6 Best Yacht Charters In Key West, Florida - Updated 2024

Rachel
Rachel 
Contributing Writer
Updated
| 3 min read

Key West is an island city in the Florida Keys, famous for its upscale beach lifestyle and many exciting things to do. It’s popular among beach lovers and water sports enthusiasts alike. The best way to experience this tropical oasis is on the water, and the best option is to stay on a private overnight boat charter to fully capture all possible opportunities to dip into the crystal blue ocean. Warmed by the gulf stream, the water in Key West maintains a perfect year-round temperature for swimming, snorkelling, diving and more. The area’s warm tropical climate also makes it irresistible to cool off in the refreshing ocean. For your next trip, read on to find out the best yacht charters in Key West, Florida, for a memorable adventure.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on May 22, 2024.

1. Transformed classic Bluewater Cruiser offering mesmerizing views of the bay

This transformed classic Bluewater Cruiser is now your cosy and stylish sanctuary, offering mesmerizing views of the bay, canal, and sandy beaches. Hop aboard the 45-foot (13.72 meter) yacht, featuring a roomy main cabin with a cushy memory foam queen bed and refreshing ocean breeze. Enjoy the fully equipped kitchen, speedy Wi-Fi, and TV entertainment. Head to the upper-level bridge with comfy cushions and a dining set to relish the stunning scenery.

Exciting extras include kayaks, a full bar, and a shuttle service to and from shore. Get ready for thrilling captained yacht charters for fishing, snorkelling, and exploring Key West Sand Bars or Dry Tortugas.

Stayed at this property?
Key West, Florida, United States
2.83 km (1.8 mi) from The Hemingway Home and Museum
20 reviews   Wifi Available
Boat 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
we made breakfast almost every morning and loved coffee out on the bow
it was peaceful had unbelievably stunning beauty and was very comfortable
Host:
the hosts went out if our way to make our stay comfortable
everything went smoothly and ali was incredibly kind and easy to work with
ali and larry were great hosts offering help when we needed
amazing sunrises and sunsets ali and her husband were extremely helpful and were outstanding hosts
these are the best hosts
Read more reviews

2. Exquisitely crafted vessel designed for pure relaxation (from USD 118)

Step aboard this exquisitely crafted vessel designed for pure relaxation, ideal for a couple seeking a touch of luxury. Drift off to dreamland on a sumptuous front bed adorned with cozy blankets and soft pillows. The living area beckons you to unwind, offering a fold-down table for dining or just chilling out. Need more space? No problem! Tuck in for the night with additional sleeping options cleverly concealed in the back cushions.

Beach lovers will adore the direct access, while a shared outdoor pool promises a delightful oasis. Adventure-seekers, you’re in for a treat with complimentary kayaks, beach cruisers, and snorkel gear at your disposal. Even your furry friends are welcome! Cook up scrumptious meals in the well-equipped kitchen boasting an induction stove, microwave, and grill.

Stayed at this property?
Key West, Florida, United States
6.97 km (4.4 mi) from The Hemingway Home and Museum
28 reviews   Wifi Available
Boat 3 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Host:
david was a great host with plenty of knowledge of the area
dave was a great host the boat was perfect for a short little getaway
friendly hosts neighbors and dock dog
Location:
close to everything fun in key west and the other keys
i fun unique place to stay
great place to stay if you want to experience what boat life is like
Read more reviews

3. Happy's Houseboat (from USD 450)

This private yacht charter in Key West is perfect for a couple seeking a unique getaway on the water. Anchored in an enclosed bay, this houseboat has a spacious main suite and a well-equipped kitchen. The large sun deck is great for suntanning in the day and stargazing at night. Guests can just hop off the deck into the warm waters of the Florida Keys and have a swim or snorkel with the marine life. Kayaks, paddle boards and bicycles are available for rent for an additional fee. The host is also happy to bring guests out to secluded swimming, fishing and snorkelling spots, so please do put in your request when making reservations.

