Paradise Boat Rental

(20 reviews)

Ian is the best! He definitely went above and beyond to make our Key West bachelorette trip so…read morespecial. Super friendly and fun to chat with, too! Boat was clean and a great time. He has one of those big floating mats, football/games, and a paddleboard to take on the water, too! We just did a 3 hour day but it was the perfect amount of time in the sun for the folks in our group who aren't Florida locals. Ian also doubled as our photographer and videographer and he rocked!!! Would highly recommend Key West Tiki Boat!

From the beginning, it was a great experience. We worked with Ian and he was awesome! He got us to…read morea fantastic spot to hang out and managed to dodge the rain! Ian made this experience so much better by being a fantastic captain and fun to hang out with our group! Highly recommend!

Stock Island Custom Charters

Jamie is fun and personable and everything you'd want from a boat captain! She knew exactly where…read moreto go to experience an awesome sandbar followed by a stop in the dolphin playground where they swam right up next to us. We capped off our trip with a zip around the coast of Key West to see locations like Mallory Square, the southernmost point, and Smathers Beach from the water. Jamie had suggestions for us as far as locations and was able to guide us through a memorable experience without ever feeling rushed. I would highly recommend this charter!

From the owner: We are a private backcountry boat charter in Key West that wants to create the most memorable day…read moreof your vacation. From trips to one of our remote sandbars to sunsets, dolphin/turtle sightings to light tackle fishing. You pick your activities and you pick your times! "It's more fun when you're not the only one having it!"

Dolphin Safari Charters

4.6

(95 reviews)

HIGHLIGHT OF OUR TRIP! We have a 2 and 6 y/o and they cannot stop talking about it. The captain…read morestarted by asking what our goals were for the outing. We wanted to 1) see dolphins, 2) snorkel, 3) spend time at a remote sandbar, 4) anything else he recommended. We were able to accomplish all 4, and then some! We had a pod of dolphins swimming around and under our boat, which was amazing. We found a very shallow sandbar and decided to snorkel there, with our kids being young. We saw fish and found a large conch shell that our 6 y/o still talks about days later. We saw the remnants of a lighthouse in the middle of nowhere. And then ended the day watching the sun go down. Just breathtaking. Cannot recommend it enough. There were also a variety of sodas, waters, and snacks available which came in handy with little ones. A nice touch that we were glad to take advantage of while in the middle of the ocean. In summary... yes, it costs more to charter a boat, but the intimate atmosphere with just your family and friends around make it absolutely priceless. I'd pay triple the price to make these memories with my family, and not have 25 strangers in the background of each picture. Splurge once and you will know EXACTLY what I'm talking about.

Did the three hour dolphin and snorkel ride for $99/person. Originally was supposed to go earlier…read morebut they called me the day before and said the weather would be bad and asked if we could postpone it and I am glad we did because the weather was much sunnier and less windy the next day. James did a great job as our captain. It's nice you can bring your own beverages and they have some snacks on board. We drove around key west stopping at a few points, then rode out to an area to snorkel for a bit where we saw tons of sponges and some little fish, and then head back toward Key West, into the marina, and then back to where we started. Honestly, we didn't see any dolphin until we were on our way back in from snorkeling, and it honestly felt like it was just pure luck that we saw one but thank goodness we did since it was the highlight of the safari. The boat was pretty nice and comfortable. There were 6 total people including Captain James. The front is definitely the best place to see things from, so try to get a seat there if you can, even though it's not under the shaded cover part. It's like $112.36 per person after tax/fees plus there's a big sign on the boat guilt tripping you into tipping at least 20%. It's fine because James did a great job and deserved the 20% tip (although if we didn't bump into that dolphin on the way in, I would've felt a bit ripped off for the price), but basically expect to be out over $130 per person for a three hour boat ride. This can get pretty expensive, especially if you have a family, and I would've felt ripped off if we didn't see a dolphin but luckily we did so it was a cool experience that I definitely recommend when the weather is nice, winds are calm. Their website had higher prices in the description than the $99 that was actually charged so I hope they don't raise their prices because that would get kind of expensive. Especially when I was just in Miami and could rent a 13 person yacht for four hours $1300 so $100/person plus tax and tip is about the most I would be willing to pay for this experience, especially since seeing dolphins isn't guaranteed so you are basically just paying for a 3 hour boat ride.

