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Stock Island, Florida Boat Rentals & Yacht Charters

Page 1 of 227 listings

Captained 42' Sailing Catamaran with 3 cabins and all the toys
Sailing in Key West · 6 guests

Captained 42' Sailing Catamaran with 3 cabins and all the toys

5.0
$320/hour
Stylish elegance and spacious comfort ... your best time ever!
Events in Key West · 12 guests

Stylish elegance and spacious comfort ... your best time ever!

5.0
$95+/hour
Sea Ray 270 Key West Experience
Tours in Key West · 6 guests

Sea Ray 270 Key West Experience

5.0
$165/hour
Ultimate speed, spacious comfort and elegant style ... Best Time Ever!
Events in Key West · 12 guests

Ultimate speed, spacious comfort and elegant style ... Best Time Ever!

5.0
$200/hour
SUV of the Seas - Top Luxury Adventure Boat in Key West, FL
Events in Stock Island · 13 guests

SUV of the Seas - Top Luxury Adventure Boat in Key West, FL

5.0
Superowner
$238+/hour
Instant Book
Private Key West Boat Experience — Swim, Sip & Soak Up the Sun!
Powerboats in Key West · 10 guests

Private Key West Boat Experience — Swim, Sip & Soak Up the Sun!

5.0
$126+/hour
Pontoon Boat !! Enjoy Paradise Like A Local!
Powerboats in Key West · 10 guests

Pontoon Boat !! Enjoy Paradise Like A Local!

5.0
$90/hour
Best Ocean Adventure in Key West – GetMyBoat Superowner and Best of 2025.
Powerboats in Key West · 8 guests

Best Ocean Adventure in Key West – GetMyBoat Superowner and Best of 2025.

5.0
$175+/hour
 Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter
Powerboats in Key West · 10 guests

Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter

5.0
$130+/hour
22ft Deluxe Pontoon with Lounge Seating - Sounds, Seat Upgrades & Dog Friendly
Powerboats in Key West · 8 guests

22ft Deluxe Pontoon with Lounge Seating - Sounds, Seat Upgrades & Dog Friendly

New
$80/hour
Hurricane Deck Boat With Upgraded Lounge Seats & Upgraded Sound (Pet Friendly)
Powerboats in Key West · 8 guests

Hurricane Deck Boat With Upgraded Lounge Seats & Upgraded Sound (Pet Friendly)

New
$150/hour
Reel Paradise Key West Sandbar + Snorkel + Private Charter + Light Tackle Fishin
Events in Key West · 12 guests

Reel Paradise Key West Sandbar + Snorkel + Private Charter + Light Tackle Fishin

5.0
$200+/hour
Instant Book
Captained 80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

Captained 80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/hour
67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Book Direct with the Owner
Events in Key West · 12 guests

67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Book Direct with the Owner

5.0
$750+/hour
88ft Lazzara with lots of Outdoor Spaces and Water Toys serving Key West
Powerboats in Stock Island · 12 guests

88ft Lazzara with lots of Outdoor Spaces and Water Toys serving Key West

5.0
$850+/hour
37' Freedom Yacht With 1400 Horse Power In Key West, Florida
Powerboats in Stock Island · 13 guests

37' Freedom Yacht With 1400 Horse Power In Key West, Florida

New
$359/hour
37’ Luxury Freeman with Bathroom, Shade & Key West Charters
Powerboats in Key West · 12 guests

37’ Luxury Freeman with Bathroom, Shade & Key West Charters

New
$250+/hour
45' Sea Ray Luxury Yacht | Direct Owner | Key West, Dry Tortugas
Events in Key West · 12 guests

45' Sea Ray Luxury Yacht | Direct Owner | Key West, Dry Tortugas

New
$500/hour
"Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West
Sailing in Key West · 6 guests

"Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West

New
$351/hour
Dry Tortugas National Park Trip — Private Charter from Key West
Events in Key West · 12 guests

