rent sailboat key west

Private & Shared Sailing Charters

Sunset sail key west.

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

Get inspired with our most popular trips!

Private sunset sail.

Chillout Lilypad Sail

Key West Daysail

Sunset Sail on When & If

Privates Charters

Discover your perfect private charter.

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

Shared Trips

Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

Three Classic Boats

View our fleet.

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Real. Fun. Sailing.

When And If is back at beautiful Stock Island Marina!

Check Out Our Ship's Store!

Wreckers' Race Season Is Back!

Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

Friends of SSKW

Legal & safety.

Florida Keys Best Yacht Sales and Charters

Charter a  catamaran plan your own private key west sailing adventure, day charters, 4-8 hours ​, multi-day charters, bare boat charters, crew available ​.

Buy or Sell A Catamaran

Brand New Build

Power or Sail

Vessels in any category

Sailing School

Take a learning vacation! 

We offer 101, 103, 104, 114, 106

COME SAIL WITH US!

Help us reach 100 reviews!

Ahoy, sailors!  In an effort to provide the best experience for our guests, we would love to hear from you! How was your experience? Would you book with us again? Please leave us a review!

Adventures to Get You Inspired

Sail Away With Us

We're in a tv show, escape from reality.

In our episodes we are going to explore the places, people, and destinations where it “all went down.” We are here to uncover the true Key West. We hope you join us along the way!

The Gallery

Now it's your turn, book your adventure today, 3/4 day sail, 1/2 day sail, sunset sail, overnight expedition, dry tortugas adventure, our contest.

Get a chance to win big! On every $25 pledge per month, claim a raffle ticket for a drawing conducted every 90 days. This is your chance to win exciting prizes including a Grand Prize of a three-day trip to Dry Tortugas, worth $15,000.

GRAND Prize

First prize, second prize, third prize, let's set sail.

Historic Seaport, 120 Margaret St C18, Key West, FL 33040

(361) 459-7245

 [email protected]

Let's Set Sail!

• Become an Anchor Captain
• List Your Boat

Basic Information

Key West Yacht Rental

Welcome to Anchor Yacht and Boat Rentals, your premier destination for the ultimate Key West boating experience. Nestled in the heart of Key West, Florida, our fleet of luxurious yachts and boats awaits, ready to provide you with an unforgettable adventure on the crystal-clear waters of the Gulf of Mexico and the Atlantic Ocean.

At Anchor Yacht and Boat Rentals, we take pride in offering a diverse selection of vessels to suit every taste and occasion. Whether you're seeking a romantic sunset cruise, a thrilling deep-sea fishing expedition, or a relaxing day of snorkeling and swimming, our boats and yachts are equipped to make your dream day on the water a reality. Our team of experienced captains and crew members are dedicated to ensuring your safety and enjoyment throughout your journey.

Our Key West boat and yacht rentals are not just about transportation; they're about creating memories that will last a lifetime. Picture yourself sipping champagne on the deck of one of our elegant yachts as the sun dips below the horizon, casting a golden glow on the sea. Imagine the thrill of reeling in a trophy fish or the wonder of exploring vibrant coral reefs teeming with marine life. These are the experiences that await you when you choose Anchor Yacht and Boat Rentals.

Whether you're a seasoned sailor or a first-time boater, our team is here to make your adventure exceptional. So, why wait? Contact us today to book your Key West boat or yacht rental and embark on an unforgettable journey with Anchor Yacht and Boat Rentals. Your dream day on the water is just a click or a call away.

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Key West, FL Sailboat

Set sail in the florida keys & enjoy a perfect day on the water, custom 33' sloop (1975), description.

A sail on this custom sloop offers a great way to see Key West from the water! Experience the joy of setting sail and shutting off the engine as we sail you through the colorful waters that surround our beautiful Island. Sail through the internationally renowned live- aboard anchorage, past Mallory square and the old Customs House and out toward Fort Zachary Taylor. Sail around Sunset Key and take a look at Key West's most fantastic National wildlife preserve. You will always have a chance to see dolphins, turtles and countless variety of sea birds. Sit back and relax or take a turn at sailing the boat. This truly is your trip!

With over 15 years experience sailing and living in the Keys, our captains and crew provide you with the local knowledge of marine life, surrounding islands as well as stories of Key West's rich and colorful history. Come sail with us in comfort and style.

Trip Includes: soft drinks, bottled water and coolers stocked with ice. You are welcome to bring any adult beverages of your choice.

Two hour sails reflect sunrise and sunset sails.

Price calendar and Availability

• Manufacturer Custom
• Model 33' Sloop
• Guest Capacity 6
• Single Beds 0
• Double Beds 1
• Bathrooms 1
• Number of engines 1
• Horsepower per engine 12
• Chart plotter
• Cocktail parties

Navigation & Safety

• Depth finder
• Life jackets
• Fire extinguisher
• First aid kit
• Cockpit table

Sports equipment

View all photos

Member since October 2015

I am a professional sailor, and a knowledgeable guide of Key West. I will work hard to make sure that you have an excellent day with us on the water.

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Location and Destination Guide

Key west attractions by boat, destination guide.

Usually this boat operates around Key West, FL .

Florida Keys is the boating paradise waiting to be discovered on board of Sailo’s top Key West sailing charters. From the many Key West attractions by boat, our favorites are snorkeling the reefs and mysterious shipwrecks, or Dry Tortugas fishing in crystal clear, turquoise waters. At the end of a long day on your yacht rental in Key West , Florida treat yourself with the perfect sunset cruise and take away memories for a lifetime.

