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Featured Houseboats in Fleming Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (118)
"Enjoy being on the water, having a full kitchen, access to all water activities, stores, and a walkable access to a restaurant. Loved it and have plans to do it again!"
The price is AU$662
includes taxes & fees
3 Mar - 4 Mar
Aqua Lodges at Hurricane Hole Marina

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

10.0 out of 10, Exceptional, (4)
"Was just a teaser initial trip to Key West but staying on the water was awesome! Beautiful views and great amenities. Kevin and Captain Philip were great throughout the whole process including great local recommendations! One thing to note, if you are 6’ plus, will need to watch your head and the steps downstairs require concentration. As a shorter person (barely 5’!) it all worked perfectly for me! Look forward to staying again and taking the boat out next time! "
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (31)
"Great time enjoying the keys like a pirate. "
34’ Catamaran Sailboat

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

9.8 out of 10, Exceptional, (18)
"Great boat...great marina...awesome aircon...the only negative is the privy rules that exist on boats"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

10.0 out of 10, Exceptional, (3)
"I didn’t really know what I was getting into, but I’m glad I didn’t cancel. This was such a beautiful experience to have shared with just myself. The bed was comfortable and I slept really well both nights. The second night, I had to rent a kayak from the marina (40) to get to the house. It was a beautiful sunset paddle. It’s easy enough, but even as an experienced paddler, it’s about 20 minutes . I had to leave around 5am to catch my flight and paddled back to the marina in pitch black. It was...
The price is AU$487
includes taxes & fees
27 Feb - 28 Feb
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!

9.8 out of 10, Exceptional, (80)
"This was a wonderful weekend sail around Key West on a very nice and large catamaran. The full amenities from kitchen, grill, four bedrooms, four "heads" and a large outdoor covered sitting area was absolutely amazing!What made it even better was the attention to detail from Elizabeth who met us at the dock, showed us around the boat while instructing us on the dos and don'ts! She went over the accommodations of the marina and the amenities of the Perry Hotel that we had full use of!Then...our...
LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!

Cozy Houseboat “Wild One”

10.0 out of 10, Exceptional, (6)
"My friend and I absolutely loved staying on this sweet houseboat!!! It is charming and has everything you need for a relaxing stay! The sunset, sunrise and stars were beautiful. The owners are fantastic! Everything was explained well and communication before and after the stay was great! If we ever make it back to Florida, we will plan our trip around this VRBO!! It’s perfect!!! "
The price is AU$795
includes taxes & fees
2 Mar - 3 Mar
Cozy Houseboat “Wild One”

Brand new VRBO exclusive offer! 50 foot motor yacht in Key West!

10.0 out of 10, Exceptional, (1)
"Having done power cat trips in BVI and Exumas we thought it would be fun to stay on a boat during our visit to Key West. Having the hotel pool and amenities made it feel like a resort stay. The boat was clean and spacious. Only negative is you can’t flush the toilet paper and have to put"
Brand new VRBO exclusive offer! 50 foot motor yacht in Key West!

Luxury 62' Yacht! In a Beautiful Resort

10.0 out of 10, Exceptional, (7)
"We had an incredible stay on ParT On. Clean, safe, excellent dining options. Highly recommend"
Luxury 62' Yacht! In a Beautiful Resort

Ocean views! <br>I didn’t do it too

10.0 out of 10, Exceptional, (14)
"Bill was a wonderful host and provided everything we needs. Much appreciated. "
Ocean views! <br>I didn’t do it too

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

8.0 out of 10, Very good, (18)
"Great weekend everyone loved it."
The price is AU$805
includes taxes & fees
7 Mar - 8 Mar
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!

10.0 out of 10, Exceptional, (4)
"Our stay was wonderful. Tom was extremely helpful with anything we needed and great person to work with.would definitely stay again. "
Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!

Ocean views! <br>Luxury suites

10.0 out of 10, Exceptional, (24)
"This is a hidden treasure. Quiet, secluded, great paddling. The hosts give great recommendations on paddling and dining. Perfect!"
Ocean views! <br>Luxury suites

The Crystalmarine Suite – Rustic Luxury on the Sea

10.0 out of 10, Exceptional, (3)
"We wanted a unique experience when visiting Key West and thought staying on the water would be fun. The house boat was charming and, even though the weather was cool, we enjoyed staying on the water. We are sure, during warmer weather, it would have been even better."
The price is AU$1,315
includes taxes & fees
3 Mar - 4 Mar
The Crystalmarine Suite – Rustic Luxury on the Sea

Happy’s Houseboat Key West

9.2 out of 10, Wonderful, (20)
"This was one of our best stays ever! This boat is not fancy but served us well. Key West is busy and full of people, we had our own little piece of paradise for 2 nights. Fished right off the boat, had a little skiff of our own to go back and forth and Vaughn treated us well. We would love to come back someday! Thank you:)"
Happy’s Houseboat Key West

Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.

10.0 out of 10, Exceptional, (2)
"We loved the settings, and Captain Mike is a wonderful, helpful host!The interior of the boat is not spacious, and is full of useful items available for our use.A highly recommended unusual stay.The pood and communal showers are excellent."
Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.

Double Cabin Luxury Power Motor Yacht in Key West

10.0 out of 10, Exceptional, (1)
"Absolutely perfect for our needs and surpassed our hopes. So close to Key West for the festivities and far enough away to relax and just enjoy our time together. Our host was fantastic and very accommodating!!"
Double Cabin Luxury Power Motor Yacht in Key West

Southern Bell is a Beautiful Houseboat cozy and relaxing.

10.0 out of 10, Exceptional, (4)
"The houseboat was great. Right next to Key West in stock island. The host and his crew were excellent, couldn’t ask for a better stay and better people!"
Southern Bell is a Beautiful Houseboat cozy and relaxing.

Reduced Rate! 46’ Yacht in Beautiful Resort!

"From start to finish communication was easy and efficient. Any concerns were immediately addressed and the check-in process was smooth. The catamaran was very clean and stocked with all the essentials and quite comfortable. My family and I especially enjoyed our eight hour excursion with Captain Jason and his mate Dru. I can’t speak highly enough of our stay and would recommend to anyone, definitely a 10 out of 10 "
Reduced Rate! 46’ Yacht in Beautiful Resort!

VRBO Exclusive Offer! 51' Catamaran Yacht located in a Beautiful Resort!

10.0 out of 10, Exceptional, (13)
"It was fun to swap a hotel experience for a boat. Thanks! "
VRBO Exclusive Offer! 51' Catamaran Yacht located in a Beautiful Resort!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Fleming Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (118)
"Enjoy being on the water, having a full kitchen, access to all water activities, stores, and a walkable access to a restaurant. Loved it and have plans to do it again!"
The price is AU$662
includes taxes & fees
3 Mar - 4 Mar
Aqua Lodges at Hurricane Hole Marina

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (803)
"Great location, clean, and good customer service. wish they had fishing rods and more to do around the property, and the AC didn't keep the upstairs cool, very hot up there at night. overall, happy about the stay."
Coconut Mallory Resort And Marina By Kees Vacations

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (372)
"The location was perfect! It was 2 or 3 blocks from Duval Street. The bed was comfortable and the room with bath clean."
Steps from Duval, Pool on Site & Bikes Included!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.