Boat vacation rentals in Monroe County

A wonderful place to stay for something a little different. Our group booked 4 nights on the Bella Maggio, and did a 24 hour sail with Captain Dan (highly recommended). Check in is very simple and communicated well. You have a dedicated person to text during your stay if you need anything - which was great. We had an AC issue one day, and they came out immediately and fixed it for us. You can enjoy the amenities of the hotel, take the free shuttle to Key West (or uber - around $25), or enjoy some cool sports on Stock Island. Overall we would not hesitate to do this again!

Our stay on the Andiamo was fabulous from start to finish. Blue Ocean Charters proactively communicates and responds very quickly with helpful details. Stephanie checked us in and made us feel right at home. She was also very responsive during our stay. The Andiamo is a very cleverly laid out boat with lots of options for lounging and enjoying the excursion. We picked up groceries and made a few of our meals on the electric grill with ease. Which was good because once we arrived we didn't want to leave! The nearby pool is lovely and Bad Boy Taqueria is great restaurant just at the end of the docks. Our 4 hr sunset cruise with Capt John and Amanda was nothing short of magical with a long encounter with a couple of pods of Bottlenose Dolphins. They mean it when they say there is no movement when the boat is docked and despite rough water, the Andiamo is quite smooth and fast.

Charles and Annette were the most wonderful hosts. So cool to be sleeping on such a lovely boat. Hosts really helpful and knowledgeable. Supermarket really close (walk), turtle hospital (short drive). Don’t look elsewhere, stay here!

Mike was an amazing host. Very friendly and responsive. The place is really nice with a nice view to the marina. Barbecue site very nice and the area Pool super clean and enjoyable. Live music and good drinks. I would definitely come back amd rent with them again.

Yaly is the best host ever! She is responsive, helpful, kind, friendly, and full of life. I was blown away by her and my stay. If you are thinking about staying here book right now…. immediately. You’ll remember this stay for the rest of your life. 10/10 ⭐️

We were interested to try a new location in the Keys and a new experience, and our stay here fit the bill! Not only was the marina RIGHT behind Publix, but very centrally located in Marathon. Staying in the boat was so cool. Clean beds, plenty of hot water, and a cold fridge- didn’t need much else! Ian was super responsive and am appreciative of the hospitality we received. We can’t wait to book again!

Being a boat-y type, it was right up my alley. First time I've ever done a non-traditional AirBnB. Ryan was great, and responsive to any questions I had. I would definitely do it again.

Great spot on a quiet dock on a live-a-board sailboat right off of Keys Fresh Seafood Market & The Docks restaurant. Hog’s Fish restaurant & bar a few steps away too. Ride one of the bikes to Dion’s for your grocery needs aboard. Easy bike rides to multiple restaurant/food truck/bar destinations on Stock Island & even into Key West. Cabin is super comfortable yet quaint. The wildlife & marine life were wonderful to enjoy as well. If you enjoy sailboats, marina life etc., then Dave’s Sail La Vie is a great place to stay to enjoy a laidback getaway. Grateful for the great time!

Great boat to stay on. Very beautiful view on the canal. I saw tons of iguanas sun bathing on the side walks, they didn’t bother anyone. The boat was clean and very cool, it is a marine environment so the bathroom was compact. It is a boat so expect small spaces. The host was very helpful in every way. When I called him he picked up immediately. Parking was very close to the boat. I would be happy to return.

Danny is the best host. Super responsive, patient, always willing to help and always understanding. The boat itself is a gem. The photos don’t do it justine, captain you should update the photos your boat is so much better in real life ! Catch a breathtaking sunset, relax, spend time fishing and cook the fishes you just caught, the purpose of life isn’t it ? We forgot to buy ice, Danny went with his taxi boat to get some for us and came back. The attention to details, he’s a very nice guy and also very interesting. Don’t hesitate, we will book again in a few months. Such a unique experience. Thank you for everything Danny 🙏🏻⚓️

A truly unique experience! Loved everything about it. Had some minor dingy issues but the host was always responsive and addressed the issues in a timely manner. Swimming in the ocean, sleeping under the stars, watching a lightning storm, grilling on a boat, kayaking around a mangrove island…it doesn’t get any better!

Remember it is a boat! Inside is a little darker than the pictures but the beds were very comfortable and sitting in the cockpit for an evening cocktail was great. Don't hesitate and go ahead and book it!

Great location and perfect for our family for a quick trip. Thank you!

My boyfriend and I stayed 2 nights on the beautiful One Heart for my birthday. It doesn’t exist enough words to explain how this was the most exciting and perfect experience ever. We went to anchor one night at Boca grande key on the night of my birthday. This was so fun trip, we fished (we caught all kind of fish like a barracuda!!) saw dolphins and had a nice snack on board with a key lime pie for my birthday cake!!! I would compare that trip as a fairy tale experience! That boat is beautiful, Jen and Tom are so carrying, attentive and generous they made this trip the best it could be! This is an experience you never forget and that stays in your thoughts as memories forever and I encourage everybody to do it! The bed on the boat was very comfortable! I would say that the only problem was that we should have stayed longer than 2 nights. It broke my heart that we had to leave! That means we have to come back next year! Best advise I could say: just do it!!!!

Before our stay we were concerned about the AC keeping up and it was great. Getting on and off while carrying luggage etc could be tricky. But it is a boat. Spacious. Friendly neighbors. Excellent location. Host answered all of our questions quickly. Would stay again. Kids loved it too!

Great experience for our mom and sons adventure! Don was very responsive, helping us with the nuances of boat living! After full days of fishing the boys enjoyed more fishing off the bow of the boat and roaming the marina, while mom took in the sunset from the upper deck with a glass of wine. We had all our meals right next to the boat at the old Tavernier restaurant or the great little Caribbean themed bar down stairs - they even cooked up our fresh catch for us!

If you want a different kind of Airbnb to tell your friends back home about, look no further! The staff is super friendly and welcoming, quickly responsive to any small issues we needed help with, and super accommodating and attentive. I had to reserve another week aboard one of the boats quickly due to Hurricane Helene and everything was situated for me within an hour or so. We came for my 40th birthday and did an 8 hour charter on one of the boats and had one of the best days out at sea that I’ve ever had! I NEVER write reviews but this was an amazing experience and I still have another week to go!! By ALL means!! Book your stay in Key West with BOYC!!! You will NOT be disappointed!!! Worth EVERY penny!!! 💗🧜🏼‍♀️🐚