Title: Book the Best BUSINESS Hotels in Winston Waterways in 2025 | 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) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Business Hotels in Winston Waterways, FL from CA $186 ![](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 Business Hotels Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) ## Top Winston Waterways Business Hotels ![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) ![Outdoor pool, open 8 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/c604580a.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) ![Snack bar](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/66659102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Key Largo Manatee Bay Key Largo 8.8/10 Excellent (1018) "Enjoyed our stay!!! " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Natasha CA $171 CA $193 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787.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/dd3dbaaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/46aade65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/ad31d180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Inn Key Largo Key Largo 8.6/10 Excellent (1587) "The staff was so nice and I loved the little beach/ pool area!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Cassandra CA $153 CA $207 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.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 Key Largo 7.6/10 Good (1007) "Clean room, nice bed, quiet" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmen CA $125 CA $186 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2238900/2238823/2ddd7c42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/3000000/2240000/2238900/2238823/6115fab2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/3000000/2240000/2238900/2238823/d8f0eaf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2240000/2238900/2238823/948e38a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gilbert's Resort Key Largo 8.6/10 Excellent (1004) "great place to stay, relax but also have fun" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) marianul CA $317 CA $357 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Key-Largo-Hotels-Gilberts-Resort.h2238823.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/41600/41514/bc450ed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/41600/41514/07624670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Balcony, Marina View | Living room](https://images.trvl-media.com/lodging/1000000/50000/41600/41514/63698252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Balcony, Marina View](https://images.trvl-media.com/lodging/1000000/50000/41600/41514/e464911a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Key Largo Key Largo 8.0/10 Very good (1002) "Property was nicely located and clean Would definitely book again" ![](https://a.travel-assets.com/egds/marks/flags/uk.svg) David CA $239 CA $269 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Key-Largo-Hotels-Courtyard-By-Marriott-Key-Largo.h41514.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach cabanas, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/8f8fe319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/92d23e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms, Pool Access, Bay View (Balcony/Patio, Private Pool) | Beach](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/10dd6c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Playa Largo Resort & Spa, Autograph Collection Key Largo 9.0/10 Wonderful (1013) "Very nice place to stay in the keys " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Yamilka CA $336 CA $455 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![32-inch LCD TV with satellite channels, TV, iPod dock](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/3b0a2582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/6e0cfc6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/1f0afa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton Key Largo 8.6/10 Excellent (1017) "Excellent hotel " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $405 CA $533 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/8147c88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/ca67d5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/be3c8b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coconut Cove Resort and Marina Islamorada 7.6/10 Good (825) "Staff was very friendly and accommodating and the facility was clean and quiet." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Dolores CA $194 CA $219 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.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=2025-10-31&endDate=2025-11-01®ionId=553248635976481538&adults=2&travelerType=business_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Winston Waterways Hotel Reviews ![Waterside Suites & Marina](//images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "This was right next to the departure point for Rainbow Reef's scuba diving boats, making it super easy to do a dive week without driving all over. The kitchen in the room was a nice addition as well." [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](//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 "Excellent hotel " [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Creekside Inn Islamorada](//images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg) ### Creekside Inn Islamorada 10/10 Excellent "Clean room nice " [](https://expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) ![Reefhouse Resort & Marina](//images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Very friendly staff. " [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ![The Pelican Key Largo Cottages](//images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg) ### The Pelican Key Largo Cottages 10/10 Excellent "Check in was simple! Cottage is amazing, clean and beds are super comfortable. Bonus is the view and activities available. Even though we were checking out they offered us to still use the kayaks before we left. Definitely would stay here again! " [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Bayside Inn Key Largo](//images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg) ### Bayside Inn Key Largo 10/10 Excellent "Who was the lady at the front desk?? She was such a sweet hostess! Realky appreciated her thoughtfulness and friendliness " [](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ![Hampton Inn Key Largo Manatee Bay](//images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233_y.jpg) ### Hampton Inn Key Largo Manatee Bay 10/10 Excellent "Enjoyed our stay!!! " [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Marina Del Mar Resort and Marina](//images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg) ### Marina Del Mar Resort and Marina 10/10 Excellent "Great views and ambience" [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Holiday Inn Key Largo by IHG](//images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg) ### Holiday Inn Key Largo by IHG 10/10 Excellent "Awesome trip stayed there for seven days had a blast down by the pool and the tiki hut and the iguanas are fun to watch as are the curly tail lizards no problem we had in the room was the toilet didn’t flush very well. It did flush but it was slow. The restaurant next-door within walking distance is nice pool tables and some other games and all we had a great time if you do go here make sure you go to Rob’s Marina feed the tarpon and go along the snorkeling trip to the lighthouse. You will be amazed. Happy travels." 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