Stayed at this property?
Key West, Florida, United States
3.1 km (2.0 mi) from The Hemingway Home and Museum
house boat 3 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Location:
amazing location in the middle of the bay very private with great views on every side
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

4. Deluxe charter boat for a group of six (from USD 225)

Moored at a small local marina, this luxury yacht charter in Key West offers a live-aboard experience that will have you feeling like a local yachtie. The yacht has four staterooms that can accommodate up to six guests and is equipped with all the basic amenities. The marina is home to local artists, who display their work throughout the quay. There is a fantastic seafood restaurant serving up delicious local catch just a few steps from the yacht. The restaurant also hosts live entertainment every Friday and Saturday, which is a great opportunity for meeting the artsy locals.

Stayed at this property?

7.01 km (4.4 mi) from The Hemingway Home and Museum
82 reviews  
yacht 6 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 3
Refund Policy :

Top guest reviews
Amenities & Room:
The boat is very spacious Beds are not plush but your on a boat
The pictures on the listing are exactly as the boat looked in person
The yacht was beautiful and immaculate
we did not use)
We sat at the top of the boat and had beautiful views
Cleanliness:
Loved it very clean
The boat was very clean and well maintained
The boat house was quite sufficient for showering water pressure was great and always had hot water
Host:
and he answered us right away
he's an awesome guy
Very friendly marina Would return
Andy was very quick to respond to the couple questions we had when we checked in
The Hogfish Bar and Grill (almost next door) is fantastic Good food drinks and service
Location:
Enjoyed learning this way of life
Also ate at Roostica Pizza on Stock Island - another great choice Thanks for everything
It is a little ways away from Duval Street in Key West but was very easily accessed by Uber for approximately $20
If" a problem arises Andy takes care of it immediately
Spent the entire month of February here and didn't want to leave
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

5. Unique stay out at sea

Ideal for an adventurous couple, the Wanderland is a 50 feet (15 metres) pleasure craft moored in an amazing location, out at sea, where beautiful sunsets are guaranteed. Jump right off the vessel into the welcoming waters to snorkel, kayak, fish and paddle board ⎯ this makes for a dream vacation for water sports enthusiasts and ocean lovers alike. Staying on the Wanderland is a little like camping but out on the ocean. Guests must bring food and drinks for their days on the boat. The barbecue onboard is perfect for grilled dinners while enjoying the amazing sunsets.

Stayed at this property?
Key West, Florida, United States
1.35 km (0.9 mi) from The Hemingway Home and Museum
86 reviews  
Boat 2 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Cleanliness:
hopefully they will repair the broken window and clean and disinfect the place before other guests arrive
Host:
robert and his crew were very helpful throughout our stay
the space was comfortable the people were so kind knowledgeable and were so accommodating
very friendly hosts
comfy beds there were some minor hiccups with the boat but robert was an amazing host responsive and friendly
it’s so spacious and private robert was such a great host and was always a call away
Location:
great location great boat great for adventurers
towards key west there are quite a few boats but they are not terribly close
Read more reviews

6. Motor yacht with mod cons

Live like a celebrity on this motor yacht and experience the exclusive lifestyle at its premium marina. This pleasure yacht can sleep up to six guests comfortably in its three rooms. It also has spacious indoor and outdoor living areas, roomy enough for everyone to spread out. It is moored at one of the best resorts in Key West, The Perry Hotel, which has luxurious waterfront swimming pools, fine dining restaurants, free shuttle service to town, and more. While the vessel will be moored during your stay, guests will be requested to book a cruise package during the reservation period to discover the beautiful ocean around Key West.

Stayed at this property?
Key West, Florida, United States
6.3 km (4.0 mi) from The Hemingway Home and Museum
28 reviews  
Boat 4 Beds 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
the marina was wonderful with great amenities a beautiful pool shuttle and at night it was peaceful
Cleanliness:
the marina was wonderful the pool bar and bathrooms were clean
Read more reviews

Stay on the water in Key West

Explore Key West like a local and spend your days lounging on a luxury yacht and exploring best places to eat. The ocean is Key West’s best feature and there is nowhere closer to the water than staying in one of these best yacht rentals in Key West.

Frequently asked questions about yacht charters in Key West


Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Rachel is a dedicated traveller who explores diverse cultures, food, festivities and museums worldwide. She has a particular interest in architecture, nature and markets. Moreover, she often...Read more

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