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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Compare 32 Houseboats in Fleming Key with updated reviews, rates, and availability.

Aqua Lodges at Hurricane Hole Marina
Exterior

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (114)
"Great getaway, yet very close to Key West. It is about a 5-10 minute drive from property to Duval Street."
The price is AED 1,021
AED 1,666 total
includes taxes & fees
20 Feb - 21 Feb
Aqua Lodges at Hurricane Hole Marina
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Miscellaneous

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

10.0 out of 10, Exceptional, (2)
"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"
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
34’ Catamaran Sailboat
Marina

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!
Beach

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

9.8 out of 10, Exceptional, (17)
"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...
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Outdoor dining

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

10.0 out of 10, Exceptional, (2)
"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! "
The price is AED 687
AED 1,104 total
includes taxes & fees
12 Feb - 13 Feb
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!
Beach

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

9.8 out of 10, Exceptional, (80)
"Loved the location, and the boat. it was a joy to stay on board "
LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!
Cozy Houseboat “Wild One”
Miscellaneous

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 AED 1,102
AED 1,855 total
includes taxes & fees
10 Feb - 11 Feb
Cozy Houseboat “Wild One”
Brand new VRBO exclusive offer! 50 foot motor yacht in Key West!
Miscellaneous

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
Miscellaneous

Luxury 62' Yacht! In a Beautiful Resort

10.0 out of 10, Exceptional, (7)
"Excellent boat, excellent stay. Would love to return."
Luxury 62' Yacht! In a Beautiful Resort
Ocean views! <br>I didn’t do it too
Exterior

Ocean views! <br>I didn’t do it too

10.0 out of 10, Exceptional, (13)
"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."
Ocean views! <br>I didn’t do it too
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Beautiful Views

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

8.2 out of 10, Very Good, (16)
"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!"
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!
Aerial view

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
Marina

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
5 star resort living w/ pool! Family sized w/ full kitchen & great views!
Sunset cruise

5 star resort living w/ pool! Family sized w/ full kitchen & great views!

6.8 out of 10, (17)
"Had alot of fun on this Classic...Host was very kind."
The price is AED 1,403
AED 2,140 total
includes taxes & fees
10 Feb - 11 Feb
5 star resort living w/ pool! Family sized w/ full kitchen & great views!
The Crystalmarine Suite – Rustic Luxury on the Sea
Room

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 AED 2,387
AED 3,027 total
includes taxes & fees
1 Mar - 2 Mar
The Crystalmarine Suite – Rustic Luxury on the Sea
Happy’s Houseboat Key West
Miscellaneous

Happy’s Houseboat Key West

9.2 out of 10, Wonderful, (19)
"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.
Marina

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

10.0 out of 10, Exceptional, (1)
Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.
Double Cabin Luxury Power Motor Yacht in Key West
Miscellaneous

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.
Property grounds

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!
Miscellaneous

Reduced Rate! 46’ Yacht in Beautiful Resort!

Reduced Rate! 46’ Yacht in 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
Exterior

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (114)
"Great getaway, yet very close to Key West. It is about a 5-10 minute drive from property to Duval Street."
The price is AED 1,021
AED 1,666 total
includes taxes & fees
20 Feb - 21 Feb
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Exterior

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (289)
"I had a great experience with my family!"
The price is AED 2,296
AED 2,686 total
includes taxes & fees
20 Feb - 21 Feb
Hyatt Vacation Club at Sunset Harbor, Key West
Coconut Mallory Resort And Marina By Kees Vacations
Exterior

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
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.

Frequently asked questions

Why book your houseboat in Fleming Key with Expedia?
Expedia makes it a breeze to find houseboats in Fleming Key — from cute and cozy options to luxurious floating palaces! If you’re sticking to a budget, choose how much you’d like to spend and the preferred star rating of your vessel. We’ll help you find the right fit whatever your getaway looks like.
How can I find cheap houseboats in Fleming Key?
If you’re looking for incredible deals on houseboats in Fleming Key, you’ll want to add several filters to your search. You can sort your results by price so that the cheapest choices appear first on the page. Then, change your filters to suit your budget. Expedia will help you find your perfect floating stay whatever your plans or budget.