Leisure Cat Adventure Tours

What an amazing day snorkeling and going to the sand bar!! Our group had an amazing time and Capt…read more Ralph was very knowledgeable. It was great to not be in one of those crowded boats with 40+ people. This private experience was one to remember. We will definitly do this trip again when we visit next year.

From the owner: Avoid the crowded boats where you snorkel with dozens of people. Wouldn't you rather experience Key…read moreWest and surrounding waters on a safe, stable, and fast power catamaran? When you book with Leisure Cat Adventure Tours, you will have many options. We are not a one-trip-boat, our boat is very versatile and can take you to the reef, Mangrove Islands, Backcountry, Sandbars, and Dolphin Playground. Because we are a quick boat and able to go into shallow water, you'll spend more time relaxing at your ultimate destination and activity. We go everywhere!

Life On the Rocks Charters

(15 reviews)

Captain Andres was prompt, gracious, thoughtful, and a very safe captain. We had a wonderful…read morerelaxing excursion and were lucky enough to see a manatee, turtles and dolphins. There was zero pressure and just an overall great time. We look forward to booking with him in the future. Highly recommend.

The trip was great! Beautiful scenery. The under water scooters were fun. Captain Andre was very…read moreknowledgeable about the area and took us to explore some great places. We also got to meet Gemini, a great bonus to the trip.

Boundless Charters Key West

A day out with Captain Derek on his gorgeous boat is worth every penny! If you want a truly…read morememorable and exciting highlight for your trip to Key West, I highly recommend Boundless charters! We had the best day on his boat last year that we booked it first thing this year! Another sensational adventure for our whole family!

From the owner: We are a private charter boat offering Island tours, sandbar, remote beaches, snorkeling, dolphin…read moreencounters, site site seeing and much more

Sun Surf and Sand Charters

Shane and scruffy were awesome. We had a bunch o ladies and we went to a few sandbars. He served…read moreus our drinks while we floated, played the music for us, provided floaties and snorkel gear. A fantastic ladies boat day! We had ten people and two boats. Best part of our trip. Bring your drinks and snacks!!

From the owner: Home of the $99 sandbar charter, dolphin watching tours and all about the smiles on the waters off…read moreKey West....

Laid Back Key West

(23 reviews)

Eric is very knowledgeable and just a great captain He…read moreknows the area and where to fish or float . You'll enjoy the time on his boat When we return, we'll be back to charter Laid Back with Eric

Second time with captain Eric. We went lobstering, saw dolphins , sharks and plenty of reef fish…read more Eric is a very flexible and friendly captain. We will be back in future visits to key west for sure

Key West Sailing Charters

4.1

(9 reviews)

Just left our charter with Captain Jeff and 1st Mate Cassie. Had a great time snorkeling on the…read morereef! Everything was relaxing and laid back, which was just what we needed. If your thinking about going with one of those big company charters where your on the boat with a bunch of other folks, rethink your choice and go with someone that cares whether or not you you have a great time. And yes, we saw these dolphins on our trip.

Had an great time on the two hour sunset tour with Captain Pete and first mate Emily! They provided…read morea large cooler for our drinks, some snacks and great conversation! We were able to sit in seats near the captain, sit on cushions up front towards the bow, or stand by the railings. Emily was super helpful if we needed anything. The sunset was awesome and it was a very pretty sight coming back in twilight. One of the highlights of our trip!!

Fury Water Adventures

4.2

(1.9k reviews)

Just being on the water was great, but the glass bottom viewing of the coral reef was wonderful!…read moreInformative and enjoyable for all ages and abilities! The sunset portion was a great ending to the trip! Friendly crew!

Glass Bottom Boat Sunset Trip. We are locals & took our visiting son & family on the trip. The…read morecaptain was on point & definitely new what she was doing in timing the sunset view, etc. Crew was knowledgeable and attentive. Wish they could offer more to see at the reef -- kind of a let down. Few fish, not much other sea life, and lots of seaweed. Also, we wished they would offer more drinks (beer/wine) & other food choices. Overall, it was an ok trip!

Danger Charters

(1k reviews)

We had a very enjoyable afternoon snorkeling trip and then a beautiful view of the sunset from the…read moresailing ship Sarah, crewed by Captain Micah & Mate James. It was everything we looked forward to!

