Title: Hotels by Hersha Hospitality in Florida Keys from CA $388 | Expedia.ca [Florida Keys Travel Guide](https://expedia.ca/Florida-Keys.dx6023765)[Hotels in Florida Keys](https://expedia.ca/Florida-Keys-Hotels.d6023765.Travel-Guide-Hotels)[Vacation Rentals in Florida Keys](https://expedia.ca/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)[Flights to Florida Keys](https://expedia.ca/Cheap-Flights-To-Florida-Keys.d6023765.Travel-Guide-Flights)[Things to do in Florida Keys](https://expedia.ca/Things-To-Do-In-Florida-Keys.d6023765.Travel-Guide-Activities)[Florida Keys Car Rentals](https://expedia.ca/Car-Rentals-In-Florida-Keys.d6023765.Car-Rental-Guide)[Florida Keys Vacation Packages](https://expedia.ca/Florida-Keys.d6023765.Destination-Travel-Guides) ![Higgs Beach which includes a beach and tropical scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63798-Florida-Keys.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels by Hersha Hospitality in Florida Keys from CA $388 ![](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 prices for these dates Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6023765&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Florida Keys Hersha Hospitality Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/b513b652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/6ec44483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Islander Suite Ocean View Two Bedroom | Private kitchen](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/20ed25e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort Matecumbe 9.2/10 Wonderful (1009) "Staff was great at the front desk. Resort was very relaxing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Summer CA $268 CA $395 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Brand New Two King Bay Front | Private kitchen](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/4b05ab7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/641fc549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/29faa902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Villas by Islander Resort Matecumbe 8.8/10 Excellent (391) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory CA $261 CA $388 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.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=2025-11-12&endDate=2025-11-13®ionId=6023765&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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%2FFlorida-Keys-Hotels-Hersha-Hospitality.0-0-d6023765--bHershaHospitality.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FFlorida-Keys-Hotels-Hersha-Hospitality.0-0-d6023765--bHershaHospitality.Travel-Guide-Filter-Hotels) ## Top Florida Keys Hotel Reviews ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Hampton Inn Key Largo Manatee Bay](//images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233_y.jpg) ### Hampton Inn Key Largo Manatee Bay 10/10 Excellent "Lovely pool and waterfront area. Well maintained and clean." [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Old Wooden Bridge Resort and Marina](//images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/92962431_y.jpg) ### Old Wooden Bridge Resort and Marina 10/10 Excellent "We absolutely loved our stay here! I’ll be honest, when I saw the pictures online, I was a little nervous about the beds because they looked like they might be on the cheaper side… but wow, I was so wrong. The beds were unbelievably comfortable — high quality, cozy, supportive, and honestly some of the best sleep I’ve had on a trip. The whole place stayed warm and inviting. The cabin has everything you need: plenty of split units to keep the rooms cool, a full kitchen and full-size refrigerator, and the location is perfect for fishing. They even rent fishing poles and sell bait right in the office, which was super convenient. And one of my absolute favorite parts — the Key deer! They came up every night to visit. It was such a peaceful and magical experience to just sit outside and see them wandering right up near the cabin. It really made the stay feel special and memorable. The only hiccup we had was arriving at about 1:00 a.m. We were originally told we’d be in one building, but the room had been changed and we weren’t notified. It was a little stressful trying to figure out which door was ours in the middle of the night, but once we found the right cabin, everything else was perfect. Other than that hiccup, verything was greatl. We’ll 100% be staying here again the next time we’re in the Keys. This place is definitely a gem! Do be aware that you do have to climb a full set of stairs to get to the houses on stilts which are the duplexes. " [](https://expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information) ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton 10/10 Excellent "peaceful" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Rock Reef Resort](//images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 10/10 Excellent "Clean, lovely grounds, park right at room" [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Reefhouse Resort & Marina](//images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Everything including the spa was fantastic. " [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "A few problems with the room, ex. Coffee maker, sink in bathroom, shower, but over all excelent " [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Courtyard by Marriott Faro Blanco Resort](//images.trvl-media.com/lodging/11000000/10560000/10554600/10554536/962eab99_y.jpg) ### Courtyard by Marriott Faro Blanco Resort 10/10 Excellent "Great infinity pool " [](https://expedia.ca/Marathon-Hotels-Courtyard-By-Marriott-Marathon-Florida-Keys.h10554536.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 "Everything was cleaning and good working order staff was wonderful." [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Packages - More ways to book - [Hotels near Christ of the Abyss](https://www.expedia.ca/Christ-Of-The-Abyss-Hotels.0-l6069273-0.Travel-Guide-Filter-Hotels) - [Hotels near John Pennekamp Coral Reef State Park](https://www.expedia.ca/John-Pennekamp-Coral-Reef-State-Park-Hotels.0-l6068611-0.Travel-Guide-Filter-Hotels) - [John Pennekamp Coral Reef State Park](https://www.expedia.ca/John-Pennekamp-Coral-Reef-State-Park-United-States-of-America.d6068611.Vacation-Attraction) - [Book Hersha Hospitality in Florida Keys on Expedia.com](https://www.expedia.com/Florida-Keys-Hotels-Hersha-Hospitality.0-0-d6023765--bHershaHospitality.Travel-Guide-Filter-Hotels)