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Cudjoe Key, Florida Boat Rentals

Page 1 of 124 listings

Chaparral 23ft Powerboat with Bimini Cover for Daily Rental
Fishing in Cudjoe Key · 8 guests

Chaparral 23ft Powerboat with Bimini Cover for Daily Rental

New
$700/day
Choose your own adventure exploring the last frontier of Florida, the Lower Florida Keys! Amazing Float Plans and secluded sandbars!
Powerboats in Cudjoe Key · 6 guests

Choose your own adventure exploring the last frontier of Florida, the Lower Florida Keys! Amazing Float Plans and secluded sandbars!

5.0
$500/day
32' Boston Whaler Conquest with large cabin & AC, in lower Florida Keys
Powerboats in Big Pine Key · 10 guests

32' Boston Whaler Conquest with large cabin & AC, in lower Florida Keys

4.9
$750+/day
Instant Book
 Hydra Sports Center Console with 225 Hp Suzuki outboard. Key West, Florida!
Powerboats in Key West · 6 guests

Hydra Sports Center Console with 225 Hp Suzuki outboard. Key West, Florida!

5.0
$105+/hour
Instant Book
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
Newer Key West Party Boat for 36 people!
Powerboats in Key West · 36 guests

Newer Key West Party Boat for 36 people!

5.0
$550/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
6 Hour Sandbar Charter in Key West
Powerboats in Key West · 6 guests

6 Hour Sandbar Charter in Key West

5.0
$160+/hour
4 Hour Sandbar Charter in Key West with Captain Zak
Powerboats in Key West · 6 guests

4 Hour Sandbar Charter in Key West with Captain Zak

5.0
$160+/hour
2-Hour Sunset Cruise in Key West - Hydrasport 25' Center Console
Powerboats in Key West · 6 guests

2-Hour Sunset Cruise in Key West - Hydrasport 25' Center Console

New
$163/hour
Key West Luxury Charters
Fishing in Key West · 12 guests

Key West Luxury Charters

New
$200/hour
Instant Book
Luxury Lagoon 440 Sailing Catamaran in Key West
Sailing in Key West · 6 guests

Luxury Lagoon 440 Sailing Catamaran in Key West

5.0
$250/hour
Experience Luxury in Key West on Your Own Terms - Key West's Premier Charter
Powerboats in Key West · 12 guests

Experience Luxury in Key West on Your Own Terms - Key West's Premier Charter

5.0
Snoozed - Active 02 Aug 2025
Best Ocean Adventure in Key West – Explore, Relax, Discover!
Powerboats in Stock Island · 8 guests

Best Ocean Adventure in Key West – Explore, Relax, Discover!

5.0
$160+/hour
84ft Lazzara Motor Yacht is a head turner with lots of outdoor spaces and toys
Powerboats in Stock Island · 12 guests

84ft Lazzara Motor Yacht is a head turner with lots of outdoor spaces and toys

5.0
$850+/hour
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

New
$320/hour
80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/hour
Key West Freestyle Adventure: 1-Hour Freelance Trip
Water Sports in Stock Island · 12 guests

Key West Freestyle Adventure: 1-Hour Freelance Trip

New
$160/hour
Key West Jet Ski Adventure: 2-Hour Tour Encircling Key West Island
Water Sports in Stock Island · 2 guests

Key West Jet Ski Adventure: 2-Hour Tour Encircling Key West Island

New
$104/hour
32ft Donzi Center Console for Fishing Charters in Key West!!
Powerboats in Key West · 6 guests

32ft Donzi Center Console for Fishing Charters in Key West!!

New
$900/day
Instant Book
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
Pontoon Boat !! Enjoy Paradise Like A Local!
Powerboats in Key West · 10 guests

Pontoon Boat !! Enjoy Paradise Like A Local!

5.0
$90/hour
"Stress Free" 20ft Mako Center Console Rental in Key West, Florida
Powerboats in Key West · 4 guests

"Stress Free" 20ft Mako Center Console Rental in Key West, Florida

New
$204/hour
2020 Sailfish 270 WAC Charter in Key West!
Powerboats in Key West · 6 guests

2020 Sailfish 270 WAC Charter in Key West!

5.0
$169+/hour

Cudjoe Key Reviews

  1. AB

    Angeline

    Newer Key West Party Boat for 36 people!

    Chad and Gino were amazing! They were accommodating and was the best event of the trip. Boat was huge and the floating mat was perfect for our group of 17 girls. We would book with Chad again and we wished we booked for longer.

  2. DP

    Dayana

    Pontoon Boat !! Enjoy Paradise Like A Local!

    My group had an amazing time, the captain took us to Snipes Key sandbar, beautiful waters. Best plans you can make to relax and enjoy the waters in key west. Luis was very attentive and accommodating also.

  3. Saurabh

    Saurabh

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

    We had the best time in the ocean with Paul. Very professional and friendly at the same time. The boat was clean and with all the equipments required.

  4. LK

    Laurel

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

    Highly recommend! Patrick was super accommodating, great with communication and setting everything up. We had captain Bridget and she hands down the best!! It was a super windy day but the boat handled great in the rough water and she took us to an amazing spot. We had the best time for my 40th bday! Can’t not recommend this boat and captain Bridget enough!

  5. AB

    Anna

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

    Booked with Patrick for a boat day in key west and I’m so glad we did! The boat was amazing, all instruction was super clear and we were paired up with Bridget who was the BEST captain! She knew all the good spots to go and made sure we had fun. Would definitely recommend both Patrick and Bridget!

  6. DM

    Dean

    Choose your own adventure exploring the last frontier of Florida, the Lower Florida Keys! Amazing Float Plans and secluded sandbars!

    We could have not scripted a better trip. Austin showed us "The Keys". We had asked for a remote location to spend some time and he more than delivered. Snorkeling, exploring, and some fishing. My son and I caught many fish including a Bonefish off the sandbar. Thanks Austin, we had a wonderful family day!