My husband and I are visiting Key West for the first time and went on a morning snorkel & kayak…read moretour on Thursday. We liked it so much when we came back to shore that we booked their sunset, snorkel, and sandbar tour two days later! Captain Anna was amazing on both trips. The crew members (shout out to Mo, Ali, Anthony, Maddy) work so hard and are really engaging with guests the entire time. It's clear they love the area and their jobs and love sharing it with visitors. Highly recommend for intimacy of a smaller tour.

SunShine Scooters

4.7

(78 reviews)

Rented a moped while in port for a cruise. Total with the insurance for 4 hours and tax is $68…read morewhich I thought was fair. Quick and easy, in and out. No problems with the scooter.

Reasonable priced scooter rental - $60 a day and $10 for insurance (worth it to not bother with…read moreyour own). Friendly and helpful service!

JV Rent'All

4.0

(40 reviews)

Hey little did I know that I would be traveling to Key West when it was 97°. Little did I know that…read morethe scavenger hunt we were on would take us literally 90 miles to accomplish. I am a Midwestern girl, so I am no idea what heatstroke was all about. I found out real quick oh, and that is when we found JV Rental. The gentleman behind the counter was as sweet as sweet could be. He understood our predicament very well, and it was literally less than five minutes from filling out the paperwork to taking off in our golf cart. We were a group from Margaritaville and Margaritaville has electric golf carts, so driving a gas, golf cart was a bit different, a little rougher, but all in all the experience was amazing. Thank you, thank you, thank you J. V. Rental. You literally saved this Midwestern girls life because apparently unbeknownst to me I had a really bad case of heat stroke. You are simply the best.

Easy to rent golf cart. Earlier opening time and after hour drop off if needed. Was a little…read morepricier than some others but we chose them because they were normal size gas carts, not electric, not too small. Would recommend. We did 24 hrs to allow us more time to explore even after they closed.

Paradise Boat Rental - boatcharters - Updated July 2026

People who viewed Paradise Boat Rental also viewed

Fun in the Sun Charters & Boat Rentals

4.4

(45 reviews)

2nd time out with Captain Kyle. He is amazing! We booked a private charter for 3 people and…read morerequested Kyle. It was such a great time! We just love him as a Captain. It couldn't be more perfect! He even found us sun on an overcast day! We will be back next year and request the best captain ever!!!

Perfect! Highly recommend! Seamless from booking to finish! We were lucky enough to have our call…read moreanswered and a last minute private charter. Everything explained perfectly and professionally handled! Captain Kyle was excellent and very much appreciated! We will definitely be back again!

Schooner Jolly II Rover

4.8

(61 reviews)

My husband booked us on this sunset cruise. We wanted a lower keyed experience and it was perfect…read more This tall ship does not serve alcohol or food only water and snacks. The positive side is you get to bring your own alcohol and food if you want. We chose to eat dinner at the Conch Republic seafood house before we boarded. And of course I brought my wine on board. We boarded at 6:15 pm and were greeted by a crew of three. Captain and two mates. They were all awesome full of knowledge answering all our questions while tending to the boat. They are known for their cannon which is fired at other ships veering too close lol. We had a quiet group of 18 souls on board but it was my first time on an actual sail boat so I totally enjoyed it. I highly recommend this as your option if want to avoid the huge boats.

My husband and I decided to board for the sunset tour and it did not disappoint!!!! It was our…read morebest experience ever (we have been on sunset tours on other vacations). This by far was the best ...it was so relaxing and we were able to interact with steering the ship and putting the sails up..no distracting music or having people trip all over you...this is a date night must or one for a good wholesome family night out with your children that will leave you with a lifetime of terrific memories!! These guys know what they are doing!!!!

Sunset Sail Key West

4.6

(62 reviews)

Great music great time. The experience was amazing. They also provide food and all the drinks that…read moreyou need or want. Absolutely a must when you visit Key West or even if you lived here.

What a great experience on a beautiful boat. They only take a handful of people out and it's not a…read moreparty boat which we appreciated. They served wine and beer and the crew had wonderful knowledge of the boat's history. What a nice and calm way to enjoy the sunset!

Cruisin Tikis Key West

(116 reviews)

We had so much fun! Brian was respectful and helped us enjoy the excursion fully. We cant wait to…read morereturn!

This is my second adventure with Cruisin Tikis Key West which rents dock space from Macs…read morerestaurant. Very laid back reservation system directly with the owner Johna. Arrived thirty minutes early to blow up our rafts and register online with an ipod. Brought our snacks and liquor onto the tiki boat with our charismatic captain, Kathy who provided mixers and a quick safety drill. We were off right on time and headed out to the sandbar in the Gulf of Mexico. Light drizzle for the first ten minutes then pure sun for the entire two hours. Loved every minute and would do it again and again. Price is $430 for two hours with a max of six people.

