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Find The Best Boat Rentals in Big Pine Key, Florida.

Page 1 of 124 listings

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
Choose your own adventure exploring the last frontier of Florida, the Lower Florida Keys! Amazing Float Plans and secluded sandbars!
Powerboats in Cudjoe Key · 6 guests

Choose your own adventure exploring the last frontier of Florida, the Lower Florida Keys! Amazing Float Plans and secluded sandbars!

5.0
$500/day
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
THE ONE AND ONLY GRADY WHITE FREEDOM
Fishing in Marathon · 8 guests

THE ONE AND ONLY GRADY WHITE FREEDOM

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

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

5.0
$220+/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
Comfortable Pontoon Boat with 4-Stroke ~ Bring the Whole Family & the Dog
Powerboats in Marathon · 12 guests

Comfortable Pontoon Boat with 4-Stroke ~ Bring the Whole Family & the Dog

5.0
$318+/day
Top Luxury Adventure Boat in Marathon, Florida
Events in Marathon · 13 guests

Top Luxury Adventure Boat in Marathon, Florida

5.0
Superowner
$238+/hour
Enjoy Endless Fun in the Sun on the Bayliner 2659 Rendezvous
Powerboats in Marathon · 6 guests

Enjoy Endless Fun in the Sun on the Bayliner 2659 Rendezvous

5.0
$125/hour
Private sandbar trip
Powerboats in Key West · 6 guests

Private sandbar trip

5.0
$85+/hour
Snorkel, Sandbar, and Fish on a Cobia 28 Center Console
Powerboats in Marathon · 6 guests

Snorkel, Sandbar, and Fish on a Cobia 28 Center Console

5.0
$150/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!

New
$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
"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
 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
2-Hour Sunset Cruise in Key West - Hydrasport 25' Center Console
Powerboats in Key West · 6 guests

2-Hour Sunset Cruise in Key West - Hydrasport 25' Center Console

New
$163/hour
6 Hour Sandbar Charter in Key West
Powerboats in Key West · 6 guests

6 Hour Sandbar Charter in Key West

5.0
$160+/hour
Explore Key West in Comfort on this Luxury Center Console
Powerboats in Key West · 6 guests

Explore Key West in Comfort on this Luxury Center Console

5.0
$250+/hour
Key West Reel Paradise Charters
Fishing in Key West · 12 guests

Key West Reel Paradise Charters

5.0
$225+/hour
 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

New
$165/hour
Luxury Lagoon 440 Sailing Catamaran in Key West
Sailing in Key West · 6 guests

Luxury Lagoon 440 Sailing Catamaran in Key West

5.0
$250/hour
Experience Luxury in Key West on Your Own Terms - Key West's Premier Charter
Powerboats in Key West · 12 guests

Experience Luxury in Key West on Your Own Terms - Key West's Premier Charter

5.0
$90+/hour

Big Pine Key Reviews

  1. MH

    Marin

    Enjoy Endless Fun in the Sun on the Bayliner 2659 Rendezvous

    Scott was amazing from the booking to the end of our trip! He made it about us; 3 young children and 2 adults, and went above and beyond to find a manatee (our oldest said it was the best day of her life!)! His laid back and informative style was exactly what we were wanting on Christmas Eve. The kids had a blast getting splashed on the boat, loved soaking up the beautiful sun and even mom and dad got some snorkeling in! Thank you, Scott, for adding to our Christmas memories!

  2. BW

    Brian

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

    The boat was immaculate and our kids really enjoyed the power of the boat. We were able to see a good portion of the Keys from both sides - traveling under the 7 mile bridge!

  3. RL

    Russell

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

    This was a great boat. Navigation was top of the line. Everything worked great for our family.

  4. 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.

  5. 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.

  6. MH

    Mark

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

    Todd's boat was great for our lobster trip to the keys! Couldn't have asked for a better setup to accommodate everyone on board. The AC was definitely a nice feature to catch a small break from the sun as well! Thanks Todd and we'll definitely be back in touch when planning our next trip down!