Title: 4 Stars Hotels in Midtown, Key West from CA $361 - Find Cheap Midtown Hotels With 4 Stars | Expedia.ca [Midtown Travel Guide](https://expedia.ca/Key-West-Midtown.dx553248635976480489)[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)[Midtown Car Rentals](https://expedia.ca/Car-Rentals-In-Midtown.d553248635976480489.Car-Rental-Guide)[Midtown Vacations](https://expedia.ca/Midtown.d553248635976480489.Destination-Travel-Guides) ![The sign says it all.](https://images.trvl-media.com/place/1187/193153ec-9280-4785-aba4-30c50138d70b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ronald Wilson # 4 Stars Hotels in Midtown, Key West from CA $361 - ![](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 Midtown 4 Star Hotels Tonight [Dec 31 - Jan 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976480489&startDate=2025-12-31&endDate=2026-01-01&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 1 - Jan 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976480489&startDate=2026-01-01&endDate=2026-01-02&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976480489&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976480489&startDate=2026-01-09&endDate=2026-01-11&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Midtown 4-star hotels ![2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/4a54e511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/dcdeb665.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/44728c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Flamingo Resort Key West [](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) New Town 8.0/10 Very good (1809) "the staff was so welcoming and nice, it was a perfect place to stay in Key West!" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Alicia CA $319 CA $436 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, beach views ](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/8f43a3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fountain](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/b4576547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/69828d6c.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 (2963) "Wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisa CA $384 CA $532 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.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) ![Sports facility](https://images.trvl-media.com/lodging/1000000/10000/1000/901/09ed2e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/1000/901/399f6b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/10000/1000/901/f89b6e1a.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 (1002) "Staff was courteous and the location is perfect for a weekend in Key West." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TIMOTHY CA $585 CA $747 total includes taxes & fees Jan 15 - Jan 16, 2026 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![6 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/0fcf571b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/15e67a67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceans Edge Key West Resort, Hotel & Marina [](https://www.expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) Stock Island 9.0/10 Wonderful (1764) "The place is great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna CA $321 CA $445 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Beach nearby, white sand](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/62b1909b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/4233d834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/5710a846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaritaville Beach House Key West [](https://www.expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) Key West 8.8/10 Excellent (1788) "Great place! I really enjoyed my time in this establishment." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elijah CA $493 CA $643 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5.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) ![49-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/4777ebf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/1fec5fac.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 (1180) "great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael CA $409 CA $545 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/3ec0a4eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/9db4ed8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King with balcony | View from room](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/024b1bb1.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 (1007) "Nice property, comfortable stay - cookies and staff are great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $339 CA $428 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![4 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/28a1790c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/99dc8f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, minibar, in-room safe, individually decorated](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/b166f8e3.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 (1217) "Excellent location, clean rooms, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vikas CA $251 CA $361 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![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) ![Room (Winslet) | Exterior](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/f458d20b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/414fe812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Truman)](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/33f2b657.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 (1098) "Clean room, quiet location, excellent staff. Breakfast and amenities were great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon CA $463 CA $591 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/7826c1a5.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/bd916166.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 (491) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ELENA CA $620 CA $779 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/aebf156d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/e0f768ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/c8d74747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Lounge](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/39a1d7db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Concha Key West, Autograph Collection [](https://www.expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) Key West Historic District 9.0/10 Wonderful (305) "The hotel was so elegant. Rooftop pool and bar had an amazing atmosphere and food. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelli CA $430 CA $530 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ![Private beach, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77.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/1000000/20000/19400/19307/f8df3f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Dockside) | Living room](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/053d9529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/d639c41f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pier House Resort & Spa [](https://www.expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1007) "All accommodations were outstanding!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bob CA $553 CA $712 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/611890d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/b515d08c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/02b8eaa6.