Search Houseboats in Sugarloaf Key

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

7 Saf. - 9 Saf.

In two weeks

14 Saf. - 16 Saf.

In one month

28 Saf. - 2 Rab. I

In two months

28 Rab. I - 30 Rab. I

Compare 19 Houseboats in Sugarloaf Key with updated reviews, rates, and availability.

"Great getaway, yet very close to Key West. It is about a 5-10 minute drive from property to Duval Street."

SAR 1,777 total

includes taxes & fees

23 Feb - 24 Feb

"Owner communication was great and Master Suite was very comfortable. AC worked great, boat has lot of bathroom space! Our charter to see the sunset was spectacular with such a great kind crew that did a professional job. Our stay overall was verand will book again on our next trip"

"We had a wonderful time. It is an older, smaller boat but we enjoyed it. There is a port a pot in the cabin but there is a huge shower and bathroom under the carport. We were able to fish right off the boat. Frank will answer texts pretty quickly. "

"Rented this nice boat for 2 nights for a two 60-somethings and three 20-somethings. From "A to Z" it meet or exceeded our expectations. Boat was a bit old, the carpets, etc. were more that a bit "dingy", and 5 adults certainly "maxed out" the space.... but we didn't care much. It was such a unique experience for our 3 younger guests who had NEVER been on a boat before. The harbor is very nice with good restaurants. etc. Jim our "check-in /out" guy was great. Jeff our captain for our 4 hour boat...

"We used our paddle boards to get back to the docks to uber around town. We also were able to pick up a pizza at the ocean wall! It was an amazing way to visit Key West! Very peaceful! Great Location! Definite ocean front! Can’t get any closer! Wonderful experience! Absolutely would do it again! "

SAR 1,079 total

includes taxes & fees

2 Mar - 3 Mar

"Our family of 5 (3 grown children) had a great two-night stay on the boat. The boat's 4 (small) bedrooms were comfortable and each had a small bathroom. Boat was very clean and the living area/outside area was pretty roomy. It is a different experience than a hotel room or house rental (less luxury), but I would recommend the experience. The boat was also docked at the marina/ Perry hotel, which was very nice (access to a nice pool, two bars, restaurant (we had a good breakfast overlooking the...

"This was an absolute dream come true vacation. The owners were incredible and very helpful. We would love to do this again! Actually we didn’t really want to leave. Tony and Ally were not only genuinely kind but also very informative. They made this stay remarkable for us."

SAR 1,902 total

includes taxes & fees

2 Feb - 3 Feb

"Excellent boat, excellent stay. Would love to return."

"Located in a very quiet bay. Houseboat is super clean and Bill is great to work with - very responsive to questions and needs. There is not much in walking distance, so a golf cart (highly recommend), scooter, or bike would be necessary."

"Owners communicated well. They had the sewage pumped out before we came & while we were there. At times we noticed an odor but Febreeze seemed to help. I am sure staying in the marina you have odors like that. I only used the microwave & it worked well - cooking free vacation. The A/C was cold, except when the breakers tripped. Glad my husband & son knew how to flip them back on. We were gone most of the time, only slept & showered there & watched OSU win!"

SAR 1,902 total

includes taxes & fees

31 Jan - 1 Feb

"Our stay was wonderful. Tom was extremely helpful with anything we needed and great person to work with.would definitely stay again. "

"This is a hidden treasure. Quiet, secluded, great paddling. The hosts give great recommendations on paddling and dining. Perfect!"

"Had alot of fun on this Classic...Host was very kind."

SAR 2,313 total

includes taxes & fees

6 Feb - 7 Feb

"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."

SAR 3,092 total

includes taxes & fees

1 Mar - 2 Mar

"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:)"

"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!!"

"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!"