Your go-to Florida Keys vacation concierge
Key West & The Lower Keys
Exploring Key West and The Lower Keys offers a beautiful balance of open-water freedom and historic island charm.
We have Center Consoles and 24'pontoon boats with an upperdeck that has two waterslides off of it available. Our Backcountry Tours are in some of the most untouched areas, with sea life all around in the water. It is great fun for everyone.
Relax and let a professional take over. A certified captain will be guiding the boat through the Florida Keys waters.
We offer fishing, sandbar, eco tours, sightseeing, lobstering, bar-hopping and more!
Would you like a hotel? Close to everything or all by yourself! Maybe a vacation home with a pool or a boat...or both! Let us help you!
Lower Keys Boat & Jetski Rental
Key West-Boat Rentals
Double Decker Slide Boat
Get ready for an adventure like no other with our Double Decker Slide Boat Charter! Step aboard our spacious double-decker pontoon boat, where the fun begins with a thrilling waterslide off the back deck. Feel the rush as you slide into the inviting turquoise waters of Key West, then soak up the sun on the top deck with panoramic views of the stunning islands and wildlife.
6 Passenger Max
Cudjoe Key-Boat Rentals
20' Glastron
20′ deck boat with a Yamaha 150 HP motor and plenty of wrap around seating for 10 people comfortably with a Yamaha 150 hp motor. Boat is equipped with GPS that has colored tracks to cool locations. This is a leisure cruise around deck boat, fishing is not allowed on this boat
Cudjoe Key-Boat Rentals
22' Crest Tri-Toon
Explore local waters aboard a 22′ Tri Toon with a Honda 150 hp motor, featuring a 9″ GPS with colored tracks to mark notable spots. The boat accommodates up to 12 people and is delivered to your dock between Sugarloaf Key and Summerland at no extra charge, delivery may apply for other locations. Enjoy flexible time on the water while observing the rental’s operational boundaries for a safe, relaxed outing.
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Delivered free to locations between Sugarloaf Key and Summerland
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Lower Keys-Jet Ski Rental
1/2 Day
Perfect for a short thrill!
Duration
4 hours
You must be 21 years old to rent. If you are 18 years old and have a Boater's license, you are allowed to operate. The minimum age to operate with a licensed adult on board the craft is 14 years old.
Our waverunners can accommodate up to 3 people, with a maximum weight capacity of 400 lbs per ski. We deliver skis for full and multiple days between the west end of Big Pine Key to Lower Sugarloaf Key.
Lower Keys-Jet Ski Rentals
Multiday Rentals
Make the most of your vacation with a multi-day jetski rental!
2- 7 day rentals delivered between 8 and 10 am and picked up between 5 and 6 pm
You must be 21 years old to rent. If you are 18 years old and have a Boater's license, you are allowed to operate. The minimum age to operate with a licensed adult on board the craft is 14 years old.
Our waverunners can accommodate up to 3 people, with a maximum weight capacity of 400 lbs per ski. We deliver skis for full and multiple days between the west end of Big Pine Key to Lower Sugarloaf Key.
Key West-Boat Rentals
13 Passenger 25' Double Decker w/ Slides
What's included
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13 Passenger Pontoon Boat Rental; 25' Double Decker with 2 Slides (Children and babies count as passengers)
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Includes two 70qt coolers and life vests!
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Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+.
Optional Add-Ons
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Paddleboards
Paddle Boarding is fun and suitable for people of all ages and abilities. -
Lily Pad
This floating foam island allows you to rest, kick-back, tan, run, and play on. Looking for a fun way to hang out? Book your Lily Pad today. -
Lower Keys Jet-Ski Rental
Full Day
We'll come to you! Enjoy a full day of thrills on our 3 passenger wave runners!
8 hours delivered between 8 and 10 am and picked up between 5 and 6 pm
You must be 21 years old to rent. If you are 18 years old and have a Boater's license, you are allowed to operate. The minimum age to operate with a licensed adult on board the craft is 14 years old.
Our waverunners can accommodate up to 3 people, with a maximum weight capacity of 400 lbs per ski. We deliver skis for full and multiple days between the west end of Big Pine Key to Lower Sugarloaf Key.
Key West-Boat Rentals
12 Passenger 25' Pontoon
What's included
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12 Passenger Pontoon Boat Rental (Children and babies count as passengers)
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Includes a 70qt cooler and life vests!
