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Browse Key West Boat Rentals.

5.0(Average of 316 reviews in this area)

All Key West Listings

Page 1 of 3 (52 listings)
Stylish elegance and spacious comfort ... your best time ever!
Events in Key West · 12 guests

Stylish elegance and spacious comfort ... your best time ever!

5.0
$95-$155hour
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
$135hour
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
$175hour
SUV of the Seas - Top Luxury Adventure Boat in Stock Island, Florida
Events in Stock Island · 13 guests

SUV of the Seas - Top Luxury Adventure Boat in Stock Island, Florida

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
$149hour
18' Party Barge Pontoon for rent in Cudjoe Key, Florida!!! We deliver only!
Powerboats in Cudjoe Key · 6 guests

18' Party Barge Pontoon for rent in Cudjoe Key, Florida!!! We deliver only!

5.0
$21hour
24' Pontoon to rent in Cudjoe Key, FL. We deliver!
Powerboats in Summerland Key · 9 guests

24' Pontoon to rent in Cudjoe Key, FL. We deliver!

5.0
$21hour
Luxury Sailing Catamaran in Key West
Sailing in Key West · 10 guests

Luxury Sailing Catamaran in Key West

5.0
$250hour
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
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
Luxury Activity Vessel - 33' Regal SAV: Private Mini Yacht for up to 13
Powerboats in Key West · 13 guests

Luxury Activity Vessel - 33' Regal SAV: Private Mini Yacht for up to 13

New
Superowner
$237-$399hour
24' Aquasport center console. Weekly or multi day rentals in Cudjoe Key, FL
Powerboats in Cudjoe Key · 8 guests

24' Aquasport center console. Weekly or multi day rentals in Cudjoe Key, FL

5.0
$155-$460day
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
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
$500day
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
2020 Sailfish 270 WAC Charter in Key West!
Powerboats in Key West · 6 guests

2020 Sailfish 270 WAC Charter in Key West!

5.0
$675day
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
Tiki Bar Boat in Key West
Powerboats in Key West · 6 guests

Tiki Bar Boat in Key West

New
$125hour
Sea Fox 24ft Center Console to Go Fishing!!! in Summerland Key, Florida
Fishing in Summerland Key · 5 guests

Sea Fox 24ft Center Console to Go Fishing!!! in Summerland Key, Florida

5.0
$186-$350day
Godfrey Sweetwater 23' Tritoon in Cudjoe Key, Florida
Powerboats in Cudjoe Key · 10 guests

Godfrey Sweetwater 23' Tritoon in Cudjoe Key, Florida

New
$22hour
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-$950hour
Newer Key West Party Boat for 36 people!
Powerboats in Key West · 36 guests

Newer Key West Party Boat for 36 people!

5.0
$550hour

Key West Reviews

  1. SH
    Shelby
    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    Anthony communicated frequently before the trip and was flexible when we wanted to change our activities based on the weather. We had a great experience and will definitely use him again when we return to Key West!

  2. DR
    Don
    18' Party Barge Pontoon for rent in Cudjoe Key, Florida!!! We deliver only!

    Mitch was super helpful and easy to communicate with when we needed him. The boat was perfect for our needs and enhanced our experience so much! It was a pleasure to work with him!

  3. 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

  4. 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.

  5. AE
    ALISA
    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    We hired Anthony for a 4 hour boat cruise and had an absolute blast. The boat (a 23' Boston Whaler) was very comfortable to ride and also provided shade when it got too hot. Anthony took us to sand bars, shared his knowledge of the Keys and even procured a 12 pack for us from a party boat when we ran out (a rookie mistake indeed!). Anthony is a very competent captain and I felt safe the entire time. We've hired several boats with captains before and Anthony is the best one by far. The bonus was he brought his 20 lb pug, Mystic, who is soooo sweet and always well-behaved. What a day!! Thank you so much, Anthony!!

  6. SF
    Sallmae
    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    Anthony was they best host and such a great fit for our group! He took us on with only a days notice and had good communication from the beginning to the end of our ride. He reassured us of any concerns from refund questions to weather questions. We have already said Anthony will be the captain we call in anytime we are in the keys... fun attentive, caring host and even gave us a tour and went beyond in helping us create lasting memories. You can't go wrong with this ride and it's captain!!