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$100-$300

Browse Key West Boat Rentals.

Page 1 of 234 listings

luxury 25'ft pontoon for Sandbar & Dolphin and Sunset  tours. Dog friendly
Powerboats in Key West · 6 guests

luxury 25'ft pontoon for Sandbar & Dolphin and Sunset tours. Dog friendly

5.0
$150hour
Private Key West Boat Adventure | Sandbars and More!
Powerboats in Stock Island · 8 guests

Private Key West Boat Adventure | Sandbars and More!

5.0
$120hour
Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports
Powerboats in Key West · 6 guests

Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

5.0
$141hour
30' Jeanneau NC 895 Weekender Cabin Cruiser Yacht
Powerboats in Stock Island · 6 guests

30' Jeanneau NC 895 Weekender Cabin Cruiser Yacht

5.0
$225hour
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-$400hour
Half Day 4hrs: Sandbar hangout/ Island Hopping/ Paddle-boarding/ snorkeling
Powerboats in Key West · 6 guests

Half Day 4hrs: Sandbar hangout/ Island Hopping/ Paddle-boarding/ snorkeling

4.9
$136-$163hour
Salty Sandbars Key West on our new Boston Whaler 23 Vantage
Powerboats in Key West · 6 guests

Salty Sandbars Key West on our new Boston Whaler 23 Vantage

4.9
$135hour
Luxury Sailing Catamaran in Key West
Sailing in Key West · 10 guests

Luxury Sailing Catamaran in Key West

5.0
$250hour
4-Hour Private Charter in Key West with Captain Zak
Powerboats in Key West · 6 guests

4-Hour Private Charter in Key West with Captain Zak

5.0
$150-$163hour
24' Aquasport Center Console in Cudjoe Key, FL
Powerboats in Cudjoe Key · 8 guests

24' Aquasport Center Console in Cudjoe Key, FL

5.0
Snoozed - Active 04 Apr 2025
Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$175-$200hour
41' Island Trader Ketch in Key West, Florida!
Sailing in Stock Island · 6 guests

41' Island Trader Ketch in Key West, Florida!

4.9
$162-$199hour
Wake Surf Wake Skate In Key West, Florida
Tours in Key West · 6 guests

Wake Surf Wake Skate In Key West, Florida

5.0
$225hour
Hydrasport 6-Hour Private Charter in Key West
Powerboats in Key West · 6 guests

Hydrasport 6-Hour Private Charter in Key West

5.0
$142hour
Rum Runner Bar Boat in Key West, Florida
Powerboats in Key West · 12 guests

Rum Runner Bar Boat in Key West, Florida

5.0
$150hour
Tiki Bar Boat in Key West
Powerboats in Key West · 6 guests

Tiki Bar Boat in Key West

New
$125hour
23ft Concept Powerboat Island Tour and Sandbar charter
Powerboats in Key West · 6 guests

23ft Concept Powerboat Island Tour and Sandbar charter

New
$175hour
Backcountry Fishing in Key West
Fishing in Stock Island · 4 guests

Backcountry Fishing in Key West

New
$190hour
Sandbar Charter and Island Tour
Powerboats in Key West · 6 guests

Sandbar Charter and Island Tour

New
$200hour
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
$163hour
Full Day Shared Charter in Key West, Florida
Fishing in Key West · 6 guests

Full Day Shared Charter in Key West, Florida

5.0
$275day
"Key West Sailfish" Sailfish 2360
Fishing in Key West · 6 guests

"Key West Sailfish" Sailfish 2360

New
$249hour
"Stress Free" 20ft Mako Center Console Rental in Key West, Florida
Powerboats in Key West · 4 guests

"Stress Free" 20ft Mako Center Console Rental in Key West, Florida

New
$204hour
Adventure escape challenge on the waters in Key West, Florida
Tours in Key West · 6 guests

Adventure escape challenge on the waters in Key West, Florida

New
$150hour

Key West Reviews

  1. Stephanie

    Stephanie

    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    My friends and I had such a great time on the water with Anthony! The boat was awesome and he took us to a couple sandbars. He was so knowledgeable about the water and area. Would definitely recommend.

  2. Holly

    Holly

    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    Anthony called us ahead of time to warn of the wind and asked if we wanted to reschedule. Due to our travel plans, we decided not to, but still had a wonderful time! Anthony was knowledgeable, friendly and knew what he was doing! We would recommend him.

  3. AB

    Ana

    luxury 25'ft pontoon for Sandbar & Dolphin and Sunset tours. Dog friendly

    Eric was the perfect captain! Took us to a great spot for our bachelorette party, glad we chose him!

  4. AV

    Alejandro

  5. LA

    Laura

    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    We all enjoyed the hole trip, it was our last day in key west and we couldn’t have asked for a better way to finish our trip to key west. We all felt save with Anthony as a captain, he told us a lot about the island as we sailed around. The biggest recommendation from us if you are looking for something to top your vacation

  6. Michele

    Michele

    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    Stop looking! THIS is your boat/captain experience. I researched the heck out of what boat to hire for our trip to Key West. And we saw a ton of other boats/captains on our sandbar sunset trip…this is the best boat and Anthony was by far the most warm, service oriented, and knowledgeable captain. And his little pug, Mystic, absolutely made the trip feel like we were on our own boat. We will be back and will use Anthony every time.