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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
$750+/day
26ft Twin Vee PowerCat
Powerboats in Marathon · 6 guests

26ft Twin Vee PowerCat

New
Snoozed - Active 02 May 2025
25ft Premier Pontoon
Tours in Marathon · 16 guests

25ft Premier Pontoon

New
Snoozed - Active 02 May 2025
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
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
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
Instant Book
20' Hydra Sports Center Console with 200 Hp Etec Motor in Key West, Florida!
Powerboats in Key West · 6 guests

20' Hydra Sports Center Console with 200 Hp Etec Motor in Key West, Florida!

5.0
$125/hour
Instant Book
Captained sail on a beautiful and comfortable 50' wooden ketch
Sailing in Key Colony Beach · 6 guests

Captained sail on a beautiful and comfortable 50' wooden ketch

New
$325/hour
#1 BOAT IN THE FLORIDA KEYS - Key Largo
Powerboats in Key Colony Beach · 8 guests

#1 BOAT IN THE FLORIDA KEYS - Key Largo

5.0
$125+/hour
Instant Book
Snorkel, Sandbar, and Fish on a Cobia 28 Center Console
Tours in Marathon · 6 guests

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

5.0
$150/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
"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
Luxury Lagoon 440 Sailing Catamaran in Key West
Sailing in Key West · 10 guests

Luxury Lagoon 440 Sailing Catamaran in Key West

5.0
$250/hour
Instant Book
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
SUV of the Seas - Top Luxury Adventure Boat in Key West, FL
Events in Key West · 13 guests

SUV of the Seas - Top Luxury Adventure Boat in Key West, FL

5.0
Superowner
$238+/hour
Hydrasport 6-Hour Private Charter in Key West
Powerboats in Stock Island · 6 guests

Hydrasport 6-Hour Private Charter in Key West

5.0
$142/hour
Reel Paradise 36 Contender Center Console!!
Fishing in Stock Island · 12 guests

Reel Paradise 36 Contender Center Console!!

New
$230/hour
Instant Book
80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/hour
Six Fins Jet Ski Rental
Water Sports in Stock Island · 3 guests

Six Fins Jet Ski Rental

New
$104/hour
32ft Donzi Center Console for Fishing Charters in Key West!!
Powerboats in Key West · 6 guests

32ft Donzi Center Console for Fishing Charters in Key West!!

New
$900/day
Instant Book
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

Big Pine Key Reviews

  1. Trisha

    Trisha

    Enjoy Endless Fun in the Sun on the Bayliner 2659 Rendezvous

    Scott is the best! Knowledgeable, fun and all around a great captain! We had a blast relaxing and learning with Scott! Highly recommend this boat trip! We had a blast snorkeling, relaxing and chatting!

  2. 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.

  3. 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.

  4. 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!

  5. MH

    Manuel

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

    Todd is a fantastic communicator! He was very patient and helpful. Very open and honest, he was flexible and helpful. I will definitely give him a call on our next trip to the Keys. If you are wondering whether or not you should rent well let me put you over the top, rent with Todd! Best deal and service in we have found!

  6. DM

    Dean

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

    We could have not scripted a better trip. Austin showed us "The Keys". We had asked for a remote location to spend some time and he more than delivered. Snorkeling, exploring, and some fishing. My son and I caught many fish including a Bonefish off the sandbar. Thanks Austin, we had a wonderful family day!