Title: Book the Best ROMANTIC Hotels in Winston Waterways, Key Largo from CA $145 - 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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/romantic.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Winston Waterways, Key Largo from CA $145 ![](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 [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-12&endDate=2025-10-13&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-13&endDate=2025-10-14&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-24&endDate=2025-10-26&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winston Waterways Romantic Hotels ![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) ![Suite, Kitchenette](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/5746e378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drift Hotel Key Largo 9.0/10 Wonderful (1007) "Helpful staff, clean, and a great location!" [](https://www.expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.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) ![Outdoor pool, a heated pool, open 9 AM to 9 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/b15145a5.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 Key Largo 9.0/10 Wonderful (1009) "Nice stay for one night" CA $137 CA $155 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Key-Largo-Hotels-Amoray-Resort.h5311313.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/8e763282.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) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/46aade65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Inn Key Largo Key Largo 8.6/10 Excellent (1583) "The staff was so nice and I loved the little beach/ pool area!" CA $153 CA $207 total includes taxes & fees Oct 14 - Oct 15 [](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) ![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) ![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) ![Sun loungers, beach umbrellas, beach towels, kayaking](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/ac9979c6.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 (1005) "Great place to stay!" CA $126 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/1000000/10000/5200/5114/d42f8885.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) ![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/1000000/10000/5200/5114/19311fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marina Del Mar Resort and Marina Key Largo 8.4/10 Very good (1619) "Great value. Huge room." CA $128 CA $184 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.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) ![Outdoor wedding area](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/9192d0b5.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 Key Largo 8.8/10 Excellent (1004) "Great beach and dock area. " CA $129 CA $145 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![2 outdoor pools, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/8e36d25e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/43b1d1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/b41300e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Key Largo by IHG Key Largo 8.6/10 Excellent (1014) "Excellent place to stay for a weekend " CA $189 CA $213 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) ![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) ![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) ![Private beach, white sand, sun loungers, kayaking](https://images.trvl-media.com/lodging/11000000/10980000/10977100/10977095/86543aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shore House | Garden view](https://images.trvl-media.com/lodging/11000000/10980000/10977100/10977095/7d19adb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Largo Resort Key Largo 9.4/10 Exceptional (291) "Amazing place to stay " CA $304 CA $435 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-Largo-Hotels-Largo-Resort.h10977095.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) ![Private beach, sun loungers, beach bar, kayaking](https://images.trvl-media.com/lodging/3000000/2240000/2238900/2238823/f52a88f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gilbert's Resort Key Largo 8.6/10 Excellent (1002) "great place to stay, relax but also have fun" CA $302 CA $340 total includes taxes & fees Oct 13 - Oct 14 [](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) ![Fireplace](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/f2f49899.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) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/b2a768a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Reefhouse Resort & Marina Key Largo 9.2/10 Wonderful (1312) "We had a great stay and will definitely stay here again and recommend to others. " CA $307 CA $401 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.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=2025-10-26&endDate=2025-10-27®ionId=553248635976481538&adults=2&travelerType=romantic&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 "The rooms have 2 levels. There’s living room and kitchen downstairs. The couch downstairs makes into bed and then the main bedroom is up stairs. If you have a friend that snores you can get away to another bedroom " [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.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 "The staff was so nice and I loved the little beach/ pool area!" [](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](//images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 10/10 Excellent "view was great ,service was great also" [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Playa Largo Resort & Spa, Autograph Collection](//images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg) ### Playa Largo Resort & Spa, Autograph Collection 10/10 Excellent "Staff was great, pool area was beautiful. Great Food and drink options. Very relaxing, did not need to leave the resort. Shout out to Matt the bartender who was amazing!" [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Sunset Cove Beach Resort](//images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/fe271bae_y.jpg) ### Sunset Cove Beach Resort 10/10 Excellent "First time there and it was very nice and clean. Staff was great!" [](https://expedia.ca/Key-Largo-Hotels-Sunset-Cove-Beach-Resort.h5027403.Hotel-Information) ![Creekside Inn Islamorada](//images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg) ### Creekside Inn Islamorada 10/10 Excellent "Great little place on the water. Easy access for boating. Hidden Gem. We will definitely be booking again soon. " [](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 "Bartender should be more helpful Saturday 10/4/25 Carlos was very helpful " [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.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 "quiet to relax .. this is the best place." [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.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 "Was very clean and comfortable. Staff was very friendly" [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Winston Waterways? > If you and your partner need a romantic vacation, we'd like to help you plan for it. If you want to explore the area, you might head to John Pennekamp Coral Reef State Park. If you're interested in staying near a particular destination, you can sort by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list. ### What is there to do in Winston Waterways? > There's nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all there is to see and do in Winston Waterways. 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[Boutique Hotels in Key Biscayne](https://www.expedia.ca/Key-Biscayne-Hotels-Boutique-Hotel.0-0-d8212-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Key Biscayne](https://www.expedia.ca/Key-Biscayne-Hotels-Historic-Hotel.0-0-d8212-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Key Biscayne](https://www.expedia.ca/Key-Biscayne-Hotels-Hotels-With-Childcare.0-0-d8212-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Key Biscayne](https://www.expedia.ca/Key-Biscayne-Hotels-Hotels-With-Kitchenettes.0-0-d8212-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Key Biscayne](https://www.expedia.ca/Key-Biscayne-Hotels-Hotels-With-Tennis-Courts.0-0-d8212-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Key Biscayne](https://www.expedia.ca/Key-Biscayne-Hotels-Shopping-Hotel.0-0-d8212-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Key Biscayne](https://www.expedia.ca/Key-Biscayne-Hotels-Spa-Hotel.0-0-d8212-tSpaHotel.Travel-Guide-Filter-Hotels) - 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[Pet-Friendly Hotels in Key Largo Village](https://www.expedia.ca/Key-Largo-Village-Key-Largo-Hotels-Pet-Friendly-Hotel.0-n553248635976468738-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Scuba Diving Hotels in Key Largo Village](https://www.expedia.ca/Key-Largo-Village-Key-Largo-Hotels-Scuba-Diving-Vacations.0-n553248635976468738-0-tscubadivingvacations.Travel-Guide-Filter-Hotels) - [Spa Hotels in Key Largo Village](https://www.expedia.ca/Key-Largo-Village-Key-Largo-Hotels-Spa-Hotel.0-n553248635976468738-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Key Largo Village](https://www.expedia.ca/Key-Largo-Village-Key-Largo-Hotels-Waterpark-Hotels.0-n553248635976468738-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Largo Gardens](https://www.expedia.ca/Largo-Gardens-Key-Largo-Hotels-Adults-Only-Resorts.0-n553248635976471939-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Largo Gardens](https://www.expedia.ca/Largo-Gardens-Key-Largo-Hotels-All-Inclusive-Hotel.0-n553248635976471939-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - 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