Title: Windley Key Houseboats from CA $399 | 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) ![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Houseboats in Windley Key from CA $399 - ![](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 In two weeks [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 months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-04-24&endDate=2026-04-26&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) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/17a61bb5.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) ![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 (118) "I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $208 CA $426 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.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) ![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w903h683x60y0-ed597f77.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) ![Books](https://images.trvl-media.com/lodging/97000000/96480000/96473300/96473229/w905h683x60y0-4fee4dcd.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 $363 CA $571 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Tavernier-Hotels-Island-Sanctuary-Islamorada.h96473229.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) ![Exterior](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/f15964b5.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 $1,722 CA $1,937 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.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) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105410000/105400100/105400060/7b127d76.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) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105410000/105400100/105400060/109eec62.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 $513 CA $631 total includes taxes & fees Jan 3 - Jan 4, 2026 [](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) ![Interior](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/737e91ed.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) ![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) ### 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) "Heidi has a little bit of paradise on her houseboat! You must plan on staying!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Toni M. CA $410 CA $685 total includes taxes & fees Jan 11 - Jan 12, 2026 [](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) ![Marina](https://images.trvl-media.com/lodging/70000000/69980000/69971900/69971899/f997cbd9.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) ### 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 $246 CA $399 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Key-Largo-Hotels-Vrbo-Property.h69971899.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/106000000/105190000/105186400/105186352/w1136h754x75y36-3d8ab231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105190000/105186400/105186352/w1134h840x75y31-dc8cc27e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105190000/105186400/105186352/w1142h1533x75y20-aa565e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105190000/105186400/105186352/w1136h1545x74y31-25c9c29d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing Yacht With Resort Amenities In The Heart Of Key Largo [](https://www.expedia.ca/Tavernier-Hotels-Amazing-Yacht-With-Resort-Amenities-In-The-Heart-Of-Key-Largo.h105186352.Hotel-Information) Key Largo 4.6/10 (7) "We enjoyed our very unique yacht stay! It was as advertised. Great location close to restaurants and activities! Super!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark K. CA $418 CA $576 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Tavernier-Hotels-Amazing-Yacht-With-Resort-Amenities-In-The-Heart-Of-Key-Largo.h105186352.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=2026-01-12&endDate=2026-01-13®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=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&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=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&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=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&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=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&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=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&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=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&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=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&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 location and staff is amazing. Would definitely recommend!" [](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "It was over the top amazing" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg) ### Coconut Cove Resort and Marina 10/10 Excellent "Everything was great thank you" [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Great view from the balcony. Quiet, spacious " [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.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 "Wonderful hotel. Great location Pool is amazing the staff was very friendly In all very good.. highly recommend " [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) ![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg) ### Drop Anchor 10/10 Excellent "Amazing and peaceful lady at front desk was amazing and friendly " [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Really enjoy our stay here. Love the mattress and pool. Will come back when we visit keys in the future." [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg) ### Marina Del Mar Resort and Marina 10/10 Excellent "Outstanding staff!" [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![The Pelican Key Largo Cottages](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg) ### The Pelican Key Largo Cottages 10/10 Excellent "Nice " [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ## Find out more about Windley Key ## Windley Key Houseboats information | Number of reviews | 366 | | ----------------- | ------------- | | Accommodation | 26 Houseboats | | Lowest Price | CA $399 | | Highest Price | CA $1,937 | ## 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) - 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