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Florida Keys, US Boat Rentals & Yacht Charters

Page 2 of 474 listings

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
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
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
Limited Availability
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
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
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
Limited Availability
2024 Yamaha 252XE Key Largo, FL
Powerboats in Key Largo · 12 guests

2024 Yamaha 252XE Key Largo, FL

4.7
Superowner
Best of 2026
$386+/day
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
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
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

5.0
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

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. LC

    Lloyd

    Super Fun Deck Boat Captain included

    Highly recommended! Everything is as listed, great service, communication and experience!

  3. Chasen

    Chasen

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

    My and girlfriends first time In the keys and we did it the right way. This boat was so fun and fast and very Clean. Our captain was absolutely the best. He was a vibe the whole time and took us to the most beautiful spots

  4. 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!

  5. 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!

  6. 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.