Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Why travelers choose Greetwell

Curated by our team

Every experience is hand selected and approved by Greetwell.

Personal concierge

Real humans available to help before, during, and after your booking.

Intimate & authentic

Including unique in-home experiences you won't find anywhere else.

Easy booking & cancellation

Reserve in minutes with free cancellation on most experiences.

Greetwell

Experiences that stay with you long after the trip

Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

About

  • Our Story
  • For Experience Providers
  • For Hospitality Partners
  • For Developers

Resources

  • Travel Guides
  • Experience Gift Cards
  • Help Center
[email protected]1-877-GREET-WELL

Safe & Secure Payments

© 2026 Greetwell, Inc. All rights reserved.
Privacy PolicyTerms
Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Best results for

Boat Rentals in Big Pine Lake, FL

Showing 25-48 of 124 results
5-Day Boat Rental in Marathon

5-Day Boat Rental in Marathon

Choose the boat and layout that fit your plans on Florida Keys waters

$1,447/ boat
21' Fishing Boat Rental in Summerland Key
Up to 6

21' Fishing Boat Rental in Summerland Key

Take the helm for fishing, snorkeling or diving

$426/ boat
23' Boat Rental in Cudjoe Key
Up to 8

23' Boat Rental in Cudjoe Key

Cruise or fish the Keys with GPS-guided local routes

5.0 • 58 reviews
$596/ boat
20' Deck Boat Rental in Cudjoe Key
Up to 10

20' Deck Boat Rental in Cudjoe Key

Cruise local waters with GPS guidance and convenient delivery

5.0 • 58 reviews
$568/ boat
18' Center Console Boat Rental in Cudjoe Key

18' Center Console Boat Rental in Cudjoe Key

Navigate Cudjoe Key waters with GPS and a 150 hp Yamaha

4.9 • 109 reviews
$448/ boat
20' Pontoon Rental in Cudjoe Key
Up to 8

20' Pontoon Rental in Cudjoe Key

Navigate Cudjoe Key’s shallow waters with a 70 hp pontoon and Garmin GPS

4.9 • 109 reviews
$460/ boat
Multi-Day Bay Boat Rental Delivered Near Marathon
Up to 5

Multi-Day Bay Boat Rental Delivered Near Marathon

Navigate bays and backcountry with fishing-ready Garmin technology

4.9 • 71 reviews
$2,605/ boat
Multi-Day Dusky 227 Boat Rental with Delivery Near Marathon
Up to 5

Multi-Day Dusky 227 Boat Rental with Delivery Near Marathon

Fishing-ready boat rental with delivery and pickup near Marathon

4.9 • 71 reviews
$2,777/ boat
Key West 26' Deck Boat Rental
Up to 9

Key West 26' Deck Boat Rental

Set your own course on a Yamaha-powered Key West deck boat

4.8 • 284 reviews
$578/ boat
Key West 22' Bay Boat Rental
Up to 6

Key West 22' Bay Boat Rental

Take the helm of a well-equipped bay boat for your Key West day on the water

4.8 • 284 reviews
$525/ boat
20' Boat Rental in Key West
Up to 5

20' Boat Rental in Key West

Chart your own Key West day aboard a 20-foot Sea Fox Viper

4.7 • 21 reviews
$397/ boat
22' Sea Fox Boat Rental in Key West

22' Sea Fox Boat Rental in Key West

Take the helm for flexible Key West boating, from a half day to a week

4.7 • 21 reviews
$426/ boat
Full-Day Boat Rental in Duck Key, Florida Keys
Up to 12

Full-Day Boat Rental in Duck Key, Florida Keys

Make the day your own on the waters of the Florida Keys

$341/ boat
20' Center Console Boat Rental in Marathon
Up to 8

20' Center Console Boat Rental in Marathon

Explore Florida Keys waters with fishing gear and swim access on board

$369/ boat
23' Carolina Skiff Boat Rental in Summerland Key
Up to 6

23' Carolina Skiff Boat Rental in Summerland Key

Take the helm and explore the Keys on your own

$511/ boat
17' Center Console Boat Rental in Cudjoe Key
Up to 6

17' Center Console Boat Rental in Cudjoe Key

Take the helm of a GPS-equipped center console for daytime Keys boating

5.0 • 58 reviews
$568/ boat
Private Bareboat Charter in Key West for Sandbars & Sunset
Up to 12

Private Bareboat Charter in Key West for Sandbars & Sunset

Explore the Florida Keys with a blend of speed, comfort, and style

$743/ boat
Cudjoe Key 21' Deck Boat Rental
Up to 8

Cudjoe Key 21' Deck Boat Rental

Navigate shallow waters on a versatile center-console deck boat

4.9 • 109 reviews
$471/ boat
19' Center Console Boat Rental in Marathon
Up to 4

19' Center Console Boat Rental in Marathon

Cruise and fish with onboard GPS, a live well, and a swim step

4.4 • 1.5K reviews
$351/ boat
22' Deck Boat Rental with Dock Delivery in Cudjoe Key
Up to 12

22' Deck Boat Rental with Dock Delivery in Cudjoe Key

GPS-guided cruising and fishing around Cudjoe Key

5.0 • 58 reviews
$596/ boat
Key West 4-Hour Pontoon Boat Rental
Up to 8

Key West 4-Hour Pontoon Boat Rental

Take the helm of a well-equipped pontoon for your Key West day on the water

4.8 • 284 reviews
$578/ boat
24' Fishing Boat Rental in Summerland Key
Up to 6

24' Fishing Boat Rental in Summerland Key

Head out fishing with room for family, friends, and gear

$482/ boat
Key West 13-Person Pontoon Rental
Up to 13

Key West 13-Person Pontoon Rental

Cruise Key West waters with onboard GPS, shade, and a cooler

4.7 • 21 reviews
$460/ boat
Private Sandbar & Sunset Boat Rental in Key West
Up to 12

Private Sandbar & Sunset Boat Rental in Key West

Make your outing your own, from beach stops to dockside dining or a sunset cruise

$403/ boat
123456
Big Pine Lake Things To Do
Boat RentalsFishing Charters234Boat Tours133Snorkeling98Yacht Charters92
More
  • Sailing78
  • Scuba Diving69
  • Car Rentals52
  • Sunrise and Sunset Tours44
  • Bike Rentals27
  • Private Fishing Charters27
  • Dolphin Watching22
Kayaking Tours20
  • Jet Skiing17
  • Scenic Flights9
  • Scavenger Hunts8
  • Scooter Rentals8
  • Dinner Cruises7
  • Ghost and Haunted7
  • Paddleboarding7
  • Bar and Pub Crawl6
  • Parasailing6
  • Private Boat Charters6
  • Water Skiing6
  • Helicopter Tours5
  • Travel guides for Boat Rentals

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide
    Best of Florida • 2026

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide

    Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.