Title: Book the Best ADVENTURE Hotels in Historic Seaport in 2025 | Expedia.ca [Historic Seaport Travel Guide](https://expedia.ca/Key-West-Historic-Seaport.dx553248635976383502)[Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Historic Seaport Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Seaport.d553248635976383502.Car-Rental-Guide)[Historic Seaport Vacations](https://expedia.ca/Historic-Seaport.d553248635976383502.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497495-mallory-square.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels & Resorts for Couples in Historic Seaport, FL from CA $187 ![](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 Historic Seaport Hotels & Resorts for Couples Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976383502&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976383502&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976383502&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976383502&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Historic Seaport Hotels & Resorts for Couples ![King Room D | Balcony](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/350337ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room B | View from room](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/4d0697b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/6492356c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Single B | View from room](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/77670d2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simonton Court Historic Inn & Cottages Key West Historic District 9.8/10 Exceptional (855) "Extremely kind, courteous staff and just great place to stay experiencing Key West" CA $251 CA $283 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Simonton-Court-Historic-Inn-Guesthouse.h37900084.Hotel-Information) ![On the beach, beach towels](https://images.trvl-media.com/lodging/28000000/27120000/27116600/27116595/549da22e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/28000000/27120000/27116600/27116595/582baf5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27116600/27116595/1f8eb641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27120000/27116600/27116595/63bae977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Galleon Resort Efficiency in the old town Key West Historic District 9.6/10 Exceptional (153) "Overall the place was just what we were looking for!" CA $386 CA $491 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Key-West-Hotels-Galleon-Resort-Efficiency-In-The-Old-Town.h27116595.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/103000000/102250000/102246100/102246019/5e4c70a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102250000/102246100/102246019/w2499h1666x1y1-c35caef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102250000/102246100/102246019/f0faf1c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102250000/102246100/102246019/7a3d3c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom Key West Home - Perfect Location & Private Pool Key West Historic District 9.6/10 Exceptional (5) "This was a great place to stay. The house was in a perfect location, close to Duval but far enough off for a quiet night. The backyard and pool were a relaxing place to hang out for a bit as well. If we do this trip again next year I hope we can get this house." CA $841 CA $1,600 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Key-West-Hotels-3-Bedroom-Key-West-Home-With-Perfect-Location-Private-Pool.h102246019.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592682/633ff310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, stereo](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592682/4aafafd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592682/b1d84406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592682/f83fd949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Waterfront at Galion Resort in Old Town Key West Historic District 9.6/10 Exceptional (92) "Enjoyed our stay at Galleon" CA $948 CA $1,201 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Key-West-Hotels-Luxury-Waterfront-At-The-Galleon-Resort-In-Old-Town.h23592682.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/97000000/96220000/96219000/96218972/727ef598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96220000/96219000/96218972/d47627bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96219000/96218972/017afd8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/97000000/96220000/96219000/96218972/w2499h1667x1y1-d6653d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Mansion in Old Town Key West with Private Pool - Sleeps 16! Key West Historic District 9.8/10 Exceptional (236) "House was great but location was even better" CA $1,122 CA $2,312 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Key-West-Hotels-Historic-Mansion-In-Old-Town-Key-West-With-Private-Pool-Sleeps-16.h96218972.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22160000/22154400/22154384/2159bdac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/23000000/22160000/22154400/22154384/068323d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22160000/22154400/22154384/11067e91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22160000/22154400/22154384/837f0429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Galleon Resort beach hotel luxury in Old Town Key West Key West Historic District 9.8/10 Exceptional (137) "Everything was excellent! My wife and I loved our stay, both the condo and amenities were wonderful, will definitely return!" CA $836 CA $1,026 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Key-West-Hotels-Galleon-Resort-Beach-Hotel-Luxury-In-Old-Town-Key-West.h22154384.