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Havana, CU Boat Rentals & Yacht Charters

Page 1 of 124 listings

33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$199+/hour
52′ Yacht with Flybridge Private Luxury Charter in Key West | Up to 10 Guests
Events in Key West · 10 guests

52′ Yacht with Flybridge Private Luxury Charter in Key West | Up to 10 Guests

5.0
$600/hour
23ft Concept Powerboat Island Tour and Sandbar charter
Powerboats in Key West · 6 guests

23ft Concept Powerboat Island Tour and Sandbar charter

New
$175/hour
Sandbar Charter and Island Tour
Powerboats in Key West · 6 guests

Sandbar Charter and Island Tour

New
$200/hour
 46ft SeaRay | Grand Admiral
Events in Key West · 12 guests

46ft SeaRay | Grand Admiral

New
$526+/hour
62ft Lagoon Yacht Charter - Create Lasting Memories in Key West!
Events in Key West · 13 guests

62ft Lagoon Yacht Charter - Create Lasting Memories in Key West!

New
$995+/hour
Instant Book
"Key West Sailfish" Sailfish 2360
Fishing in Key West · 6 guests

"Key West Sailfish" Sailfish 2360

New
$249/hour
''Miss Carolina'' Carolina Classic 35 Express Rental in Key West, Florida
Events in Key West · 10 guests

''Miss Carolina'' Carolina Classic 35 Express Rental in Key West, Florida

New
$512/hour
Egg Harbor 35ft Sportfisher for Offshore Adventures!
Fishing in Key West · 6 guests

Egg Harbor 35ft Sportfisher for Offshore Adventures!

New
$225/hour
45ft Lagoon | Somewhere
Sailing in Key West · 12 guests

45ft Lagoon | Somewhere

New
$740+/hour
Adventure escape challenge on the waters in Key West, Florida
Tours in Key West · 6 guests

Adventure escape challenge on the waters in Key West, Florida

New
$150/hour
New SeaRay 250 SDX Salty SandBars Key West
Powerboats in Key West · 6 guests

New SeaRay 250 SDX Salty SandBars Key West

5.0
$135+/hour
Lets go boating like a local Sandbar hangout/ Island Hopping/ Paddle-boarding
Powerboats in Key West · 6 guests

Lets go boating like a local Sandbar hangout/ Island Hopping/ Paddle-boarding

4.9
$158+/hour
Boston Whaler 24ft Sandbar Hangout Key West
Powerboats in Key West · 6 guests

Boston Whaler 24ft Sandbar Hangout Key West

5.0
$130/hour
The Tiki Boat Fast, Fun, and Spacious Up to 12 Passengers
Powerboats in Key West · 12 guests

The Tiki Boat Fast, Fun, and Spacious Up to 12 Passengers

New
$250/hour
 Key West Party Boat for 6- 36 people!
Powerboats in Key West · 36 guests

Key West Party Boat for 6- 36 people!

5.0
$550/hour
See Vee 27' Center Console up to 6 people!
Powerboats in Key West · 6 guests

See Vee 27' Center Console up to 6 people!

New
$150+/hour
Key West Sandbar hangout SeaRay 250 SDX Salty Sandbars Key West
Powerboats in Key West · 6 guests

Key West Sandbar hangout SeaRay 250 SDX Salty Sandbars Key West

5.0
$169+/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
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
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
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
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

Havana Reviews

  1. WD

    Whit

    Boston Whaler 24ft Sandbar Hangout Key West

    Anthony was a great captain and guide for our 4 hour trip, going out of his way to find us some unique spots in the sandbars. Would definitely recommend Anthony to anyone else looking for a relaxed tour around the area.

  2. db

    daniel

    Boston Whaler 24ft Sandbar Hangout Key West

    We had an incredible day out on the water with Captain Anthony! He took us out to Mud Keys and Snipes, and both spots were absolutely stunning. Anthony is a fantastic captain-- professional, knowledgeable about the local waters, and made sure the entire trip felt relaxed and seamless. Whether you're looking for a hidden sandbar to lounge on or want to explore the unique scenery of the keys, he knows exactly where to go to beat the crowds. Ilf you're looking for an authentic and stress-free Key West boat day, we can't recommend Anthony enough. Well definitely be booking with him again next time we're in town!

  3. 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. ⭐️⭐️⭐️⭐️⭐️

  4. JB

    Jessi

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

    Fantastic trip, gorgeous boat, great crew!

  5. Robert

    Robert

    Boston Whaler 24ft Sandbar Hangout Key West

    Reservation & pre trip communication with Anthony was easy & straight forward. The boat was perfect and in great shape. Captain Zack was personable, knowledgeable and fun to chill with. we alk enjoyed a fabulous day!!

  6. CF

    Corinne

    New SeaRay 250 SDX Salty SandBars Key West

    We had the best time out on the water and to the sand bars with Captain Mike! He’s incredibly knowledgeable on all things Key West and more! He kept us very entertained with his facts and stories. The boat was pristine and included all of the amenities listed. I would highly recommend this tour!