Navigational lights
  • Life jackets for all passengers (required by law)

🌊 Pirate Flag Pontoons Guided Tours

AM Tour – 9:00 AM to 12:30 PM
$119 per person

Begin your morning with a guided adventure along the beautiful shoreline of Blackwater Sound. Cruise past stunning million-dollar homes, wind through Lake Surprise, and explore the scenic waters of Jewfish Creek. Along the way, enjoy a stop at Black Siren before heading south to admire the eclectic floating homes and decorated houseboats that make this area so unique.

Sunset Cruise – 3:30 PM to 8:00 PM
$139 per person

Spend your evening soaking in the golden hour with a relaxing guided cruise. Follow the same scenic route of luxury homes, hidden creeks, and colorful houseboats—but at sunset, the entire experience transforms with breathtaking skies and calm waters.

🚤 What’s Included

  • Professional guide on every tour
  • Complimentary day pass to JD’s Marina & Beach
    • Relax on the sandy beach
    • Fish from the dock
  • Free on-site parking

🏝️ Full-Day Rentals – Islamorada Sandbar

Looking for a longer adventure? Mini boat rentals are also available for the famous Islamorada Sandbar.

  • $340 for 6 hours
  • $360 for 8 hours

Please message us directly for details and availability.

⚠️ Important Notes

  • Rentals are for 2 people max — no exceptions
  • Minimum age to operate: 18
  • Weather: We monitor conditions and may reschedule for safety
  • We recommend packing light — there is no onboard storage besides the cooler and mesh bag
  • No glass bottles or illegal substances allowed

🧳 What to Bring

  • Sunscreen
  • Water
  • Water shoes or sandals
  • Small towel
  • Drinks, snacks, & ice (we provide the cooler)
  • Bluetooth speaker if you want your own tunes
  • A good attitude — you're going to love this!

🌴 Private Tours (Weekdays Only)

Looking for something more customized or want to bring a group? A knowledgeable local host will guide your group to some of the best sandbars and scenic spots in South Florida.

Perfect for:

  • Small group outings
  • Corporate Team Building
  • Birthday celebrations
  • Bachelorette gatherings
  • Scenic sandbar hopping from Haulover to Key Biscayne or beyond

Private tours are by request only and require a 8-person minimum (4 boats). Itineraries can be customized based on location, weather, and group vibe.

📲 Text 305-771-5002 to request a quote or check weekday availability.

📍Located at 104100 Overseas Highway, Key Largo, FL 33037

Contact us

Got questions about our rentals or private tours? Want to check availability before booking? Drop us a message below and we’ll get back to you ASAP!

📲 Prefer to text? You can also reach us directly at 305-771-5002

🕒 Operating Hours (Rentals by Appointment)

Weekend Rentals:
Sat–Sun: 8:00 AM – 8:00 PM

Weekday Private Tours:
Available by request (Offered on Wednesdays)

📧 Email: [email protected]

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