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EXPERIENCE SAILING IN SOUTH FLORIDA ON A Custom 33.0 BOAT RENTAL IN Key West

Welcome to one of the most famous year-round boating destinations in the world! Hop aboard your yacht charter in Key West, FL and enjoy this amazing floating playground for both beginners and experienced sailors. The boat rental in Key West, FL you have selected is a Custom Sail boat - a popular choice to explore the natural beauty of Florida’s coast. Sailing on a FL, Key West yacht charter is an experience you should not miss if you decide to visit the boating capital of the world. Picture yourself on romantic  sunset cruise on this FL, Key West boat rental, or having fun with your family or friends on a sightseeing tour along the coast. For more ideas about things to do on your boat rental or yacht charter in Key West, FL, make sure to check our destination guide for Sailing in South Florida !

We invite you to browse through hundreds of Sailo boats perfect for sailing in Florida, and choose the dream Sail boat rental or yacht charter for your nautical adventure. Whether you are looking to spend a relaxed afternoon on a classy motorboat or sailboat, or have a fun on a sporty catamaran, our team here to make sure you will be making the best out of your time on the water.  For details about this Custom 33.0 boat rental in Key West, FL, or to make special arrangements for your trip, please click on the “Message Owner “ blue button to send a direct message to the boat representative.

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SERENITY NOW

Private Charters Key West Florida

Private crewed sailing packages.

Set sail on your own private catamaran and explore the only living coral reef in the continental United States.  Sail the pristine turquoise waters of the Florida Keys and enjoy a relaxing afternoon on a secluded beach.  As a private charter you, and up to 5 of your guests, have the option to customize your adventure.

Full Day Sail  Adventure Lunch and Optional Snorkeling

Starting at $1200

Half Day Sailing Adventure with

Optional lunch and snorkeling.

Starting at $600

Sunset Sailing Adventure with  Appetizer  and optional Snorkeling

Sailing catamaran "serenity now".

Up to 6 Passangers max

S/V "Serenity Now"  is a Fountaine Pajot Lipari 41.  She has a large comfortable trampoline on her bow and a spacious covered cockpit on her stern. Inside you will find a settee with seating for six along with four cabins and two large heads.

About Your Crew

Captain Tom and his wife Denise have been sailing for over two decades.   Over the course of the last three years they have sailed over 4,000 nm along the east coast of US and the Caribbean Sea.  Tom holds a USCG OUPV Captain's License.  Prior to their most recent adventure, Tom was a Research Physicist and his wife a Public Relations Manager.  Bow and Harry our French Hounds server at the pleasure of our guest or vacation at a nearby pet resort during charters.

6810 Font Street

Key West FL 33040

[email protected]

410-849-9199

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Exclusive Excursions

Water Adventures For Private Groups

Elevate your event with Fury Signature Charters, where every detail is uniquely yours. We understand that your event is special, and our dedicated event planning team is here to ensure everything is executed to perfection. You can craft a custom private charter itinerary with us, blending various Fury excursions, delicious cuisine, and beverages. And because Fury has the largest fleet with the most deck space in Key West, you’ll get the variety of options you need to make your event Signature!

Key West Private Charters

Completely Customizable

Guaranteed best price when you book direct.

GROUPS OF 8 OR MORE CALL FOR DISCOUNT Flexible & Refundable Reservations.

Reserve a private Fury Charter or customize your own!

At Fury, we specialize in crafting unique event experiences for charter enthusiasts. With our spacious catamarans and the largest deck space in Key West, we can accommodate charters of any size. Our dedicated crew ensures flawless execution, offering tailored excursions, exquisite cuisine, and refreshing beverages for a truly extraordinary charter occasion.

• Perfect for groups of any size.
• Customizable starting at 1.5 hours.
• Starting at $1,650* (*Gratuity and service fee not included)

“We almost signed up to go again the next night, but I was afraid that I had worn myself out. My wife and I highly recommend this charter!”

This is a 10 out of 10!! It was an awesome day, professional, friendly staff all the way around! Thanks for a great day in Key West!

“ Our friends booked a private charter to a sandbar as a birthday celebration and it did not disappoint! Captain Jude and Tomas were top-notch during the entire trip. Music, drinks, food, entertainment and overall enjoyment were major priorities! Highly recommend these guys! “

“ Extremely knowledgeable staff! We saw so many dolphins, and let’s not forget the great playlist. I will not hesitate to charter them again! Cheers! “

“ This was my second charter with Fury and another great full day on the water! This is a well-oiled machine. The crew was amazing, the food was really good and the activities kept you going! I highly recommend this trip when you visit Key West! “

“ The charter captain took the time to stop and show us the dolphins swimming while the crew talked about them on our way back. Overall, it was a fantastic experience, and I can’t wait to do it again.”

45' Power Catamaran

• Capacity of 30 Passengers
• One Restroom
• Fresh Water Rinse
• Covered Seating Area

Call (877) 561-8825 to book or send inquiry below

57' Power Catamaran

• Capacity of 49 Passengers
• Two Restrooms
• Shaded Area
• Seated Sun Deck
• Open Netted Seating Area

65' Sailing Catamaran

• Capacity of 122 Passengers
• Shaded Lounge Area
• Large Sun Deck

WHAT'S INCLUDED

Types of charters.

• Associate Reward Trips
• Corporate Events
• Group Outings
• Graduations
• For Wedding Charters Click Here

PRICING & ADDITIONAL SERVICES

To Reserve you must call (877) 561-8825 to book or submit inquiry below.

Additional services may be provided such as catering, full bar & live music bands for an additional fee.

• Name * First Last
• Phone Number
• Event Type Please select Associate Rewards Trip Corporate Event Group Outing Birthday Graduation Wedding Other
• Charter Date MM slash DD slash YYYY
• Number of Guests

Places To Explore With Your Charter Boat Rental

For those seeking to enjoy ocean adventures on their own schedule, renting a private charter boat is the perfect option! We offer half and full day rates for state-of-the-art catamaran rentals with convenient departure points located right on the Key West Harbor. Here’s a sampling of extraordinary sites to explore with a Key West private boat charter from Fury.

