19 boat rentals in Islamorada, FL
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Rent a Boat in Islamorada, Florida with Sailo!
Looking for the right Islamorada boat rental with a captain? Boating in Florida is a thrilling experience and one best savoured with your own private yacht charter in Islamorada, FL. Choose your perfect boat rental in Islamorada and step aboard with your family or friends for a spectacular day on the water. Escape the crowds and enjoy some of the most beautiful scenery in Florida from the deck of your own yacht charter.
Our premium private boat rentals with a captain in Islamorada
Want to rent a boat in Islamorada, FL? You’ll find 11 boats waiting for you to take them on an adventure here on Sailo. Choose from our sailboat charters in Islamorada. A catamaran is also a great choice, with catamarans in Islamorada. Fans of luxury motor yachts will be spoiled for choice with our motor yachts in Islamorada. Florida is an excellent place to enjoy a boat party, so discover our party boats in Islamorada for 13+ guests in Islamorada and see for yourself.
How to find the best boat charter in Islamorada, FL?
Choosing the perfect boat charter in Islamorada, FL is easy and quick thanks to our advanced filters! First we recommend filtering by date and trip duration. Whether you look for a 2, 4 hrs or a full day rental in Islamorada, the group size is very important, as well as the type of boat you want for your adventure in the waters of Florida. Use the price filter to see only options according to your budget and click on the 'Crew' button to choose if you want a boat with a captain or you want to drive it yourself (option Bareboat). Once a Islamorada charter catches your eye, click on it to see the boat page with more photos and a detailed description. Check the reviews and send a direct message to the boat owner to ask more details!
How much does it cost to rent a boat in Islamorada, FL?
Islamorada boat charters prices vary significantly. You can find great cheap boat rentals in Islamorada starting from $250 for a daily trip. Luxury or party yacht rentals for the day can cost up to $6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in Islamorada with captain and/or crew, fuel cost, special requests for pick-up and drop-off or other special arrangements you may want to make with the owner.
What is Sailo’s cancellation policy?
As long as the booking request hasn't been accepted by the Islamorada boat charter owner, the renter can cancel the request without any charge. If the renter cancels after the booking request has been accepted, the booking will be subject to the terms of the cancellation policy in place for each boat. The renter should check the cancellation policy with the boat owner, as some of the professional operators have specific cancellation policies which supersede that of Sailo. Whenever a boat owner doesn't have a specific cancellation policy,Sailo's Standard Cancellation policy will apply.
Responsible boating guidelines
However long you’re on a boat, it’s always a thrilling and fun experience. Here at Sailo, we like to make sure that the stunning beauty of the seas, lakes and rivers of our planet stay as pristine as possible. If you’re going to charter a yacht, from a few hours to week, try to follow these sustainable boating tips:
- Take your rubbish home
- Use eco-friendly sunblock
- Avoid single use plastic
Much of the world’s plastic ends up in the sea, so reduce, reuse and recycle. Read more about responsible boating.
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| Number of boats | 19 boats available |
|---|---|
| Types of boats | Motor, Party, Sailboat, Catamaran |
| Average price | $784 per day |
| Minimum price | $450 per day |
| Maximum price | $2,000 per day |
| Manufacturers | Beneteau, Jeanneau, Sea Ray, Lagoon, Bali, Bavaria, Catalina, Azimut |
In 2026, Islamorada remains a premier destination: Pontoons and Deck Boats (perfect for the sandbar) average $150–$350 per hour; Center Consoles (for fishing and snorkeling) range from $200 to $500 per hour; and Luxury Adventure Boats or high-end sportfishers typically range from $450 to $1,500+ per hour including a captain. Expect to spend roughly $900 to $2,500 for a full-day private experience.
The 'Islamorada Trifecta' includes: 1) Anchoring at the famous Holiday Isle Sandbar (Whale Harbor) for a waist-deep water party; 2) Snorkeling the vibrant patch reefs at Alligator Reef Lighthouse; and 3) Exploring the historic ruins of Indian Key State Historic Site, which is only accessible by boat. For anglers, a 'backcountry' trip into the mangroves of Everglades National Park is world-class.
Islamorada is surrounded by 'skinny water'—shallow seagrass flats that can be treacherous for those unfamiliar with the local tides. A USCG-licensed captain (usually included or available for $50–$100/hr) ensures you won't run aground or damage the protected seagrass, which carries heavy fines in 2026. Plus, they know exactly where the dolphins are playing.
Most charters depart from Plantation Yacht Harbor Marina (at Founders Park), Safe Harbor Islamorada, or the iconic Bud n' Mary's Fishing Marina. Many luxury listings also offer pickups at the docks of resorts like Cheeca Lodge or Postcard Inn for a more seamless 'door-to-dock' experience.
Absolutely. Islamorada is the heart of the Keys. A motorboat can reach Key Largo (to the north) or Marathon (to the south) in about 45 to 60 minutes. These are popular choices for full-day 'Island Hopping' itineraries, allowing you to see the Seven Mile Bridge or the Christ of the Abyss statue in a single trip.
Most rentals are BYOB, but Islamorada is the king of 'Dock-and-Dine.' You can have your captain pull up to the Lorelei Cabana Bar or Lazy Days for a fresh-catch lunch. For a 2026 'VIP' experience, many hosts offer catering add-ons featuring local stone crab claws and key lime treats. Pro tip: Most boats have a 'No Red Wine' policy to protect the decks.
If you were born on or after January 1, 1988, Florida law requires a Boating Safety Education ID Card. If you book a captained rental, you are exempt as the captain is the legal operator. For bareboat (self-drive) rentals, this card is mandatory (visitors can obtain a 90-day temporary certificate online).
For standard 2-to-4-hour sandbar trips or local sightseeing, fuel is frequently included. For full-day offshore fishing or high-speed runs to the Everglades, fuel is typically charged based on consumption at the end of the trip (the 'full-to-full' policy). Always check the 'Price Includes' section for 2026 fuel specifics.
Standard private '6-pack' charters are limited to 6 guests, while larger luxury '12-pack' yachts allow up to 12. For bigger celebrations like a wedding party or corporate retreat, Islamorada features unique Tiki Boats and large Catamarans on Sailo licensed to carry up to 18–40 passengers.
For the best 'glassy' water and snorkeling visibility, aim for May or June. If you're coming for the famous fishing, March through May is prime for tarpon and sailfish. Be aware that Hurricane Season (June–November) can bring afternoon storms, but your Sailo captain will monitor the radar to ensure you stay in the 'blue' and away from the 'gray.'