Search Houseboats in Fleming Key from CA $105

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Aug 8 - Aug 10
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Aug 29 - Aug 31
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Sep 26 - Sep 28

Browse Select Fleming Key Houseboats

Aqua Lodges at Hurricane Hole Marina
Accommodations float on calm waters, offering serene views of the surrounding landscape.

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"The stay was beautiful "
The price is CA $105
CA $350 total
includes taxes & fees
Aug 10 - Aug 11
Aqua Lodges at Hurricane Hole Marina
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Enjoy the serene view of the calm body of water from the comfort of your room.

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

10.0 out of 10, Exceptional, (7)
"The ideal getaway, I brought a grill and a pan and did all the cooking outside on the deck. Took paddle boards through mangrove tunnels and saw tons of fish. Had a baby sea turtle swim up to the boat. "
The price is CA $223
CA $371 total
includes taxes & fees
Aug 11 - Aug 12
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Super-cozy boat in 5 Star Key West Marina.
Marina

Super-cozy boat in 5 Star Key West Marina.

10.0 out of 10, Exceptional, (1)
"We had the best experience in this charming boathouse - it was just the right size for our group of four. From the moment we stepped inside, we felt right at home in its cozy and comfortable atmosphere, it felt like a bit of home away from home, but with the added novelty of being right on the water. Lori's thoughtful touches throughout made the small space extra inviting and relaxing. She and her husband were amazing hosts and always responded quickly to answer any of our questions, I loved...
Super-cozy boat in 5 Star Key West Marina.
34’ Catamaran Sailboat
Step aboard and enjoy the view from this cozy cabin, featuring a comfortable bench, a fully equipped kitchenette, and a control panel for your convenience.

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (35)
"Great time enjoying the keys like a pirate. "
34’ Catamaran Sailboat
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Guests can enjoy stunning marina views from the hotel's elevated balconies.

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

7.4 out of 10, Good, (10)
"We were here celebrating 55th birthdays and had a blast. Great location and communication with Capt. We will return for sure, hoping to make it an annual get together."
The price is CA $384
CA $1,019 total
includes taxes & fees
Aug 11 - Aug 12
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Brand new VRBO exclusive offer! 50 foot motor yacht in Key West!
Step aboard and enter the interior through the glass door.

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!
Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!
Relax by the resort pool surrounded by palm trees and a paved walkway.

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

10.0 out of 10, Exceptional, (5)
"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!
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew
Relax on the spacious deck with a comfortable seating area and flat-screen TV.

Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew

The price is CA $8,264
CA $10,397 total
includes taxes & fees
Aug 20 - Aug 21
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew
KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.
Step into the charming Hogfish Bar Grill, a rustic restaurant nestled among tropical vegetation on Stock Island.

KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.

9.0 out of 10, Wonderful, (106)
"Our stay was great! Host was very accommodating! We took advantage of chartering the smaller boat the host has out to the sandbar for a fun day out in the water. Would definitely recommend!Boat amenities were as expecting. They are on the process of making upgrades to the boat. They just did new flooring before our stay. "
KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Experience the charm of Key West at The Perry Hotel, where a beautifully designed sign welcomes you to a tropical oasis with lush greenery and stunning views.

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

7.8 out of 10, Good, (22)
"Great weekend everyone loved it."
The price is CA $344
CA $698 total
includes taxes & fees
Aug 11 - Aug 12
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.
Relax on the beach, surrounded by a tranquil atmosphere and a thatched-roof structure.

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.
Ocean views! <br>I didn’t do it too
Enjoy meals and relaxation on the covered deck with seating and kitchen area.

Ocean views! <br>I didn’t do it too

10.0 out of 10, Exceptional, (21)
"Successful"
Ocean views! <br>I didn’t do it too
2 Bedrooms, 1 Bath-42' Hatteras in Key West
Relax by the pool surrounded by palm trees and lounge chairs.

2 Bedrooms, 1 Bath-42' Hatteras in Key West

The price is CA $828
CA $1,523 total
includes taxes & fees
Aug 1 - Aug 2
2 Bedrooms, 1 Bath-42' Hatteras in Key West
TRAVEL THE KEYS OR JUST RELAX AT THE DOCK
Relax on the beach with comfortable seating and umbrellas, surrounded by calm waters and a boat on the horizon.

TRAVEL THE KEYS OR JUST RELAX AT THE DOCK

9.4 out of 10, Exceptional, (28)
"The marina is the perfect location! There are 4 bedrooms so it is perfect for a group of friends (all individual beds except the master). The kitchen was well stocked to make all means and the grill on the top deck was great!"
TRAVEL THE KEYS OR JUST RELAX AT THE DOCK
SPECIAL OFFER! 50 Foot Luxury Sailing Catamaran in Five Star Resort, Key West!
Relax by the resort pool overlooking the marina, surrounded by lounge chairs and palm trees.

SPECIAL OFFER! 50 Foot Luxury Sailing Catamaran in Five Star Resort, Key West!

SPECIAL OFFER! 50 Foot Luxury Sailing Catamaran in Five Star Resort, Key West!
Amazing 4 Bdrm, 4 Bath Catamaran - Purpus
Relax by the pool overlooking the marina, surrounded by palm trees and lounge chairs.

Amazing 4 Bdrm, 4 Bath Catamaran - Purpus

10.0 out of 10, Exceptional, (2)
"Boat was immaculate, and very roomy for the 8 of us. Property manager very pleasant and responsive to communication. Location was perfect, area was quiet, the hotel amenities and marina amenities were wonderful. Pools at hotel were beautiful and well maintained. We loved our stay! The shuttle to downtown key west, an amazing bonus, saved us lots of uber fairs."
Amazing 4 Bdrm, 4 Bath Catamaran - Purpus
Happy’s Houseboat Key West
Experience the nautical charm of this cozy cabin, complete with a control station, cushioned bench, and stunning water views.

Happy’s Houseboat Key West

9.2 out of 10, Wonderful, (20)
"We enjoyed the time there"
Happy’s Houseboat Key West
Waterfront & Heated Pool - Awai's Floating Villa
Enjoy waterfront views and serene surroundings from the spacious deck area with large windows and outdoor furniture.

Waterfront & Heated Pool - Awai's Floating Villa

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay. The boat was comfortable, clean and at a perfect location. Having coffee on the rooftop each morning, was a perfect way to start the day. Shuttle service to Downtown was perfect, no need for a rental car. "
The price is CA $581
CA $1,129 total
includes taxes & fees
Aug 11 - Aug 12
Waterfront & Heated Pool - Awai's Floating Villa
Southern Bell is a Beautiful Houseboat cozy and relaxing.
Enjoy a serene view of the calm waters and distant shoreline from the comfort of your boat.

Southern Bell is a Beautiful Houseboat cozy and relaxing.

10.0 out of 10, Exceptional, (6)
"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.
Cozy Houseboat “Wild One”
Property grounds

Cozy Houseboat “Wild One”

9.8 out of 10, Exceptional, (10)
"We loved our stay! It was a perfect getaway/honeymoon spot for us. Ally and Tony communicated well and we loved their house boat. It was a fun, relaxing experience."
The price is CA $275
CA $524 total
includes taxes & fees
Aug 11 - Aug 12
Cozy Houseboat “Wild One”
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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Top Fleming Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"We had an awesome girls trip here! The staff were accommodating in putting our two rooms next to each other. The 3 pools/pool bars are great and have fun activities daily! It’s so close to everything either a quick walk or Uber got us everywhere we needed to go. We will definitely be back!"
Emma 4-night trip
Posted 21 hours ago
Southernmost Beach Resort and Guesthouses