Sand Key (24° 27.138’N, 81° 52.573’W)

If it’s the coral reef you’re craving, then head to Sand Key, seven miles south of Key West. This popular snorkel spot is home to a historic lighthouse and its shallow reef formations are ideal for novice and experienced snorkelers alike. Your boat captain will tie up to one of the white-and-blue mooring buoys and you’ll be ready to swim among the rainbows of colorful reef fish. This area is specially protected, so please take only photos and leave only bubbles!

Western Dry Rocks (24° 26.692N, 81° 55.581’W)

Southwest of Key West along the reef tract is Western Dry Rocks. Like Sand Key, it has large rows of shallow coral reef alternating with sand channels, making it a great snorkel spot for scoping colorful fish, the occasional angelfish or even a blue tang!

Boca Chica Sandbar (24° 33.295’N, 81° 42.935’W)

In search of sand-between-your-toes relaxation closer to Key West? Then the sandbar south of Boca Chica is just the place for you! Though civilization is within sight, you’ll feel worlds away surrounded by white sand and shallow clear water. You may even be lucky enough to spot a Bahama sea star or queen conch, but be sure to leave nature in its place since both are protected animals.

We require payment in full at time of booking for the private charters.

Yes! You can choose to charter a specific Fury tour if you wish or customize your own.

The most popular private charter is a 4 hour trip with snorkeling, kayaking and relaxing at the sand bar. Depending on when your trip is booked, it’s possible to even watch the sunset.

Yes! Fury operates 365 days a year.

We do not provide professional photography. Our crew may take boarding photos and can take photos throughout the trip for an additional fee.

No, we do not offer any wifi on our vessels.

All charters include beer, wine, champagne, sodas and water. We do have a catering options and bar upgrades available for an additional fee. We do not allow outside catering or drinks on our charters.

Yes. All guests are provided with Buoyancy Compensators for snorkeling. Life jackets are onboard for everyone in case of emergency.

No, we do not provide parking at any of our check in locations, but you can use street parking, pay to park lots or parking garages.

Fury tours will not depart in unsafe weather conditions. The Captain will assess the weather and should the Captain determine that the conditions are unsafe to run the tour, the tour may be postponed or it will be canceled. Every effort will be made to reschedule your tour during your stay. If you are unable to re-schedule your tour, you will have the option of receiving a voucher for a future trip. Every effort will be made to run tours, as advertised. Should Fury have to amend or alter your tour due to extraneous circumstances, tickets remain non-refundable on tours taken.

We have a 20% non refundable deposit. Within 30-15 days of your charter, we are able to refund 50% of the trip, and within 15 days of your charter we do not offer a refund. We do offer a full refund if we cancel the charter due to weather conditions.

Fury allows service animals only. A service animal is any dog that has been trained to perform tasks to benefit an individual. The work performed must be directly related to the individuals disability. According the ADA service animals for emotional support, therapy, comfort or companionship are not considered service animals.

The guest requiring the service animal must be in possession of the animal at all times. ​Due to the nature of Fury tours, guest and service animal may be required to remain on the boat for the entirety of the tour . This is to ensure the guest’s safety as well as that of the service animal, Key West wildlife, other guests, captain and crew.

LET'S TURN UP THE HEAT ON SAVINGS!

Sign up to receive an email with a one time offer code to use on select trips.

Combo Package SAVE $100

Package with Reef Snorkel, Parasail or Glass Bottom Boat & Save

TRIP DETAILS

Commotion On The Ocean Sunset Cruise

Key West’s Original Live Music Sunset Cruise

• Departs 6:30pm

Save up to $8*

Dolphin Watch Eco Tour

Founding member of NOAA Dolphin Smart Program

• Departs 9:00am, 12:30pm & 5:00pm

Dolphin Watch Sunset Cruise Combo

Eco Tour • Backcountry Snorkel • Sunset (Available Seasonally)

Double Dip Snorkel Sunset Combo

Snorkel 2 Reef Locations • Sunset (Available Seasonally)

• Departs 10:30am & 2:00pm

Double Dip Snorkel Trip

Visit Two Living Coral Reef Locations

Fury’s Island Adventure Eco Tour

Remote Sanctuary Reserved For Locals

• Departs 10:00am & 3:30pm
• Food & Beverages

Save up to $15*

Glass Bottom Boat

Taking Visitors To Key West’s Reefs For Over 70 Years

• Departs 12:00pm, 2:00pm & 6:00pm
• Approx. 2 hrs

Save up to $7*

Glass Bottom Boat & Sunset Cruise

Island Adventure & Sunset Cruise Combo

Eco Tour • Snorkel • Kayak • Paddleboard • Sunset Combo Option

Key West Jet Ski Tours

Brand New SeaDoo Jet Skis

• Departs 8:30am-5:30pm

Key West Parasailing

Tandem + Triple Rides Largest Parasailing Fleet in Key West

• Departs 9:00am-3:00pm, 4:15pm & 5:15pm

Key West Snorkeling

Start Your Day Aboard Key West’s Most Spacious Catamaran

• Departs 9:30am

Save up to $5*

Key West Sunset Cruise

Tranquil Ocean Setting

• Departs 6:45pm

New! Ultimate Adventure H2.0

Key West's Largest & Only State Certified Ocean Waterpark • All Activities Included!

• Departs 10:00am & 1:00pm

Save up to $30* with code 10X

Reef & Ritas Snorkeling Trip

Afternoon Adventure Aboard Key West’s Most Spacious Catamaran

• Departs 1:00pm

Save up to $6*

Rum & Reggae Snorkel Sunset Combo

Reef Adventure by Day, Sunset Magic by Night

• Departs 5:00pm

• Best listings 1st
• Price - Low to high
• Average Rating - Highest rated 1st

Our charter advisors are here to assist you.

