Title: Book the Best ROMANTIC Hotels in Winston Waterways, Key Largo from CA $248 - Winston Waterways Romantic Getaways | 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) ![](https://images.trvl-media.com/place/553248635976481538/ecdd89c4-e539-4429-8ffb-e8e2551fcc04.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Romantic Hotels Tonight [Feb 3 - Feb 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-02-03&endDate=2026-02-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Feb 4 - Feb 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-02-04&endDate=2026-02-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Winston Waterways romantic hotels ![Exterior](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/59d69f79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/2602f29d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/28719020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite 10 Not Pet-Friendly | Living area](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/85f959a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Cove Beach Resort [](https://www.expedia.ca/Key-Largo-Hotels-Sunset-Cove-Beach-Resort.h5027403.Hotel-Information) Key Largo 9.0/10 Wonderful (1,002 reviews) "I enjoyed staying here, very cute hotel on the beach " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emi CA $240 CA $269 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Key-Largo-Hotels-Sunset-Cove-Beach-Resort.h5027403.Hotel-Information) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/f42604af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Water view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/3997e962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront King Suite w/ Kitchen & Private Balcony](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/d0b4fd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drop Anchor [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) Islamorada 8.8/10 Excellent (1,009 reviews) "Clean room, beautiful view and loved being able to walk out to the beach. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $198 CA $270 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/c05305d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/193fd781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/09a2540f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/19311fed.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 (1,708 reviews) "Another awesome stay. Staff was very friendly and helpful, location is great and check in check out was super easy and fast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin CA $255 CA $326 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![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) ![Executive Suite, Kitchenette, Oceanfront (Accessible)](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/712986cd.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) ![Kayaking](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/a8fec8e4.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 (1,003 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $391 CA $455 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.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) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/2984df2f.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) ![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 (1,005 reviews) "Very friendly staff, clean room, great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Duane CA $221 CA $248 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/11000000/10980000/10977100/10977095/5adafa75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Grand Lodge | Living area](https://images.trvl-media.com/lodging/11000000/10980000/10977100/10977095/6076fc3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Grand Lodge | Beach/ocean view](https://images.trvl-media.com/lodging/11000000/10980000/10977100/10977095/50ab344b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/11000000/10980000/10977100/10977095/fa794c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Largo Resort [](https://www.expedia.ca/Key-Largo-Hotels-Largo-Resort.h10977095.Hotel-Information) Key Largo 9.4/10 Exceptional (298 reviews) "Alex was amazing and highly recommend for future stays. Bungalow serenity was so nice and spacious. Had some trouble with the getting the TV to work but the pool and views was stunning. A great place to get away from everyday stresses and relax. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $317 CA $447 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Key-Largo-Hotels-Largo-Resort.h10977095.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2240000/2238900/2238823/40b1f344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/3000000/2240000/2238900/2238823/4c887e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room](https://images.trvl-media.com/lodging/3000000/2240000/2238900/2238823/2c9a2986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/3000000/2240000/2238900/2238823/67274cae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gilbert's Resort [](https://www.expedia.ca/Key-Largo-Hotels-Gilberts-Resort.h2238823.Hotel-Information) Key Largo 8.6/10 Excellent (1,002 reviews) "Great place to stay for relax and have fun! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tatiana [](https://www.expedia.ca/Key-Largo-Hotels-Gilberts-Resort.h2238823.Hotel-Information) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/b2a768a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/86c2e00e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach views, serves lunch, dinner, and happy hour](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/9cf56c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Reefhouse Resort & Marina [](https://www.expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) Key Largo 9.4/10 Exceptional (1,346 reviews) "Would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $421 CA $528 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/ad31d180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/78ecf44f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier One Bedroom Waterfront Suite Bayview with Sofabed](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/8552ad16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier One Bedroom Waterfront Suite Bayview with Sofabed](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/5288c949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Inn Key Largo [](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) Key Largo 8.6/10 Excellent (1,668 reviews) "Spotless rooms, staff is so friendly and helpful! Amazing place to stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jeannie CA $214 CA $274 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/42d47c50.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) ![Beach/ocean view](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/2d6f6a20.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) ### 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 (1,003 reviews) "Nice place. Excellent location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmen CA $311 CA $394 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.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=2026-02-17&endDate=2026-02-18®ionId=553248635976481538&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Winston Waterways Hotel Reviews ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton 10/10 Excellent "Clean room and the view was spectacular " [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.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 "Friendly staff and beautiful spot " [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Our room was huge! Two floors, a bath and half and a full kitchen. Loved the view from the balcony. " [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Awesome place!!" [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.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 "The walls, doors, and baseboards could use a good scrub and maybe some fresh paint. Otherwise, it was very nice. " [](https://expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.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 "Another awesome stay. Staff was very friendly and helpful, location is great and check in check out was super easy and fast!" [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Would stay again" [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.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 rooms were very clean. And the breakfast was delicious with different options to enjoy. The staff was very welcoming and friendly. Our bed was made daily. And fresh towels were given. I would recommend this hotel if you are in the area. I will definitely come back in the future with my family." [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Bayside Inn Key Largo](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg) ### Bayside Inn Key Largo 10/10 Excellent "The location! " [](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Winston Waterways? ### What is there to do in Winston Waterways? ## 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) - [Hotels with Hot Tubs in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Hotels-With-Hot-Tubs.0-n6240961-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - 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