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 (1002) "Great hotel, great beach, had a really good stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristian Mihai CA $448 CA $586 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.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/18000000/17450000/17442800/17442701/6cf9bef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/3ac97dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/acfeb5a7.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 (1017) "Our stay was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $574 CA $699 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/a383df35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Harbor View King with Balcony | View from property](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/7692f964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/e32c81ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Marker Key West Harbor Resort [](https://www.expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) Key West Historic District 9.2/10 Wonderful (1005) "Perfect location.. close to the wharf for the best dining experience." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marty CA $471 CA $616 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/a299c4a1.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) ![Suite, 1 Bedroom, Partial Harbor View](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/66a642ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/08834b0e.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 (1003) "Location, large rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) george CA $609 CA $791 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/becea015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/305f8d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/c957f1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/68402caa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Havana Cabana at Key West [](https://www.expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information) New Town 8.8/10 Excellent (1695) "Enjoyed stay, friendly staff and good shuttle bus" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul CA $313 CA $445 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/920000/911000/910922/8aacf584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/920000/911000/910922/c395702b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/1000000/920000/911000/910922/a99e5d74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury 2 bedroom Bi-level Garden View Suite | Balcony view](https://images.trvl-media.com/lodging/1000000/920000/911000/910922/5fa9c353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Santa Maria Suites [](https://www.expedia.ca/Key-West-Hotels-Santa-Maria-Suites.h910922.Hotel-Information) Old Town Key West 9.6/10 Exceptional (1001) "Awesome place we loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josh CA $669 CA $846 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Key-West-Hotels-Santa-Maria-Suites.h910922.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/4000000/3840000/3830600/3830519/853cc84c.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) ![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) ### Southernmost House [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-House-Hotel.h3830519.Hotel-Information) Old Town Key West 9.4/10 Exceptional (1002) "Great place to stay. Staff was very friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob CA $503 CA $693 total includes taxes & fees Jan 15 - Jan 16, 2026 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-House-Hotel.h3830519.Hotel-Information) ![Room 27C - Economy - Queen Bed - Adults Only 21+](https://images.trvl-media.com/lodging/104000000/103380000/103373900/103373822/976e1cc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 22 - Standard - King Bed - Adults Only 21+ | Terrace/patio](https://images.trvl-media.com/lodging/104000000/103380000/103373900/103373822/97ab2ff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 33 - Premium - King Bed - Adults Only 21+ | Terrace/patio](https://images.trvl-media.com/lodging/104000000/103380000/103373900/103373822/02978c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 26 - Premium - King Bed - Adult Only 21+ | Terrace/patio](https://images.trvl-media.com/lodging/104000000/103380000/103373900/103373822/7a34532f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bishop Hotel Key West [](https://www.expedia.ca/Key-West-Hotels-Bishop-Hotel-Key-West.h103373822.Hotel-Information) Old Town Key West 9.8/10 Exceptional (346) "This place was awesome." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven [](https://www.expedia.ca/Key-West-Hotels-Bishop-Hotel-Key-West.h103373822.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Midtown-Key-West-Hotels.s40-n553248635976480489-0.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Midtown-Key-West-Hotels.s40-n553248635976480489-0.Travel-Guide-Filter-Hotels) ## Top Midtown 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 "Excellent breakfast! Conveniently located and nice walks! Can't wait to stay there again!" [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782_y.jpg) ### Margaritaville Beach House Key West 10/10 Excellent "Many pros: friendly staff especially Levan at the bar, waitress Anita and front desk Chrissy and multiple drivers on the shuttles! Thank you again. Memorable decor. Bedroom suit layout is perfect. Location is awesome with close proximity to the beach, airport and downtown Duval St. Restaurant has good food and coffee with just enough variety to keep you coming back. Afternoon slushies were a nice touch. Beach sunrise priceless. mentionable cons: loud heavy metal doors that slam shut behind you. There should be a courtesy fee for guests to use the chairs and umbrellas at the beach. $50 a day is too expensive for 2 chairs and an umbrella especially when the pool area is crowded. Shallow Beach was clean but with little shade options. " [](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) ![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/becea015_y.jpg) ### Havana Cabana at Key West 10/10 Excellent "Great " [](https://expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.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 "Staff was amazing " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "Room was clean. Even though it’s a little bit from Duval st. There is a free shuttle. Kim is awesome. I’d stay there solely to have her shuttle us downtown." [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.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 "Everything was amazing. Staff was great and service was top notch. Weather this time of year is paradise. Only thing is bring your wallet, it ain’t cheap. " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.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 "Bed was not so great rest was" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.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 "The best " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent "We didn't know there was breakfast until this survey! How did we miss it? The pet friendliness was great. Our dog was happy about the grass out front and the availability of ice. She loves ice." 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