An expert will find you the best offers

Sailboat rental in Key West, United States

Rent a boat in Key West to expore the island. You can also rent a catmaran in Key West if you prefer.

Our other types of boats

Best deals at sea.

Find the best prices for boat rentals & yacht charters with or without a skipper.

Quality control

Boat listings are checked regularly to guarantee the highest standards possible

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Customer Care

A team of charter experts to help you seven days a week

Key West Boat Rentals

The original est. 2005, boat rentals kw key west florida, making memories to last a life time.

It’s your day and your way!

Book 305-797-8954

Our family owned business, since 2005, is crazy about boating in the Florida Keys !

Offering the widest selection of Pontoons, Deck Boats, Center Consoles and Charters for any occasion.

Deck boat Rentals

We have you covered.

• Tiki Boat Charters

Eco Tours & More!

• Center Console Rentals

Choose from different sizes

Sandbar & Kayak Watersports

Eco Adventures!

• Island Charters

Are you ready to relax?

Pontoon Boat Rentals & Tritoons

Check out these rental options for a fun day!

Book Direct and Save!

Rent a Boat KW

What makes us different?

Key West has beautiful Back Country . You can find your own private fishing hole, sand bar, or even snorkel on the reef.  Florida Keys Boat Rentals   provides you with a wide range of rentals, charters and watersports to choose from.

We show you the fishing holes, snorkeling spots and local hangouts to make the best of your self guided boating tour on the beautiful waters of Key West, Florida. We have a boat rental for any occasion.

Boat the clear waters of Key West, zip around the Back Country , find your own private fishing hole, scuba dive spot or a snorkel spot on the reef. Florida Keys Boat Rentals makes this all possible. Set your own schedule and choose from a wide range of reliable, comfortable rental boats. All of our rental boats are perfect from a day of diving, snorkeling or private sunset cruises in Key West.

Boat Rentals KW Key West Florida FL.

Key West Boat Rentals and Sandbar Charters reviews

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• Boat Rentals
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• Rum Runner Tour
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• Luxury Private Charter
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• Sunset Dinner Cruise
• All Day Adventure – Do it All
• Key West Parasailing
• Jet Ski & Wave Runner Tour
• Mangrove Boat Tours
• Key West Sip & Sail Sunset Cruise
• Key West Sunset Snorkel Sail
• Key West Dolphin Watch, Snorkel & Sunset
• Guided Kayak Eco tour 2 hour
• Contact Info
• 305 797 8954

Pick A Boat • Call us at 305-296-2554

KEY WEST BOAT RENTALS

Be your own captain, personalize your trip & add a captain for just $250, now $50 off full day rentals, quick   highlights.

Cruise Ship INCLUDES:

Half or Full-Day Rental & Pet Friendly!

Clock START TIME & DURATION:

9am or 1pm, 4 Hour (half Day) or 8 Hours (Full Day)

Map Marker DEPARTURE LOCATION:

Cow Key Marina, 5001 5th Ave, Key West Island

Star Outline REVIEWS:

Over 2,563 5 star reviews, click Here to Read Reviews

NEW PONTOON RENTAL   BOATS

22ft Deluxe Pontoon Boat With Lounge Seating EQUIPPED: 115HP, BIMINI TOP, RADIO, COMFORT SEATING & READY FOR YOUR KEY WEST ADVENTURE.

Online Special: $50 off Full Day

• Full Day Price: $ 625 Now $575
• Half Day Price: $500
• Boat Type: Pontoon with lounge
• Up To 8 People

22ft Premier Pontoon Boat With Lounge Seating & Sun Bed EQUIPPED: 115HP, BIMINI TOP, RADIO, COMFORT SEATING. PERFECT FOR YOUR TRIP TO THE SANDBAR

➔ Half Day – 4 Hours (9AM – 1PM or 1PM – 5PM) ➔ Full Day – 8 Hours (9 AM – 5 PM) ➔ LOWEST Prices Guaranteed ➔ Full-Service Marina Bait, Drinks & More! ➔ Over 38 Years in Key West ➔ Award-Winning Watersports Company

Book with Confidence

Check available dates:, available rental boats.

NEW BOAT: 22ft Deluxe Pontoon Boat With Lounge Seating EQUIPPED: 115HP, BIMINI TOP, RADIO, COMFORT SEATING & READY FOR YOUR KEY WEST ADVENTURE!

NEW BOAT: 22ft Premier Pontoon Boat With Lounge Seating & Sun Bed EQUIPPED: 115HP, BIMINI TOP, RADIO, COMFORT SEATING. PERFECT FOR YOUR TRIP TO THE SANDBAR!

22ft Hurricane Deck Boat With Upgraded Lounge Seating EQUIPPED: 150HP, BIMINI TOP, RADIO, COMFORT SEATING. DECK BOATS ARE PERFECT FOR ALL TYPES OF TRIPS FROM SANDBARS, SNORKELING, DOLPHIN WATCHING & MORE.

• Full Day Price: $ 575 Now $525
• Half Day Price: $450
• Boat Type: Deck Boat

21ft Key West Center Console (Luxury Edition) Sound & Seat Upgrades EQUIPPED: 250HP, BIMINI TOP, RADIO, READY TO FISH. THIS BOAT IS BUILT FOR COMFORT & PERFORMANCE.