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Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+
Optional Add-Ons
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Paddleboards
Paddle Boarding is fun and suitable for people of all ages and abilities. -
Lily Pad
This floating foam island allows you to rest, kick-back, tan, run, and play on. Looking for a fun way to hang out? Book your Lily Pad today. -
Key West-Boat Rentals
13 Passenger Double Decker w/ Slide 30'
What's included
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13 Passenger Pontoon Boat Rental; 30' Double Decker with 3 Slides (Children and babies count as passengers)
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Includes two 70qt coolers and life vests!
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Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+.
Optional Add-Ons
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Paddleboards
Paddle Boarding is fun and suitable for people of all ages and abilities. -
Lily Pad
This floating foam island allows you to rest, kick-back, tan, run, and play on. Looking for a fun way to hang out? Book your Lily Pad today. -
Key West-Boat Rentals
Tiki Party Boat w/ Slide 30'
What's included
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13 Passenger Tiki Boat Rental
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Includes a 70qt cooler and life vests!
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Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+.
Optional Add-Ons
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Paddleboards
Paddle Boarding is fun and suitable for people of all ages and abilities. -
Lily Pad
This floating foam island allows you to rest, kick-back, tan, run, and play on. Looking for a fun way to hang out? Book your Lily Pad today. -
Key West-Boat Rentals
23' Everglades
6 Passenger
Create your own adventure: fish, snorkel, paddleboard, or just cruise in style!
The newest boat in our rental fleet! Our 23ft Everglades provides plenty of space and shade while you make your way through our beautiful local waterways!
What's included
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6 Passenger Everglades 230DC Boat Rental
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live well
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fresh & saltwater rinse down
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70qt cooler
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Bluetooth speaker
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head/ toilet
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Key West-Boat Rentals
13 Passenger 25' Double Decker w/ Slides
What's included
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13 Passenger Pontoon Boat Rental; 25' Double Decker with 2 Slides (Children and babies count as passengers)
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Includes two 70qt coolers and life vests!
-
Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+.
Optional Add-Ons
-
Paddleboards
Paddle Boarding is fun and suitable for people of all ages and abilities. -
Lily Pad
This floating foam island allows you to rest, kick-back, tan, run, and play on. Looking for a fun way to hang out? Book your Lily Pad today. -
Key West Boat-Rentals
Release Center Console Fishing Boats
The newest fleet in town! Release Center Console PANGA fishing boat now available! Make your way through our beautiful local waterways in style! Book now for your next off-shore and back country fishing excursion.
What's included
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Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+. We sell ice!
Optional Add-Ons
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Paddleboards
Paddle Boarding is fun and suitable for people of all ages and abilities. -
Lily Pad
This floating foam island allows you to rest, kick-back, tan, run, and play on. Looking for a fun way to hang out? Book your Lily Pad today. -
Key West-Boat Rentals
13 Passenger Double Decker w/ Slide 30'
What's included
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13 Passenger Pontoon Boat Rental; 30' Double Decker with 3 Slides (Children and babies count as passengers)
-
Includes two 70qt coolers and life vests!
-
Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+.
Optional Add-Ons
-
Paddleboards
Paddle Boarding is fun and suitable for people of all ages and abilities. -
Lily Pad
This floating foam island allows you to rest, kick-back, tan, run, and play on. Looking for a fun way to hang out? Book your Lily Pad today. -
Key West-Boat Rentals
21' Pathfinder
Total # of Passengers
2-4
Half Day and Full Day Rentals Available
OPENING FISHING BOAT
WITH EVERYTHING YOU NEED TO FISH
JUST RENT POLLS AND BUY BAIT
Rates
Half Day Rental (4 Hours) – $500 8am-1200pm or 1230-430pm
Full Day Rental (8 Hours) – $600 8am-430pm
Must be at least 23 years of age. PREVIOUS BOATING EXPERIENCE REQUIRED. Private Captains are available for hire.
Key West-Boat Rentals
Boatyard 23' Century
Total # of Passengers
2-6
Half Day and Full Day Rentals Available
OPENING FISHING BOAT
WITH EVERYTHING YOU NEED TO FISH
JUST RENT POLLS AND BUY BAIT
Rates
Half Day Rental (4 Hours) – $500 8am-1200 or 1230pm to 430pm
Full Day Rental (8 Hours) – $600 8am-430pm
Must be at least 23 years of age. PREVIOUS BOATING EXPERIENCE REQUIRED. Private Captains are available for hire.
