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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Fleming Key houseboats

Exterior

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (190 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is ￥16,699
￥45,832 total
includes taxes & fees
Jul 7 - Jul 8
Aqua Lodges at Hurricane Hole Marina
Smart TV, DVD player, books

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Stock Island
9.2 out of 10, Wonderful, (11 reviews)
"Everything was in place nice place to if you want peace and to just chill perfect spot also too be on the water is a plus."
United States
Shenicka B.
The price is ￥29,041
￥51,932 total
includes taxes & fees
Jul 7 - Jul 8
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Exterior

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.4 out of 10, Good, (38 reviews)
"Perfect location! Had options of 2 pools to enjoy on property. The marina serves complimentary coffee. "
United States
Crystal A.
The price is ￥29,364
￥65,908 total
includes taxes & fees
Aug 4 - Aug 5
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
1 bedroom, WiFi, bed sheets

Cozy Houseboat

Cozy Houseboat
Stock Island
The price is ￥29,041
￥77,685 total
includes taxes & fees
Jul 16 - Jul 17
Cozy Houseboat
Marina

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, (6 reviews)
"We loved staying on this beautiful boat and all the amenities of the Perry Marina. Will definitely stay again: highly recommend "
United States
Erin S.
The price is ￥39,085
￥65,006 total
includes taxes & fees
Jul 8 - Jul 9
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
Pool

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (61 reviews)
"Great would definitely stay again "
United States
Zach C.
The price is ￥67,763
￥84,300 total
includes taxes & fees
Jul 6 - Jul 7
Living the Dream Key West Style
Dining

Key West Sailboat Getaway

Key West Sailboat Getaway
Stock Island
The price is ￥25,653
￥42,776 total
includes taxes & fees
Jul 16 - Jul 17
Key West Sailboat Getaway
Marina

Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West

Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Stock Island
10.0 out of 10, Exceptional, (1 review)
"The marina was beautiful boat was quiet, relaxing close to everything but far enough away from the craziness of downtown. Plentyto do close by in and it’s a short drive to Key West my girlfriend said it was by far the best Mother’s Day ever couldn’t be happier. "
United States
Tyler L.
The price is ￥36,302
￥72,140 total
includes taxes & fees
Jul 16 - Jul 17
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Smart TV, stereo

Docked in Paradise

Docked in Paradise
Stock Island
9.0 out of 10, Wonderful, (7 reviews)
"Houseboat was lovely! We truly enjoyed our stay. Josh was very responsive and helpful and the amenities at the marina and hotel were excellent."
United States
Susan T.
The price is ￥41,948
￥83,453 total
includes taxes & fees
Jul 7 - Jul 8
Docked in Paradise
Property grounds

Luxury 2 stateroom Yacht FREE TIME

Luxury 2 stateroom Yacht FREE TIME
Stock Island
10.0 out of 10, Exceptional, (2 reviews)
"My family and I had a wonderful stay on the boat. We had everything we could possibly need and then some. We would love to book the boat again next time we are down in Key West. Thank you for such a great experience. Cor (host) was great with our last minute booking and JD did a fantastic job setting everything up for us. A BIG Thank You from your Texas friends."
United States
Jennifer S.
The price is ￥86,978
￥159,404 total
includes taxes & fees
Jul 8 - Jul 9
Luxury 2 stateroom Yacht FREE TIME
Marina

Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West

Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
Stock Island
The price is ￥36,302
￥76,295 total
includes taxes & fees
Jul 20 - Jul 21
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
Smart TV, music library, stereo

Key West Luxury Houseboat

Key West Luxury Houseboat
Stock Island
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay in Key West. Brad was very welcoming."
United States
Christopher A.
The price is ￥100,918
￥161,714 total
includes taxes & fees
Jul 7 - Jul 8
Key West Luxury Houseboat
Outdoor dining

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

Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West
Stock Island
9.0 out of 10, Wonderful, (2 reviews)
"We thoroughly enjoyed our stay on "Somewhere" and the excursion was the highlight. The Yacht Club was also fantastic - great pool and we had a chance to meet fellow boaters and joined them for yoga. The boat was more spacious than we thought. "
United States
Michelle C.
The price is ￥80,509
￥173,462 total
includes taxes & fees
Jul 6 - Jul 7
Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West
Marina

Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
The price is ￥59,050
￥118,242 total
includes taxes & fees
Jul 6 - Jul 7
Waterfront & Heated Pool - Break Awai Floating Villa
1 bedroom, desk, bed sheets

Affordable, Adventurous Houseboat on-the-water in Key West Florida

Affordable, Adventurous Houseboat on-the-water in Key West Florida
Stock Island
10.0 out of 10, Exceptional, (1 review)
"Wonderful getaway on the water! Quite the adventure! Comfy bed! Clean and well stocked! Would do it again!"
United States
lisa w.
The price is ￥44,570
￥65,831 total
includes taxes & fees
Jul 12 - Jul 13
Affordable, Adventurous Houseboat on-the-water in Key West Florida
Property grounds

Waterfront & Heated Pool - Away Awai Floating Villa

Waterfront & Heated Pool - Away Awai Floating Villa
Stock Island
9.6 out of 10, Exceptional, (5 reviews)
"A unique location with all you need"
United States
Stefanie S.
The price is ￥59,534
￥121,369 total
includes taxes & fees
Jul 6 - Jul 7
Waterfront & Heated Pool - Away Awai Floating Villa
Outdoor pool

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

40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
Stock Island
10.0 out of 10, Exceptional, (1 review)
The price is ￥85,349
￥165,233 total
includes taxes & fees
Jul 6 - Jul 7
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
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
Stock Island
The price is ￥145,045
￥255,423 total
includes taxes & fees
Jul 12 - Jul 13
Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
Marina

Oceanfront - Break Awai x Away Awai Floating Villas

Oceanfront - Break Awai x Away Awai Floating Villas
Stock Island
The price is ￥145,206
￥259,838 total
includes taxes & fees
Jul 6 - Jul 7
Oceanfront - Break Awai x Away Awai Floating Villas
Interior

Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL

Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL
Meadows
The price is ￥121,005
￥173,804 total
includes taxes & fees
Jul 20 - Jul 21
Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL
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

8/10 Good
"I loved that Southernmost Resort had direct access to the beach, 3 pools, a spa. A concierge that could connect you to any tour or restaurant recommendation to anything on the Island. You never had to leave their space if you did not want. you could opt for a quiet stay to recharge and disconnect from the world or be involved in all the fun goings on each day at the resort or steps away from shops, museums, tours. It was a perfect week away for a solo traveler looking to find a bit of respite from the world while trying some new and exciting things like snorkeling the reef, and kayaking the mangroves. Seeing dolphins, tropical fish, manatees, turtles all within an arms reach........GLORIOUS!!"
Mary 7-night trip
Posted 1 hour ago
Southernmost Beach Resort and Guesthouses

Find out more about Fleming Key

Fleming Key Houseboats information

Number of reviews
220
Accommodation
61 Houseboats
Lowest Price
￥42,776
Highest Price
￥259,838

Frequently asked questions

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How can I find cheap houseboats in Fleming Key?
If you're on the lookout for terrific deals on houseboats in Fleming Key, add a few filters to your search. Start by sorting your results by price so that the cheapest options show up first. Then, change your filters to match your budget. Also, be sure to join our free rewards program, One Key™, for exclusive member deals. Expedia can help you find your perfect floating stay whatever your plans or budget.

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