• Full Day Price: $ 600 Now $550
• Boat Type: Center Console
• Up To 6 People

(New) 21ft Nautic Star With Comfort Seating & Ready For Fishing EQUIPPED: 115HP, T-TOP, RADIO, UPGRADE COMFORT SEATING & SOUND. THE PERFECT ALL AROUND ADVENTURE BOAT. READY FOR FISHING, SANDBARS, SNORKELING & MORE

• Full Day Price: $ 550 Now $500
• Half Day Price: $400

21ft Contender Performance & Ready For Fishing EQUIPPED: 200HP, T-TOP, RADIO. THIS BOAT IS READY FOR EVERYTHING FISHING, SNORKELING, SANDBARS & MORE. THE CONTENDER BRAND IS BUILT FOR PERFORMANCE

• Half Day Price: $475

22ft Cobia Center Console EQUIPPED: 150HP, BIMINI TOP, RADIO, ROD HOLDERS, ONBOARD COOLER. 

• Full Day Price: $ 525 Now $475

19ft Boston Whaler EQUIPPED: 115HP, BIMINI TOP, RADIO, COMFORT SEATING.

15ft Boston Whaler (Cozy Cruiser) EQUIPPED: 60HP, BIMINI TOP, RADIO, COMFORT SEATING. THE PERFECT RENTAL BOAT FOR UP TO 3 PEOPLE.

•   Full Day Price:  $475  Now $425
•   Half Day Price: $350
•   Boat Type: Center Console
•   Up To 3 People

SEE THE ADVENTURE

KEY WEST BOAT RENTAL   DETAILS

Captain your own Key West adventure. We have the largest fleet of rental boats in Key West. Select the boat that best fits your needs. We have everything from pontoons and deck boats with space to lounge to center console fishing boats, all available from our marina in Key West. Our rental boats range in size and space, based on your rental needs. You can rent a small, personal 2 person boat up to a 12 person pontoon. Our boats are perfect for trips to the sandbar, fishing, snorkeling & more.

Now Available: Reserve a floating lil pad mat, snorkel gear, fishing poles and more from our onsite marina store.

Pet Friendly: Dogs are welcome our your boat rentals. 2 Max

Boats are available for rent for half day (4 hours) or full day (8 hours) rentals. Half-day boat rentals must be scheduled at 9 am and returned by 1, or 1 pm and returned by 5 pm. Please note, renters must be 25+ to drive.

Do you want to rent a boat but not familiar with the Key West waterways? No problem, add one of our experienced, local captains for an additional cost (please call our office to reserve at least 3 days in advance. Full-day captain cost is $350 and half-day cost is $250).

This activity is operated by Sunset Boat Rentals & Tours Inc. Rental boats are proudly powered by Mercury

• Chevron down Rental Requirements
• A Credit Card Authorization for $1000 is required for deposit.

Guests are responsible for gas. The boat will be filled back up at the marina.

You must be 25 years of age to rent a boat & have previous boating experience.

Dive tanks are not allowed on rental boats per Florida state law.

• Rental boats must remain within 10 miles from the marina.
• All guests must be present at check-in to sign liability waivers
• Chevron down Location

• Chevron down Florida Boaters Safety Test

Required – Florida Boaters Safety: Florida Law requires everyone born after Jan 1, 1988 to take a boaters safety test to drive a boat. Each driver must present a passed boaters safety test prior to departure. Tests can be taken online, click here.

• Chevron down Can I Bring Dogs On Your Rental Boats?

Absolutely, feel free to bring your dog with you on your rental boat.

• Chevron down What We Offer
• Pontoon Boats
• Snorkeling Boats
• Fishing Boats
• Knowledgable & Friendly Staff With The Best Spots To Explore
• Great For Family & Group Trips To Local Sandbars & Hotspots
• Lowest Price Guaranteed
• Chevron down Our Fleet

Click HERE to view photos of our boats.

• Half-day – $525 | Full-day – $600
• Up to 12 people
• Equipped: 150hp, bimini top, radio, comfort seating
• Half-day – $500 | Full-day – $575
• Up to 8 people
• Equipped: 60hp, bimini top, radio, comfort seating
• Half-day – $450 | Full-day – $525
• Equipped: 150hp, bimini top, radio, rod holders, on-board cooler
• Half-day – $400 | Full-day – $475
• Up to 6 people
• Equipped: 115hp, bimini top, radio, comfort seating
• Half-day – $300 | Full-day – $375
• Up to 3 people
• Chevron down Full Service Marina
• Stock Rock Cafe
• Live & Frozen Bait & Tackle
• Convenience Store
• Snacks & Beverages
• Snorkel Equipment Rental
• Fishing Equipment Rental

22ft Deluxe Pontoon Boat With Lounge Seating

• Dollar Full Day Price: $625 Now $575
• Dollar Half Day Price: $500
• Cruise Ship Boat Type: Pontoon with lounge
• Users Up To 8 People

22ft Premier Pontoon Boat

26ft pontoon boat.

• Dollar Full Day Price: $650 Now $600
• Dollar Half Day Price: $525
• Cruise Ship Boat Type: Pontoon
• Users Up To 12 People

22ft Deck Boat

• Dollar Full Day Price: $575 Now $525
• Dollar Half Day Price: $450
• Cruise Ship Boat Type: Deck Boat

Key West Center Console

• Dollar Full Day Price: $600 Now $550
• Cruise Ship Boat Type: Center Console
• Users Up To 6 People

21ft Nautic Star

• Dollar Full Day Price: $550 Now $500
• Dollar Half Day Price: $400

21ft Contender

• Dollar Half Day Price: $475
• Dollar Full Day Price: $525 Now $475

19ft Boston Whaler

15ft boston whaler.

• Dollar Full Day Price: $475 Now $425
• Dollar Half Day Price: $350
• Users Up To 3 People

BOAT RENTAL REVIEWS

The boat rental folks at Sunset Watersports were extremely helpful and fun! The crew had winning personalities that made the trip extremely enjoyable and the staff at our boat rental day went out of their way to be helpful during shuttle service and getting us set up with fun GPS coordinates for our pontoon boat rental day. Thank you for the good times!

