A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Search Houseboats in Windley Key from CA $295

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Windley Key houseboats

A row of floating cottages with balconies and outdoor seating, docked along a waterway.

1. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (185 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is CA $157
CA $378 total
includes taxes & fees
Nov 17 - Nov 18
Treasure Harbor
A parking area with covered parking spaces and a building with a balcony.

2. ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ???

ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ???
Key Largo
6.4 out of 10, (22 reviews)
"Nice boat, everything was in working order. Would stay here again. "
United States
Kevin J.
The price is CA $218
CA $352 total
includes taxes & fees
Nov 16 - Nov 17
ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ???
A white boat docked at a marina with a clear sky, palm trees, and a flag.

3. Perfect 3-bedroom boat in Key Largo for a relaxing getaway

Perfect 3-bedroom boat in Key Largo for a relaxing getaway
Key Largo
The price is CA $231
CA $332 total
includes taxes & fees
Dec 4 - Dec 5
Perfect 3-bedroom boat in Key Largo for a relaxing getaway
A compact living space with a kitchenette, a dining area with a round table, and a seating area with a blue sofa.

4. Amazing boat in the heart of key largo with hotel amenities

Amazing boat in the heart of key largo with hotel amenities
Key Largo
The price is CA $244
CA $295 total
includes taxes & fees
Nov 16 - Nov 17
Amazing boat in the heart of key largo with hotel amenities
Property grounds

5. Nature Retreat Sailboat Escape

Nature Retreat Sailboat Escape
Silver Shores
8.2 out of 10, Very good, (43 reviews)
"My family and I had a wonderful time."
United States
Carrie C.
The price is CA $397
CA $654 total
includes taxes & fees
Nov 21 - Nov 22
Nature Retreat Sailboat Escape
A boat with a covered deck, a flag, and a welcome mat.

6. Florida Keys Houseboat - Rooftop Deck, Luxury & Adventure - Walk to Dining & Fun

Florida Keys Houseboat - Rooftop Deck, Luxury & Adventure - Walk to Dining & Fun
Tavernier
9.8 out of 10, Exceptional, (220 reviews)
"Our host was amazing! Great location with lots to do! "
United States
Jamie B.
The price is CA $374
CA $625 total
includes taxes & fees
Nov 16 - Nov 17
Florida Keys Houseboat - Rooftop Deck, Luxury & Adventure - Walk to Dining & Fun
A marina with a building labeled "Sea Horse" featuring a covered deck area, railings, and a clear view of the water.

7. 1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.

1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.
Tavernier
9.6 out of 10, Exceptional, (5 reviews)
"Very clean and great stay. Would defend it again "
United States
Ryan K.
The price is CA $535
CA $648 total
includes taxes & fees
Nov 16 - Nov 17
1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.
A wooden deck with two folding chairs and a small table, overlooking a calm body of water during sunset.

8. Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (4 reviews)
"Great experience ! Will do it again"
United States
Deivys
The price is CA $1,162
CA $1,308 total
includes taxes & fees
Nov 16 - Nov 17
Premium Floating Bungalow by Stay Ombi
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 Windley Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"The room was clean and felt newly renovated. The shower door is farm slide style glass that is very heavy and difficult to use. There is not much sound insulation between the rooms. Our upstairs neighbors were very loud and were up super early which caused us to lose sleep. Not the hotels fault but annoying regardless. The location was great and very close to numerous activities and restaurants."
Robert 3-night trip
Posted 1 hour ago
Chesapeake Beach Resort

Find out more about Windley Key

Windley Key Houseboats information

Number of reviews
436
Accommodation
18 Houseboats
Lowest Price
CA $295
Highest Price
CA $1,308

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