Fleming Key Houseboat Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22

Our top choices for Fleming Key houseboats

Smart TV, DVD player, books
Party Like A Local in Key West, 2 bedroom 1 bath yacht at marina.

Party Like A Local in Key West, 2 bedroom 1 bath yacht at marina.

Party Like A Local in Key West, 2 bedroom 1 bath yacht at marina.
Stock Island
$395 nightly
The price is $439
Dec 27 - Dec 28
Total with taxes and fees
Party Like A Local in Key West, 2 bedroom 1 bath yacht at marina.
Marina
Living the Dream Key West Style

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
9.8 out of 10, Exceptional, (36)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
$476 nightly
The price is $529
Jan 12 - Jan 13, 2026
Total with taxes and fees
Living the Dream Key West Style
Dining
Key West Luxury Houseboat

Key West Luxury Houseboat

Key West Luxury Houseboat
Stock Island
9.6 out of 10, Exceptional, (8)
"This was our first houseboat vacation and it didn’t disappoint! We love seeing all the hustle and bustle of Key West but loved coming back to our peace and tranquillity each night and waking up and having coffee on one of the decks! We will definitely do it again!"
United States
Trish R.
$927 nightly
The price is $1,029
Jan 4 - Jan 5, 2026
Total with taxes and fees
Key West Luxury Houseboat
Exterior
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

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

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
$462 nightly
The price is $513
Jan 4 - Jan 5, 2026
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Property grounds
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown

43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown

43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
Stock Island
10.0 out of 10, Exceptional, (1)
"The owners are very attentive and interested in making sure that our stay was great on every level. Top notch communication and they went above and beyond with the hospitality. Thanks so much. "
United States
Marc B.
$347 nightly
The price is $385
Jan 5 - Jan 6, 2026
Total with taxes and fees
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
Outdoor dining
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew

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

Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew
Stock Island
$6,852 nightly
The price is $7,602
Dec 31 - Jan 1, 2026
Total with taxes and fees
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew
Exterior
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
$382 nightly
The price is $430
Jan 5 - Jan 6, 2026
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Marina
Wake up aboard your private yacht by Luxury Sea Charters in Key West - One Heart

Wake up aboard your private yacht by Luxury Sea Charters in Key West - One Heart

Wake up aboard your private yacht by Luxury Sea Charters in Key West - One Heart
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (2)
"Absolutely amazing place to stay… better than we imagined! The host, Tom was fantastic and made us feel right at home. We loved the views and the amenities, Truely an awesome place to stay!"
United States
John C.
$418 nightly
The price is $463
Jan 4 - Jan 5, 2026
Total with taxes and fees
Wake up aboard your private yacht by Luxury Sea Charters in Key West - One Heart
Property grounds
Docked in Paradise

Docked in Paradise

Docked in Paradise
Stock Island
$513 nightly
The price is $569
Jan 8 - Jan 9, 2026
Total with taxes and fees
Docked in Paradise
Smart TV
Wake up Aboard your private yacht by Luxury Sea Charters in Key West - FREE TIME

Wake up Aboard your private yacht by Luxury Sea Charters in Key West - FREE TIME

Wake up Aboard your private yacht by Luxury Sea Charters in Key West - FREE TIME
Stock Island
10.0 out of 10, Exceptional, (1)
"Tom & Jen were great hosts! Prompt with communication before and during our stay. They shopped for and delivered our groceries, along with welcoming us with a tour of the marina & boat. Very personable. The boat was very clean with all necessities on board. Highly recommend staying aboard Free Time!"
United States
Melissa G.
$740 nightly
The price is $821
Jan 4 - Jan 5, 2026
Total with taxes and fees
Wake up Aboard your private yacht by Luxury Sea Charters in Key West - FREE TIME
Marina
Cozy Houseboat

Cozy Houseboat

Cozy Houseboat
2.0 star property
Stock Island
$581 nightly
The price is $645
Dec 25 - Dec 26
Total with taxes and fees
Cozy Houseboat
Property grounds
Waterfront & Heated Pool - Awai's Floating Villa

