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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
Instant Book
36’ Contender – Triple 350s, Sandbar, Snorkel, Key West Run
Fishing in Marathon · 12 guests

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

New
$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
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
Instant Book
Top Luxury Adventure Boat in Marathon, Florida
Events in Marathon · 13 guests

Top Luxury Adventure Boat in Marathon, Florida

5.0
Superowner
$238+/hour
 Hydra Sports Center Console with 225 Hp Suzuki outboard. Key West, Florida!
Powerboats in Key West · 6 guests

Hydra Sports Center Console with 225 Hp Suzuki outboard. Key West, Florida!

5.0
$105+/hour
Instant Book
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
Instant Book
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
Newer Key West Party Boat for 36 people!
Powerboats in Key West · 36 guests

Newer Key West Party Boat for 36 people!

5.0
$550/hour
4 Hour Sandbar Charter in Key West with Captain Zak
Powerboats in Key West · 6 guests

4 Hour Sandbar Charter in Key West with Captain Zak

5.0
$160+/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
Key West Luxury Charters
Fishing in Key West · 12 guests

Key West Luxury Charters

New
$225+/hour
Instant Book
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
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
$600+/hour
Instant Book
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

New
$850+/hour
Instant Book

Big Pine Key Reviews

  1. MC

    Marcy

    Enjoy Endless Fun in the Sun on the Bayliner 2659 Rendezvous

    We booked Scott last minute and very happy we did. Communication was great and he was able to pick us up at our rental house on the water. Game changer. Very knowledgeable about the area and accommodating to everything we wanted to do and see. Thanks, Scott!

  2. MB

    Mike

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

    The boat was great, accommodated our party of 11 perfectly. The GPS was perfect for navigating, and we also received a map with several must visit spots. Great communication, everything was as advertised, definitely would rent again in the future. Thanks!

  3. JR

    Jorge

    Hydra Sports Center Console with 225 Hp Suzuki outboard. Key West, Florida!

    Great charter and great captain. Attentive to the guest. Well versed in the boat and water life. Great music and great vibes! A++++++++ service great for families!Amazing service will definitely book with Eric again!

  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!