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Florida Keys, US Boat Rentals & Yacht Charters

Page 2 of 473 listings

Private Key West Charter: Sandbar, Snorkel, Sunset & Reef
Powerboats in Key West · 8 guests

Private Key West Charter: Sandbar, Snorkel, Sunset & Reef

5.0
$142+/hour
Key West Sandbar Hangout Aboard Sea Ray 250 SDX Yacht
Powerboats in Key West · 6 guests

Key West Sandbar Hangout Aboard Sea Ray 250 SDX Yacht

5.0
$169+/hour
23' Mako Center console for rent in Key Largo, Florida!
Powerboats in Key Largo · 6 guests

23' Mako Center console for rent in Key Largo, Florida!

4.6
$75/hour
Top Luxury 2021 Brabus Shadow 500 Cabin Adventure Boat in Marathon, Florida!
Events in Marathon · 13 guests

Top Luxury 2021 Brabus Shadow 500 Cabin Adventure Boat in Marathon, Florida!

5.0
Superowner
$225+/hour
Ride the 24ft Bowrider in Key Largo, Florida
Powerboats in Key Largo · 12 guests

Ride the 24ft Bowrider in Key Largo, Florida

4.9
$120/hour
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
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

4.4
Superowner
$225+/hour
25ft Premier Pontoon Experience Big Pine Key Verado 250HP
Powerboats in Big Pine Key · 16 guests

25ft Premier Pontoon Experience Big Pine Key Verado 250HP

5.0
$80/hour
Premium Islamorada Boat Rental | 29' Grady-White Freedom
Powerboats in Islamorada · 8 guests

Premium Islamorada Boat Rental | 29' Grady-White Freedom

5.0
$125+/hour
37ft Midnight Express Open Luxury Yacht on The Waters of Key West!
Events in Key West · 12 guests

37ft Midnight Express Open Luxury Yacht on The Waters of Key West!

5.0
$175+/hour
Snorkel, Sandbar, and Fish on a Cobia 28 Center Console with Captain Brad
Powerboats in Marathon · 6 guests

Snorkel, Sandbar, and Fish on a Cobia 28 Center Console with Captain Brad

5.0
$150/hour
36’ Contender Marathon – Triple 350s, Sandbar, Snorkel, Key West Run
Events in Marathon · 12 guests

36’ Contender Marathon – Triple 350s, Sandbar, Snorkel, Key West Run

5.0
$220+/hour
 Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter
Powerboats in Key West · 10 guests

Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter

5.0
$135+/hour
24ft Cobia 237 Center Console for rent in Big Pine RV park
Fishing in Big Pine Key · 8 guests

24ft Cobia 237 Center Console for rent in Big Pine RV park

5.0
$100/hour
Premium 29' Grady-White Freedom Center Console In Key Largo
Powerboats in Key Largo · 8 guests

Premium 29' Grady-White Freedom Center Console In Key Largo

5.0
$775+/day
Super Fun Deck Boat Captain included
Powerboats in Islamorada · 6 guests

Super Fun Deck Boat Captain included

5.0
$85/hour
67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Celebrations and Getaways
Events in Key West · 12 guests

67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Celebrations and Getaways

5.0
$750+/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
2017 Sea Fox Commander Reef Fishing, Offshore Fishing, Snorkeling and Sand Bar
Fishing in Marathon · 6 guests

2017 Sea Fox Commander Reef Fishing, Offshore Fishing, Snorkeling and Sand Bar

5.0
$125+/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
2022 Yamaha 252EX Islamorada, FL
Powerboats in Key Largo · 12 guests

2022 Yamaha 252EX Islamorada, FL

New
Superowner
Best of 2026
$118/hour
88ft Lazzara Yacht with lots of Outdoor Spaces and Water Toys serving Key West
Events in Stock Island · 12 guests

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

5.0
$850+/hour
Private Islamorada Charters in the Florida Keys aboard 23' Hurricane Fun Deck
Powerboats in Islamorada · 6 guests

Private Islamorada Charters in the Florida Keys aboard 23' Hurricane Fun Deck

5.0
$135/hour
28ft Contender - Center Console
Powerboats in Islamorada · 6 guests

28ft Contender - Center Console

New
$150/hour

Florida Keys Reviews

  1. TW

    Tim

    Snorkel, Sandbar, and Fish on a Cobia 28 Center Console with Captain Brad

    We hired Brad to help my wife and me to go to a coral reef to spread my parent’s ashes. My wife got seasick but Brad did everything possible to get her feeling better. He was very respectful of the reason for the trip and even took off his hat when the “ceremony” started. I did a little snorkeling but came back to the boat to get my wife on shore. Once we docked, I took my wife to the jeep and turned on the air. Brad was so nice that he rinsed off in fresh water all the equipment and brought it to the jeep. Brad was very courteous, respectful, polite, & capable. His boat was immaculate and ran like a dream and it was a 1999 boat! You very rarely find an individual who checked all the boxes and he did!!

  2. TG

    Todd

    Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter

    Paul you were great - thanks so much for everything and we greatly appreciated you giving us an amazing sunset experience.

  3. CZ

    Chris

    Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter

    Captain Paul gave our family one of the most memorable experiences of our entire Florida Keys trip. From the moment we stepped on the boat, he was friendly, knowledgeable, and focused on making sure everyone had a great time. The day was the perfect mix of sightseeing, exploring, relaxing, and even a little fishing. We caught several mangrove snapper, and Liam even landed a barracuda, which was the highlight of his vacation. Along the way, we encountered a few unexpected challenges, but Paul stayed calm, positive, and professional, making sure our family was taken care of and still having fun. To top it all off, he filleted our catch and prepared fresh sashimi right on the boat. It doesn’t get much fresher than that. What could have been just another day on the water turned into an adventure our family will be talking about for years. If you’re looking for a captain who genuinely cares about his guests and goes above and beyond to create an unforgettable experience, Captain Paul is your guy.

  4. GT

    Greg

    Private Key West Charter: Sandbar, Snorkel, Sunset & Reef

    David was a great host. No surprise charges and very accommodating in all aspects. Captain Dustin and Christina were very knowledgeable on local spots to avoid the wind and were great to hang out with for the day. We would highly recommend spending a day touring with them.

  5. Jason

    Jason

    Key West Sandbar Hangout Aboard Sea Ray 250 SDX Yacht

    We had an absolute fantastic day. Anthony knows the spots to find that moment you are looking for in a special trip to the Keys. My wife and I had a magical trip, visiting a remote island and sharing a romantic sunset together. He even took pictures for us along with being a fantastic host. Next time we are in the Keys, we will be giving Anthony a call again as our Captain. Thank you from A and J for taking us to the Edge of Heaven!

  6. PG

    Patrick

    Key West Sandbar Hangout Aboard Sea Ray 250 SDX Yacht

    Just spent 8 hours on the Boston Whaler with my three daughters. We had an amazing time. Anthony is the perfect host - laid back, funny, kind and most of all knowledgeable of the places to go and see. We visited two sandbars, got to see some baby hammerheads, a stingray, the sunset (which was amazing), and on our ride back to dock we also saw a family of dolphins. The boat was very clean, larger than expected, had the toys we wanted (full face snorkeling equipment, paddle boats, and the water mat). The cooler was stocked and there were chips as well. We would do it again in a heartbeat! Worth every penny for a relaxing day on the water with an amazing host!