The 7 Best Boat Rentals in Naples Florida with Hidden Gems Included


Welcome to my unofficial guide to Best Boat Rentals in Naples Florida!

After spending the last few weeks in Naples (FL) we have done the unthinkable with my girlfriend; that’s right we have tried and tested boat rental companies to bring you the best of the best; meanwhile, I’ve forgotten to pack sunscreen (more than once) and she will never let me hear the end of it.


Finding the right boat rental comes down to three things, to the boat you want, what you want to do and your budget. As soon as you know this it’s super easy to choose the right company.

You see I met my lovely girlfriend while wandering through the USA. She was a wanderer as well and since then we have been together. Sometimes we play the role of secret shoppers without benefits yet we blog about our experiences.

Since we love Naples FL so much we thought it would be a great idea to see which are the best rental companies for boats. We have tested them all and these are our results.

I’m ranking the top 7 best companies on customer service, ease of rental process, boat options, and of course price.

You can rest assured that no matter which you choose from the list below you will have a great time. There are only the best companies listed.

Let me see them already!




#1 On the Pontoon Boat – Best Pontoon Boat Rentals Naples Florida

This rental service was the most recommended one from them all so I’ve decided that we will try this one first.

It’s the perfect way to explore the beauty of Naples and Keewaydin Island.

I can’t rave enough about the staff. You name it they have it on board. Let it be cool drinks or anything that you want.

Heads up! Getting to Keewaydin Island will be about an hour. And it’s not boring at all. You can frequently see dolphins and other wildlife.

Here’s why it’s my #1 pick:

  • The staff members were pleasant, knowledgeable, and incredibly helpful.
  • The trip to the island was lovely, but be warned that it takes about an hour.
  • Brace yourself this boat can really sprint!
  • The boat was in excellent condition and fully met our expectations.
  • Their instructions and map were extremely helpful.
  • We managed to get a beautiful view of dolphins

#2 Captain Joey D Charters – Boat Rental With Captain Naples Florida

Next I wanted to try a bit of fishing. I’m no master fisherman not even by a long shot still I managed to catch a few for bragging rights.

There’s no real adventure without some danger.

We were out on the open sea with my girlfriend, and we were having the time of our lives. As mentioned I’ve caught a few fish, and it was a blast! Then, out of nowhere, the fog rolled in. We couldn’t see a thing. I started to get worried, but the captain reassured us that he had everything under control.

Sure enough, he managed to get us back to port safely. I was so relieved! It was a great experience, and I would highly recommend Captain Joe D Charters to anyone looking for a fun fishing trip. Thanks, Captain Jason! You’re the best!

These are the reasons why you should choose to rent this boat:

  • The crew is knowledgeable and friendly
  • They provide a great experience for people who have no prior fishing experience
  • The captain is helpful and makes sure everyone has a good time
  • You can catch a lot of fish
  • The captain cleans and fillets the fish for you
  • Beats the hell out of owning and maintaining your own boat
  • If you’re interested in history or architecture you can have your learn all about it

#3 Pure Florida Charter – Best Private Boat Rentals Naples Florida

My birthday was coming up and my girlfriend had given me a gift certificate for a fishing charter. Plus we wanted to test them out so we would be hitting two birds with one stone.

I booked an 8-hour charter with Captain Mike and first mate Nick. Both men were professional and gracious. We went to at least 5 locations, hey the more places you go the chances are higher for a great catch.

Now from the 3 of us man sadly I caught the least amount of fish. At least I’ve got a few so I have a story to tell to our friends at home. Even my girlfriend managed to catch one and like a true professional she quit while she was ahead.

We had a blast on this charter.

Here are the top reasons why you should rent them:

  • The crew is professional and experienced
  • You don’t need to worry about bait or gear
  • You just focus on spending the day and having a good time
  • They go to at least 5 locations, so you have a good chance of catching fish
  • The boat is in great condition and it’s super comfortable
  • It’s a great option for groups or families
  • It’s a great value

#4 Island Sailing – Best Boat Rental Near Me

We weren’t ready for this boat. The pictures don’t do justice for it.

As we boarded the enormous sailboat, I couldn’t help but feel a sense of excitement.

We decided to take a day trip out to see the sights of Naples from the sea. We were greeted by the captain, who was a serious man with a welcoming smile.

After a quick safety lesson, we were off.

The journey was peaceful and relaxing as we sailed by the beautiful homes and yachts that lined the coast.

Our captain was happy to give us a tour of the area, and we were all entranced by his stories of life on the sea. As the sun began to set, he turned off the engine and opened up the sails.

We sat back and enjoyed the gentle breeze as the sun slowly disappeared behind the horizon. It was a truly magical experience, and I was so grateful to have had the chance to do it.

If you’re looking for a unique way to see Naples, I would highly recommend taking a boat trip with Island Sailing.

Here’s why I would rent them out:

  • The Naples pier was easily accessible as the meeting spot
  • The boat was huge and clean, and everything fitted even the kitchen sink
  • If you’re looking for a fun and exciting way to see the city this is the best choice
  • The boat is fitted with both an engine and sail and if you want to enjoy some quiet you can glide with the sails only

#5 Destination Boat Clubs – Best Naples Boat Rentals

Full disclosure time. We love Naples so we decided to join a boat club.

If I happened to get a boat my girlfriend would probably walk me over the ledge. Plus we’re traveling a lot so there’s no way for me to maintain or even enjoy my own boat (I’m not writing this under duress).

