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Premium Islamorada Boat Rental | 29' Grady-White FreedomPremium Islamorada Boat Rental | 29' Grady-White FreedomPremium Islamorada Boat Rental | 29' Grady-White FreedomPremium Islamorada Boat Rental | 29' Grady-White Freedom

Premium Islamorada Boat Rental | 29' Grady-White Freedom

Captain Optional

100% refund within 24 hours of your trip
  • Looks Good

    This date is available.

Easy, low-stress days exploring the Florida Keys, with smooth outings that feel like a highlight of the trip and make guests eager to come back.
Clean, mechanically solid setup that runs reliably, with comfortable space for groups; only minor feedback notes the Bluetooth audio can be tricky to use.
Consistently praised for clear communication, professionalism, and going out of the way to help, creating a smooth, confidence-boosting rental experience.
Renters say this listing is great for:
Family TimeSightseeingRelaxationDate Nights
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AI Overview

Owner's Description

Experience the Florida Keys Like a Local There's no better way to experience the Florida Keys than from the water—and there's no better boat to do it from than our premium 29' Grady-White Freedom. Whether you're looking to snorkel the crystal-clear waters of Alligator Reef Lighthouse, spend the afternoon relaxing at the famous Islamorada Sandbar, explore hidden mangrove channels, enjoy waterfront restaurants, or do a little fishing, this boat is built for it all. Powered by twin Yamaha 300 HP engines, our Grady-White delivers a smooth, dry ride with plenty of power, while premium Garmin navigation and sonar systems make exploring effortless. Comfortable seating, plenty of shade, a Bluetooth stereo, freshwater shower, and a fully enclosed head make it the perfect boat for families, couples, and groups of friends. Unlike many rental boats, our vessel is professionally maintained, meticulously cleaned before every trip, and equipped with everything you need for an unforgettable day on the water. Features • Twin Yamaha 300 HP Engines • Premium Garmin Navigation & Sonar • Bluetooth Stereo • Freshwater Shower • Fully Enclosed Head (Bathroom) • Comfortable Seating & Shade • Snorkeling, Sandbar & Waterfront Restaurant Friendly Good to Know - Self-operated rentals available for qualified boaters. - Independent captains are available upon request. - Fuel is not included. - 20-mile offshore operating limit. - We typically respond to inquiries in under one hour. Whether you're celebrating a special occasion or simply looking for an unforgettable day exploring the Florida Keys, we'd love to help you create an amazing experience on the water.

Serge

Serge

19 total bookings
Capacity
8 guests
Powerboats, Pontoons, & RIBs
Center Console

Reviews

5.0 (6 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. Premium Islamorada Boat Rental | 29' Grady-White Freedom
  2. Premium Islamorada Boat Rental | 29' Grady-White Freedom
  3. Premium Islamorada Boat Rental | 29' Grady-White Freedom
  4. Premium Islamorada Boat Rental | 29' Grady-White Freedom
  5. Premium Islamorada Boat Rental | 29' Grady-White Freedom
5 photos have been added by reviewers who booked this listing.
  1. KL

    Kris

    We had an incredible experience renting from Serge! From start to finish, the process was simple and seamless. Serge was professional, responsive, and extremely accommodating—he made sure everything was clear and easy for us, which we really appreciated. The boat itself was exactly what we were looking for: clean, in great condition, and ran perfectly. It was the perfect setup for getting a group of friends out on the water together. We’re already looking forward to our next outing and fully intend to rent with Serge again in the future. Highly recommend!

  2. Dave
    Dave

    Great boat and experience! Serge and Bob went out of their way and the boat was a highlight of our trip to the Keys. A+++

  3. Paul
    Paul

    Everything as described. Communication was fantastic. Vessel was mechanically well maintained.

  4. RO

    Rebecca

    The GW was perfect for us. We needed a boat large enough to take out 7 people but also capable of being comfortable for our elderly family members. The boat was very clean and taken care of. Todd was helpful at the dock with showing how to work everything. We had a great day on the water. I would certainly rent again the next time we come down to the Keys for vacation.

  5. Shane
    Shane

    The 29’ Grady White that I rented was perfect for our trip. It was clean and was in great mechanical condition. I would recommend this boat to any of my friends or family visiting the middle keys.

Serge

Serge

19 total bookings

After years of the hustle and bustle of New York City, I found my escape in the stunning beauty of the Florida Keys. This is my happy place—a paradise where you can truly relax, recharge, and embrace life on the water. But like so many others, I was frustrated with the lack of quality boat rentals. The same poorly maintained, low-quality boats just didn’t match the magic of this destination. That’s why I decided to build a fleet of higher-end boats that my customers and captains love. Our goal is to provide the highest quality boats, and we pride ourselves on safety, customer satisfaction, and exceptional experiences. Whether you’re fishing, snorkeling, island-hopping, or simply soaking in a spectacular sunset, my team and I are here to make your time on the water unforgettable. For me, it’s more than just renting boats—it’s about helping you embrace the adventure, relax in luxury, and experience the Keys the way they’re meant to be enjoyed. Thank you for your consideration

Features & Details

  • Grady-White
  • Grady-White 285 Freedom
  • Capacity: 8 people max

Safety Equipment

Life Jackets (8)

Operating Equipment

GPS ChartPlotter
Depth Sounder

Guest Amenities

Cabins (1)
Sun Protection
Toilets (1)

Leisure & Entertainment Equipment

Bluetooth
Sound System

Accessories

Fish Finder

Departure Location

The boat's approximate location on a map

You’ll get helpful information for your departure after your booking is confirmed.

Street Address For Arrival

Street Address For Arrival

80460 Overseas Highway
Islamorada, Florida, 33036
United States
Departure Location

Departure Location

Same as Street Address

Cancellation Policy

Free cancellation up to 1 day before your trip.

Additional Terms & Information

Please review the following before booking: - Self-operated rentals are available for qualified boaters with prior boating experience. We reserve the right to verify experience and decline a rental if the operator is not deemed qualified. - Independent captains are available upon request. Captain fees are separate from the boat rental. - Fuel is not included and will be charged based on actual usage upon return. - A $1,000 security allowance is required and may be used for fuel, damage, missing equipment, excessive cleaning, or violations of the rental agreement. - The vessel is limited to 20 miles offshore and must remain within the approved operating area. - No towing, racing, overnight use, or operation while under the influence of alcohol or drugs. - Please arrive 20–30 minutes before your scheduled departure for check-in, vessel orientation, and safety briefing. - Renters are responsible for complying with all Florida boating laws and operating the vessel in a safe and responsible manner. - Weather cancellations due to unsafe boating conditions may be rescheduled or refunded at our discretion. - We take great pride in maintaining one of the cleanest and best-equipped rental boats in the Florida Keys and ask that all guests return the vessel in the same condition it was received. Our goal is simple: provide a safe, hassle-free, and unforgettable day on the water. If you have any questions before booking, we're happy to help and typically respond within an hour.

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  • Multi-Day Trips
  • With Captain
  • Self-Captain