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Browse Islamorada Boat Rentals.

All Islamorada Listings

Page 1 of 124 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 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
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
Discover Your Own Private Paradise
Powerboats in Islamorada · 6 guests

Discover Your Own Private Paradise

5.0
$185/hour
Yamaha 242XE - Top of line entertainment boat for any adventure - Islamorada
Powerboats in Islamorada · 11 guests

Yamaha 242XE - Top of line entertainment boat for any adventure - Islamorada

5.0
Superowner
$150/hour
Super Fun Deck Boat Captain included
Powerboats in Islamorada · 6 guests

Super Fun Deck Boat Captain included

5.0
$130/hour
Private Islamorada Charters in the Florida Keys
Powerboats in Islamorada · 6 guests

Private Islamorada Charters in the Florida Keys

5.0
$135/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
Private Luxury Adventure Boat - Islamorada
Events in Islamorada · 13 guests

Private Luxury Adventure Boat - Islamorada

New
Superowner
$225+/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
Mako Marine 33' Express Cabin
Powerboats in Islamorada · 6 guests

Mako Marine 33' Express Cabin

5.0
$250/hour
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
Famous Islamorada Sandbar and Snorkeling
Powerboats in Islamorada · 6 guests

Famous Islamorada Sandbar and Snorkeling

New
$150/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
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
36' Invincible Open Fisherman Center Console
Powerboats in Islamorada · 6 guests

36' Invincible Open Fisherman Center Console

New
$125+/hour
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. Jordan

    Jordan

    2022 Sea Chaser 22 HFC Rental in Tavernier, Florida

    Awesome day on the water in Braxton's boat. It was clean, in great condition, and the navigation system was flawless. Will definitely rent again from Braxton. His communication was really great and super helpful.

  2. Chase

    Chase

    22ft Sea Fox 226 Commander

    Had a great day on the water. Boat was spotless & ran great. Everything was perfect. Will definitely be renting from Braxton again when in the Keys.

  3. 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!

  4. DP

    David

    22ft Sea Fox 226 Commander

    5 star Service and Product. Will be renting from Braxton again I the near future.

  5. 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!

  6. 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!