Title: Book the Best Cow Key LUXURY Hotels - Upscale Hotels in Cow Key, FL | Expedia.ca [Cow Key Travel Guide](https://expedia.ca/Cow-Key.dx180163)[Hotels in Cow Key](https://expedia.ca/Cow-Key-Hotels.d180163.Travel-Guide-Hotels)[Vacation Rentals in Cow Key](https://expedia.ca/Cow-Key-Vacation-Rentals.d180163.Travel-Guide-VacationRentals)[Cow Key Car Rentals](https://expedia.ca/Car-Rentals-In-Cow-Key.d180163.Car-Rental-Guide)[Cow Key Vacation Packages](https://expedia.ca/Cow-Key.d180163.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/luxury.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/luxury.jpeg?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 Cow Key Luxury Hotels Tonight [Jan 30 - Jan 31](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-01-30&endDate=2026-01-31&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-01-31&endDate=2026-02-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-01-30&endDate=2026-02-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=180163&startDate=2026-02-06&endDate=2026-02-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Cow Key luxury hotels ![Marina](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/deb8b21f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/c805ef87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/948eecb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/bfe6eb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Perry Hotel & Marina Key West [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) Stock Island 9.4/10 Exceptional (1,200 reviews) "great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael CA $543 CA $696 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![4 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/cf132c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/87058123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free beach shuttle, kayaking](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/b549f4a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/314846dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parrot Key Hotel & Villas [](https://www.expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) Northside Resort 9.0/10 Wonderful (1,257 reviews) "Friendly staff, great pools" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $446 CA $579 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/f2c5f58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/0acd853b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/137c65ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/841e73b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Opal Key Resort & Marina, Key West [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) Old Town Key West 9.2/10 Wonderful (1,034 reviews) "Great location great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $644 CA $778 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cd9b522f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/200c01e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/6b2435f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/ad75486a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree Resort by Hilton Grand Key - Key West [](https://www.expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) Key West 8.2/10 Very good (1,000 reviews) "Nice place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $538 CA $651 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Oceanfront Walkout Suite - King | View from room](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62.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/1000000/20000/12400/12346/4caaa3f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/1b169515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/7df2a82d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Marina Key West, Curio Collection by Hilton [](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) Old Town Key West 8.4/10 Very good (520 reviews) "Beautiful historic hotel, room was spacious, lots of amenities, friendly staff, terrific views, can walk to town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dallas CA $761 CA $947 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Couples treatment rooms, facials, massages](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/70df70cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/1441613f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/3bfd19eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southernmost Beach Resort and Guesthouses [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) Old Town Key West 8.8/10 Excellent (3,053 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) denise CA $627 CA $804 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/b5f8742c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Train station shuttle](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/193f2662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/9a7bf2b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winslow's Bungalows - Key West Historic Inns [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) Old Town Key West 9.2/10 Wonderful (1,138 reviews) "Beautiful place, clean, friendly and good location to everywhere!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $659 CA $810 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, Ocean View](https://images.trvl-media.com/lodging/1000000/10000/1000/901/8f0e07a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, ocean views ](https://images.trvl-media.com/lodging/1000000/10000/1000/901/cd7c9771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, Ocean View | Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1000/901/c6f4724b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Key West Resort and Spa [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1,009 reviews) "Our room was clean, staff was very friendly and accommodating. The location was perfect…plan to return. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $604 CA $773 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![Private beach, scuba diving, sailing, kayaking](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/bc3021c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/2fd2eeb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/123aeac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/dc04826f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Reach Key West, Curio Collection by Hilton [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) Old Town Key West 8.6/10 Excellent (1,000 reviews) "Nice place and nice staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffery B CA $619 CA $788 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/a299c4a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/2317df22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/05980c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/fc1e65ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Key Resort - A Noble House Resort [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.Hotel-Information) Key West Historic District 9.2/10 Wonderful (1,004 reviews) "Clean room and front desk very friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer Renee CA $808 CA $1,014 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.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=2026-02-13&endDate=2026-02-14®ionId=180163&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Top Cow Key Hotel Reviews ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg) ### Winslow's Bungalows - Key West Historic Inns 10/10 Excellent "Room was neat and staff was very courteous" [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Duval House](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9_y.jpg) ### Duval House 10/10 Excellent "Clean room" [](https://expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "Cleanliness, staff and the spacious room" [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Wonderful staff. Beautiful " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "Shuttle" [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "Everything was great. " [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Overall a great experience. Pool and hot tub were amazing and the shuttle was great. Check you bill though, I was being billed for parking (I don’t have a car in FL lol)" [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg) ### Ibis Bay Beach Resort 10/10 Excellent "We had a last minute cancellation on our VRBO. Ibis Bay was able to accommodate us immediately. The staff was awesome and the room was clean." [](https://expedia.ca/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "This place exceeded our expectations!! The rooms were spacious and clean, and we somehow lucked out with incredible water and marina views from the top floor. Food at the Yellowfin restaurant was better than we could have imagined (a few delicious fish dishes, belgian waffle breakfast, and even something as simple as a chicken quesadilla was great. Great coffee and breakfast cocktail selection as well.) I will say that leading up to the resort, we had our reservations, but the resort itself was perfect for a relaxing few days. 6 heated pools, a few outside games, ample outdoor lounge chairs and cabanas for laying out, and a beautiful marina setting and full bar to cater to just about everyones needs. Shuttle is very close by and comes every hour to take you downtown to enjoy a day or night out. Staff was also very accomodating. And with a quick ten minute drive from the airport, the planes that flew over the resort was very cool touch. If you want a vacation where you can choose to have a few drinks (or not at all, as my wife is pregnant) in a very relaxing serene setting, I wouldn't sleep on this place. We would go back here again in a second!!" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ## Frequently asked questions ### Are you searching for the perfect hotel for your luxury getaway to Cow Key? ### When can I expect good weather in Cow Key? ### What's there to see and do in Cow Key? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Flamingo ](https://www.expedia.ca/Flamingo-Hotels-Adults-Only-Resorts.0-0-d553248635074842070-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Flamingo ](https://www.expedia.ca/Flamingo-Hotels-Beach-Hotel.0-0-d553248635074842070-tBeachHotel.Travel-Guide-Filter-Hotels) - 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