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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
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
$850+/day
Private sandbar trip
Powerboats in Key West · 6 guests

Private sandbar trip

5.0
$85+/hour
Ultimate speed, spacious comfort and elegant style ... Best Time Ever!
Events in Key West · 12 guests

Ultimate speed, spacious comfort and elegant style ... Best Time Ever!

5.0
$200/hour
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
Instant Book
"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
Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests
Sailing in Key West · 6 guests

Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests

New
$210/hour
Explore Key West in Comfort on this Luxury Center Console
Powerboats in Key West · 12 guests

Explore Key West in Comfort on this Luxury Center Console

5.0
$175+/hour
Dry Tortugas National Park Trip — Private Charter from Key West
Powerboats in Key West · 12 guests

Dry Tortugas National Park Trip — Private Charter from Key West

New
$250/hour
Instant Book
Reel Paradise Key West Sandbar + Snorkel + Private Charter + Light Tackle Fishin
Events in Key West · 12 guests

Reel Paradise Key West Sandbar + Snorkel + Private Charter + Light Tackle Fishin

5.0
$200+/hour
Instant Book
 Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter
Powerboats in Key West · 6 guests

Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter

New
$200/hour
Sea Ray 270 Key West Experience
Tours in Key West · 6 guests

Sea Ray 270 Key West Experience

5.0
$165/hour
88ft Lazzara with lots of Outdoor Spaces and Water Toys serving Key West
Powerboats in Stock Island · 12 guests

88ft Lazzara with lots of Outdoor Spaces and Water Toys serving Key West

5.0
$850+/hour
Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas
Sailing in Key West · 12 guests

Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas

New
$560+/hour
Best Ocean Adventure in Key West – GetMyBoat Superowner and Best of 2025.
Powerboats in Key West · 8 guests

Best Ocean Adventure in Key West – GetMyBoat Superowner and Best of 2025.

5.0
$175+/hour
45' Sea Ray Luxury Yacht | Direct Owner | Key West, Dry Tortugas
Events in Key West · 12 guests

45' Sea Ray Luxury Yacht | Direct Owner | Key West, Dry Tortugas

New
$300+/hour
67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Book Direct with the Owner
Events in Key West · 12 guests

67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Book Direct with the Owner

5.0
$750+/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

5.0
$320/hour
Captained 80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

Captained 80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/hour
2024 Yamaha VX | The Best 2-Hour Flagship Guided Jet Ski Tour
Water Sports in Key West · 2 guests

2024 Yamaha VX | The Best 2-Hour Flagship Guided Jet Ski Tour

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
21' Nauticstar - Explore Key West Snorkeling and Remote Beaches with a captain
Powerboats in Key West · 6 guests

21' Nauticstar - Explore Key West Snorkeling and Remote Beaches with a captain

New
$160+/hour
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
Private Key West Boat Experience — Swim, Sip & Soak Up the Sun!
Powerboats in Key West · 10 guests

Private Key West Boat Experience — Swim, Sip & Soak Up the Sun!

5.0
$126+/hour

Cudjoe Key Reviews

  1. Brandon

    Brandon

    Captained 42' Sailing Catamaran with 3 cabins and all the toys

    Highly recommended Captain Aaron and his crew Brook... they did an amazing job of hosting and tending to our wants. Very nice boat with ample toys and things to do on the water. Will definitely join them again. ⭐️⭐️⭐️⭐️⭐️

  2. Heath

    Heath

    Ultimate speed, spacious comfort and elegant style ... Best Time Ever!

    Great boat and the trip was amazing. Everything was as described and Captain Brian was awesome!!!

  3. TR

    Tim

    67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Book Direct with the Owner

    Great communication throughout! Boat and crew were first class!!! You will not be disappointed!!!

  4. RK

    Richard

    Reel Paradise Key West Sandbar + Snorkel + Private Charter + Light Tackle Fishin

    Perfect day on the boat with captain Mikey. Very straightforward communication

  5. TM

    Ted

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

    Five stars, all the way. The boat was great and what we wanted, but better, Todd was right there, great with the handover, totally immediate with questions/responses, and just basically an all-round great person. Highly recommend! Like the boating area all around this Key as well, totally beautiful.

  6. MK

    Mike

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

    Our family had a great experience with Todd. The rental was easy and efficient. Todd provided a thorough overview of the boat, cabin, and electronics. The cabin was great to have for the family. Our toddler took a two hour nap in the A/C in the cabin which allowed us to stay on the water all day. We had a great experience and will be renting with Todd again in the future.