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Group Size (2)

Browse Key West Boat Rentals.

Page 1 of 352 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
EXPLORE Natural Beauty of the Keys on our 27FT SEABORN!!
Events in Stock Island · 6 guests

EXPLORE Natural Beauty of the Keys on our 27FT SEABORN!!

5.0
Superowner
Best of 2023
$140hour
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
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
Private Key West Boat Adventure | Sandbars and More!
Powerboats in Stock Island · 8 guests

Private Key West Boat Adventure | Sandbars and More!

5.0
$100-$105hour
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
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
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
$137-$385day
Jeanneau NC 895 Luxury Yacht - Private Key West Boat Charter
Events in Stock Island · 6 guests

Jeanneau NC 895 Luxury Yacht - Private Key West Boat Charter

5.0
$150-$225hour
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
$175-$225hour
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
$138-$478day
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
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
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
Glastron Deck Boat 150 HP Yamaha
Powerboats in Cudjoe Key · 8 guests

Glastron Deck Boat 150 HP Yamaha

New
$175-$490day
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
Wake Surf Wake Skate In Key West, Florida
Tours in Key West · 6 guests

Wake Surf Wake Skate In Key West, Florida

5.0
Snoozed - Active 02 Jan 2025
Hydrasport 6-Hour Private Charter in Key West
Powerboats in Stock Island · 6 guests

Hydrasport 6-Hour Private Charter in Key West

5.0
$142hour
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

New
$115-$150hour
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
$125hour
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. AB

    Alicia

    4-Hour Private Charter in Key West with Captain Zak

    Zack was very knowledgeable and customized our day for us. He was friendly and easy going and made sure we have a great time.

  2. SW

    Staci

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

    We had a great day on the water with Eric. Weather/Wind didn't agree with us that day however Eric went to the best areas to ensure we still had the best day possible. Highly recommend!

  3. DJ

    Deanna

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

    Captain Eric was knowledgeable, friendly and so fun! We had a great time on the sandbar. We highly recommend him and his boat, Sandy.

  4. shannon

    shannon

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

    Was very pleased with Pats professionalism with this booking. He was quick and very helpful with all the details of my trip. We were a group of ladies visiting from all different places so I was nice to get to experience some time together out on the water. Can’t wait to do it again! 5 star service

  5. FL

    Felicia

    EXPLORE Natural Beauty of the Keys on our 27FT SEABORN!!

    Jorge and Nicole were very attentive and treated us like we were on a 100ft Yacht. Jorge was extremely friendly and the seven of us felt safe, the 4 hour sail was extremely relaxing. Our booking was at night: therefore, we didn't take advantage of using the jet ski or floaty, but having the option was great. Nicole was beautiful inside and out. Everything we asked she assisted us with a smile. Not having to lift a finger during the sail was the icing on the cake. This excursion was great way to end our girls trip. We are looking forward to a repeat.

  6. Beauty

    Beauty

    EXPLORE Natural Beauty of the Keys on our 27FT SEABORN!!

    Jorge and Louis were amazing treated my family very well the entire trip my brother is visually impaired and they treated them with kindness and respect. Kind and friendly to the two kids on the boats. I am a navy veteran and DIsc Jockey for FM318 live and they were very respectful and helpful like I was DJ Khalid. They deserve a raise. They also like my Dominican culture music!!!