Title: Windley Key Houseboats from CA $372 | Expedia.ca [Windley Key Travel Guide](https://expedia.ca/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Vacation Rentals in Windley Key](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[Flights to Windley Key](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Windley Key Car Rentals](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[Windley Key Vacation Packages](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides) ![Theater of the Sea](https://images.trvl-media.com/place/6069249/5a39f3a2-0de6-49e9-a8f9-b4e8e17b70ba.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Houseboats in Windley Key from CA $372 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windley Key houseboats ![Exterior](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/ee0752b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/1641bbd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/17a61bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/92a650b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treasure Harbor [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) Islamorada 9.0/10 Wonderful (121) "Great spot! Will be back someday hopefully. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Diane CA $159 CA $372 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) ![55-inch Smart TV with digital channels, books](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/96d842c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/c244835e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/dc4f4949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/a7f8b8c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premium Floating Bungalow by Stay Ombi [](https://www.expedia.ca/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information) Key Largo CA $1,556 CA $1,751 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information) ![2 bedrooms, in-room safe, desk, bed sheets](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w903h683x61y0-6a8ad40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w905h683x60y0-4fee4dcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w905h683x60y0-23f3304c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w903h683x60y0-ed597f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Sanctuary Islamorada [](https://www.expedia.ca/Tavernier-Hotels-Island-Sanctuary-Islamorada.h96473229.Hotel-Information) Tavernier 9.8/10 Exceptional (13) "It exceeded our expectations, and we are so glad we found this location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenn H. CA $365 CA $554 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Tavernier-Hotels-Island-Sanctuary-Islamorada.h96473229.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105410000/105400100/105400060/09082025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105410000/105400100/105400060/109eec62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105410000/105400100/105400060/58d1ec74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/106000000/105410000/105400100/105400060/132cb1f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds. [](https://www.expedia.ca/Tavernier-Hotels-15-Bedroom.h105400060.Hotel-Information) Tavernier 10/10 Exceptional (2) "The property manager was SO nice. She made sure we were comfortable as we brought a big dog. They made sure that the boat we chose was big enough for us! This was a super fun stay. We would absolutely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah B. CA $515 CA $644 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Tavernier-Hotels-15-Bedroom.h105400060.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/895e45f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/012c4b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/1379ede6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/737e91ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures [](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Luxury-Houseboat.h32791186.Hotel-Information) Tavernier 9.8/10 Exceptional (210) "Absolutely wonderful property in every way!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher K. CA $412 CA $687 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Luxury-Houseboat.h32791186.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69980000/69971900/69971899/b95fc421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/70000000/69980000/69971900/69971899/2393760f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69980000/69971900/69971899/d748da89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/70000000/69980000/69971900/69971899/f997cbd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ??? [](https://www.expedia.ca/Key-Largo-Hotels-Vrbo-Property.h69971899.Hotel-Information) Key Largo 6.4/10 (20) "Small cozy great location, but it’s not a clean I got charged for a cleaning fee it does not look like it cleaned up " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nora A. CA $292 CA $458 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Key-Largo-Hotels-Vrbo-Property.h69971899.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2026-01-19&endDate=2026-01-20®ionId=553248635976197663&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=VILLA) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-08&d2=2026-04-08&lodging=HOUSE_BOAT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Houseboats.d553248635976197663-aaHouseboats.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Houseboats.d553248635976197663-aaHouseboats.Travel-Guide-Accommodation) ## Top Windley Key Hotel Reviews ![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg) ### Fisher Inn Resort & Marina 10/10 Excellent "Beautiful view" [](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Lovely Spacious clean accommodation" [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg) ### Creekside Inn 10/10 Excellent "It is an awesome experience with wonderful views, the location is a big advantage for this hotel" [](https://expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) ![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg) ### Drop Anchor 10/10 Excellent "The staff was personable, great location, having the bicycles and kayaks were a great touch" [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Holiday Inn Key Largo by IHG](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg) ### Holiday Inn Key Largo by IHG 10/10 Excellent "Comfortable and convenient. Enjoyed the shade of the tiki huts." [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) ![Playa Largo Resort & Spa, Autograph Collection](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg) ### Playa Largo Resort & Spa, Autograph Collection 10/10 Excellent "Courteous staff, clean, many extra like hot chocolate bar, s’mores station and coffee station. Nice stay!" [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Great staff and facility" [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ![Rock Reef Resort](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 10/10 Excellent "Cute hotel a great location for our trip through the Keys.. the room was clean and comfortable and the staff was friendly and helpful.. " [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Entire resort was clean and beautiful. Quiet location with beautiful rooms. We will return." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ## Find out more about Windley Key ## Windley Key Houseboats information | Number of reviews | 362 | | ----------------- | ------------- | | Accommodation | 26 Houseboats | | Lowest Price | CA $372 | | Highest Price | CA $1,751 | ## Explore a world of travel with Expedia - Lodging - Packages - Cars - More ways to book - [2 Star Hotels in Plantation Key ](https://www.expedia.ca/2Star-Plantation-Key-Hotels.s20-0-d553248635083898347.Travel-Guide-Filter-Hotels) - [B&B in Coopertown ](https://www.expedia.ca/Coopertown-Bed-And-Breakfast.d6177715-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Coopertown ](https://www.expedia.ca/Coopertown-Guest-Houses.d6177715-aaGuestHouses.Travel-Guide-Accommodation) - [B&B in Elliott Key ](https://www.expedia.ca/Elliott-Key-Bed-And-Breakfast.d553248621532652848-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Elliott Key ](https://www.expedia.ca/Elliott-Key-Condos.d553248621532652848-aaCondos.Travel-Guide-Accommodation) - 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