Lower Keys Charters
Key West-Charters
Sandbar Charters
Fun In The Sun has mastered the art of sandbar charters, guiding you to the most picturesque and secluded spots. Our local, knowledgeable crew will lead you to off-the-beaten-path beaches and the finest sandbars in the Florida Keys, ensuring a memorable and exclusive adventure. Book your sandbar
Key West-Charters
Private Bar Crawl
Get ready to soak up the sun and enjoy the best drinks and vibes Key West has to offer at places like Geiger Key Marina and Fish Camp, The Docks Restaurant + Raw Bar, Stock Rock Cafe, Badboy Burrito, Hurricane Hole Key West, Oceans Edge Resort & Marina Key West, Dante’s, Half Shell Raw Bar, and more!
At Fun in The Sun, we’re all about maximizing the fun, so we’ve crafted the perfect 3-hour Boat Bar Crawl. Trust us, three hours is enough time to hit up all our favorite watering holes along the way!
Key West-Charters
Sandbar Trip
Experience and relax on the same sandbars and remote beaches visited by Jimmy Buffet in his Key West years. Visit Boca Grande, Woman Key, Ballast Key (the true Southernmost spot in the U.S.) or Snipe point. Jump in, cool off, grab a floaty and enjoy your favorite beverage – this is where your vacation starts!
Key West-Charters
Scatter Ashes at Sea
Celebrate the life and honor the final wishes of a loved one on the waters surrounding Key West. Each request is unique and tailored to your special requests. We consider your expectations and wishes. Locations may include sunsets, viewing wild dolphins, peaceful nature settings or your special requests.
Key West-Charters
Snorkeling
Our snorkeling sites are off-the-beaten-path and in shallow, calm water. Explore coral reefs, shallow shipwrecks, underwater sandbars covered with sand dollars – visit Sting Ray alley! All equipment, flotation and patient instruction provided. This activity is for families and children of all ages and abilities.
Key West-Charters
Seaport Cruises - Mac's Place Dock
Our daily 2-hour Seaport Cruises fit perfectly into your Key West sightseeing trip. Enjoy your tiki adventure on the glistening crystal blue waters and look for the abundant Florida Keys wildlife both in the air and sea. Your captain will tell you interesting Key West fun facts and history while cruisin'.
Key West-Charters
Swim Stop Cruise- Mac's Place Dock
Our daily 2-hour Swim Stop Cruises fit perfectly into your Key West sightseeing trip. You will cruise out to a special spot in the Gulf of Mexico to take a dip and cool off. Enjoy your tiki adventure on the glistening crystal blue waters and look for the abundant Florida Keys wildlife both in the air and sea. Your captain will tell you interesting Key West fun facts and history while cruisin’.
Key West-Charters
Custom Charter
Whether you want to explore serene sandbars, enjoy a private boat bar crawl, or simply soak up the sun, our knowledgeable local captain will ensure every detail is catered to your preferences. Enjoy the freedom to design your own itinerary, relax on our top-of-the-line boat, and make unforgettable memories with friends and family. Book your custom 6-person charter today and let Fun In The Sun turn your Key West dreams into reality!
Key West-Charters
26' Pathfinder
Our 26 foot 2023 Pathfinder 2600 HPS was built for exactly the water we fish. At 26 feet with a Yamaha 300 on the transom, she’s got the range to run offshore when the bite calls for it and the deck space to fish up to five guests comfortably. Add in the stability when the chop picks up, and you’ve got a serious fishing platform that doesn’t punish you for spending all day on it.
Key West-Charters
Combination Trips
We lose the crowds – You plan the day! With your private charter we offer you the option to combine activities as you plan your time on the water. This is the perfect way for you to experience several activities in the time frame and expense of only one trip! It’s your special day, just ask and we will do all we can to accommodate your needs. Special requests always welcome!
Key West-Charters
Dolphin Watch
Observe “Safari Style” our resident pods of dolphin that feed, play and socialize in the shallow waters North and West of Key West. This is a peaceful, no impact connection with these beautiful animals and a great photo opportunity. This can be followed up with snorkeling or a tour into one of our wildlife refuges. Enjoy a painlessly educational nature experience – birders and naturalists welcome.
Key West-Charters
Fishing
Light tackle, low stress and calm water – this is the best combination for a fun day of fishing in the pristine waters of the Florida Keys backcountry. We focus on plenty of action, light tackle and practice catch and release. We have the patience for the beginner and the experience for the expert! All tackle, bait, license and helpful hints provided. Novices and families welcome!
Key West-Charters
Sunset Cruise - Mac's Place Dock
Take in the sunset without the crowds on one of our Cruisin' Tikis Key West! Enjoy the sunset tiki style as you glide through the aqua blue waters of the keys with your friends, family, small group, or on a romantic trip for two. We will cruise around the harbor, past Sunset Pier and Mallory Square ending with the beautiful Key West Sunset.