Absolutely incredible boat rental. The crew were fantastic. Christie and Bridget did a wonderful job at Cow Key Marina. If you want a great boat rental in the Key West area, this is the place to go! We rented a pontoon boat and they directed us to a beautiful sandbar for the best day ever!!

We did a full day rental if the 22 foot center console fishing boat. Service was great before and after rental. I selected the incorrect boat when booking online and called in to change the order. They were very accommodating. Staff was very helpful with pointing out spots to check out and when going over the boat. Built in cooler and swim ladder. Overall a great experience!

Sunset Watersports boat rental crew made it easy to rent. The shop had fishing pole rentals, snorkeling rentals and bait. Helped us download the navionics app on our smartphones and prepared us for what the waterways were like. Great guys!

My wife and I were in Key West to celebrate her birthday. The staff were very helpful. They advised us the 21' center console fishing boat would be a better option due to the weather conditions which was a good choice, as it had been renovated recently and had better equipment. The staff prepared us for our outing, we took their advice and had a great day. We cruised around the entire island. Encountered a group of dolphins who joined us for about 30 minutes, playing in our wake and leaping out of the water. It was fantastic! Went to the sandbar and enjoyed relaxing in the ocean. Big thumbs ups from us!

BOAT RENTAL FAQs

• Chevron down What kind of boats do you have?
• Equipped: 90hp, bimini top, radio, comfort seating
• Chevron down Can I hire a captain?

Yes! Captain hire cost is $350 per Full Day and $250 per Half Day.

• Island Hopping
• Sandbar Excursions
• Explore With A Local Tour Guide
• Remember to bring your bathing suits, sun glasses, sunscreen, towel, hats and favorite beverages

We also have fishing & snorkeling equipment for rent at the marina!

• Chevron down How old do I have to be to rent?
• Chevron down Do your boats have GPS

We have partnered with Navionics, a GPS app that utilizes your phone to provide up to date mobility on the water. Navionics is a cutting-edge navigation app that serves as your ultimate marine companion. With detailed charts, real-time weather, and community-sourced data, it provides boaters and outdoor enthusiasts with the essential tools for safe and enjoyable adventures on the water. You may download Navionics ahead of time to familiarize yourself with the app or our boat rental crew can show you how to use it at time of check-in.

• Chevron down Can I bring dive tanks?
• Chevron down Am I responsible for gas?
• Chevron down What sandbars should we go to in Key West?

Key West is surrounded by some of the Florida Keys best sandbars. Here are some of our favorites. 

Snipes point sandbar boat rentals:.

Located east of the mangrove isles of Mud Keys, its easily one of the favorite local sandbar hangouts. This sandbar gets even more popular on weekends, where you can find tons of locals from the middle to lower Florida Keys. Snipes Point water is crystal clear and shallow.

Jewfish Basin Sandbar Boat Rentals:

Located just 7 miles north of Key West you will find a series of beautiful sandbars tucked away in between the Harbor Keys & Mud Keys. These sandbars are perfect inlets for boat rentals & very close to our marina dock at Cow Key Marina.

Mud Keys Sandbar Boat Rentals:

The only reason this location is number 3 on the list is due to the difficulty navigating. The Mud Keys are a series of mangrove islands and shallow water way passages. This location is much less popular, not because of it’s beauty but due to it’s true seclusion. We highly recommend asking our company for a guide to help navigate these tough passages.

Boca Grande Sandbar Boat Rentals:

Boca Grande is another amazing sandbar located in just off of Key West. Boca Grande is about 15 miles west of Key West and is a 180 acre uninhabited island located in the Mule Keys. This sandbar is great for exploring & socializing among other visitors. This sandbar is outside of the range of our standard boat rental but you can hire a guide with one of our boat rentals to explore this incredible island.

Boca Chica Sandbar Boat Rentals:

The closest and most accessible of Key West’s sandbars is located just off the island of Boca Chica. This sandbar is about a mile from the marina and is frequented by jetski tours, boat rentals and charters alike. This shallow water haven is ideal for your first stop no matter if you are going snorkeling, sandbar hopping or even fishing.

KEY WEST BOAT RENTALS VIDEO

Key West Discounts & Deals?

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Matt Weidert

Key West Bareboat Charter | Sailing Adventure to the Dry Tortgas

Planning and our last-minute booking, boat trouble a-brewing.

Sailing to Dry Tortugas - our catamaran finally gets underway

What to expect from the Key West Bareboat Charter cruising grounds

• Few protected anchorages
• Mostly anchoring, limited moorings available
• Longer passages
• Dodging the lobster trap buoys was very frustrating - here's my advice: charter a boat with good visibility from the helm station and go farther south on your route to the park (time and weather permitting)
• I asked the operator of the Yankee Freedom (high speed catamaran that takes tourists to the park daily) if there was a better route to avoid the buoys - they confirmed there is no better route than the one we took
• Less predictable weather - shiftier trade winds, hurricane season, and cold fronts in the winter

Fishing en route to the Dry Tortugas

Dry Tortugas fishing totals - I give us a C+

• 3 barracuda (one of which was the biggest I've ever caught...and I seem to catch a lot of them)
• 2 king mackerels 
• 1 little tunny

Exploring Fort Jefferson and Garden Key

Heading ashore at Dingy Beach

Homeward bound - back to civilization.

Our last day and a change in plans

Not qualified to do a Key West bareboat charter on your own yet?

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Overnight Boat Rental Key West

by "Charter Booker" | Dec 23, 2017 | Overnight Yacht Vacation Rentals

Overnight boat rental in Key West, Florida is a popular option.  Many people like to take in a sunset sail or a full day excursion, snorkeling, swimming, relaxing and sailing.  There’s so many reasons why you’ll love an overnight boat rental in Key West, Florida, as alternative accommodation, but here’s 5 of our favorites:

Guaranteed water views!