Waterfront & Heated Pool - Awai's Floating Villa

Waterfront & Heated Pool - Awai's Floating Villa
Stock Island
9.4 out of 10, Exceptional, (3)
"Very clean and modern. Marina view was beautiful. "
United States
Christy V.
$973 nightly
The price is $1,080
Jan 1 - Jan 2, 2026
Total with taxes and fees
Waterfront & Heated Pool - Awai's Floating Villa
Private kitchen
Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West

Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West

Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West
Stock Island
$854 nightly
The price is $948
Jan 5 - Jan 6, 2026
Total with taxes and fees
Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West
Dining
Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West

Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West

Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
Stock Island
$1,427 nightly
The price is $1,583
Jan 6 - Jan 7, 2026
Total with taxes and fees
Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
Outdoor pool
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6

40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6

40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
Stock Island
$918 nightly
The price is $1,019
Jan 1 - Jan 2, 2026
Total with taxes and fees
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
Fridge, stovetop, coffee/tea maker, toaster
Super-Cozy boat in Key West!

Super-Cozy boat in Key West!

Super-Cozy boat in Key West!
Key West
8.0 out of 10, Very Good, (1)
"Yes, Troy was very welcoming. Met me at the airport and gave me a ride to his boat. Very accomodating. 2 diff.options for sleeping and boat was very comfortable. Plenty of fresh towels.Picked up whatever I needed and brought it out to me. Thx!"
United States
rachael K.
$283 nightly
The price is $314
Jan 6 - Jan 7, 2026
Total with taxes and fees
Super-Cozy boat in Key West!
Fridge, microwave, oven, coffee/tea maker
Beautiful Houseboat in Key West

Beautiful Houseboat in Key West

Beautiful Houseboat in Key West
Stock Island
10.0 out of 10, Exceptional, (1)
"Went with my girlfriend and we had an amazing time, so much fun. I recommend to anyone.if you have a partner, friends and family or even by yourself this is a great experience "
United States
Antonio M.
$629 nightly
The price is $698
Jan 3 - Jan 4, 2026
Total with taxes and fees
Beautiful Houseboat in Key West
Interior
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools
Stock Island
6.0 out of 10, (1)
" Host’s communication needs to improve! When we checked in, beddings didnt look fresh, so I asked: Me: sent pic & asked “this is how bed? Sheets washed/clean? Her reply: If we are going to have these kinds of problems because how I choose to make my bed then your more than welcome to try a room at the hotel ( copied & pasted from her text)"
United States
Myra
$277 nightly
The price is $308
Dec 25 - Dec 26
Total with taxes and fees
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools
Outdoor pool
Charming 1-Bedroom, Sailboat in wonderful Key West

Charming 1-Bedroom, Sailboat in wonderful Key West

Charming 1-Bedroom, Sailboat in wonderful Key West
Stock Island
2.0 out of 10, (1)
"The people were the only thing that was acceptable "
United States
Michael
$541 nightly
The price is $600
Jan 10 - Jan 11, 2026
Total with taxes and fees
Charming 1-Bedroom, Sailboat in wonderful Key West
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Fleming Key Hotel Reviews

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Everything was wonderful."
Tracy 2-night trip
Posted 13 hours ago
Hyatt Vacation Club at Beach House, Key West

Find out more about Fleming Key

Fleming Key Houseboats information

Number of reviews
244
Accommodation
53 Houseboats
Lowest Price
$308
Highest Price
$7,602

Frequently asked questions

Why book your houseboat in Fleming Key with Expedia?
Expedia makes it easy to find houseboats in Fleming Key — from cute and comfy options to floating palaces! If you have a certain budget, select how much you want to spend and your preferred star rating. We'll help you find the right fit whatever your getaway looks like.
How can I find cheap houseboats in Fleming Key?
Expedia's filters make it a breeze to find cheap houseboats in Fleming Key. Tailor your search results by your budget and preferred star rating — lower-rated houseboats are lighter on the hip pocket. You can also join Expedia Rewards for free to reel in discounts on your floating stay.

Explore a world of travel with Expedia