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Browse Islamorada Boat Rentals.

Page 1 of 121 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
$85/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
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
Instant Book
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
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
Super Fun Deck Boat Captain included
Powerboats in Islamorada · 6 guests

Super Fun Deck Boat Captain included

5.0
$130/hour
Private Luxury Adventure Boat - Islamorada
Events in Islamorada · 13 guests

Private Luxury Adventure Boat - Islamorada

New
Superowner
$225+/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
26' Shearwater - Custom Islamorada Tours, Alligator Lighthouse, Sandbar, Snorkel
Powerboats in Islamorada · 6 guests

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

New
$120/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
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 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. SV

    Sandi

    Super Fun Deck Boat Captain included

    Captain Chris is an expert boater, so we felt really safe. He also made the day so wonderful. The floaties, paddle board, and most delicious burgers were such a special touch. He was the best captain at the sandbar - very fun.

  2. Tamela

    Tamela

    Private Islamorada Charters in the Florida Keys

    Dawid "David" was great! Our family chose his charter services to celebrate our dad's 70th birthday, and our expectations were exceeded. We had a blast! He's very accommodating and chill. He is an EMT and paramedic, which added an extra level of peace of mind. His price is also very affordable for the services offered. Book with him; you won't be disappointed!

  3. DV

    Diane

    2022 Sea Chaser 22 HFC Rental in Tavernier, Florida

    Wonderful trip with Braxton! Perfect way to spend an afternoon on the water. Braxton was a great host and tour guide. Good price for this fun and safe adventure!

  4. David

    David

    2022 Sea Chaser 22 HFC Rental in Tavernier, Florida

    Braxton was awesome to work with. His boat was in fantastic shape and perfect for our family boat outing. I highly recommend Braxton and his boat.

  5. 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!

  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!