Forget a room with a view…stay in the view, on a yacht in Key West, Florida! You’re at water level on a yacht in Key West. See fish and other marine wildlife swim right up to your yacht. Manatees are common marine wildlife you can see while staying overnight on a yacht in Key West, Florida.  From time to time it is not uncommon to see a dolphin or two swim by on a boat in Key West, Florida.

Wow factor on an overnight boat rental

Get a slice of laid back luxury in your life on a yacht in Key West, Florida.  It’s common to stay at a hotel or in a house, but how common is it to stay overnight on a vacation rental that floats in Key West?  Book your next vacation rental on a yacht today in Key West. Stay overnight, take a sunset sail, or enjoy a full day excursion out on the water while being in your home on a boat in Key West, Florida.

Family friendly overnight boat rental 

Kids can have their own cabin. Most of our yachts in Key West will sleep a couple families making this amazing stay on a yacht in Key West an incredible vacation. They can jump on many of our yacht’s trampolines, fish, and for those daring, can even jump off the yacht in Key West into the ocean blue water.  Overnight on a yacht in Key West is a vacation rental dream come true.

Quality time

Swap the screens for open skies & stars. There’s nothing better than laying on the deck of your favorite boat in Key West, under the stars, unplugged, and taking all that Mother Nature has to offer staying on a boat in Key West, Florida.

Save money with an overnight boat rental 

All this for less than a hotel room in Key West, Florida. Many hotels in Key West, Florida are over-priced due to the fact that Key West, Florida draws overnight vacation rentals from all over the world.  Vacation rental customers do not know how inexpensive it is to stay on a yacht in Key West Florida.  Whether you are looking to rent a boat in Key West, Florida, the cost savings can be huge. https://blueoceanyachtcharters.com/contact/

Happy Sailing,

“Charter Booker!”

(Charter Booker, manages Blue Ocean Yacht Charters in Key West and writes many of the company’s blogs.  He has experience both on the water and off the water helping customers experience the best possible yacht charter.  Carrying American Sailing Association certifications with extensive knowledge of boat safety and regulations makes him the charter authority.  Call 305-923-4152 and ask for “Charter Booker” when booking your next yacht charter in Key West, Florida.)

Get 10% off with code BOOK10 when you book through our website.

Boat Rentals

Make Your Vacation Memorable!

26’ Rendezvous Deck Boats

20’ Hurricane Deck Boat

22' Angler Panga

23’ Sea Fox

23' hurricane fun deck.

21’ Pathfinder

• 701 Palm Ave. Key West, FL 33040
• 305-296-8826

SEVERAL BOAT OPTIONS!

25′ SINGLE DECK PONTOON

UP TO 12 PEOPLE Half, Full & Multi-Day Rates

Optional Add On: Snorkeling, Paddleboard, LillyPad, Sandbar Adventure, Mangrove Tour, Dolphin Cruise, Booze Cruise, Sunset Cruise*, Wine and Sunset Experience*

*Sunset Cruise & Wine & Sunset Experiences require a Captain. Captains can be requested upon checkout. (Renter is required to pay captain directly).

25′ DOUBLE DECKER PONTOON BOAT W/ DOUBLE SLIDES

UP TO 15 PEOPLE Half, Full & Multi-Day Rates – Two Slides – Two 70qt Coolers

30′ DOUBLE DECKER PONTOON BOAT W/ THREE SLIDES

UP TO 15 PEOPLE Half, Full & Multi-Day Rates – Three Slides – Two 70qt Coolers

RELEASE PANGA FISHING BOATS

UP TO 7 PEOPLE Half, Full & Multi-Day Rates -Rent a Release PANGA fishing boat for your off-shore and back country fishing excursion -Live wells, GPS & More -Brand new boats for 2023 -Medium to advanced boating operator skills required -Fishing equipment not included

Optional Add On: Snorkeling, Paddleboard, LillyPad, Sandbar Adventure, Mangrove Tour, Dolphin Cruise, Booze Cruise, Sunset Cruise, Wine and Sunset Experience

27′ LUXURY CENTER CONSOLE FISHING BOAT

Half, Full & Multi-Day Rates -Rent a 27′ Boston Whaler center console fishing boat and add a captain for your off-shore and back country fishing excursion. -Twin 225 -Starting at $800 -Live wells, GPS & More -Fishing equipment not included & pricing does not include fuel, tax, or captain.

*Please Note:  A Captain is required to rent the Luxury Center Console.

21′ BOSTON WHALER

Half, Full & Multi-Day Rates -Rent a 21′ Boston Whaler fishing boat for your fishing excursion. -Spacious and comfortable seating, complete with a sizable sun lounge on the bow -Equipped with cutting-edge GPS, Bluetooth Stereo, swim ladder, and additional amenities -Immaculate, brand new vessel of the 2023 model year -Can accommodate up to 9 People or 1488 LBS -Discover unparalleled luxury aboard our esteemed family day boat.

*Please Note:  This vessel necessitates medium to advanced boating operator skills.

Optional Add On: -Enhance your experience with available snorkeling gear and Lily Pads. -For detailed rates, availability, and further inquiries, please reach out to us.

Key Features:

I’M READY TO BOOK MY BOATING ADVENTURE!

Beach Weekend Key West is located just outside of Key West on Stock Island on the Ocean Side of US1. We are a full-service marina with wet slips, high and dry forklift service, as well as a full ship’s store.

Our brand new fleet of pontoon rentals will include 25′ Harris Cruisers, 25′ Solid Craft Double Decker with Double Slides, and 30′ Solid Craft Double Decker with Double Slide Pontoons, featuring a restroom and freshwater shower. Fuel is also available to the public and conveniently located.