SV Argo Navis

(52 reviews)

We have sailed the sunset cruise 3 years in a row. Top notch…read moreboat and crew. Great night

Had a sunset cruise last night. What an amazing experience. The captain and crew were friendly,…read moreprofessional and just when you thought they couldn't be any better at sailing, they started making drinks and appetizers! Can't wait to do it again !

Schooner Appledore

(113 reviews)

Just took this sunset cruise in Key West. Captain Joe, Christina and Brandon were top notch crew…read more Beautiful Schooner, and fabulous views. I highly recommend tis cruise.

There's something about stepping aboard the Appledore Schooner that hits you square in the chest in…read morea good way. The wood creaks just enough to whisper stories, the sails stretch like they've seen a hundred lifetimes, and even knowing it's a polished replica, it still feels like you've signed up for a voyage out of another century. The breeze rolls in warm and salty, drinks are flowing, food's dialed in, and the crew runs a tight ship without killing the charm. It's not just a boat ride it's a floating time machine with just enough modern comfort to keep you from questioning your life choices. Now toss in my crew a full-blown cast of characters that could rival The Hangover. One guy shows up dressed like a budget pirate, fully committed. Another thinks every moment is an opportunity for a prank. Then you've got the intellectual who knows everything, the guy who drinks like it's a competitive sport, the jokester, the snob and me, somewhere in the middle just trying to keep the ship from turning into a crime scene. I swear, the energy alone had "we're getting kicked off" written all over it before we even left the dock. And sure enough, chaos found us. A "harmless" prank turned into a domino effect one bumped shoulder, one spilled drink, one very offended passenger, and suddenly we're apologizing while trying not to laugh. At one point, our drunk friend got a little too bold near the edge, and let's just say there was a moment where we all collectively realized how quickly a sunset cruise could turn into a rescue mission. Words were exchanged, tensions flared, and for a split second it looked like fists might fly but somehow, like all great misadventures, it smoothed itself out into laughter, stories, and another round of drinks. End of the day? Absolutely worth it. Get on that boat, bring your people, and don't just take the ride make it a story you'll be telling for years.

Brightwild Adventures

(12 reviews)

This was an amazing tour with amazing tour guide guides! Captain Dave, and his first mate Presley…read morewere super professional and friendly. We would absolutely book with this company again and might go back on this very same adventure. We took a sandbar boat trip out of Key West and it was awesome! Lunch and all the drinks you could want were provided and they had lots of water toys. Super fun!!

We took a sunset cruise that was fantastic. It helped that…read moreit was a beautiful night for it. The lady that was the first mate did an excellent job hosting. They offered beer,wine, champagne and non alcoholic beverages to drink. They had Cuban sandwiches to eat with chips and pastries. She took pictures of all the couples right at sun down & did a great job with them. I felt it was a GREAT experience from beginning to end I highly recommend them.

Ware's The Fish Charters

(11 reviews)

We had an awesome day with Captain Al!! Caught a few beautiful black tip tuna using kites which is…read morea skill all it's own that Captain Al made look easy. Also a few small sharks and then we hooked a 7 to 8 foot Hammerhead shark it took my son and I about 50 minutes to bring it along side. It was a pretty amazing experience and we also did a little barracuda fishing for some live action again lots of fun. The boat is very clean extremely well equipped and the captain being retired Coast Guard you know he will keep you safe. Next time in the Keys we will set up another trip for sure.

We had a great fishing trip with Dave…read more We caught a bunch of Maui Maui and tuna. We had fun and I will definitely re book next time and am in key west

Salty Bonez Adventures

4.4

(7 reviews)

Absolutely reserve Anthony for a private boat trip while in the Keys. From start to finish this…read moretrip was amazing for my family. Anthony's boat is top notch, all the equipment is new and nice (paddle boards, masks, etc). Anthony's knowledge and experience of navigating the Key's waterways is outstanding; your family will be safe on this trip! We will definitely book again.

Captain Anthony and his pup Mystic were the highlight of our trip! Perfect boat to go to the sand…read morebars in and float in the beautiful water. Fits 6 guests very comfortably and plenty of storage area for your bags. Giant cooler filled with ice was the perfect touch.

Six Fins Charter