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Florida Keys, US Boat Rentals & Yacht Charters

Page 2 of 4 • 77 listings

2025 Yamaha AR250 Key Largo, FL
Powerboats in Key Largo · 12 guests

2025 Yamaha AR250 Key Largo, FL

5.0
Superowner
Best of 2026
$425+/day
2022 Yamaha 252XE Islamorada, FL
Powerboats in Key Largo · 12 guests

2022 Yamaha 252XE Islamorada, FL

5.0
Superowner
Best of 2026
$575+/day
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
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
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
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
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
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
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
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
 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
Super Fun Deck Boat Captain included
Powerboats in Islamorada · 6 guests

Super Fun Deck Boat Captain included

5.0
$85/hour
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
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
Key West 67' Luxury Power Catamaran | 6 Cabins, Jet Ski, Parties & Getaways
Events in Key West · 12 guests

Key West 67' Luxury Power Catamaran | 6 Cabins, Jet Ski, Parties & 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
Limited Availability
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
Perfect Sandbar Rental! 2024 Hurricane 205-SS Deck Boat
Powerboats in Big Pine Key · 10 guests

Perfect Sandbar Rental! 2024 Hurricane 205-SS Deck Boat

New
$75/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

Florida Keys Reviews

  1. Daren

    Daren

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

    Jay was great at explaining the local waterways and the boat electronics had accurate charts of the channels and shallow water locations. Jay went over a map with us before departure and showed us points of interest and local dockside restaurants and how to get from the ocean side of the island to the bay side.

  2. AO

    Amanda

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

    Absolutely the best! Easy paperwork, easy instructions and we had a blast. The boat worked perfectly well in all the areas we went to. We were able to snorkel, resort hop thanks to guest docks and ride around. The full tank lasted all 3 days we had the boat. Everything was in working order. Jay was so informative with options, places to go and where to stop at. Very kind. Worth the money for sure. Best price around! Loved renting for 3 days and going/returning on our schedule.

  3. 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!

  4. 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!

  5. WG

    William

    Key West Sandbar Hangout Aboard Sea Ray 250 SDX Yacht

    Anthony was amazing! We made a last minute booking and he answered within minutes to quickly get us booked for 3 o’clock departure… which was within the hour of reaching out to him. When arriving to the marina it looked as if a storm was approaching and anthony did everything to make sure we didnt waste our money and go out and get stuck in the storm. About an hour later the storm passed so we reached out to see if it was too late to go out, and he said he stuck around just incase the storm passed and to meet back at the marina. We ended up having an amazing evening with great weather and he took us out to a beautiful sandbar! The evening was amazing and his professionalism was awesome. Would book again, no question about it.

  6. Yaritza

    Yaritza

    Key West Sandbar Hangout Aboard Sea Ray 250 SDX Yacht

    Anthony is an amazing and the BEST captain! Our trip couldn’t have been any more perfect. He was so friendly, experienced, accommodating and communicative. His boat was so comfortable and beautiful. He also took us out to the best spots. Our trip wouldn’t have been the same without his navigational skills and knowledge of the area. We will definitely be back and will recommend to our friends and family.