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Islamorada, Florida Boat Rentals

Page 1 of 120 listings

22ft Sea Fox 226 Commander
Powerboats in Tavernier · 8 guests

22ft Sea Fox 226 Commander

5.0
$100/hour
2022 Sea Chaser 22 HFC Rental in Tavernier, Florida
Powerboats in Tavernier · 8 guests

2022 Sea Chaser 22 HFC Rental in Tavernier, Florida

5.0
$100/hour
31ft Contender Center Console - Captained Custom Tours in Islamorada, Florida
Powerboats in Islamorada · 6 guests

31ft Contender Center Console - Captained Custom Tours in Islamorada, Florida

5.0
$150/hour
Private Luxury Adventure Boat - Islamorada
Events in Islamorada · 13 guests

Private Luxury Adventure Boat - Islamorada

5.0
Superowner
$225+/hour
Instant Book
Luxury Adventure Boat: Brabus of the Seas - Up to 13ppl - Islamorada/Key Largo
Events in Islamorada · 13 guests

Luxury Adventure Boat: Brabus of the Seas - Up to 13ppl - Islamorada/Key Largo

4.4
Superowner
$225+/hour
Private Tiki Boat Charters for up to 18 Passengers
Events in Islamorada · 18 guests

Private Tiki Boat Charters for up to 18 Passengers

5.0
$333+/hour
Discover Your Own Private Paradise
Powerboats in Islamorada · 6 guests

Discover Your Own Private Paradise

5.0
$185/hour
The ULTIMATE Florida Keys Boat – 29' Grady-White Freedom
Powerboats in Islamorada · 8 guests

The ULTIMATE Florida Keys Boat – 29' Grady-White Freedom

5.0
$125+/hour
Super Fun Deck Boat Captain included
Powerboats in Islamorada · 6 guests

Super Fun Deck Boat Captain included

5.0
$85/hour
26' Shearwater - Custom Islamorada Tours, Alligator Lighthouse, Sandbar, Snorkel
Powerboats in Islamorada · 6 guests

26' Shearwater - Custom Islamorada Tours, Alligator Lighthouse, Sandbar, Snorkel

New
$125/hour
Instant Book
Captain-Included Custom Charter — Fish, Snorkel, sandbar and more!
Powerboats in Tavernier · 6 guests

Captain-Included Custom Charter — Fish, Snorkel, sandbar and more!

New
$150/hour
''Pescado Loco''Atlantic Sportfish Motor Yacht Rental in Islamorada, Florida
Fishing in Islamorada · 6 guests

''Pescado Loco''Atlantic Sportfish Motor Yacht Rental in Islamorada, Florida

New
$332/hour
All-Inclusive SANDBAR, Snorkeling, BBQ, Sightseeing & Sunset 26’ Boat
Powerboats in Islamorada · 6 guests

All-Inclusive SANDBAR, Snorkeling, BBQ, Sightseeing & Sunset 26’ Boat

New
$175+/hour
Famous Islamorada Sandbar and Snorkeling
Powerboats in Islamorada · 6 guests

Famous Islamorada Sandbar and Snorkeling

New
$150/hour
Scenic boat tour on 25-foot Sea Fox Commander
Powerboats in Islamorada · 6 guests

Scenic boat tour on 25-foot Sea Fox Commander

New
$150+/hour
Sandbar Charter Party Aboard Triton Pontoon
Powerboats in Islamorada · 6 guests

Sandbar Charter Party Aboard Triton Pontoon

New
$163/hour
Full Day Gulfstream Charters in Islamorada onboard 42' Liberty Express
Fishing in Islamorada · 6 guests

Full Day Gulfstream Charters in Islamorada onboard 42' Liberty Express

New
$1,800/day
Swordfish Charters - Private Charter up to 6 people in Islamorada, Florida!
Fishing in Islamorada · 6 guests

Swordfish Charters - Private Charter up to 6 people in Islamorada, Florida!

New
$2,500/day
Fishing Charter on 40' Henriques Sportfish Boat in Islamorada, Florida
Fishing in Islamorada · 6 guests

Fishing Charter on 40' Henriques Sportfish Boat in Islamorada, Florida

New
$163+/hour
Full Day Reef + Wreck Charters - Private Charter for up to 6 People
Fishing in Islamorada · 6 guests

Full Day Reef + Wreck Charters - Private Charter for up to 6 People

New
$1,800/day

Islamorada Reviews

  1. Florin

    Florin

    22ft Sea Fox 226 Commander

    Best Captain, great communication, best itinerary, best boat ,well priced. Looking forward to coming back and book with Cpt Braxton! 100% recommended !

  2. EF

    Eric

    22ft Sea Fox 226 Commander

    We had a fantastic experience renting a boat from Why Knot Boat Rentals in Key Largo over Thanksgiving weekend. Braxton was incredibly flexible when some minor weather challenges popped up, and he made the entire process smooth and stress-free. Before we headed out, he gave clear and helpful instructions and shared great recommendations for places to explore on the water. The boat itself was in excellent condition, exactly as described, and performed perfectly the entire day. We would absolutely recommend Why Knot Boat Rentals to anyone looking for a great day on the water in the Keys, and we’ll definitely be renting from them again on a future trip!

  3. Tristan

    Tristan

    22ft Sea Fox 226 Commander

    Braxton Why Knott Exclusive Rentals is super awesome and a class act. Everything went great- we snorkelled the reefs he recommended at chicken and hen and saw dolphins on our ride. Smooth and flawless, highly recommended . Check out their website for all the cool spear fishing trips they do!

  4. MICHAEL

    MICHAEL

    2022 Sea Chaser 22 HFC Rental in Tavernier, Florida

    We had an amazing experience renting from Braxton! He was incredibly flexible with our dates and group size, making the whole process smooth and stress-free. What really stood out was his thoughtfulness—he provided toys, snorkel gear, and fishing rods for the kids, which made the trip even more special. The boat was clean, well-maintained, and perfect for a fun day on the water. Braxton was friendly, professional, and went above and beyond to ensure we had everything we needed. Highly recommend renting from him for a hassle-free and memorable outing!

  5. Robert

    Robert

    2022 Sea Chaser 22 HFC Rental in Tavernier, Florida

    5-Star Boating Tour with Captain Braxton! We had an amazing time on our boat tour with Captain Braxton! From start to finish, he made the experience seamless and enjoyable. We started with snorkeling in the bay, where he took us to a cool spot with clear waters and marine life. Afterward, we cruised to a beautiful sandbar where we could relax and soak up the sun. Captain Braxton’s knowledge of the area was impressive—he knew exactly where to go for the best experience. He was also incredibly friendly, accommodating, and made sure we were comfortable the entire time. If you’re looking for an stress-free and fun boating adventure, we highly recommend booking with Captain Braxton!

  6. Jonathan

    Jonathan

    2022 Sea Chaser 22 HFC Rental in Tavernier, Florida

    Braxton was an exceptional captain! He treated our family with incredible kindness and went above and beyond to ensure we had a fantastic time. His attentive service made our experience truly memorable. We’ll definitely be back and can’t recommend him highly enough!