Title: Book the Best Beachside LUXURY Hotels - Upscale Hotels in Beachside, Key West | Expedia.ca [Beachside Travel Guide](https://expedia.ca/Key-West-Beachside.dx864982244484468736)[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)[Beachside Car Rentals](https://expedia.ca/Car-Rentals-In-Beachside.d864982244484468736.Car-Rental-Guide)[Beachside Vacations](https://expedia.ca/Beachside.d864982244484468736.Destination-Travel-Guides) ![Smathers Beach featuring tropical scenes and a sandy beach as well as a small group of people](https://images.trvl-media.com/place/6069255/1aa27092-0b99-4293-aebe-1ab333ed908a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Luxury Hotels in Beachside, Key West - ![](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 Beachside Luxury Hotels Tonight [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-12-01&endDate=2025-12-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-12-02&endDate=2025-12-03&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-12-05&endDate=2025-12-07&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-12-12&endDate=2025-12-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Beachside Luxury Hotels ## Top Beachside 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 "Would stay again. Great location and nice hotel." [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "Love this hotel ! One of my favorite here at the Keys ! Beautiful view and hotel ! " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.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 "Very clean" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "This suite was fabulous. There is nothing more to add." [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.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 "." [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.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 "Nice resort. Good food. Nice pool. Friendly staff." [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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 "Nice room. Friendly staff. Great ocean views. " [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "Excellent " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Room was very clean and staff was v" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your stay in Beachside? > Expedia can help you arrange a flight to Key West Intl. Airport (EYW) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are an important consideration when you plan a vacation, so we make it easy to find what you'd like to make your stay relaxing and comfortable. If you want a posh hotel that has a spa, an indoor pool, or luxury bedding, Expedia can help you find the best luxury hotel experience that Beachside has to offer. Beachside has some interesting things to see and do including Smathers Beach and Florida Keys Beaches, so you might want to take in the local sights during your visit. ### What's there to see and do in Beachside? > Experience Beachside with a stop at Smathers Beach, Florida Keys Beaches, and Duval Street. If you have extra time while you're in the area, you might want to see Clarence S. 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[Oceanfront Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Oceanfront-Hotels.0-n553248635976481798-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Pet-Friendly-Hotel.0-n553248635976481798-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Romantic-Hotel.0-n553248635976481798-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Shopping-Hotel.0-n553248635976481798-0-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Ski-Hotel.0-n553248635976481798-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Spa-Hotel.0-n553248635976481798-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Wedding-Hotels.0-n553248635976481798-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - 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