Best of all there are many boats to choose from so there’s no way to get bored in the near future. Plus they are upgrading the fleet so you can even choose a different boat every week.

Best of all it’s super affordable and they won’t charge you an arm and a leg.

Here’s why they are a great choice:

  • The club offers a wide variety of boats to choose from, ensuring that you can find the perfect one for your needs
  • The customer service is consistently excellent, with kind and helpful personnel
  • The president of Destination Boat Club, Dirk, is incredibly helpful and responsive to members’ needs
  • The cost of membership is reasonable when compared to private boat ownership, and you’ll have access to boats in multiple locations
  • You don’t have to deal with the hassle and aggravation of maintaining your own boat when you’re a member of Destination Boat Club

#6 Freedom Boat Club

Just our luck we’ve managed to book it on the hottest day of the year.

The sun was beating down mercilessly, and the humidity was suffocating. We had been looking forward to this day all week long, and we couldn’t wait to get out on the water.

We climbed into my boat and the captain started the engine. The cool, refreshing water was calling our name. We headed out of the marina.

As we made our way through the narrow channels, the captain kept my eye out for any signs of wildlife. Suddenly, we saw a large splash off in the distance. He quickly steered my boat towards the commotion.

As we got closer, we could see that it was a bunch of dolphins. They were swimming and playing in the water, and they didn’t seem to mind my presence. We sat back and enjoyed the show for a while before heading back to the marina.

Here’s why they are a great choice:

  • Freedom Boat Club offers access to a variety of boats, so you can find the perfect one for your needs.
  • You don’t have to worry about cleaning or maintaining the boat – everything is done for you.
  • You can keep the boat overnight if you need to, which is great if you’re on a fishing trip and want to stay out late
  • The boats are all in great condition and are well-maintained
  • The staff is friendly and helpful, and they’re always available to answer any questions you may have
  • The dock masters are fantastic and will help you with anything you need.

#7 Island Hopper Boat Rental

Finally we booked Island Hopper.

Chase was our guide on the Island Hopper Boat Rental. As we cruised down the river, he showed us different wildlife and told me about the area.

He was very knowledgeable and informative, and we learned a lot about the Ten Thousand Islands.

We stopped at White Horse Key for a while before heading back to the mainland. I was amazed by how beautiful the beaches were, and my girlfriend collected a few shells as souvenirs.

Chase let us open it up once we were out of the canal/minimum wake zone, which was one of the highlights. We had all of the benefits of a tour with some of the freedom and privacy you’d get from renting your own boat.

It was a lot of fun, and I would recommend it to anyone visiting the Naples area.

Here’s why they are an excellent choice:

  • Island Hopper Boat Rental is a great choice because their guides are knowledgeable and passionate about their work.
  • They offer a variety of tours that cater to different interests.
  • They have a variety of boats that can accommodate different groups sizes.
  • Their prices are affordable and they offer packages that include discounts on multiple tours.
  • They have a convenient location that is easy to find.
  • They offer a unique experience that is perfect for adults and children alike.
  • They provide an amazing opportunity to see wildlife up close and personal.

What are Cheap Boat Rentals Naples Florida?

Here’s a list of Cheap Boat Rentals Naples Florida:

  • Park Shore Marina and Boat Rentals
  • Extreme Family Fun Spot
  • Bayfront Boat Rentals
  • Port O Call Marina

Which companies offer Party Boat Rental Naples Florida?

Here’s a list of companies that do Party Boat Rental Naples Florida:

  • Pontoon Boat Rental
  • Boat Rentals at Naples Bay Resort
  • Naples Boat Rentals, by On The Pontoon Boat Inc.

Are there Boat Rentals on Marco Island?

Yes there are Boat Rentals on Marco Island and here’s the list:

  • Gator Boat Rentals
  • Southwest Florida Boat Club & Rentals
  • Big Marco Boat Rentals
  • Rose Marina
  • Dolphin Cove Marina

Is there a Groupon for Boat Rentals in Naples Florida?

Yes, currently there’s a Groupon for Boat Rentals in Naples Florida for Extreme Family Fun which is up to 37% off.

Conclusions on Best Boat Rentals in Naples Florida

We had a great time on these boat rentals. Each of them had something unique to offer. If you simply can’t get a boat then renting one out for a few hours or days is the next best thing.

From fishing to private tours you name it these have a lot to offer. We have reached the end of this journey and the next one is soon to come.

I hope you have found the right rental company for the job. They are all excellent and they are the best of the best.

Maybe you can help me out by sharing this post if you found it useful? It would help us a lot. Thank you!

Frequently Asked Questions:

How much does it cost to rent a boat in Naples Florida?

To rent a boat in Naples Florida will cost you anywhere from $36 to $600 an hour. According to the price it can be with a captain or bareboat and you can rent it for a half-day or a full one. Plus you can do fishing or visit the neighboring areas and islands.

How much does it cost to rent a fishing boat in Florida?

To rent a fishing boat in Florida really depends on the location for example in Naples FL you can rent it from $45/h to up to $4000/h in a more popular location and with all the bells and whistles.

How do you get to Keewaydin Island?

The best way to get to Keewaydin Island is by getting to Rose Marina in Marco Island and taking the Hemingway Water Shuttle. By far it’s the easiest because it’s running 7 times a day.

How much is it to rent a boat in Fort Myers?

To rent a boat in Fort Myers will set you back anywhere from $40 to $400 an hour depending on what kind of boat you want and what you want to do with it. Also, these can come with a captain or bareboat.

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