Title: Book the Best ADVENTURE Hotels in Sugarloaf Shores in 2025 | Expedia.ca [Flights to Summerland Key](https://expedia.ca/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.ca/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Sugarloaf Shores Car Rentals](https://expedia.ca/Car-Rentals-In-Sugarloaf-Shores.d6270983.Car-Rental-Guide)[Sugarloaf Shores Vacations](https://expedia.ca/Sugarloaf-Shores.d6270983.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498222-sugarloaf-key.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels & Resorts for Couples in Sugarloaf Shores, FL from CA $282 ![](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 Sugarloaf Shores Hotels & Resorts for Couples Tonight [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Sugarloaf Shores 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) ![Exterior](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/6492356c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37910000/37900100/37900084/49f6e3c6.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) ### Simonton Court Historic Inn & Cottages Key West Historic District 9.8/10 Exceptional (859) "Extremely kind, courteous staff and just great place to stay experiencing Key West" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bill CA $250 CA $282 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Simonton-Court-Historic-Inn-Guesthouse.h37900084.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) ![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) ![Mansion Room #106 - Ocean View w/ Direct Pool Access - Adults Only](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/4498aa15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southernmost House Old Town Key West 9.4/10 Exceptional (1000) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa Frances CA $251 CA $412 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-House-Hotel.h3830519.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/107000000/106170000/106161400/106161399/w1600h1197x0y3-686d442a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106170000/106161400/106161399/77506a7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106170000/106161400/106161399/6899b386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106170000/106161400/106161399/12e38f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HIDDEN OASIS 3 blocks from Duval Old Town Key West 9.6/10 Exceptional (94) "We absolutely loved this place! It was quaint and quiet location. It was beautifully landscaped and I loved the Hidden Oasis unit and would stay there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn W. CA $571 CA $1,208 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-HIDDEN-OASIS-3-Blocks-From-Duval.h106161399.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285348/97c2dee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285348/78a3af3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285348/af7284a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285348/9a940095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LA CASA CUBANA @ Cuban Club Suites Old Town Key West 9.6/10 Exceptional (70) "Cute, clean and perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gretchen B. CA $482 CA $976 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Key-West-Hotels-LA-CASA-CUBANA-Cuban-Club-Suites.h106285348.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) ![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) ![Breakfast, lunch, dinner served; Cuban cuisine, pool views ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/a7282e8e.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 (1746) "Great resort " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shaw Rostin CA $201 CA $315 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/73acf8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/22584e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/bea2cf35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/f620b37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Time #110 Ocean Views - Cudjoe Key Cudjoe Key 9.4/10 Exceptional (10) "Greta property, really enjoyed the water view and the bbq grill " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William B. CA $294 CA $868 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/3c8eff21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/c7065ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/5498fbd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/w2500h1666x0y1-8de3e595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Lobster Lodge - Venture Out #543 - Cudjoe Key Cudjoe Key 9.2/10 Wonderful (7) "Close to Key West. Would stay there again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) elisa b. CA $264 CA $831 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/a0a288d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/96aae30a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/d7fdd1bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/62b4ca8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key Cudjoe Key 9.0/10 Wonderful (7) "Place was perfect for our trip. Staff was super nice and helpful as well. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca G. CA $331 CA $915 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Summerland-Key-Hotels-Salty-Breeze-161-Canal-Front-Venture-Out-Home-On-Cudjoe-Key.h106911727.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/6e8a6b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/8879ca02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/88047f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/10da66f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Dockage, just minutes to Key West Cudjoe Key 9.2/10 Wonderful (155) "A beautiful stay, we plan to come back again in the future!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sabastian M. CA $210 CA $442 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/22000000/21710000/21701900/21701863/caca8733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21710000/21701900/21701863/20368b2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21710000/21701900/21701863/fb79651c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/22000000/21710000/21701900/21701863/62bd25b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking Key West 9.2/10 Wonderful (156) "Nice place to stay with washer/dryer and parking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobbi M. CA $185 CA $493 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Dog-Friendly-Sunrise-Suites-Condo-With-Pool.h21701863.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=2025-11-06&endDate=2025-11-07®ionId=6270983&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top Sugarloaf Shores Hotel Reviews ![Hampton Inn Key West FL](//images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg) ### Hampton Inn Key West FL 10/10 Excellent "Very friendly staff. Loved the shuttle to downtown Key West. Awesome place to stay!" [](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](//images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "The hotel was very clean, nice staff, the room was beautiful and comfortable " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "This hotel is beautiful. Great view from the room. Staff is amazing " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](//images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent "👍" [](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](//images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "A great place to stay!" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](//images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Shuttle was great and the staff was great" [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Blue Flamingo Resort Key West](//images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "The hotel is amazing. Rooms are super clean. Staff is rude which is sad since the hotel is really nice. " [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![The Perry Hotel & Marina Key West](//images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "We loved this hotel! For Key West the price was great, which is the main reason we chose this hotel. And then we were pleasantly surprised. The room itself was beautiful! Very spacious w/ beautiful tile on the floor & shower. The lobby was beautiful, & we loved the pool area, which is right on the beautiful marina! Definitely would stay here again if ever in Key West!" [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Beachside Resort & Residences](//images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Great!!! As advertised " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ## 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) - [Cheap Hotels in Bay Point](https://www.expedia.ca/Bay-Point-Hotels-Cheap-Hotels.0-0-d553248635976383913-tCheapHotels.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Big Coppitt Key](https://www.expedia.ca/Big-Coppitt-Key-Hotels-Beach-Hotel.0-0-d553248635975850102-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Big Coppitt Key](https://www.expedia.ca/Big-Coppitt-Key-Hotels-Cheap-Hotels.0-0-d553248635975850102-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Big Coppitt Key](https://www.expedia.ca/Big-Coppitt-Key-Hotels-Luxury-Hotel.0-0-d553248635975850102-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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