Title: Book the Best Winston Waterways Hotels with FREE PARKING in 2026 | Expedia.ca [Flights to Key Largo](https://expedia.ca/Cheap-Flights-To-Key-Largo.d8369.Travel-Guide-Flights)[Things to do in Key Largo](https://expedia.ca/Things-To-Do-In-Key-Largo.d8369.Travel-Guide-Activities)[Winston Waterways Car Rentals](https://expedia.ca/Car-Rentals-In-Winston-Waterways.d553248635976481538.Car-Rental-Guide)[Winston Waterways Vacations](https://expedia.ca/Winston-Waterways.d553248635976481538.Destination-Travel-Guides) ![Clearwater Beach Pier Panorama](https://images.trvl-media.com/place/553248635976481538/ecdd89c4-e539-4429-8ffb-e8e2551fcc04.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Free Parking in Winston Waterways, FL from CA $167 - ![](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 availability on Winston Waterways Hotels with Free Parking Tonight [Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-01-06&endDate=2026-01-07&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 7 - Jan 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-01-07&endDate=2026-01-08&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winston Waterways hotels with parking ![Room, 1 King Bed, Bay View | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/66659102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/d369153c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/c052003d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Key Largo Manatee Bay [](https://www.expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) Key Largo 8.8/10 Excellent (1018) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elior CA $187 CA $211 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![On the beach, sun loungers, snorkeling, kayaking](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/f3e504e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, snorkeling, kayaking](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/70c7ac71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/1508fc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/0065f64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drift Hotel [](https://www.expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.Hotel-Information) Key Largo 9.0/10 Wonderful (1011) "Yes my family had a great stay and will absolutely be returning in the future. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $197 CA $237 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/de0ac7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/9d3b800e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/9c95fe9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterside Suites & Marina [](https://www.expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) Key Largo 9.0/10 Wonderful (1186) "Clean room and staff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim CA $197 CA $261 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/9a9545cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/af88a0b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/bf4f58dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marina Del Mar Resort and Marina [](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) Key Largo 8.4/10 Very good (1685) "Wonderful place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tempie CA $141 CA $198 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/2a78a3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/e8b845d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/cb9ea3a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/3dad51c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seafarer Key Largo [](https://www.expedia.ca/Key-Largo-Hotels-Seafarer-Key-Largo.h111555855.Hotel-Information) Rock Harbor 9.4/10 Exceptional (139) "We loved this spot - nice room, extremely kind and helpful staff and great beach access. We would definetly stay here again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susie CA $184 CA $227 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Key-Largo-Hotels-Seafarer-Key-Largo.h111555855.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Cabin, 1 King Bed, Bay View](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/w1498h1001x2y0-11d0c529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/528adcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/w1485h1001x15y0-19c35a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rock Reef Resort [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) Rock Harbor 9.2/10 Wonderful (1080) "Would stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $186 CA $210 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3.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) ![Exterior](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/ee0752b0.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 [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/e12ff0a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/38a88171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/e0609cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/485a14f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amoray Dive Resort [](https://www.expedia.ca/Key-Largo-Hotels-Amoray-Resort.h5311313.Hotel-Information) Key Largo 9.2/10 Wonderful (1008) "warm pool, great clean room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heidi CA $194 CA $257 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Key-Largo-Hotels-Amoray-Resort.h5311313.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/4ac8a422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/eec761cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/340e7f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/aed267ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dove Creek Resort & Marina, Trademark Collection by Wyndham [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.Hotel-Information) Key Largo 7.6/10 Good (1008) "Amazing hotel and staff! Highly recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alisa CA $174 CA $239 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/b5cef261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, kayaking, rowing, fishing](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/a2a4b9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite | Beach/ocean view](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/ae06d5c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Pelican Key Largo Cottages [](https://www.expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) Key Largo 9.0/10 Wonderful (1009) "Very clean room, friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lani CA $148 CA $167 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.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=2026-01-20&endDate=2026-01-21®ionId=553248635976481538&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Winston Waterways 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) ![Hampton Inn Key Largo Manatee Bay](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233_y.jpg) ### Hampton Inn Key Largo Manatee Bay 10/10 Excellent "The check-in worker was very friendly and welcoming. She described the property details and offered dining options. The grounds were lovely, and we took advantage of the heated pool, Tiki bar, and enjoyed lounging by the water as the sun set. The room was clean. We also had breakfast on the day of our departure, which was good." [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Ocean Pointe Suites at Key Largo](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/c6c81bd5_y.jpg) ### Ocean Pointe Suites at Key Largo 10/10 Excellent "Very clean. Beautiful views!" [](https://expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.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) ![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) ![Drift Hotel](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/f3e504e7_y.jpg) ### Drift Hotel 10/10 Excellent "Can't wait to go back. Perfect location, clean, updated and peaceful." [](https://expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.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) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Adults-Only-Resorts.0-n6240961-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Casino Hotels in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Casino-Hotel.0-n6240961-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Couples-Resorts-Hotels.0-n6240961-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Hotel-With-Early-Check-In.0-n6240961-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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