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/108000000/107910000/107901200/107901117/503b06e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107910000/107901200/107901117/007d891a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/108000000/107910000/107901200/107901117/69c6e5fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107910000/107901200/107901117/3114b6bb_edited_133b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skip the Hotel - Stay on the Water aboard a 46 foot Yacht in Key West Stock Island 10/10 Exceptional (1) "Absolutely amazing place to stay… better than we imagined! The host, Tom was fantastic and made us feel right at home. We loved the views and the amenities, Truely an awesome place to stay!" CA $16 CA $187 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Key-West-Hotels-Skip-The-Hotel-Stay-On-The-Water-Aboard-A-46-Foot-Yacht-In-Key-West.h107901117.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/1b750a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/ce6ab55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/1e98017f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, Mobility Accessible](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/ee02c68f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Havana Cabana at Key West New Town 8.8/10 Excellent (1749) "Great place to stay!" CA $178 CA $289 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information) ![Mansion Room #201 - Ocean View with private balcony - Adults Only | Terrace/patio](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/9dea706f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/f12b1e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/853cc84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/d08fe38f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southernmost House Old Town Key West 9.4/10 Exceptional (1008) "Loved this hotel so much! I really loved the atmosphere of this hotel and how close to the water you were. We will definitely be staying here again." CA $257 CA $420 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-House-Hotel.h3830519.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/1809a710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/1739e347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/967dbb83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/5cbc0ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CORTEZ ~ Adults Only, Poolview King Room at Azul Mansion! Old Town Key West 9.6/10 Exceptional (138) "Great property. Lots of thoughtful amenities. Management friendly and responsive. " CA $122 CA $328 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Key-West-Hotels-CORTEZ-Adults-Only.h57737081.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=2025-10-30&endDate=2025-10-31®ionId=553248635976383502&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Seaport Hotel Reviews ![Ridley House - Key West Historic Inns](//images.trvl-media.com/lodging/5000000/4960000/4959000/4958964/e470d82d_y.jpg) ### Ridley House - Key West Historic Inns 10/10 Excellent "Clean room, includes breakfast, 2m walking distance for everything; like restaurants, bars, stores and marinas. Highly recommended. " [](https://expedia.ca/Key-West-Hotels-Kimpton-Ridley-House.h4958964.Hotel-Information) ![Fitch Lodge - Key West Historic Inns](//images.trvl-media.com/lodging/2000000/1400000/1397700/1397643/76c68788_y.jpg) ### Fitch Lodge - Key West Historic Inns 10/10 Excellent "Clean room. Friendly. " [](https://expedia.ca/Key-West-Hotels-Kimpton-Fitch-Lodge.h1397643.Hotel-Information) ![Pier House Resort & Spa](//images.trvl-media.com/lodging/1000000/20000/19400/19307/ed076ab9_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "This was a great place. We will return. " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![The Marquesa Hotel](//images.trvl-media.com/lodging/1000000/890000/889900/889862/d2b2f582_y.jpg) ### The Marquesa Hotel 10/10 Excellent "Multiple pools in an awes garden setting. Vintage property but with modern comfort." [](https://expedia.ca/Key-West-Hotels-The-Marquesa-Hotel.h889862.Hotel-Information) ![Heron House Court - Adult Only](//images.trvl-media.com/lodging/1000000/910000/902100/902014/4d24feec_y.jpg) ### Heron House Court - Adult Only 10/10 Excellent "Very friendly " [](https://expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) ![The Marker Key West Harbor Resort](//images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3_y.jpg) ### The Marker Key West Harbor Resort 10/10 Excellent "Very nice place to stay . Great location and walking distance to a lot of places." [](https://expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) ![La Concha Key West, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/3900/3853/a3b28d11_y.jpg) ### La Concha Key West, Autograph Collection 10/10 Excellent "Awesome property , would 100% stay again. Staff was awesome. Only downside was one of the elevators wasn’t working and the room was a bit small…….. but no problem at all. Enjoyed our stay very much !!! Thanks " [](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ![Eden House](//images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/365028d8_y.jpg) ### Eden House 10/10 Excellent "Room was clean and our stay was great as it was before. " [](https://expedia.ca/Key-West-Hotels-Eden-House.h1709243.Hotel-Information) ![Ocean Key Resort - A Noble House Resort](//images.trvl-media.com/lodging/1000000/20000/16700/16682/a299c4a1_y.jpg) ### Ocean Key Resort - A Noble House Resort 10/10 Excellent "Beautiful ocean views with sunsets and great spa and pool area." 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