LEARN ABOUT OUR BOAT CLUB

All the great things about boating | none of the bad.

Our brand new boat club in Key West gives you access to the pristine waters without all of the hassles of maintenance, expense, and time squandered maintaining a boat. Also, our custom “Beach Weekend Boat Club App”, offers you the convenience of scheduling your reservations, as well as adding additional services, such as ice, water sport activities, and more!

Boat Club membership is the premier way to experience the boating lifestyle! You will enjoy all the advantages of boat ownership without the enormous sticker shock of a boat!

Reserve Boat Storage!

We’re building brand-new boat storage! Call for details and  make your reservation today!

What Our Customers Say

My family came into town for a short trip. Decided to rent a pontoon boat for the day. Nicest boat we have ever rented. The staff was out of this world. Would recommend them to everyone!

Great company! Easy to talk to and the staff really does everything they can to make it an enjoyable vacation. I will be booking through them for years to come.

Vinnie Chulk

The staff at beach weekend are beyond amazing. My family has such a great time and the pontoons were all new and looked great. All the staff was so helpful with anything that we needed. We will definitely be booking again.

Ruth Halpine

We had an awesome day out on the water. The staff are some of the nicest people you’ll ever meet. The boats are brand new, and the facilities are incredible. We’ll definitely be back soon!

Brett Divine

The staff at beach weekend are beyond helpful. Alexis was such a pleasure to talk with over to the phone and answer all my silly questions! My family has such a great time and the pontoons were all new and looked great. We will definitely be booking again.

Bailey Miller-Hollenbeck

Recent Posts

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• 2009 August
• https://beachweekendkeywest.com/kw/
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The Best Boat Rentals in Key West

Browse, book, and get out onto the water with local captains and boat owners., our favorite boat rentals in key west.

5 (352 reviews)

• Boat Rentals

the United States

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

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

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

Private Key West Boat Adventure | Sandbars and More!

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

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

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

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

4-Hour Private Charter in Key West with Captain Zak

Jeanneau NC 895 Luxury Yacht - Private Key West Boat Charter

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

Salty Sandbars Key West on our new Boston Whaler 23 Vantage

Suggested searches, types of boats popular in key west.

From mid-size to mega yachts, these luxury boats are great for groups and celebrations

₽12,810-₽104,310

• Fishing Charters

Let a captain do the driving while you do the fishing

₽10,520-₽45,750

Explore local waters with a boat rental dedicated to sightseeing and exploration

₽10,520-₽82,350

Perfect for casual cruising, sandbar stops, swimming, and parties

₽11,440-₽15,560

Fishing Boats

Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts

Who says you need a motor to have fun on the water?

₽13,730-₽100,650

Set sail with these traditional wind-powered boats

₽14,640-₽43,460

Wakeboarding Boats

A high-octane powerboat designed and outfitted for wakeboard towing

Get off the boat and into the water with offshore snorkeling trips

Top Boat Rental Locations Near Key West

Florida Keys , Florida

109 listings

Stock Island , Florida

17 listings

Most Popular Yacht Rentals in Key West

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

Newer Key West Party Boat for 36 people!

"Princess Flybridge Yacht" Viking Princess

''Miss Carolina'' Carolina Classic 35 Express Rental in Key West, Florida

Most popular fishing charters in key west.

"Key West Sailfish" Sailfish 2360

Egg Harbor 35ft Sportfisher for Offshore Adventures!

Backcountry Fishing in Key West

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

Most popular boat tours in key west.

BackCountry Sandbars Key West

Adventure escape challenge on the waters in Key West, Florida

Experience Luxury in Key West on Your Own Terms - Key West's Premier Charter

Recent Reviews in Key West

We had an amazing experience with this boat rental. The boat was perfect and large enough for our family. The communication and all the details were a breeze. We would definitely rent this boat again and will share with friends. Thank you!

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

Eric was extremely friendly and his boat was great! We really enjoyed our time out in the sun and he took us to the best spots! He provided a cooler w ice, a mat to lay on and two floats! Definitely book with him if you are in Key West!!

We had a great time with Captain Michael. He was very professional and helpful. Will definitely come back again!

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

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!

Full of experience we loved everything

Top Boat Rental Locations in the United States

Miami , Florida

923 listings

Miami Beach , Florida

432 listings

Tampa , Florida

444 listings

Los Angeles , California

405 listings

Chicago , Illinois

282 listings

Hollywood , Florida

272 listings

How To Book on Getmyboat

Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.

Inquire & Book

Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.

Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

Dive into Our Journal

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Getmyboat's Guides to the World of Boating

Frequently asked questions.

Boat rentals in Key West cost between $100/hour for a small powerboat rental up to $1,800/day for private yacht rentals . The average price for a boat rental in Key West is around $300/hour for a motor yacht or pontoon rental .

The best time of year to visit Key West is late spring and early summer, between April and June, to avoid Spring Break crowds and the high temperatures of peak summer. Fall is also a good time to visit; September and October are good months to travel to Key West.

The journey from Miami to Key West takes 3-4 hours by boat. You can charter a boat from Miami to Key West for a scenic trip.

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Boat Rentals

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We're your number one source for boat rentals in Key West, FL!

Book Today!

If you’re looking to spend the day fishing, cruising around the island shore or just looking to take the family out and explore our crystal blue waters, we have the perfect boat for you!

Key West is a fantastic destination with plenty of sites to see. You can choose from a wide variety of vessels including Skiffs, Center Consoles, and Deck Boats.

We want to make your boat rental experience as smooth as possible so if you have any questions or would like to reserve your boat or jetski today, just call the number listed below!

Fishing Charters

Dolphin Tours

Scuba Diving