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Browse Islamorada Boat Rentals.

Page 1 of 120 listings

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
$80/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
Instant Book
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

4.3
Superowner
$225+/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
STOP Settling for Crowded, Generic Tours – Discover Your Own Private Paradise
Powerboats in Islamorada · 6 guests

STOP Settling for Crowded, Generic Tours – Discover Your Own Private Paradise

5.0
$150/hour
Instant Book
Super Fun Deck Boat Rental Caps included
Powerboats in Islamorada · 6 guests

Super Fun Deck Boat Rental Caps included

5.0
$130/hour
21' Shearwater - Captained Islamorada Sandbar, Snorkeling, or Sunset Cruise
Powerboats in Islamorada · 5 guests

21' Shearwater - Captained Islamorada Sandbar, Snorkeling, or Sunset Cruise

5.0
$125/hour
Instant Book
Private Hurricane Deck Boat Charters in the Florida Keys
Powerboats in Islamorada · 6 guests

Private Hurricane Deck Boat Charters in the Florida Keys

5.0
$135/hour
Comfortable Keys Cruising & Striking Sunsets
Events in Islamorada · 6 guests

Comfortable Keys Cruising & Striking Sunsets

New
$124/hour
Mako Marine 33' Express Cabin
Powerboats in Islamorada · 6 guests

Mako Marine 33' Express Cabin

5.0
$250/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
''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
Sandbar Charter Party Aboard Triton Pontoon
Powerboats in Islamorada · 6 guests

Sandbar Charter Party Aboard Triton Pontoon

New
$163/hour
Catch and sea charters fishing and eco-tours
Fishing in Tavernier · 6 guests

Catch and sea charters fishing and eco-tours

New
$125/hour
Instant Book
Full Day Gulfstream Charters in Islamorada onboard air-conditioned 42' Liberty Express
Fishing in Islamorada · 6 guests

Full Day Gulfstream Charters in Islamorada onboard air-conditioned 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
36' Invincible Open Fisherman Center Console
Powerboats in Islamorada · 6 guests

36' Invincible Open Fisherman Center Console

New
$125+/hour
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 in Islamorada, Florida!
Fishing in Islamorada · 6 guests

Full Day Reef + Wreck Charters - Private Charter for up to 6 People in Islamorada, Florida!

New
$1,800/day

Islamorada Reviews

  1. DS

    Deborah

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

    Nous avons passé un moment merveilleux avec René ! En plus d être sympathique, il a vraiment tout mis en œuvre pour faire plaisir à chacun! Mes filles ont adoré la bouée tractée ! René connaît parfaitement la région et a su nous faire profiter au maximum de cet après midi en mer!

  2. MC

    Mark

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

    When your vacation guests say the number one memory of their time in South Florida was the boat trip around Islamorada, you know it was worth every penny. My wife and I had family members visit from the UK, and we wanted to give them an experience of the Keys from the water. They had never been on a private speedboat before, and Rene was the perfect boat captain, guide, and host for them. He was super relaxed, even when we arrived a few minutes behind schedule after being held up by a road traffic accident, and he tailored an itinerary ideal for them so they had the best time possible. And they certainly had that. Rene's boat is awesome, with plenty of space to relax on, gear to use, and coolers to chill the drinks. He set up the boat so my 15-year-old niece could link her music to the boat speakers and provide the soundtrack to our day, and she got to take her best Instagram pics on board (which for a teenage girl is super important, apparently). Sitting alongside Rene, she also got an introduction to boating as he answered her questions about boat driving. We snorkelled in a couple of spots, including at the Alligator Reef lighthouse, which was filled with amazing fish; we played on his floating mat, which wowed our 11-year-old niece; and we all chilled at the Islamorada sandbar. Standing in knee-deep water in the middle of the sea was a mind-blowing experience for everyone. Safety-conscious, fun, and customer-focused, Rene is someone you become fast friends with. We had a superb day and made memories that will last a lifetime. I look forward to going out on the water with him in the future.

  3. CM

    Caroline

    Private Hurricane Deck Boat Charters in the Florida Keys

    we loved our trip with Dinorah! he was so chill which we loved in our experience on being on a boat. he was so sweet and accommodating with our needs!

  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. RK

    Ryan

    2022 Sea Chaser 22 HFC Rental in Tavernier, Florida

    Braxton was great to deal with very communicative and timely. The boat was in great shape and met our needs.

  6. 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!