Dry Tortugas National Park Trip — Private Charter from Key West

New
$250/hour
Instant Book
(2018) 45ft Lagoon 450F Sailing Catamaran in Miami with 4 Cabins and Crew
Sailing in Key West · 13 guests

(2018) 45ft Lagoon 450F Sailing Catamaran in Miami with 4 Cabins and Crew

New
$1,050+/hour
21ft Key West Center Console (Luxury Reef Edition) With Sound & Seat Upgrades
Powerboats in Key West · 6 guests

21ft Key West Center Console (Luxury Reef Edition) With Sound & Seat Upgrades

New
$125/hour
Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas
Sailing in Key West · 12 guests

Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas

New
$560+/hour
21' Nauticstar - Explore Key West Snorkeling and Remote Beaches with a captain
Powerboats in Key West · 6 guests

21' Nauticstar - Explore Key West Snorkeling and Remote Beaches with a captain

New
$160+/hour

Stock Island Reviews

  1. AM

    Alessandra

    Pontoon Boat !! Enjoy Paradise Like A Local!

    We had an absolutely amazing experience with Louis! We booked it for my friend’s bachelorette in Key West. There were a few logistics to work through before our trip, but once everything was confirmed according to our original booking, he made sure we were taken care of and the experience exceeded our expectations. The boat itself was beautiful, comfortable, and exactly what we were hoping for. The real highlight, though, was our captain. He was fantastic, knowledgeable, professional, fun, and knew exactly where to take us to make the most of our day on the water. He was more than just a captain; he became a great addition to the party and helped create an unforgettable experience. From start to finish, once we were out on the water, everything was perfect. We had an absolute blast. I would happily book with them again and again, and wouldn’t hesitate to recommend them to anyone looking for a great day on the water.

  2. CZ

    Chris

    Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter

    Captain Paul gave our family one of the most memorable experiences of our entire Florida Keys trip. From the moment we stepped on the boat, he was friendly, knowledgeable, and focused on making sure everyone had a great time. The day was the perfect mix of sightseeing, exploring, relaxing, and even a little fishing. We caught several mangrove snapper, and Liam even landed a barracuda, which was the highlight of his vacation. Along the way, we encountered a few unexpected challenges, but Paul stayed calm, positive, and professional, making sure our family was taken care of and still having fun. To top it all off, he filleted our catch and prepared fresh sashimi right on the boat. It doesn’t get much fresher than that. What could have been just another day on the water turned into an adventure our family will be talking about for years. If you’re looking for a captain who genuinely cares about his guests and goes above and beyond to create an unforgettable experience, Captain Paul is your guy.

  3. TP

    Taranjeet

    Sea Ray 270 Key West Experience

    He was simply fantastic! He made our experience even better by being his awesome self in addition to the most beautiful boat on the entire dock! He had prices it perfectly! We were a party of 5, with my best friends for over 25 years, and he also took phenomenal photos for us. We are coming again in June and will definitely go to him again!

  4. BC

    Bryan

    Captained 42' Sailing Catamaran with 3 cabins and all the toys

    Aaron was super fun and extremely knowledgeable. Our group of five has so much fun sailing the rougher, windier seas. We then made for a secluded spot to fish and swim while we waited for sunset. It was a glorious view and truly checked off a bucket list item for me. Bryan - Oregon

  5. Kyla Rae

    Kyla Rae

    Pontoon Boat !! Enjoy Paradise Like A Local!

    We had a blast! Our captain, Jorge, was on time, communicated very well and had iced coolers ready to go. We had a nice boat ride out to the sandbar and had so much fun playing mermaids and looking for treasure. Great family experience!

  6. BL

    Bill

    Reel Paradise Key West Sandbar + Snorkel + Private Charter + Light Tackle Fishin

    We booked a charter with Carlos. He responded quickly and with a great price. Captain Mikey picked us up on time and the boat was so clean and nice. He took us to three old lighthouses off the coast where we enjoyed the clear water and sunshine. We enjoyed the entire trip and got some great photos. Thanks guys for a wonderful day out in the Keys. Bill n Vicki.